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An efficient green synthesis of novel 1H-imidazo[1,2-a]imidazole-3-amine and imidazo[2,1-c][1,2,4]triazole-5-amine derivatives via Strecker reaction under controlled microwave heating

  • Kamal Usef Sadek , Afaf Mohamed Abdel-Hameed EMAIL logo , Hisham A. Abdelnabi and Yasser Meleigy
Published/Copyright: September 27, 2018
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Green Processing and Synthesis
From the journal Green Processing and Synthesis Volume 8 Issue 1

Abstract

A highly efficient multi-component one-pot synthesis of novel 1H-imidazo[1,2-a]imidazole-3-amine and imidazo[2,1-c][1,2,4]triazole-5-amine derivatives has been developed through the reaction of easily available aromatic aldehydes, benzoyl cyanide and either 2-aminoimidazole-4,5-dicarbonitrile or 3-amino-1,2,4-triazole in pyridine under controlled microwave heating. The process is environmentally friendly, is operationally simple, with short reaction time and with high yields.

Keywords: catalyst free; imidazo [1,2-a]imidazoles; imidazo[2,1-c][1,2,4]triazoles; microwave heating; multi-component reaction; Strecker reaction

1 Introduction

Nitrogen containing heterocycles widely occur in synthetic drugs and natural products. A privileged theme of such heterocycles is the ability to act as bond donor and/or acceptor that effectively influences the medicinal scaffold and its target interaction [[1], [2], [3]. 1H-imidazo[1,2-a]imidazoles as [5+5] bicyclic guanidines exhibit a wide range of applications in fields related to pharmaceuticals and material science. Imidazo[1,2-a]imidazoles serve as lymphocyte function-associated nitrogen (LFA-1) inhibitors 4], [[5], specifically inhibiting [3H] diazepam binding 6]. In addition, guanidinium cations are extensively utilized as sensors for anion recognition [7]. Chiral imidazo[1,2-a]imidazoles act as a asymmetric catalyst in enantio-selective synthesis of α-amino nitriles and α-amino acids in Strecker reaction [8], [[9]. Very limited reported strategies for the synthesis of imidazo[1,2-a]imidazoles are known. It mainly involves the construction of a α-bicyclic scaffold starting from a monocyclic guanidine. Thus, Langer et al. 10] reported an interesting synthesis of imidazo[1,2-a]imidazoles via the [3+2] cyclization of oxaldiimidoyl chlorides and 2-aminoimidazoles in dimethylformamide (DMF) and catalytic amount of triethylamine and heating under reflux for 4 h with moderate yields (47%–77%). Aerobic oxidative intramolecular C-H amination of substituted 2(1-H-imidazol-1-yl)-N-alkyl benzene amines utilizing cupper acetate in the presence of 1,10-phenanthroline (phen) as ligand using dioxygen as an oxidant in m-xylene and heating under reflux at 155°C for 24–55 h has been recently reported by Wang et al., which afforded the target molecule with a variety of molecular diversity and excellent yields [11]. Although these methods have their specific merits, they require long reaction times, harsh reaction conditions and, sometimes, low yields.

Imidazo[2,1-c][1,2,4]triazole derivatives have received considerable interest due to their potential biological activities. For instance, they have applications as anti-inflammatory [12], antimicrobial [13], anti-fungicidal [12], [[14], [15] and analgesic agents 12]. To the best of our knowledge, few articles describe the synthesis of imidazo[2,1-c][1,2,4]triazole derivatives. The different approaches for the synthesis of such scaffold consist of construction of a bicyclic system starting from 3-amino-1,2,4-triazole. These approaches mainly involve coupling of 5-diazoimidazoles with nitro, chloro, bromo and acetyl amino malonic acid diethyl ester and subsequent cyclization of the coupling product via heating under reflux in DMF [16]. The Groebke reaction of 3-amino-1,2,4-triazole, aldehydes and aliphatic isonitriles in methanol in the presence of ammonium chloride under reflux for 15 h afforded the corresponding N-alkylidene-4-imidazotriazole-6-amine in moderate yields. Though these protocols are quite useful, they require harsh reaction conditions, use of hazardous and expensive reagents and long reaction times [17], [[18]. Although there are several reports on the utility of trimethylsilyl cyanide (TMSCN), cyanamide (NH2CN) or cyanohydrin as cyanide source of Strecker reaction, it is well documented that such reagents are toxic and hazardous. This prompted us to develop an efficient catalyst-free multi-component reaction for the synthesis of imidazo[1,2-a]imidazole-3-amine and imidazo[2,1-c][1,2,4]triazole-5-amine derivatives by the reaction of 2-aminoimidazole-4,5-dicarbonitrile 1a and 3-amino-1,2,4-triazole with aromatic aldehydes 2 and benzoyl cyanide 3 in pyridine under controlled microwave heating. The use of microwave technology has advantageous features of operational simplicity, enhanced reaction rates with short reaction times, high yields and purity of products 19].

In conjunction to our interest in performing green, general and efficient synthesis of biologically relevant heterocycles utilizing controlled microwave heating [20], [21], [22], [23], [24], we have developed convenient multi-component reaction for the synthesis of imidazo[1,2-a]imidazole-3-amine and imidazo[2,1-c][1,2,4]triazole-5-amine derivatives.

2 Materials and methods

2.1 General information

All the reactions were carried out in a Milestone START Microwave Lab Station (temperature controlled by infrared sensor). Melting points are uncorrected and were determined with a Gallenkamp instrument. 1H nuclear magnetic resonance (NMR) and 13C NMR spectra were carried out using a Bruker DPX instrument (Billerica, MA, USA) at 400 MHz for 1H NMR and 100 MHz for 13C NMR using DMSO-d6 as solvent and TMS as internal standard. Chemical shifts are expressed in δ ppm. Mass spectra were made using a GCMS DFS Thermo spectrometer with the EI (70 ev) mode. Analytical thin-layer chromatography was performed with silica gel plates using silica gel 60 PF254 (Merck). Starting materials were obtained from Aldrich (Mumbai, India) and used directly.

2.2 General procedure for the synthesis of imidazo[1,2-a]imidazole-3-amine and imidazo[2,1-c][1,2,4]triazole-5-amine derivatives (4, 5, 8, 9)

A mixture of 2-aminoimidazole-1,3-dicarbonitrile 1 or 3-amino-1,2,4-triazole 6 (1 mmol), aromatic aldehydes 2 (2 mmol) and benzoyl cyanide 3 (1 mmol) in pyridine (10 ml) was heated under reflux in a Milestone Microwave Lab Station at 120°C for 30 minutes. After concentration under reduced pressure and cooling to room temperature, addition of 10 ml H2O and acidification with HCl, the resulting solid product was collected by filtration, washed with EtOH, dried and recrystallized from appropriate solvent.

2.2.1 (E)-3-((4-methoxybenzylidene)amino)-2-(4-methoxyphenyl)-1H-imidazo[1,2-a]imidazole-5,6-dicarbonitrile (4a)

Dark yellow crystals from DMF, yield 90%, mp: 332–334°C. 1H NMR (400 MHz, DMSO-d6): δ 3.35 (s, 3H, OCH3), 3.48 (s, 3H, OCH3), 7.04–7.07 (m, 4H, Ar-H), 7.73 (d, 2H, J=8.4 Hz, Ar-H), 7.88 (d, 2H, J=8.4 Hz, Ar-H), 8.83 (d, 1H, J=14.8 Hz, arylidene CH), (NH imidazole, not seen, [25]). 13C NMR (100 MHz, DMSO-d6): δ 55.83, 56.01, 99.39, 114.92, 115.22, 128.86, 129.56, 130.68, 160.30, 162.85. Anal. Calcd. For C22H16N6O2: C, 66.66; H, 4.07; N, 21.20; Found: C, 66.71; H, 4.18; N, 21.37.

2.2.2 (E)-3-((4-chlorobenzylidene)amino)-2-(4-chlorophenyl)-1H-imidazo[1,2-a]imidazole-5,6-dicarbonitrile (4b)

Yellow crystals from DMF, yield 82%; mp: 357–359°C; 1H NMR (400 MHz, DMSO-d6): δ 7.36–7.40 (m, 4H, Ar-H), 7.50 (d, 2H, J=8.4 Hz, Ar-H), 7.76 (d, 2H, J=8.4 Hz, Ar-H), 8.57 (s, 1H, arylidene CH), 13.15 (s, 1H, imidazole NH). 13C NMR (100 MHz, DMSO-d6): δ 111.74, 113.37, 114.01, 120.50, 123.09, 124.97, 125.34, 126.74, 127.89, 128.19, 129.07, 129.22, 129.50, 129.77, 129.77, 129.3, 131.57, 134.21, 135.22, 136.96. Anal. Calcd. For C20H10Cl2N6: C, 59.28; H, 2.49; Cl, 17.50; N, 20.74; Found: C, 59.43; H, 2.61; Cl, 17.63, N, 20.89.

2.2.3 (E)-3-((3-nitrobenzylidene)amino)-2-(3-nitrophenyl)-1H-imidazo[1,2-a]imidazole-5,6-dicarbonitrile (4c)

Dark orange crystals from DMF; yield 83%; mp: 257–259°C; 1H NMR (400 MHz, DMSO-d6): δ 7.46–7.56 (m, 2H, Ar-H), 7.84 (d, 1H, J=7.6 Hz, Ar-H), 7.94 (d, 1H, J=7.2 Hz, Ar-H), 8.04 (s, 1H, Ar-H), 8.08 (d, 1H, J=8.4 Hz, Ar-H), 8.23 (d, 1H, J=8 Hz, Ar-H), 8.40 (s, 1H, Ar-H), 8.90 (d, 1H, J=14.8 Hz, arylidene CH), (NH imidazole, not seen [25]). 13C NMR (100 MHz, DMSO-d6): δ 97.18, 113.50, 114.38, 121.64, 122.37, 122.45, 124.72, 124.76, 125.67, 129.98, 130.80, 133.09, 133.31, 133.87, 138.44, 148.07, 148.63, 151.65. Anal. Calcd. For C20H10N8O4: C, 56.34; H, 2.36; N, 26.28; Found: C, 56.50; H, 2.19; N, 26.32.

2.2.4 (E)-3-((3,4-dimethoxybenzylidene)amino)-2-(3,4-dimethoxyphenyl)-1H-imidazo[1,2-a]imidazole-5,6-dicarbonitrile (4d)

Greenish yellow crystals from DMF, yield 86%; mp: 328–330°C; 1H NMR (400 MHz, DMSO-d6): δ (ppm) 3.74 (s, 3H, OCH3), 3.76 (s, 3H, OCH3), 3.79 (s, 3H, OCH3), 3.84 (s, 3H, OCH3), 6.94 (d, 1H, J=7.6 Hz, Ar-H), 7.00 (d, 1H, J=8 Hz, Ar-H), 7.16 (d, 1H, J=6.4 Hz, Ar-H), 7.29 (s, 1H, Ar-H), 7.46 (d, 1H, J=8.4 Hz, Ar-H), 7.54 (s, 1H, Ar-H), 8.64 (s, 1H, arylidene CH), 13.22 (s, 1H, imidazole NH). 13C NMR (100 MHz, DMSO-d6): δ 55.93, 56.07, 56.38, 117.10, 120.95, 121.03, 121.26, 123.52, 124.24, 126.22, 126.87, 128.14, 132.02, 132.17, 133.89, 136.91, 144.64, 153.52, 156.99, 159.70. Anal. Calcd. For C24H20N6O4: C, 63.15; H, 4.42; N, 18.41; Found: C, 63.22; H, 4.38; N, 18.29.

2.2.5 (E)-3-((2-methoxybenzylidene)amino)-2-(2-methoxyphenyl)-1H-imidazo[1,2-a]imidazole-5,6-dicarbonitrile (4e)

Bright yellow crystals from DMF, yield 58%; mp: 298–300°C; 1H NMR (400 MHz, DMSO-d6): δ 3.74 (s, 3H, OCH3), 3.78 (s, 3H, OCH3), 7.01–7.96 (m, 8H, Ar-H), 8.67 (s, 1H, arylidene CH), 13.17 (s, 1H, imidazole NH); 13C NMR (100 MHz, DMSO-d6): δ 56.10, 56.35, 112.48, 113.10, 114.13, 117.07, 121.05, 121.25, 123.42, 124.34, 126.79, 128.14, 132.04, 132.17, 133.98, 136.90, 144.62, 153.49, 157.01, 159.64. Anal. Calcd. For C22H16N6O2: C, 66.66; H, 4.07; N, 21.20; Found: C, 66.57; H, 3.97; N, 21.06.

2.2.6 3-Amino-2-phenyl-1H-imidazo[1,2-a]imidazole-5,6-dicarbonitrile (5)

Light purple from DMF, yield 84%; mp: 282–284°C; 1H NMR (400 MHz, DMSO-d6): δ 7.54–8.06 (m, 5H, Ar-H), (NH2, not seen [25]), 12.34 (s, 1H, imidazole NH).13C NMR (100 MHz, DMSO-d6): δ 111.70, 128.67, 128.79, 129.08, 132.34, 133.39, 145.15, 150.12, 166.36. Anal. Calcd. For C13H8N6: C, 62.90; H, 3.25; N, 33.85; Found: C, 62.71; H, 3.17; N, 33.97.

2.2.7 6–(4-Methoxyphenyl)-7H-imidazo[2,1-c][1,2,4]triazole-5-amine (8a)

Yellow crystals from ethanol; yield 82%; mp: 282–285°C; 1H NMR (400 MHz, DMSO-d6): δ 3.86 (s, 3H, OCH3), 7.02–7.12 (m, 3H, Ar-H), 7.39–7.60 (m, 3H, 1 ArH, 2H NH2), 7.61 (s, 1H, triazole), 8.04 (brs, 1H, imidazole NH). 13C NMR (100 MHz, DMSO-d6): δ 55.83, 111.40, 119.51, 120.59, 122.47, 128.06, 130.46, 150.03, 156.13. MS: m/z (%) 229 (M+) (45), 198 (25), 171 (85), 146 (100), 116 (44), 91 (30), 71 (12). Anal. Calcd. For C11H11N5O: C, 57.63; H, 4.84; N, 30.55; Found: C, 57.75; H, 4.76; N, 30.36.

2.2.8 (E)-N-(4-chlorobenzylidene)-6-(4-chlorophenyl)-7H-imidazo[2,1-c][1,2,4]triazol-5-amine (9b)

Yellow crystals from ethanol; yield 80%; mp: 212–214°C; 1H NMR (400 MHz, DMSO-d6): δ 7.58–7.63 (m, 5H, Ar-H), 7.95–7.97 (m, 2H, ArH), 8.12–8.14 (m, 3H, 1 ArH, 1H arylidene, 1H triazole), 9.45 (s, 1H, imidazole NH). 13C NMR (100 MHz, DMSO-d6): δ 120.08, 120.18, 129.28, 129.30, 129.63, 130.18, 133.40, 136.16, 139.04, 141.13, 146.03, 150.16, 152.14. MS: m/z (%) 356 (M+1, 65), 355 (M+, 100), 328 (28), 191 (18), 156 (43), 138 (55), 111 (18), 89 (15), 75 (12). Anal. Calcd. For C17H11Cl2N5: C, 57.32, H, 3.11, Cl, 19.91, N, 19.66; Found: C, 57.40, H, 3.20, Cl, 19.86, N, 19.57.

2.2.9 (E)-N-(3-nitrobenzylidene)-6-(3-nitrophenyl)-7H-imidazo[2,1-c][1,2,4]triazol-5-amine (9c)

Yellowish crystals from ethanol; yield 84%; mp: 252–254°C; 1H NMR (400 MHz, DMSO-d6): δ 7.67–8.74 (m, 10H, 8 Ar-H, 1 arylidene, 1H triazole), 9.30 (s, 1H, imidazole NH). 13C NMR (100 MHz, DMSO-d6): δ 126.29, 126.62, 129.39, 129.55, 129.59, 130.25, 130.45, 130.49, 131.01, 131.53, 132.04, 132.19, 143.28, 143.34, 143.39, 147.57, 147.62. MS: m/z (%) 377 (M+, 22), 314 (15), 300 (30), 286 (10), 241 (5), 213 (5), 163 (7), 135 (35), 121 (100), 93 (15), 76 (20). Anal. Calcd. For C17H11N7O4: C, 54.11, H, 2.94, N, 25.99; Found: C, 54.32, H, 3.01, N, 26.12.

2.2.10 (E)-N-benzylidene-6-phenyl-7H-imidazo[2,1-c][1,2,4]triazol-5-amine (9f)

Yellow crystals from ethanol; yield 85%; mp: 262–264°C; 1H NMR (400 MHz, DMSO-d6): δ 7.50–7.53 (m, 4H, Ar-H), 7.56–7.61 (m, 4H, Ar-H), 7.70–7.72 (m, 2H, Ar-H), 7.96 (s, 1H arylidene), 7.99 (s, 1H triazole), 8.21 (brs, 1H, imidazole NH). 13C NMR (100 MHz, DMSO-d6): δ 119.43, 128.70, 129.17, 129.64, 130.83, 131.17, 131.66, 133.26, 134.36, 140.60, 142.85, 152.66, 162.34. MS: m/z (%) 287 (M+, 28), 185 (16), 171 (12), 129 (42), 83 (46), 73 (92), 57 (100). Anal. Calcd. For C17H13N5: C, 71.06, H, 4.56, N, 24.37; Found: C, 71.18, H, 4.63, N, 24.50.

3 Results and discussion

With the initial aim of optimizing the reaction conditions, we explored the reaction of equimolar amounts of 1, 2a and 3 in ethanol in the presence of three drops of piperidine, and the reaction was promoted by microwave heating at 70°C over 30 minutes. The process led to the formation of a low yield (35%) of the reaction product 4a. Pyridine was also examined and found to be convenient for such reaction, and higher yields were obtained. The structure of 4a could be established based on analytical and spectral data. 1H NMR showed arylidine CH at δ=8.83 ppm (J=14.8 Hz, which is characteristic for E configuration), aromatic protons and two methoxy functions. 13C NMR spectrum was in support of the proposed structure. We noticed that the yield was increased to 90% when two equivalents of aldehyde 2a were utilized. Similarly multi-component reaction of 1 two equivalents of 2b–e and 3 under the same reaction conditions afforded 4b–e in excellent yields. However, the reactions of 1a, 2f and 3 afford 5 without further condensation with another molecule of aldehyde 2f. The proposed structures for the reaction products were established on spectral and analytical data (Scheme 1).

Scheme 1: Synthesis of imidazo[1,2-a]imidazole derivatives.
Scheme 1:

Synthesis of imidazo[1,2-a]imidazole derivatives.

The same reaction protocol was applied to the reaction of 3-amino-1,2,4-triazole 6 with aromatic aldehyde 2b and benzoyl cyanide 3 (Scheme 2). A product 9b of molecular formula was obtained, which showed M+ 355 (100%). 1H NMR spectra of the product showed signals for aromatic protons, arylidene CH as well as imidazole NH at δ=9.45 ppm. Structure 9b was established for the reaction product via formation of the corresponding imidazo[2,1-c][1,2,4]triazole and subsequent reaction of another molecule of aldehyde 2b. The energy difference for 6a,b was computed and found to be 4.2 kcal/mol in favor of 6b [26]. Moreover, the NH group of 6b renders more nucleophilic than the NH group of 6a due to the presence of adjacent electron-withdrawing endocyclic nitrogen atom. In addition, the regioselectivity for the reaction of 3-amino-1,2,4-triazole with nucleophilic reagents has been reported to be solvent dependent. It includes the initial reaction with exocyclic amino function and subsequent cyclization with endocyclic NH of 6a in acidic medium or NH of 6b in protic or basic medium [25]. This ruled out the possible formation of 7 and its subsequent reaction with another molecule of 2b. If the reaction product was 7, the imidazole NH will appear at downfield shift (≈12.43 ppm) [27], [28]. Similarly, compound 6b reacted with 2a,c,f to afford the corresponding 8a and 9b,c,f.

Scheme 2: Synthesis of imidazo[2,1-c][1,2,4]triazole derivatives.
Scheme 2:

Synthesis of imidazo[2,1-c][1,2,4]triazole derivatives.

A proposed mechanism for the formation of the reaction products displayed involves the formation of Schiff base 10 from the reaction of 2-aminoimidazole -1,3-dicarbonitriles 1 or 3-amino-1,2,4 triazole 6 with aromatic aldehydes and subsequent Strecker reaction with benzoyl cyanide to afford the corresponding aminonitrile 11. Attack of the imidazole or triazole ring nitrogen ion pair to the CN function would result in the formation of the bicyclic imine product 12. 1,3-Proton shift followed by aromatization led to the formation of the corresponding imidazo[1,2-b]imidazole-3-amine 5 or imidazo[2,1-c]-1,2,4-triazole -5-amine 8. Further reaction with another molecule of aldehyde 2 affords the corresponding N-arylidine derivatives 4 and 9. The enhancement of the reaction under microwave heating can be rationalized based on medium effects and mechanistic effects. As a result of the material-wave interaction, the greater the polarity of a molecule of either the solvent or reactant with the rise of temperature resulted in a more pronounced microwave effect. Concerning mechanistic effects, when the polarity is increased during the reaction proceeding from the ground state to the transition state leading to intermediates 10, 11, stabilization of such transition will decrease the activation energy and reactivity will be enhanced (Scheme 3).

Scheme 3: Proposed mechanism for the formation of imidazo[1,2-a]imidazole derivatives and imidazo[2,1-c][1,2,4]triazole derivatives.
Scheme 3:

Proposed mechanism for the formation of imidazo[1,2-a]imidazole derivatives and imidazo[2,1-c][1,2,4]triazole derivatives.

4 Conclusion

In conclusion, we have developed a convenient synthesis of novel imidazo[1,2-a]imidazole-3-amine and imidazo[2,1-c][1,2,4]triazole-5-amine derivatives from three component reactions of 2-aminoimidazole-1,3- dicarbonitril or 3-amino-1,2,4-triazole with aromatic aldehyde and benzoyl cyanide in pyridine under controlled microwave heating. The process proved to be a simple, green and efficient methodology for the synthesis of target molecules. To the best of our knowledge, very limited methodologies for the synthesis of these scaffolds have been reported in the literature.

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Received: 2018-05-12
Accepted: 2018-08-06
Published Online: 2018-09-27
Published in Print: 2019-01-28

©2019 Walter de Gruyter GmbH, Berlin/Boston

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

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  4. Reduction of free fatty acids in waste oil for biodiesel production by glycerolysis: investigation and optimization of process parameters
  5. Saccharin: a cheap and mild acidic agent for the synthesis of azo dyes via telescoped dediazotization
  6. Optimization of lipase-catalyzed synthesis of polyethylene glycol stearate in a solvent-free system
  7. Green synthesis of iron oxide nanoparticles using Platanus orientalis leaf extract for antifungal activity
  8. Ultrasound assisted chemical activation of peanut husk for copper removal
  9. Room temperature silanization of Fe3O4 for the preparation of phenyl functionalized magnetic adsorbent for dispersive solid phase extraction for the extraction of phthalates in water
  10. Evaluation of the saponin green extraction from Ziziphus spina-christi leaves using hydrothermal, microwave and Bain-Marie water bath heating methods
  11. Oxidation of dibenzothiophene using the heterogeneous catalyst of tungsten-based carbon nanotubes
  12. Calcined sodium silicate as an efficient and benign heterogeneous catalyst for the transesterification of natural lecithin to L-α-glycerophosphocholine
  13. Synergistic effect between CO2 and H2O2 on ethylbenzene oxidation catalyzed by carbon supported heteropolyanion catalysts
  14. Hydrocyanation of 2-arylmethyleneindan-1,3-diones using potassium hexacyanoferrate(II) as a nontoxic cyanating agent
  15. Green synthesis of hydratropic aldehyde from α-methylstyrene catalyzed by Al2O3-supported metal phthalocyanines
  16. Environmentally benign chemical recycling of polycarbonate wastes: comparison of micro- and nano-TiO2 solid support efficiencies
  17. Medicago polymorpha-mediated antibacterial silver nanoparticles in the reduction of methyl orange
  18. Production of value-added chemicals from esterification of waste glycerol over MCM-41 supported catalysts
  19. Green synthesis of zerovalent copper nanoparticles for efficient reduction of toxic azo dyes congo red and methyl orange
  20. Optimization of the biological synthesis of silver nanoparticles using Penicillium oxalicum GRS-1 and their antimicrobial effects against common food-borne pathogens
  21. Optimization of submerged fermentation conditions to overproduce bioethanol using two industrial and traditional Saccharomyces cerevisiae strains
  22. Extraction of In3+ and Fe3+ from sulfate solutions by using a 3D-printed “Y”-shaped microreactor
  23. Foliar-mediated Ag:ZnO nanophotocatalysts: green synthesis, characterization, pollutants degradation, and in vitro biocidal activity
  24. Green cyclic acetals production by glycerol etherification reaction with benzaldehyde using cationic acidic resin
  25. Biosynthesis, characterization and antimicrobial activities assessment of fabricated selenium nanoparticles using Pelargonium zonale leaf extract
  26. Synthesis of high surface area magnesia by using walnut shell as a template
  27. Controllable biosynthesis of silver nanoparticles using actinobacterial strains
  28. Green vegetation: a promising source of color dyes
  29. Mechano-chemical synthesis of ammonia and acetic acid from inorganic materials in water
  30. Green synthesis and structural characterization of novel N1-substituted 3,4-dihydropyrimidin-2(1H)-ones
  31. Biodiesel production from cotton oil using heterogeneous CaO catalysts from eggshells prepared at different calcination temperatures
  32. Regeneration of spent mercury catalyst for the treatment of dye wastewater by the microwave and ultrasonic spray-assisted method
  33. Green synthesis of the innovative super paramagnetic nanoparticles from the leaves extract of Fraxinus chinensis Roxb and their application for the decolourisation of toxic dyes
  34. Biogenic ZnO nanoparticles: a study of blueshift of optical band gap and photocatalytic degradation of reactive yellow 186 dye under direct sunlight
  35. Leached compounds from the extracts of pomegranate peel, green coconut shell, and karuvelam wood for the removal of hexavalent chromium
  36. Enhancement of molecular weight reduction of natural rubber in triphasic CO2/toluene/H2O systems with hydrogen peroxide for preparation of biobased polyurethanes
  37. An efficient green synthesis of novel 1H-imidazo[1,2-a]imidazole-3-amine and imidazo[2,1-c][1,2,4]triazole-5-amine derivatives via Strecker reaction under controlled microwave heating
  38. Evaluation of three different green fabrication methods for the synthesis of crystalline ZnO nanoparticles using Pelargonium zonale leaf extract
  39. A highly efficient and multifunctional biomass supporting Ag, Ni, and Cu nanoparticles through wetness impregnation for environmental remediation
  40. Simple one-pot green method for large-scale production of mesalamine, an anti-inflammatory agent
  41. Relationships between step and cumulative PMI and E-factors: implications on estimating material efficiency with respect to charting synthesis optimization strategies
  42. A comparative sorption study of Cr3+ and Cr6+ using mango peels: kinetic, equilibrium and thermodynamic
  43. Effects of acid hydrolysis waste liquid recycle on preparation of microcrystalline cellulose
  44. Use of deep eutectic solvents as catalyst: A mini-review
  45. Microwave-assisted synthesis of pyrrolidinone derivatives using 1,1’-butylenebis(3-sulfo-3H-imidazol-1-ium) chloride in ethylene glycol
  46. Green and eco-friendly synthesis of Co3O4 and Ag-Co3O4: Characterization and photo-catalytic activity
  47. Adsorption optimized of the coal-based material and application for cyanide wastewater treatment
  48. Aloe vera leaf extract mediated green synthesis of selenium nanoparticles and assessment of their In vitro antimicrobial activity against spoilage fungi and pathogenic bacteria strains
  49. Waste phenolic resin derived activated carbon by microwave-assisted KOH activation and application to dye wastewater treatment
  50. Direct ethanol production from cellulose by consortium of Trichoderma reesei and Candida molischiana
  51. Agricultural waste biomass-assisted nanostructures: Synthesis and application
  52. Biodiesel production from rubber seed oil using calcium oxide derived from eggshell as catalyst – optimization and modeling studies
  53. Study of fabrication of fully aqueous solution processed SnS quantum dot-sensitized solar cell
  54. Assessment of aqueous extract of Gypsophila aretioides for inhibitory effects on calcium carbonate formation
  55. An environmentally friendly acylation reaction of 2-methylnaphthalene in solvent-free condition in a micro-channel reactor
  56. Aegle marmelos phytochemical stabilized synthesis and characterization of ZnO nanoparticles and their role against agriculture and food pathogen
  57. A reactive coupling process for co-production of solketal and biodiesel
  58. Optimization of the asymmetric synthesis of (S)-1-phenylethanol using Ispir bean as whole-cell biocatalyst
  59. Synthesis of pyrazolopyridine and pyrazoloquinoline derivatives by one-pot, three-component reactions of arylglyoxals, 3-methyl-1-aryl-1H-pyrazol-5-amines and cyclic 1,3-dicarbonyl compounds in the presence of tetrapropylammonium bromide
  60. Preconcentration of morphine in urine sample using a green and solvent-free microextraction method
  61. Extraction of glycyrrhizic acid by aqueous two-phase system formed by PEG and two environmentally friendly organic acid salts - sodium citrate and sodium tartrate
  62. Green synthesis of copper oxide nanoparticles using Juglans regia leaf extract and assessment of their physico-chemical and biological properties
  63. Deep eutectic solvents (DESs) as powerful and recyclable catalysts and solvents for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones/thiones
  64. Biosynthesis, characterization and anti-microbial activity of silver nanoparticle based gel hand wash
  65. Efficient and selective microwave-assisted O-methylation of phenolic compounds using tetramethylammonium hydroxide (TMAH)
  66. Anticoagulant, thrombolytic and antibacterial activities of Euphorbia acruensis latex-mediated bioengineered silver nanoparticles
  67. Volcanic ash as reusable catalyst in the green synthesis of 3H-1,5-benzodiazepines
  68. Green synthesis, anionic polymerization of 1,4-bis(methacryloyl)piperazine using Algerian clay as catalyst
  69. Selenium supplementation during fermentation with sugar beet molasses and Saccharomyces cerevisiae to increase bioethanol production
  70. Biosynthetic potential assessment of four food pathogenic bacteria in hydrothermally silver nanoparticles fabrication
  71. Investigating the effectiveness of classical and eco-friendly approaches for synthesis of dialdehydes from organic dihalides
  72. Pyrolysis of palm oil using zeolite catalyst and characterization of the boil-oil
  73. Azadirachta indica leaves extract assisted green synthesis of Ag-TiO2 for degradation of Methylene blue and Rhodamine B dyes in aqueous medium
  74. Synthesis of vitamin E succinate catalyzed by nano-SiO2 immobilized DMAP derivative in mixed solvent system
  75. Extraction of phytosterols from melon (Cucumis melo) seeds by supercritical CO2 as a clean technology
  76. Production of uronic acids by hydrothermolysis of pectin as a model substance for plant biomass waste
  77. Biofabrication of highly pure copper oxide nanoparticles using wheat seed extract and their catalytic activity: A mechanistic approach
  78. Intelligent modeling and optimization of emulsion aggregation method for producing green printing ink
  79. Improved removal of methylene blue on modified hierarchical zeolite Y: Achieved by a “destructive-constructive” method
  80. Two different facile and efficient approaches for the synthesis of various N-arylacetamides via N-acetylation of arylamines and straightforward one-pot reductive acetylation of nitroarenes promoted by recyclable CuFe2O4 nanoparticles in water
  81. Optimization of acid catalyzed esterification and mixed metal oxide catalyzed transesterification for biodiesel production from Moringa oleifera oil
  82. Kinetics and the fluidity of the stearic acid esters with different carbon backbones
  83. Aiming for a standardized protocol for preparing a process green synthesis report and for ranking multiple synthesis plans to a common target product
  84. Microstructure and luminescence of VO2 (B) nanoparticle synthesis by hydrothermal method
  85. Optimization of uranium removal from uranium plant wastewater by response surface methodology (RSM)
  86. Microwave drying of nickel-containing residue: dielectric properties, kinetics, and energy aspects
  87. Simple and convenient two step synthesis of 5-bromo-2,3-dimethoxy-6-methyl-1,4-benzoquinone
  88. Biodiesel production from waste cooking oil
  89. The effect of activation temperature on structure and properties of blue coke-based activated carbon by CO2 activation
  90. Optimization of reaction parameters for the green synthesis of zero valent iron nanoparticles using pine tree needles
  91. Microwave-assisted protocol for squalene isolation and conversion from oil-deodoriser distillates
  92. Denitrification performance of rare earth tailings-based catalysts
  93. Facile synthesis of silver nanoparticles using Averrhoa bilimbi L and Plum extracts and investigation on the synergistic bioactivity using in vitro models
  94. Green production of AgNPs and their phytostimulatory impact
  95. Photocatalytic activity of Ag/Ni bi-metallic nanoparticles on textile dye removal
  96. Topical Issue: Green Process Engineering / Guest Editors: Martine Poux, Patrick Cognet
  97. Modelling and optimisation of oxidative desulphurisation of tyre-derived oil via central composite design approach
  98. CO2 sequestration by carbonation of olivine: a new process for optimal separation of the solids produced
  99. Organic carbonates synthesis improved by pervaporation for CO2 utilisation
  100. Production of starch nanoparticles through solvent-antisolvent precipitation in a spinning disc reactor
  101. A kinetic study of Zn halide/TBAB-catalysed fixation of CO2 with styrene oxide in propylene carbonate
  102. Topical on Green Process Engineering
https://doi.org/10.1515/gps-2018-0093
Keywords for this article
catalyst free; imidazo [1,2-a]imidazoles; imidazo[2,1-c][1,2,4]triazoles; microwave heating; multi-component reaction; Strecker reaction
Creative Commons
BY 4.0

Articles in the same Issue

  1. Regular Articles
  2. Studies on the preparation and properties of biodegradable polyester from soybean oil
  3. Flow-mode biodiesel production from palm oil using a pressurized microwave reactor
  4. Reduction of free fatty acids in waste oil for biodiesel production by glycerolysis: investigation and optimization of process parameters
  5. Saccharin: a cheap and mild acidic agent for the synthesis of azo dyes via telescoped dediazotization
  6. Optimization of lipase-catalyzed synthesis of polyethylene glycol stearate in a solvent-free system
  7. Green synthesis of iron oxide nanoparticles using Platanus orientalis leaf extract for antifungal activity
  8. Ultrasound assisted chemical activation of peanut husk for copper removal
  9. Room temperature silanization of Fe3O4 for the preparation of phenyl functionalized magnetic adsorbent for dispersive solid phase extraction for the extraction of phthalates in water
  10. Evaluation of the saponin green extraction from Ziziphus spina-christi leaves using hydrothermal, microwave and Bain-Marie water bath heating methods
  11. Oxidation of dibenzothiophene using the heterogeneous catalyst of tungsten-based carbon nanotubes
  12. Calcined sodium silicate as an efficient and benign heterogeneous catalyst for the transesterification of natural lecithin to L-α-glycerophosphocholine
  13. Synergistic effect between CO2 and H2O2 on ethylbenzene oxidation catalyzed by carbon supported heteropolyanion catalysts
  14. Hydrocyanation of 2-arylmethyleneindan-1,3-diones using potassium hexacyanoferrate(II) as a nontoxic cyanating agent
  15. Green synthesis of hydratropic aldehyde from α-methylstyrene catalyzed by Al2O3-supported metal phthalocyanines
  16. Environmentally benign chemical recycling of polycarbonate wastes: comparison of micro- and nano-TiO2 solid support efficiencies
  17. Medicago polymorpha-mediated antibacterial silver nanoparticles in the reduction of methyl orange
  18. Production of value-added chemicals from esterification of waste glycerol over MCM-41 supported catalysts
  19. Green synthesis of zerovalent copper nanoparticles for efficient reduction of toxic azo dyes congo red and methyl orange
  20. Optimization of the biological synthesis of silver nanoparticles using Penicillium oxalicum GRS-1 and their antimicrobial effects against common food-borne pathogens
  21. Optimization of submerged fermentation conditions to overproduce bioethanol using two industrial and traditional Saccharomyces cerevisiae strains
  22. Extraction of In3+ and Fe3+ from sulfate solutions by using a 3D-printed “Y”-shaped microreactor
  23. Foliar-mediated Ag:ZnO nanophotocatalysts: green synthesis, characterization, pollutants degradation, and in vitro biocidal activity
  24. Green cyclic acetals production by glycerol etherification reaction with benzaldehyde using cationic acidic resin
  25. Biosynthesis, characterization and antimicrobial activities assessment of fabricated selenium nanoparticles using Pelargonium zonale leaf extract
  26. Synthesis of high surface area magnesia by using walnut shell as a template
  27. Controllable biosynthesis of silver nanoparticles using actinobacterial strains
  28. Green vegetation: a promising source of color dyes
  29. Mechano-chemical synthesis of ammonia and acetic acid from inorganic materials in water
  30. Green synthesis and structural characterization of novel N1-substituted 3,4-dihydropyrimidin-2(1H)-ones
  31. Biodiesel production from cotton oil using heterogeneous CaO catalysts from eggshells prepared at different calcination temperatures
  32. Regeneration of spent mercury catalyst for the treatment of dye wastewater by the microwave and ultrasonic spray-assisted method
  33. Green synthesis of the innovative super paramagnetic nanoparticles from the leaves extract of Fraxinus chinensis Roxb and their application for the decolourisation of toxic dyes
  34. Biogenic ZnO nanoparticles: a study of blueshift of optical band gap and photocatalytic degradation of reactive yellow 186 dye under direct sunlight
  35. Leached compounds from the extracts of pomegranate peel, green coconut shell, and karuvelam wood for the removal of hexavalent chromium
  36. Enhancement of molecular weight reduction of natural rubber in triphasic CO2/toluene/H2O systems with hydrogen peroxide for preparation of biobased polyurethanes
  37. An efficient green synthesis of novel 1H-imidazo[1,2-a]imidazole-3-amine and imidazo[2,1-c][1,2,4]triazole-5-amine derivatives via Strecker reaction under controlled microwave heating
  38. Evaluation of three different green fabrication methods for the synthesis of crystalline ZnO nanoparticles using Pelargonium zonale leaf extract
  39. A highly efficient and multifunctional biomass supporting Ag, Ni, and Cu nanoparticles through wetness impregnation for environmental remediation
  40. Simple one-pot green method for large-scale production of mesalamine, an anti-inflammatory agent
  41. Relationships between step and cumulative PMI and E-factors: implications on estimating material efficiency with respect to charting synthesis optimization strategies
  42. A comparative sorption study of Cr3+ and Cr6+ using mango peels: kinetic, equilibrium and thermodynamic
  43. Effects of acid hydrolysis waste liquid recycle on preparation of microcrystalline cellulose
  44. Use of deep eutectic solvents as catalyst: A mini-review
  45. Microwave-assisted synthesis of pyrrolidinone derivatives using 1,1’-butylenebis(3-sulfo-3H-imidazol-1-ium) chloride in ethylene glycol
  46. Green and eco-friendly synthesis of Co3O4 and Ag-Co3O4: Characterization and photo-catalytic activity
  47. Adsorption optimized of the coal-based material and application for cyanide wastewater treatment
  48. Aloe vera leaf extract mediated green synthesis of selenium nanoparticles and assessment of their In vitro antimicrobial activity against spoilage fungi and pathogenic bacteria strains
  49. Waste phenolic resin derived activated carbon by microwave-assisted KOH activation and application to dye wastewater treatment
  50. Direct ethanol production from cellulose by consortium of Trichoderma reesei and Candida molischiana
  51. Agricultural waste biomass-assisted nanostructures: Synthesis and application
  52. Biodiesel production from rubber seed oil using calcium oxide derived from eggshell as catalyst – optimization and modeling studies
  53. Study of fabrication of fully aqueous solution processed SnS quantum dot-sensitized solar cell
  54. Assessment of aqueous extract of Gypsophila aretioides for inhibitory effects on calcium carbonate formation
  55. An environmentally friendly acylation reaction of 2-methylnaphthalene in solvent-free condition in a micro-channel reactor
  56. Aegle marmelos phytochemical stabilized synthesis and characterization of ZnO nanoparticles and their role against agriculture and food pathogen
  57. A reactive coupling process for co-production of solketal and biodiesel
  58. Optimization of the asymmetric synthesis of (S)-1-phenylethanol using Ispir bean as whole-cell biocatalyst
  59. Synthesis of pyrazolopyridine and pyrazoloquinoline derivatives by one-pot, three-component reactions of arylglyoxals, 3-methyl-1-aryl-1H-pyrazol-5-amines and cyclic 1,3-dicarbonyl compounds in the presence of tetrapropylammonium bromide
  60. Preconcentration of morphine in urine sample using a green and solvent-free microextraction method
  61. Extraction of glycyrrhizic acid by aqueous two-phase system formed by PEG and two environmentally friendly organic acid salts - sodium citrate and sodium tartrate
  62. Green synthesis of copper oxide nanoparticles using Juglans regia leaf extract and assessment of their physico-chemical and biological properties
  63. Deep eutectic solvents (DESs) as powerful and recyclable catalysts and solvents for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones/thiones
  64. Biosynthesis, characterization and anti-microbial activity of silver nanoparticle based gel hand wash
  65. Efficient and selective microwave-assisted O-methylation of phenolic compounds using tetramethylammonium hydroxide (TMAH)
  66. Anticoagulant, thrombolytic and antibacterial activities of Euphorbia acruensis latex-mediated bioengineered silver nanoparticles
  67. Volcanic ash as reusable catalyst in the green synthesis of 3H-1,5-benzodiazepines
  68. Green synthesis, anionic polymerization of 1,4-bis(methacryloyl)piperazine using Algerian clay as catalyst
  69. Selenium supplementation during fermentation with sugar beet molasses and Saccharomyces cerevisiae to increase bioethanol production
  70. Biosynthetic potential assessment of four food pathogenic bacteria in hydrothermally silver nanoparticles fabrication
  71. Investigating the effectiveness of classical and eco-friendly approaches for synthesis of dialdehydes from organic dihalides
  72. Pyrolysis of palm oil using zeolite catalyst and characterization of the boil-oil
  73. Azadirachta indica leaves extract assisted green synthesis of Ag-TiO2 for degradation of Methylene blue and Rhodamine B dyes in aqueous medium
  74. Synthesis of vitamin E succinate catalyzed by nano-SiO2 immobilized DMAP derivative in mixed solvent system
  75. Extraction of phytosterols from melon (Cucumis melo) seeds by supercritical CO2 as a clean technology
  76. Production of uronic acids by hydrothermolysis of pectin as a model substance for plant biomass waste
  77. Biofabrication of highly pure copper oxide nanoparticles using wheat seed extract and their catalytic activity: A mechanistic approach
  78. Intelligent modeling and optimization of emulsion aggregation method for producing green printing ink
  79. Improved removal of methylene blue on modified hierarchical zeolite Y: Achieved by a “destructive-constructive” method
  80. Two different facile and efficient approaches for the synthesis of various N-arylacetamides via N-acetylation of arylamines and straightforward one-pot reductive acetylation of nitroarenes promoted by recyclable CuFe2O4 nanoparticles in water
  81. Optimization of acid catalyzed esterification and mixed metal oxide catalyzed transesterification for biodiesel production from Moringa oleifera oil
  82. Kinetics and the fluidity of the stearic acid esters with different carbon backbones
  83. Aiming for a standardized protocol for preparing a process green synthesis report and for ranking multiple synthesis plans to a common target product
  84. Microstructure and luminescence of VO2 (B) nanoparticle synthesis by hydrothermal method
  85. Optimization of uranium removal from uranium plant wastewater by response surface methodology (RSM)
  86. Microwave drying of nickel-containing residue: dielectric properties, kinetics, and energy aspects
  87. Simple and convenient two step synthesis of 5-bromo-2,3-dimethoxy-6-methyl-1,4-benzoquinone
  88. Biodiesel production from waste cooking oil
  89. The effect of activation temperature on structure and properties of blue coke-based activated carbon by CO2 activation
  90. Optimization of reaction parameters for the green synthesis of zero valent iron nanoparticles using pine tree needles
  91. Microwave-assisted protocol for squalene isolation and conversion from oil-deodoriser distillates
  92. Denitrification performance of rare earth tailings-based catalysts
  93. Facile synthesis of silver nanoparticles using Averrhoa bilimbi L and Plum extracts and investigation on the synergistic bioactivity using in vitro models
  94. Green production of AgNPs and their phytostimulatory impact
  95. Photocatalytic activity of Ag/Ni bi-metallic nanoparticles on textile dye removal
  96. Topical Issue: Green Process Engineering / Guest Editors: Martine Poux, Patrick Cognet
  97. Modelling and optimisation of oxidative desulphurisation of tyre-derived oil via central composite design approach
  98. CO2 sequestration by carbonation of olivine: a new process for optimal separation of the solids produced
  99. Organic carbonates synthesis improved by pervaporation for CO2 utilisation
  100. Production of starch nanoparticles through solvent-antisolvent precipitation in a spinning disc reactor
  101. A kinetic study of Zn halide/TBAB-catalysed fixation of CO2 with styrene oxide in propylene carbonate
  102. Topical on Green Process Engineering
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