Startseite Visible-light-assisted base-catalyzed, one-pot synthesis of highly functionalized cinnolines
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Visible-light-assisted base-catalyzed, one-pot synthesis of highly functionalized cinnolines

  • Ahmed Elkamhawy , Laila Jaragh-Alhadad , Ramadan Ahmed Mekheimer , Omeima Abdullah , Mohamed Abd-Elmonem , Moustafa Sherief Moustafa , Afaf Abdel-Hameed , Tahany Mahmoud Mohamed und Kamal Usef Sadek EMAIL logo
Veröffentlicht/Copyright: 3. November 2023
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Green Processing and Synthesis
Aus der Zeitschrift Green Processing and Synthesis Band 12 Heft 1

Abstract

The synthesis of cinnolines has found great interest due to their diverse biological and industrial potency. Yet, the reported synthetic protocols for their synthesis showed limitations that involve harsh reaction conditions such as strong acidic or basic medium, low reaction yields, and using expensive and high loading catalysts. The C–H functionalization has been recognized as intriguing synthetic approach for the synthesis of aromatic/heteroaromatic scaffolds over the past two decades. Here, we reported a novel metal-catalyzed free photocatalytic synthesis of polyfunctionally substituted cinnolines. When ethyl 1-aryl-5-cyano-4-methyl-6-oxo-1,6-dihydropyridazine-3-carboxylates and nitrostyrene derivatives are irradiated with white light (LED 30 W) in ethanol in the presence of piperidine (30 mol%) in open air for 8 h at room temperature, the corresponding polyfunctionally substituted cinnolines are obtained in excellent yields (90–95%) via C–H activation of pyridazine methyl group and nitrostyrene (–N═O) function. Several merits were achieved, which are as follows: (1) the reaction is metal-free; (2) the reaction proceeds with increasing energy efficiency; (3) diversity of functionally substituted cinnolines; (4) high EcoScale value, which reflects the greens of the reaction; and (5) ease handling either in conducting the reaction or in the isolation of products.

Graphical abstract

Keywords: C–H functionalization; visible-light; metal-catalyst free; one-pot synthesis; polyfunctionally substituted cinnolines

1 Introduction

Nitrogen-containing heterocycles are ubiquitous in pharmaceutical and biologically active scaffolds [1,2]. In this regard, cinnoline and its derivatives as aromatic bicycles contain two adjacent nitrogen atoms in the same six-membered ring, which represent an interesting and important class of heterocycles that constitute the core structure of numerous dyes [3,4], drugs [5,6,7], natural products [8], materials [9] as well as optical [10] and luminescent reagents [11]. Also, they exemplified intriguing anti-inflammatory [12], analgesic [13], antimicrobial [14,15], antimalarial [16], and anticancer [17,18,19,20] potencies owing to their ability to interact with several molecular receptors and enzymes [21,22,23]. The examples of biologically active cinnolines are illustrated in Figure 1.

Figure 1 Examples of biologically relevant cinnolines.
Figure 1

Examples of biologically relevant cinnolines.

Cinnoline was first synthesized in 1883 by Von Richter [24] via the ring closure of in situ formed phenyldiazonium ions onto ortho alkyl function in the presence of hydrochloric or hydrobromic acid. Other classical methods were followed, involving the cyclization of aryl hydrazines [25], aryl hydrazones [26,27], triazines [28], and phenyl diazonium salts [29].

Several disadvantages were associated with these protocols involving harsh reaction conditions such as strong acidic or basic ones, elevated temperatures, as well as low reaction yields, formation of side products, and limited scope. In this regard, atom economical efficient approaches for cinnoline synthesis have been achieved via the transition metal-catalyzed methodologies.

Transition metal-catalyzed reactions have recently recognized as an efficient and reliable strategy for carbon–carbon and carbon–heteroatom bond formation [30]. In recent years, green and atom economical approaches for cinnoline synthesis have been realized using the transition metal-catalyzed conditions. A novel two-step copper-catalyzed synthesis to build this interesting scaffold was developed by Willis’s group [31] via intermolecular annulations of aryl-alkenyl dihalides and N,N-disubstituted hydrazines. Ge et al. [32] have developed appealing work for cinnoline synthesis via the aerobic copper-catalyzed dehydrogenative cyclization of N-methyl-N-phenylhydrazones. A novel cascade copper-catalyzed radical cyclization of arylsulfonylhydrazones derived from ortho-alkynyl arylketones was recently reported by Wang’s group [33] to afford the corresponding cinnolines in good yields.

A novel cross-dehydrogenative coupling reaction of N-phosphorylhydrazones using copper catalyst has been reported – for the first time – to afford the corresponding cinnoline derivatives in good to excellent yields [34]. Rh-catalyzed tandem redox-neutral annulation C–H and C–N formation has been reported by Lin’s group [35] starting from azo and diazo precursors. The process revealed a diversity of substrate scope. Very recently, Pd(ii)-catalyzed cross-dehydrogenative regioisomeric coupling of 1‑aryl-indazolones and subsequent [4 + 2] annulations using allenoate precursor was reported by Sakhuja et al. [36] to afford either internal or exocyclic double-bond cinnoline derivatives depending on the applied reaction conditions. Despite the merits of using transition metals in cinnoline synthesis, sometimes they are expensive and potentially toxic and their selectivity is difficult to be controlled.

Although these reactions have their achievements, the need for novel, greener, efficient, and atom-economical procedures using available precursors and simple reaction courses to access polyfunctionally substituted cinnolines is highly desirable.

Given the increased requests for atom-economic, green, and sustainable chemical transformations, visible-light photocatalysis are emerging strategies that can meet such demand. Such process continuously using photons as a green energy source. The inexpensive, practical nature selectivity, and ease handle of visible light to conduct chemical transformations have attracted extensive attention, and immense development was achieved in the past few years [37]. It is worth mentioning that visible light has lower energy than ultraviolet traditionally applied for photocatalysis. In recent years, the metal-free photocatalysis transformation has become one of the highly demanding strategies in chemical processes [38].

As a part of our continuing efforts to develop green and efficient methodologies for the synthesis of biologically relevant heterocycles [39–45], we report herein, for the first time, the visible light-promoted synthesis of polyfunctionally substituted cinnolines via the metal-free reaction of ethyl 1-aryl-5-cyano-4-methyl-6-oxo-1,6-dihydropyridine-2-carboxylates 3a–d with nitrostyrenes 4a–f in ethanol (EtOH) containing a catalytic amount of piperidine at room temperature (Scheme 1).

Scheme 1 Synthesis of cinnoline derivatives 5a–t.
Scheme 1 Synthesis of cinnoline derivatives 5a–t.
Scheme 1

Synthesis of cinnoline derivatives 5a–t.

2 Materials and methods

2.1 Chemistry

All chemicals and solvents were purchased from Aldrich or Merck companies. Melting points were recorded using open capillaries in a Gallenkamp melting point apparatus and are uncorrected. 1H and 13C NMR spectra were run in a Bruker (600 MHz) for 1H NMR and (150 MHz) for 13C NMR spectrometer; using dimethyl sulfoxide-d 6 as a solvent and tetramethylsilane as internal standard, and the chemical shifts are expressed in δ ppm. Mass spectra were measured on a VG Autospec-Q MS 30 with electron ionization (70 eV) mode. All reactions were monitored by thin-layer chromatography (TLC) on aluminum sheets pre-coated with silica gel and were carried out until starting materials were completely consumed. The reaction mixture was placed in open air under irradiation from white LED lamp (30 W) at room temperature. Microanalytical data were obtained from the Microanalytical Data Unit at Kuwait University.

2.2 General procedure for the synthesis of cinnoline derivatives 5a–t

Method (A) (visible light): To a suspension of 3a–d (1 mmol) and nitrostyrenes 4a–f (1 mmol) in absolute EtOH (10 mL), piperidine (30 mol%) was added. The reaction mixture was irradiated with LED white lamb (30 W) in open air for 8 h, and the reaction progress was monitored by TLC. The resulting solid product was collected by filtration, washed with EtOH, dried, and recrystallized from EtOH.

Method (B) (Conventional heating): A suspension of 3a–d (1 mmol), 4a–f (1 mmol), and piperidine (30 mol%) in absolute EtOH was heated under reflux for 3–5 h (monitored by TLC). After concentration and cooling to room temperature, the precipitated solid product was collected by filtration, washed with EtOH, dried, and recrystallized from EtOH.

3 Results and discussions

Initially, visible-light-assisted reaction of ethyl 5-cyano-4-methyl-6-oxo-1-phenyl-1,6-dihydropyridazine-3-carboxylate (3a), which prepared via the reaction of ethyl 3-oxo-2-(2-phenyl-hydrazineylidene)butanoate (1a) with ethyl cyanoacetate (2) in the presence of ammonium acetate/acetic acid and heating under microwave irradiation at 70°C for 3 min. [46], and nitrostyrene 4a was chosen as a model to optimize the reaction conditions. The reaction was conducted by reacting 1 mmol of 3a and nitrostyrene 4a in ethanol as a solvent and catalytic amount of piperidine in a system open to air. Irradiation was carried out by white LED (30 W) for 8 h. We are delighted to achieve excellent yield (95%) of the corresponding cinnoline derivative 5a (entry 16). As shown in Table 1, when several solvents including tetrahydrofuran (THF), dimethylformamide (DMF), acetonitrile (CH3CN), and dioxane, with piperidine were used as a catalyst, a lower yield was achieved (Table 1). Other bases, such as sodium carbonate (Na2Co3), sodium bicarbonate (NaHCO3), and triethylamine (Et3N), were examined, and piperidine proved to be the best catalyst, affording the best yields. No reaction occurred in the absence of basic catalyst, suggesting its involvement in some steps (entry 17). When the reaction was carried out under nitrogen or argon atmosphere, only a trace amount of 5a was detected with nitrogen; however, no product was observed in argon atmosphere, which both serve as a protective shield to prevent air oxygen, implying that the presence of O2 (air) is essential for the reaction. Besides, performing the reaction under blue or green LED lights affords no product, and the reactants were recovered almost unchanged even after exposure to light for a longer time (12 h). This could be rationalized for the energy of these photons at these wavelengths, which is insufficient to reach the threshold energy of the reaction. In order to determine the exact pathway, either thermal or photochemical, the reaction mixture was monitored by inserting thermometer in the reaction mixture. The temperature reached during light exposure did not exceed the room temperature (25°C), which ruled out the possibility of thermal reaction pathway.

Table 1

Different reaction conditions screened to get the best yield of products*

Entry Solvent Base LED (yield%) Conventional heating (yield%)
1 THF Na2CO3 65 60
2 THF NaHCO3 60 55
3 THF Et3N 70 64
4 THF Piperidine 73 68
5 DMF Na2CO3 78 73
6 DMF NaHCO3 76 72
7 DMF Et3N 80 75
8 DMF Piperidine 80 77
9 CH3CN Na2CO3 80 75
10 CH3CN NaHCO3 77 70
11 CH3CN Et3N 86 80
12 CH3CN Piperidine 89 83
13 EtOH Na2CO3 85 80
14 EtOH NaHCO3 80 75
15 EtOH Et3N 88 80
16 EtOH Piperidine 95 82
17 EtOH — NR NR
18 Dioxane Na2CO3 82 79
19 Dioxane NaHCO3 75 70
20 Dioxane Et3N 82 78
21 Dioxane Piperidine 86 80

*Optimized reaction conditions: open air and irradiation of visible light with 30 W white LED; 4-methyl-pyridazine 3a and nitrostyrene (4a), equimolar amounts, base (30 mol%), solvent (10 mL), temperature (rt, 25°C), and time (8 h).

In order to evaluate the privilege of visible-light-induced reaction, the reaction of 3a with 4a in EtOH/piperidine under conventional heating for 3–5 h was examined. The desired product 5a was obtained in lower yield (83%) than the corresponding visible-light methodology. (Table 1).

The structure of 5a was established based on its analytical and spectral data. 1H NMR revealed the absence of ethoxy (OC₂H5) pyridazine function at C-5, which showed the involvement of this group in the cyclization step, in addition to the doublet signal at δ = 2.98 ppm and the triplet signal at δ = 5.69 ppm assigned for cinnoline C-5 and C-6 protons, respectively. 13C NMR and mass spectrum were in agreement with the proposed structure (Supplementary Information). Using optimized visible light, the photocatalytic reaction variety of pyridazine derivatives 3a–d and nitrostyrenes 4a–f was screened, and the results revealed the accessibility of our protocol to achieve excellent yields irrespective of the nature of pyridazine or nitrostyrene aryl group either electron-donating or electron-attracting (Scheme 1).

After synthesizing the diversity of cinnoline derivatives, some controlled experiments were performed to clarify the mechanism. The standard reaction under dark or open-air conditions at ambient temperature was conducted, and no product was obtained even after prolonged reaction time up to 24 h, which revealed that the radical pathway is involved in the reaction course [47].

EcoScale [48] is a novel semi-quantitative tool to evaluate the greenest of a particular reaction based on yield, cost, safety, technical steps, temperature, ease of workup, and purification. It is assigned by a range of penalty points of such metrics subtracted from the total of 100 points.

The EcoScale of compound 5a has been calculated and compared with other key methods in order to evaluate the greens of our protocol. We found that our methodology has a value of 96 in terms of EcoScale, which is the highest among others (Table 2).

Table 2

Comparison of EcoScale of literature reported synthesis of cinnoline derivatives

Product Solvent Catalyst Temp (°C) Time (h) Yield (%) EcoScale
Dioxane CuI/DMEDA/K2CO3 90 18 86 77 [31]
DMF Py/CF3SO3H (3.5:01), O2 (1 atm) 110 14 96 82 [32]
DCE/CH3OH (3:1) Cu(OAc)2, (5 mol%), TBHP (3.0 equiv), K2CO3 (1.0 equiv) 40, N2 5 86 73 [33]
Toluene Cu(OAc)2.H2O 110 11 94 81 [34]
PivOH/DCE [RhCp*Cl2]2/AgSbF6 50 24 93 79 [35]
Dioxane Pd(OAc)2 (15 mol%), NaOAc (100 mol%) 100 5 87 76 [36]
Ethanol Piperidine (30 mol%) Rt 8 95 96

In order to obtain insights into the reaction mechanism, control experiment was conducted via adding 1.0 mol% of 1,4-benzoquinone inhibitor to the reaction mixture under optimized conditions. After 8 h, no product was detected, indicating that radical intermediates are involved in the product formation. It is worth to mention that in visible-light-driven catalyst-free synthesis, at least one of the starting materials can absorb the light and activates the single electron transfer pathway to generate radical substrate [49].

A plausible mechanism to account for the formation of the reaction products 5a–t is depicted in Scheme 2. First, pyridazine 3 with its active methyl function acts as a light-absorbing molecule that undergoes catalyst-free single electron transfer providing pyridazine radical I and followed by coupling of radical I with nitrostyrene 4 forming intermediate II, which abstracts hydrogen radial introducing intermediate III, which undergoes tautomerization to afford the corresponding intermediate IV. Abstraction of hydrogen proton from methylene moiety adjacent to nitro group in IV by base gives intermediate V. The latter intermediate V undergoes intramolecular cyclization via the attack of carbanion to ester carbonyl group followed by the loss of one molecule of EtOH to give the final isolable product 5.

Scheme 2 Plausible mechanism to account for the formation of the cinnoline derivatives 5a–t.
Scheme 2

Plausible mechanism to account for the formation of the cinnoline derivatives 5a–t.

4 Conclusion

We have developed a highly efficient atom economical and environmentally friendly metal-free visible-light aerobic photocatalytic one-pot synthesis of polyfunctionally substituted cinnolines in excellent yields. The method showed diverse advantages such as inexpensive and laboratory available starting materials, simple workup of the reaction, and good functional group tolerance. The use of visible light instead of thermal heating constitutes a green and trending synthesis of great interest. The mechanism to account for the formation of end product was demonstrated to go through a free radical process. Moreover, the presence of base is crucial for the final cyclization step leading to the final end product.

Acknowledgement

The authors would like to thank the Deanship of Scientific Research at Umm Al-Qura University for supporting this work by grant code (23UQU4280008DSR007).

  1. Author contributions: Ahmed Elkamhawy: validation, resources, funding acquisition, and formal analysis; Laila Jaragh-Alhadad: validation, formal analysis, investigation, and software; Ramadan Ahmed Mekheimer: writing – original draft, data curation, formal analysis, and resources; Omeima Abdullah: formal analysis, funding acquisition, validation, and resources; Mohamed Abd-Elmonem: methodology, software, data curation, and resources; Moustafa Sherief Moustafa: formal analysis, investigation, software, and resources; Afaf Abdel-Hameed: project administration, data curation, formal analysis, and resources; Tahany Mahmoud Mohamed: validation, formal analysis, and data curation; Kamal Usef Sadek: conceptualization, writing – original draft, validation, and supervision.

  2. Conflict of interest: The authors state no conflict of interest.

  3. Data availability statement: The datasets generated during and/or analyzed during the current study are available from the corresponding author on a reasonable request.

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Received: 2023-07-07
Accepted: 2023-10-01
Published Online: 2023-11-03

© 2023 the author(s), published by De Gruyter

This work is licensed under the Creative Commons Attribution 4.0 International License.

Artikel in diesem Heft

  1. Research Articles
  2. Value-added utilization of coal fly ash and recycled polyvinyl chloride in door or window sub-frame composites
  3. High removal efficiency of volatile phenol from coking wastewater using coal gasification slag via optimized adsorption and multi-grade batch process
  4. Evolution of surface morphology and properties of diamond films by hydrogen plasma etching
  5. Removal efficiency of dibenzofuran using CuZn-zeolitic imidazole frameworks as a catalyst and adsorbent
  6. Rapid and efficient microwave-assisted extraction of Caesalpinia sappan Linn. heartwood and subsequent synthesis of gold nanoparticles
  7. The catalytic characteristics of 2-methylnaphthalene acylation with AlCl3 immobilized on Hβ as Lewis acid catalyst
  8. Biodegradation of synthetic PVP biofilms using natural materials and nanoparticles
  9. Rutin-loaded selenium nanoparticles modulated the redox status, inflammatory, and apoptotic pathways associated with pentylenetetrazole-induced epilepsy in mice
  10. Optimization of apigenin nanoparticles prepared by planetary ball milling: In vitro and in vivo studies
  11. Synthesis and characterization of silver nanoparticles using Origanum onites leaves: Cytotoxic, apoptotic, and necrotic effects on Capan-1, L929, and Caco-2 cell lines
  12. Exergy analysis of a conceptual CO2 capture process with an amine-based DES
  13. Construction of fluorescence system of felodipine–tetracyanovinyl–2,2′-bipyridine complex
  14. Excellent photocatalytic degradation of rhodamine B over Bi2O3 supported on Zn-MOF nanocomposites under visible light
  15. Optimization-based control strategy for a large-scale polyhydroxyalkanoates production in a fed-batch bioreactor using a coupled PDE–ODE system
  16. Effectiveness of pH and amount of Artemia urumiana extract on physical, chemical, and biological attributes of UV-fabricated biogold nanoparticles
  17. Geranium leaf-mediated synthesis of silver nanoparticles and their transcriptomic effects on Candida albicans
  18. Synthesis, characterization, anticancer, anti-inflammatory activities, and docking studies of 3,5-disubstituted thiadiazine-2-thiones
  19. Synthesis and stability of phospholipid-encapsulated nano-selenium
  20. Putative anti-proliferative effect of Indian mustard (Brassica juncea) seed and its nano-formulation
  21. Enrichment of low-grade phosphorites by the selective leaching method
  22. Electrochemical analysis of the dissolution of gold in a copper–ethylenediamine–thiosulfate system
  23. Characterisation of carbonate lake sediments as a potential filler for polymer composites
  24. Evaluation of nano-selenium biofortification characteristics of alfalfa (Medicago sativa L.)
  25. Quality of oil extracted by cold press from Nigella sativa seeds incorporated with rosemary extracts and pretreated by microwaves
  26. Heteropolyacid-loaded MOF-derived mesoporous zirconia catalyst for chemical degradation of rhodamine B
  27. Recovery of critical metals from carbonatite-type mineral wastes: Geochemical modeling investigation of (bio)hydrometallurgical leaching of REEs
  28. Photocatalytic properties of ZnFe-mixed oxides synthesized via a simple route for water remediation
  29. Attenuation of di(2-ethylhexyl)phthalate-induced hepatic and renal toxicity by naringin nanoparticles in a rat model
  30. Novel in situ synthesis of quaternary core–shell metallic sulfide nanocomposites for degradation of organic dyes and hydrogen production
  31. Microfluidic steam-based synthesis of luminescent carbon quantum dots as sensing probes for nitrite detection
  32. Transformation of eggshell waste to egg white protein solution, calcium chloride dihydrate, and eggshell membrane powder
  33. Preparation of Zr-MOFs for the adsorption of doxycycline hydrochloride from wastewater
  34. Green nanoarchitectonics of the silver nanocrystal potential for treating malaria and their cytotoxic effects on the kidney Vero cell line
  35. Carbon emissions analysis of producing modified asphalt with natural asphalt
  36. An efficient and green synthesis of 2-phenylquinazolin-4(3H)-ones via t-BuONa-mediated oxidative condensation of 2-aminobenzamides and benzyl alcohols under solvent- and transition metal-free conditions
  37. Chitosan nanoparticles loaded with mesosulfuron methyl and mesosulfuron methyl + florasulam + MCPA isooctyl to manage weeds of wheat (Triticum aestivum L.)
  38. Synergism between lignite and high-sulfur petroleum coke in CO2 gasification
  39. Facile aqueous synthesis of ZnCuInS/ZnS–ZnS QDs with enhanced photoluminescence lifetime for selective detection of Cu(ii) ions
  40. Rapid synthesis of copper nanoparticles using Nepeta cataria leaves: An eco-friendly management of disease-causing vectors and bacterial pathogens
  41. Study on the photoelectrocatalytic activity of reduced TiO2 nanotube films for removal of methyl orange
  42. Development of a fuzzy logic model for the prediction of spark-ignition engine performance and emission for gasoline–ethanol blends
  43. Micro-impact-induced mechano-chemical synthesis of organic precursors from FeC/FeN and carbonates/nitrates in water and its extension to nucleobases
  44. Green synthesis of strontium-doped tin dioxide (SrSnO2) nanoparticles using the Mahonia bealei leaf extract and evaluation of their anticancer and antimicrobial activities
  45. A study on the larvicidal and adulticidal potential of Cladostepus spongiosus macroalgae and green-fabricated silver nanoparticles against mosquito vectors
  46. Catalysts based on nickel salt heteropolytungstates for selective oxidation of diphenyl sulfide
  47. Powerful antibacterial nanocomposites from Corallina officinalis-mediated nanometals and chitosan nanoparticles against fish-borne pathogens
  48. Removal behavior of Zn and alkalis from blast furnace dust in pre-reduction sinter process
  49. Environmentally friendly synthesis and computational studies of novel class of acridinedione integrated spirothiopyrrolizidines/indolizidines
  50. The mechanisms of inhibition and lubrication of clean fracturing flowback fluids in water-based drilling fluids
  51. Adsorption/desorption performance of cellulose membrane for Pb(ii)
  52. A one-pot, multicomponent tandem synthesis of fused polycyclic pyrrolo[3,2-c]quinolinone/pyrrolizino[2,3-c]quinolinone hybrid heterocycles via environmentally benign solid state melt reaction
  53. Green synthesis of silver nanoparticles using durian rind extract and optical characteristics of surface plasmon resonance-based optical sensor for the detection of hydrogen peroxide
  54. Electrochemical analysis of copper-EDTA-ammonia-gold thiosulfate dissolution system
  55. Characterization of bio-oil production by microwave pyrolysis from cashew nut shells and Cassia fistula pods
  56. Green synthesis methods and characterization of bacterial cellulose/silver nanoparticle composites
  57. Photocatalytic research performance of zinc oxide/graphite phase carbon nitride catalyst and its application in environment
  58. Effect of phytogenic iron nanoparticles on the bio-fortification of wheat varieties
  59. In vitro anti-cancer and antimicrobial effects of manganese oxide nanoparticles synthesized using the Glycyrrhiza uralensis leaf extract on breast cancer cell lines
  60. Preparation of Pd/Ce(F)-MCM-48 catalysts and their catalytic performance of n-heptane isomerization
  61. Green “one-pot” fluorescent bis-indolizine synthesis with whole-cell plant biocatalysis
  62. Silica-titania mesoporous silicas of MCM-41 type as effective catalysts and photocatalysts for selective oxidation of diphenyl sulfide by H2O2
  63. Biosynthesis of zinc oxide nanoparticles from molted feathers of Pavo cristatus and their antibiofilm and anticancer activities
  64. Clean preparation of rutile from Ti-containing mixed molten slag by CO2 oxidation
  65. Synthesis and characterization of Pluronic F-127-coated titanium dioxide nanoparticles synthesized from extracts of Atractylodes macrocephala leaf for antioxidant, antimicrobial, and anticancer properties
  66. Effect of pretreatment with alkali on the anaerobic digestion characteristics of kitchen waste and analysis of microbial diversity
  67. Ameliorated antimicrobial, antioxidant, and anticancer properties by Plectranthus vettiveroides root extract-mediated green synthesis of chitosan nanoparticles
  68. Microwave-accelerated pretreatment technique in green extraction of oil and bioactive compounds from camelina seeds: Effectiveness and characterization
  69. Studies on the extraction performance of phorate by aptamer-functionalized magnetic nanoparticles in plasma samples
  70. Investigation of structural properties and antibacterial activity of AgO nanoparticle extract from Solanum nigrum/Mentha leaf extracts by green synthesis method
  71. Green fabrication of chitosan from marine crustaceans and mushroom waste: Toward sustainable resource utilization
  72. Synthesis, characterization, and evaluation of nanoparticles of clodinofop propargyl and fenoxaprop-P-ethyl on weed control, growth, and yield of wheat (Triticum aestivum L.)
  73. The enhanced adsorption properties of phosphorus from aqueous solutions using lanthanum modified synthetic zeolites
  74. Separation of graphene oxides of different sizes by multi-layer dialysis and anti-friction and lubrication performance
  75. Visible-light-assisted base-catalyzed, one-pot synthesis of highly functionalized cinnolines
  76. The experimental study on the air oxidation of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid with Co–Mn–Br system
  77. Highly efficient removal of tetracycline and methyl violet 2B from aqueous solution using the bimetallic FeZn-ZIFs catalyst
  78. A thermo-tolerant cellulase enzyme produced by Bacillus amyloliquefaciens M7, an insight into synthesis, optimization, characterization, and bio-polishing activity
  79. Exploration of ketone derivatives of succinimide for their antidiabetic potential: In vitro and in vivo approaches
  80. Ultrasound-assisted green synthesis and in silico study of 6-(4-(butylamino)-6-(diethylamino)-1,3,5-triazin-2-yl)oxypyridazine derivatives
  81. A study of the anticancer potential of Pluronic F-127 encapsulated Fe2O3 nanoparticles derived from Berberis vulgaris extract
  82. Biogenic synthesis of silver nanoparticles using Consolida orientalis flowers: Identification, catalytic degradation, and biological effect
  83. Initial assessment of the presence of plastic waste in some coastal mangrove forests in Vietnam
  84. Adsorption synergy electrocatalytic degradation of phenol by active oxygen-containing species generated in Co-coal based cathode and graphite anode
  85. Antibacterial, antifungal, antioxidant, and cytotoxicity activities of the aqueous extract of Syzygium aromaticum-mediated synthesized novel silver nanoparticles
  86. Synthesis of a silica matrix with ZnO nanoparticles for the fabrication of a recyclable photodegradation system to eliminate methylene blue dye
  87. Natural polymer fillers instead of dye and pigments: Pumice and scoria in PDMS fluid and elastomer composites
  88. Study on the preparation of glycerylphosphorylcholine by transesterification under supported sodium methoxide
  89. Wireless network handheld terminal-based green ecological sustainable design evaluation system: Improved data communication and reduced packet loss rate
  90. The optimization of hydrogel strength from cassava starch using oxidized sucrose as a crosslinking agent
  91. Green synthesis of silver nanoparticles using Saccharum officinarum leaf extract for antiviral paint
  92. Study on the reliability of nano-silver-coated tin solder joints for flip chips
  93. Environmentally sustainable analytical quality by design aided RP-HPLC method for the estimation of brilliant blue in commercial food samples employing a green-ultrasound-assisted extraction technique
  94. Anticancer and antimicrobial potential of zinc/sodium alginate/polyethylene glycol/d-pinitol nanocomposites against osteosarcoma MG-63 cells
  95. Nanoporous carbon@CoFe2O4 nanocomposite as a green absorbent for the adsorptive removal of Hg(ii) from aqueous solutions
  96. Characterization of silver sulfide nanoparticles from actinobacterial strain (M10A62) and its toxicity against lepidopteran and dipterans insect species
  97. Phyto-fabrication and characterization of silver nanoparticles using Withania somnifera: Investigating antioxidant potential
  98. Effect of e-waste nanofillers on the mechanical, thermal, and wear properties of epoxy-blend sisal woven fiber-reinforced composites
  99. Magnesium nanohydroxide (2D brucite) as a host matrix for thymol and carvacrol: Synthesis, characterization, and inhibition of foodborne pathogens
  100. Synergistic inhibitive effect of a hybrid zinc oxide-benzalkonium chloride composite on the corrosion of carbon steel in a sulfuric acidic solution
  101. Review Articles
  102. Role and the importance of green approach in biosynthesis of nanopropolis and effectiveness of propolis in the treatment of COVID-19 pandemic
  103. Gum tragacanth-mediated synthesis of metal nanoparticles, characterization, and their applications as a bactericide, catalyst, antioxidant, and peroxidase mimic
  104. Green-processed nano-biocomposite (ZnO–TiO2): Potential candidates for biomedical applications
  105. Reaction mechanisms in microwave-assisted lignin depolymerisation in hydrogen-donating solvents
  106. Recent progress on non-noble metal catalysts for the deoxydehydration of biomass-derived oxygenates
  107. Rapid Communication
  108. Phosphorus removal by iron–carbon microelectrolysis: A new way to achieve phosphorus recovery
  109. Special Issue: Biomolecules-derived synthesis of nanomaterials for environmental and biological applications (Guest Editors: Arpita Roy and Fernanda Maria Policarpo Tonelli)
  110. Biomolecules-derived synthesis of nanomaterials for environmental and biological applications
  111. Nano-encapsulated tanshinone IIA in PLGA-PEG-COOH inhibits apoptosis and inflammation in cerebral ischemia/reperfusion injury
  112. Green fabrication of silver nanoparticles using Melia azedarach ripened fruit extract, their characterization, and biological properties
  113. Green-synthesized nanoparticles and their therapeutic applications: A review
  114. Antioxidant, antibacterial, and cytotoxicity potential of synthesized silver nanoparticles from the Cassia alata leaf aqueous extract
  115. Green synthesis of silver nanoparticles using Callisia fragrans leaf extract and its anticancer activity against MCF-7, HepG2, KB, LU-1, and MKN-7 cell lines
  116. Algae-based green AgNPs, AuNPs, and FeNPs as potential nanoremediators
  117. Green synthesis of Kickxia elatine-induced silver nanoparticles and their role as anti-acetylcholinesterase in the treatment of Alzheimer’s disease
  118. Phytocrystallization of silver nanoparticles using Cassia alata flower extract for effective control of fungal skin pathogens
  119. Antibacterial wound dressing with hydrogel from chitosan and polyvinyl alcohol from the red cabbage extract loaded with silver nanoparticles
  120. Leveraging of mycogenic copper oxide nanostructures for disease management of Alternaria blight of Brassica juncea
  121. Nanoscale molecular reactions in microbiological medicines in modern medical applications
  122. Synthesis and characterization of ZnO/β-cyclodextrin/nicotinic acid nanocomposite and its biological and environmental application
  123. Green synthesis of silver nanoparticles via Taxus wallichiana Zucc. plant-derived Taxol: Novel utilization as anticancer, antioxidation, anti-inflammation, and antiurolithic potential
  124. Recyclability and catalytic characteristics of copper oxide nanoparticles derived from bougainvillea plant flower extract for biomedical application
  125. Phytofabrication, characterization, and evaluation of novel bioinspired selenium–iron (Se–Fe) nanocomposites using Allium sativum extract for bio-potential applications
  126. Erratum
  127. Erratum to “Synthesis, characterization, and evaluation of nanoparticles of clodinofop propargyl and fenoxaprop-P-ethyl on weed control, growth, and yield of wheat (Triticum aestivum L.)”
https://doi.org/10.1515/gps-2023-0121
Schlagwörter für diesen Artikel
C–H functionalization; visible-light; metal-catalyst free; one-pot synthesis; polyfunctionally substituted cinnolines
Creative Commons
BY 4.0

Artikel in diesem Heft

  1. Research Articles
  2. Value-added utilization of coal fly ash and recycled polyvinyl chloride in door or window sub-frame composites
  3. High removal efficiency of volatile phenol from coking wastewater using coal gasification slag via optimized adsorption and multi-grade batch process
  4. Evolution of surface morphology and properties of diamond films by hydrogen plasma etching
  5. Removal efficiency of dibenzofuran using CuZn-zeolitic imidazole frameworks as a catalyst and adsorbent
  6. Rapid and efficient microwave-assisted extraction of Caesalpinia sappan Linn. heartwood and subsequent synthesis of gold nanoparticles
  7. The catalytic characteristics of 2-methylnaphthalene acylation with AlCl3 immobilized on Hβ as Lewis acid catalyst
  8. Biodegradation of synthetic PVP biofilms using natural materials and nanoparticles
  9. Rutin-loaded selenium nanoparticles modulated the redox status, inflammatory, and apoptotic pathways associated with pentylenetetrazole-induced epilepsy in mice
  10. Optimization of apigenin nanoparticles prepared by planetary ball milling: In vitro and in vivo studies
  11. Synthesis and characterization of silver nanoparticles using Origanum onites leaves: Cytotoxic, apoptotic, and necrotic effects on Capan-1, L929, and Caco-2 cell lines
  12. Exergy analysis of a conceptual CO2 capture process with an amine-based DES
  13. Construction of fluorescence system of felodipine–tetracyanovinyl–2,2′-bipyridine complex
  14. Excellent photocatalytic degradation of rhodamine B over Bi2O3 supported on Zn-MOF nanocomposites under visible light
  15. Optimization-based control strategy for a large-scale polyhydroxyalkanoates production in a fed-batch bioreactor using a coupled PDE–ODE system
  16. Effectiveness of pH and amount of Artemia urumiana extract on physical, chemical, and biological attributes of UV-fabricated biogold nanoparticles
  17. Geranium leaf-mediated synthesis of silver nanoparticles and their transcriptomic effects on Candida albicans
  18. Synthesis, characterization, anticancer, anti-inflammatory activities, and docking studies of 3,5-disubstituted thiadiazine-2-thiones
  19. Synthesis and stability of phospholipid-encapsulated nano-selenium
  20. Putative anti-proliferative effect of Indian mustard (Brassica juncea) seed and its nano-formulation
  21. Enrichment of low-grade phosphorites by the selective leaching method
  22. Electrochemical analysis of the dissolution of gold in a copper–ethylenediamine–thiosulfate system
  23. Characterisation of carbonate lake sediments as a potential filler for polymer composites
  24. Evaluation of nano-selenium biofortification characteristics of alfalfa (Medicago sativa L.)
  25. Quality of oil extracted by cold press from Nigella sativa seeds incorporated with rosemary extracts and pretreated by microwaves
  26. Heteropolyacid-loaded MOF-derived mesoporous zirconia catalyst for chemical degradation of rhodamine B
  27. Recovery of critical metals from carbonatite-type mineral wastes: Geochemical modeling investigation of (bio)hydrometallurgical leaching of REEs
  28. Photocatalytic properties of ZnFe-mixed oxides synthesized via a simple route for water remediation
  29. Attenuation of di(2-ethylhexyl)phthalate-induced hepatic and renal toxicity by naringin nanoparticles in a rat model
  30. Novel in situ synthesis of quaternary core–shell metallic sulfide nanocomposites for degradation of organic dyes and hydrogen production
  31. Microfluidic steam-based synthesis of luminescent carbon quantum dots as sensing probes for nitrite detection
  32. Transformation of eggshell waste to egg white protein solution, calcium chloride dihydrate, and eggshell membrane powder
  33. Preparation of Zr-MOFs for the adsorption of doxycycline hydrochloride from wastewater
  34. Green nanoarchitectonics of the silver nanocrystal potential for treating malaria and their cytotoxic effects on the kidney Vero cell line
  35. Carbon emissions analysis of producing modified asphalt with natural asphalt
  36. An efficient and green synthesis of 2-phenylquinazolin-4(3H)-ones via t-BuONa-mediated oxidative condensation of 2-aminobenzamides and benzyl alcohols under solvent- and transition metal-free conditions
  37. Chitosan nanoparticles loaded with mesosulfuron methyl and mesosulfuron methyl + florasulam + MCPA isooctyl to manage weeds of wheat (Triticum aestivum L.)
  38. Synergism between lignite and high-sulfur petroleum coke in CO2 gasification
  39. Facile aqueous synthesis of ZnCuInS/ZnS–ZnS QDs with enhanced photoluminescence lifetime for selective detection of Cu(ii) ions
  40. Rapid synthesis of copper nanoparticles using Nepeta cataria leaves: An eco-friendly management of disease-causing vectors and bacterial pathogens
  41. Study on the photoelectrocatalytic activity of reduced TiO2 nanotube films for removal of methyl orange
  42. Development of a fuzzy logic model for the prediction of spark-ignition engine performance and emission for gasoline–ethanol blends
  43. Micro-impact-induced mechano-chemical synthesis of organic precursors from FeC/FeN and carbonates/nitrates in water and its extension to nucleobases
  44. Green synthesis of strontium-doped tin dioxide (SrSnO2) nanoparticles using the Mahonia bealei leaf extract and evaluation of their anticancer and antimicrobial activities
  45. A study on the larvicidal and adulticidal potential of Cladostepus spongiosus macroalgae and green-fabricated silver nanoparticles against mosquito vectors
  46. Catalysts based on nickel salt heteropolytungstates for selective oxidation of diphenyl sulfide
  47. Powerful antibacterial nanocomposites from Corallina officinalis-mediated nanometals and chitosan nanoparticles against fish-borne pathogens
  48. Removal behavior of Zn and alkalis from blast furnace dust in pre-reduction sinter process
  49. Environmentally friendly synthesis and computational studies of novel class of acridinedione integrated spirothiopyrrolizidines/indolizidines
  50. The mechanisms of inhibition and lubrication of clean fracturing flowback fluids in water-based drilling fluids
  51. Adsorption/desorption performance of cellulose membrane for Pb(ii)
  52. A one-pot, multicomponent tandem synthesis of fused polycyclic pyrrolo[3,2-c]quinolinone/pyrrolizino[2,3-c]quinolinone hybrid heterocycles via environmentally benign solid state melt reaction
  53. Green synthesis of silver nanoparticles using durian rind extract and optical characteristics of surface plasmon resonance-based optical sensor for the detection of hydrogen peroxide
  54. Electrochemical analysis of copper-EDTA-ammonia-gold thiosulfate dissolution system
  55. Characterization of bio-oil production by microwave pyrolysis from cashew nut shells and Cassia fistula pods
  56. Green synthesis methods and characterization of bacterial cellulose/silver nanoparticle composites
  57. Photocatalytic research performance of zinc oxide/graphite phase carbon nitride catalyst and its application in environment
  58. Effect of phytogenic iron nanoparticles on the bio-fortification of wheat varieties
  59. In vitro anti-cancer and antimicrobial effects of manganese oxide nanoparticles synthesized using the Glycyrrhiza uralensis leaf extract on breast cancer cell lines
  60. Preparation of Pd/Ce(F)-MCM-48 catalysts and their catalytic performance of n-heptane isomerization
  61. Green “one-pot” fluorescent bis-indolizine synthesis with whole-cell plant biocatalysis
  62. Silica-titania mesoporous silicas of MCM-41 type as effective catalysts and photocatalysts for selective oxidation of diphenyl sulfide by H2O2
  63. Biosynthesis of zinc oxide nanoparticles from molted feathers of Pavo cristatus and their antibiofilm and anticancer activities
  64. Clean preparation of rutile from Ti-containing mixed molten slag by CO2 oxidation
  65. Synthesis and characterization of Pluronic F-127-coated titanium dioxide nanoparticles synthesized from extracts of Atractylodes macrocephala leaf for antioxidant, antimicrobial, and anticancer properties
  66. Effect of pretreatment with alkali on the anaerobic digestion characteristics of kitchen waste and analysis of microbial diversity
  67. Ameliorated antimicrobial, antioxidant, and anticancer properties by Plectranthus vettiveroides root extract-mediated green synthesis of chitosan nanoparticles
  68. Microwave-accelerated pretreatment technique in green extraction of oil and bioactive compounds from camelina seeds: Effectiveness and characterization
  69. Studies on the extraction performance of phorate by aptamer-functionalized magnetic nanoparticles in plasma samples
  70. Investigation of structural properties and antibacterial activity of AgO nanoparticle extract from Solanum nigrum/Mentha leaf extracts by green synthesis method
  71. Green fabrication of chitosan from marine crustaceans and mushroom waste: Toward sustainable resource utilization
  72. Synthesis, characterization, and evaluation of nanoparticles of clodinofop propargyl and fenoxaprop-P-ethyl on weed control, growth, and yield of wheat (Triticum aestivum L.)
  73. The enhanced adsorption properties of phosphorus from aqueous solutions using lanthanum modified synthetic zeolites
  74. Separation of graphene oxides of different sizes by multi-layer dialysis and anti-friction and lubrication performance
  75. Visible-light-assisted base-catalyzed, one-pot synthesis of highly functionalized cinnolines
  76. The experimental study on the air oxidation of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid with Co–Mn–Br system
  77. Highly efficient removal of tetracycline and methyl violet 2B from aqueous solution using the bimetallic FeZn-ZIFs catalyst
  78. A thermo-tolerant cellulase enzyme produced by Bacillus amyloliquefaciens M7, an insight into synthesis, optimization, characterization, and bio-polishing activity
  79. Exploration of ketone derivatives of succinimide for their antidiabetic potential: In vitro and in vivo approaches
  80. Ultrasound-assisted green synthesis and in silico study of 6-(4-(butylamino)-6-(diethylamino)-1,3,5-triazin-2-yl)oxypyridazine derivatives
  81. A study of the anticancer potential of Pluronic F-127 encapsulated Fe2O3 nanoparticles derived from Berberis vulgaris extract
  82. Biogenic synthesis of silver nanoparticles using Consolida orientalis flowers: Identification, catalytic degradation, and biological effect
  83. Initial assessment of the presence of plastic waste in some coastal mangrove forests in Vietnam
  84. Adsorption synergy electrocatalytic degradation of phenol by active oxygen-containing species generated in Co-coal based cathode and graphite anode
  85. Antibacterial, antifungal, antioxidant, and cytotoxicity activities of the aqueous extract of Syzygium aromaticum-mediated synthesized novel silver nanoparticles
  86. Synthesis of a silica matrix with ZnO nanoparticles for the fabrication of a recyclable photodegradation system to eliminate methylene blue dye
  87. Natural polymer fillers instead of dye and pigments: Pumice and scoria in PDMS fluid and elastomer composites
  88. Study on the preparation of glycerylphosphorylcholine by transesterification under supported sodium methoxide
  89. Wireless network handheld terminal-based green ecological sustainable design evaluation system: Improved data communication and reduced packet loss rate
  90. The optimization of hydrogel strength from cassava starch using oxidized sucrose as a crosslinking agent
  91. Green synthesis of silver nanoparticles using Saccharum officinarum leaf extract for antiviral paint
  92. Study on the reliability of nano-silver-coated tin solder joints for flip chips
  93. Environmentally sustainable analytical quality by design aided RP-HPLC method for the estimation of brilliant blue in commercial food samples employing a green-ultrasound-assisted extraction technique
  94. Anticancer and antimicrobial potential of zinc/sodium alginate/polyethylene glycol/d-pinitol nanocomposites against osteosarcoma MG-63 cells
  95. Nanoporous carbon@CoFe2O4 nanocomposite as a green absorbent for the adsorptive removal of Hg(ii) from aqueous solutions
  96. Characterization of silver sulfide nanoparticles from actinobacterial strain (M10A62) and its toxicity against lepidopteran and dipterans insect species
  97. Phyto-fabrication and characterization of silver nanoparticles using Withania somnifera: Investigating antioxidant potential
  98. Effect of e-waste nanofillers on the mechanical, thermal, and wear properties of epoxy-blend sisal woven fiber-reinforced composites
  99. Magnesium nanohydroxide (2D brucite) as a host matrix for thymol and carvacrol: Synthesis, characterization, and inhibition of foodborne pathogens
  100. Synergistic inhibitive effect of a hybrid zinc oxide-benzalkonium chloride composite on the corrosion of carbon steel in a sulfuric acidic solution
  101. Review Articles
  102. Role and the importance of green approach in biosynthesis of nanopropolis and effectiveness of propolis in the treatment of COVID-19 pandemic
  103. Gum tragacanth-mediated synthesis of metal nanoparticles, characterization, and their applications as a bactericide, catalyst, antioxidant, and peroxidase mimic
  104. Green-processed nano-biocomposite (ZnO–TiO2): Potential candidates for biomedical applications
  105. Reaction mechanisms in microwave-assisted lignin depolymerisation in hydrogen-donating solvents
  106. Recent progress on non-noble metal catalysts for the deoxydehydration of biomass-derived oxygenates
  107. Rapid Communication
  108. Phosphorus removal by iron–carbon microelectrolysis: A new way to achieve phosphorus recovery
  109. Special Issue: Biomolecules-derived synthesis of nanomaterials for environmental and biological applications (Guest Editors: Arpita Roy and Fernanda Maria Policarpo Tonelli)
  110. Biomolecules-derived synthesis of nanomaterials for environmental and biological applications
  111. Nano-encapsulated tanshinone IIA in PLGA-PEG-COOH inhibits apoptosis and inflammation in cerebral ischemia/reperfusion injury
  112. Green fabrication of silver nanoparticles using Melia azedarach ripened fruit extract, their characterization, and biological properties
  113. Green-synthesized nanoparticles and their therapeutic applications: A review
  114. Antioxidant, antibacterial, and cytotoxicity potential of synthesized silver nanoparticles from the Cassia alata leaf aqueous extract
  115. Green synthesis of silver nanoparticles using Callisia fragrans leaf extract and its anticancer activity against MCF-7, HepG2, KB, LU-1, and MKN-7 cell lines
  116. Algae-based green AgNPs, AuNPs, and FeNPs as potential nanoremediators
  117. Green synthesis of Kickxia elatine-induced silver nanoparticles and their role as anti-acetylcholinesterase in the treatment of Alzheimer’s disease
  118. Phytocrystallization of silver nanoparticles using Cassia alata flower extract for effective control of fungal skin pathogens
  119. Antibacterial wound dressing with hydrogel from chitosan and polyvinyl alcohol from the red cabbage extract loaded with silver nanoparticles
  120. Leveraging of mycogenic copper oxide nanostructures for disease management of Alternaria blight of Brassica juncea
  121. Nanoscale molecular reactions in microbiological medicines in modern medical applications
  122. Synthesis and characterization of ZnO/β-cyclodextrin/nicotinic acid nanocomposite and its biological and environmental application
  123. Green synthesis of silver nanoparticles via Taxus wallichiana Zucc. plant-derived Taxol: Novel utilization as anticancer, antioxidation, anti-inflammation, and antiurolithic potential
  124. Recyclability and catalytic characteristics of copper oxide nanoparticles derived from bougainvillea plant flower extract for biomedical application
  125. Phytofabrication, characterization, and evaluation of novel bioinspired selenium–iron (Se–Fe) nanocomposites using Allium sativum extract for bio-potential applications
  126. Erratum
  127. Erratum to “Synthesis, characterization, and evaluation of nanoparticles of clodinofop propargyl and fenoxaprop-P-ethyl on weed control, growth, and yield of wheat (Triticum aestivum L.)”
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Heruntergeladen am 3.12.2025 von https://www.degruyterbrill.com/document/doi/10.1515/gps-2023-0121/html
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