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The first in situ synthesis of 1,3-dioxan-5-one derivatives and their direct use in Claisen-Schmidt reactions

Synthesis of dioxanones and their Claisen-Schmidt reactions
  • M. Javad Poursharifi , Mohammad M. Mojtahedi EMAIL logo , M. Saeed Abaee and Mohammad M. Hashemi
Published/Copyright: May 31, 2019
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Heterocyclic Communications
From the journal Heterocyclic Communications Volume 25 Issue 1

Abstract

A method is developed for in situ generation of 1,3-dioxan-5-one derivatives 2. These compounds are simple precursors for accessing carbohydrate structures and previously had to be produced via stepwise procedures using excessive amounts of reagents. In the present work, three different derivatives of 2 were synthesized via the reaction of trialkoxyalkanes with dihydroxyacetone dimer 1 in the presence of acetic acid as the catalyst. In the same pot, derivatives of 2 were reacted with aromatic aldehydes and 30 mol% of pyrrolidine to obtain high yields of the respective bischalcones 3 within short time periods.

Keywords: 1,3-dioxan-5-one; trioses; Claisen-Schmidt reaction; dihydroxyacetone; one-pot reactions

Introduction

Trioses are among the smallest monosaccharide biomolecules playing important roles in cellular respiration [1]. In the course of glycolysis, fructose-1,6-bisphosphate is cleaved to glyceraldehyde-3-phosphate and dihydroxyacetone phosphate (DHAP) [2]. The latter in turn could convert to lactic acid and pyruvic acid [3]. In the nature, DHAP can lead to more complex carbohydrates stereoselectively via enzyme-catalyzed aldol reactions [4]. The chemical equivalent to DHAP is dihydroxyacetone (1, DHA, Scheme 1) which is the only ketotriose and does not exist in enantiomeric forms and is therefore achiral [5]. DHA and its derivatives are successfully employed as C3 building blocks through synthetic manipulations for asymmetric synthesis of various compounds of interest [6].

Scheme 1 Important structures derived from ketones 2 (a synthon for 1).
Scheme 1

Important structures derived from ketones 2 (a synthon for 1).

The limitation in the chemistry of DHA is that the compound usually exists in relatively inactive dimeric form [7, 8] and researchers have to use its protected heterocyclic synthon, 1,3-dioxan-5-one 2 derivatives instead [9, 10]. In this context, Enders introduced a simple and biomimetic approach for direct proline-catalyzed asymmetric synthesis of several carbohydrate structures and their related compounds through one-step aldol reactions of 2 [11, 12, 13, 14]. Majewski reported stereodivergent synthesis of both enantiomers of glycero-allo-heptose from similar starting ketone 2 [15] and organocatalyzed synthesis of L-deoxymannojirimycin and L-deoxyidonojirimycin via syn-aldol reaction of 2 with (S)-isoserinal hydrate [16]. Interestingly, several applications of this chemistry are reported for the synthesis of natural compounds of interest such as total synthesis of (±)-isophellibiline [17], (±)-cortistatin J [18], and (±)-erythroidines [19].

The difficulties associated with the preparation of derivatives of 2 have persuaded synthetic chemists to design and attempt new methods to obtain 2 via more convenient reactions and by performing less synthetic steps [20, 21, 22, 23]. In the framework of our studies to develop new synthetic procedures in heterocyclic chemistry [24, 25, 26, 27], herein we introduce a new method for in situ preparation of three various derivatives of 2 starting from 1 and trialkoxyalkanes (RCR’3) and acetic acid as catalyst. Then, ketones 2 are reacted in the same pot with aldehydes

to get the respective bischalcone derivatives 3 via Claisen-Schmidt condensation reactions at room temperature. The importance of chalcone functionalities in heterocyclic chemistry from synthetic [28, 29] and biological points of view is well documented [30, 31].

Results and discussion

We first optimized the conditions for the synthesis of 2a by reacting 1 with MeC(OMe)3 and various catalysts (Table 1). Under the conditions reported by Müller et al [32], camphor-10-sulfonic acid (CSA) in dioxane caused 81% formation of 2a after 24 h (entry 1). Use of Lewis acids almost led to minor quantities of the desired product even at a higher temperature or a longer reaction time (entries 2-5). Acetic acid improved the result to give 80% of 2a at 60 °C and after a much shorter time period (entry 6). Also, less amounts of the solvent (entry 7) or the reagent (entry 8) led to comparable results. Other carboxylic acids did not behave better than CH3COOH (entries 9-10). These optimum conditions were applied successfully to prepare two other derivatives of 2 in high yields (entries 11-12).

With these results, we were persuaded to use the optimum conditions to prepare derivatives of 2 and subject them to react with an aromatic aldehyde to evaluate the possibility of the synthesis of bischalcone derivatives 3 in

Table 1

Optimization of the synthesis of 2.

EntryCatalystTemperature (°C)Time (h)ProductYield (%)a
1CSA60242a (R = Me,81
R’ = OMe)
2MgBr260482a< 5
3MgBr280722a< 5
4LiBr60482a< 5
5LiBr80722a< 5
6CH3CO2H6082a80
7CH3CO2Hb6082a83
8CH3COHb,c26082a83
9H2C2O4b,c80722a< 5
10PhCO2Hb,c80722a< 5
11CH3CO2Hb,c6082b (R = Me,85
R’ = OEt)
12CH3CO2Hb,c6082c (R = H,80d
R’ = OMe)

  1. aIsolated yields. bDioxane (2 mL). cMeC(OMe)3 (2.0 equiv). dGC yield.

the same reaction pot (Table 2). For this purpose, when monitoring of the reaction showed maximum formation of 2a, the mixture was treated with an alkaline hydroxides followed by addition of 4-ClC6H4CHO. As a result, use of NaOH (entries 1-2) or KOH (entries 3-4) in aqueous or solvent-free conditions gave no minor amounts of 3a. However, when organocatalysts were used, pyrrolidine (entry 5) gave 3a in 83% yield after 15 min, while Et2NH (entry 6) or Et3N (entry 7) produced 63% or 41% of the same product after similar time period.

Table 2

Optimization of the synthesis of 3a.

EntryConditions (30 mol%)SolventTime (min)Yield (%)a
1NaOHnone24< 5
2NaOHH2O24< 5
3KOHnone24< 5
4KOHH2O24< 5
5pyrrolidinenone1583
6Et2NHnone1563
7Et3Nnone1541

  1. aIsolated yields.

To show the generality of the process, we synthesized various derivatives of 3 by subjecting 2a to react with different aldehydes bearing electron withdrawing groups (Scheme 2). Thus 3a-f were obtained in high yields. Also, the reaction with benzaldehyde itself led to the same observations and 3g was obtained in 80%. Similarly, use of 2b or 2c produced the target products (3h-3n) in 85-95% yields. The condensation step for all reactions occurred within 15-20 min and products precipitated in the mixtures spontaneously.

Scheme 2 One-pot synthesis of various derivatives of 3.
Scheme 2

One-pot synthesis of various derivatives of 3.

Conclusion

In summary, we succeeded to prepare derivatives of 2, which could be either isolated from the reaction mixtures or further subjected to Claisen-Schmidt reactions in the same pot. Thus various derivatives of 2 and 3 could be prepared efficiently. After the prevailing reaction conditions, the products were solidified in the reaction vessels and required no expensive and time consuming chromatographic separations. In addition, synthesis of 2 succeeded by using much less amounts of solvent and the required orthoesters.

Experimental

Melting points are uncorrected. FT-IR spectra were recorded using KBr disks on a Bruker Vector-22 spectrometer. NMR spectra were obtained on a FT-NMR Bruker Ultra ShieldTM (500 MHz for 1H and 125 MHz for 13C) as DMSO-d6 solutions using TMS as internal standard reference. Elemental analyses were performed using a Thermo Finnigan Flash EA 1112 instrument. MS spectra were obtained on a Finnigan Mat 8430 instrument at ionization potential of 70 eV. TLC experiments were carried out on pre-coated silica gel plates using petroleum ether/EtOAc as the eluent. Chemicals and starting materials were purchased from commercial sources. Aldehydes were redistilled or recrystallized before being used. Products 3a, 3f, 3g, and 3k were known [33, 34]. All other products were new and were characterized by analyzing their 1H NMR, 13C NMR, IR, and mass spectra.

General procedure for the synthesis of 2

Acetic acid (125 μl, 20 mol%) was added dropwise to a mixture of dihydroxyacetone dimer 1 (1.01 g, 5.6 mmol) in dioxane (2 mL), while being heated at 60 °C under argon atmosphere. After 10 min, a trialkyl orthoacetate (23 mmol) was added to the mixture and was stirred for another 8 h. The mixture was concentrated under reduced pressure and the residue was distilled to obtain derivatives of 2. Products 2a-b are known [32, 34].The structure of 2c is inferred from the final products (3m and 3n) containing this central ring.

General procedure for one-pot synthesis of 3

Acetic acid (125 μl, 20 mol%) was added dropwise to a mixture of dihydroxyacetone dimer 1 (1.01 g, 5.6 mmol) in dioxane (2 mL), while being heated at 60 °C under argon atmosphere. After 10 min, trialkyl orthoacetate (23 mmol) was added to the mixture and the mixture was stirred for another 8 h. TLC (petroleum ether/EtOAc 4:1) showed complete conversion of the starting materials to 2 after 8 h. The heating source was removed and an aldehyde (18.6 mmol) and pyrrolidine (3.36 mmol, 277 μl, 30 mol%) were added and mixing was continued at room temperature for 10-15 min. The completion of the reaction was monitored with TLC (petroleum ether/EtOAc:10:1). The product precipitated in the mixture. The crude solid product was purified by recrystallization from EtOH and solid products 3 were obtained.

Spectral data of new products

4,6-Bis((Z)-4-bromobenzylidene)-2-methoxy-2-methyl-1,3-dioxan-5-one (3b) Mp: 224-225 ˚C; IR (KBr) ν 2940, 1578, 1464 cm-1; 1H NMR (500 MHz, DMSO-d6) δ 7.79 (d, J = 8.5 Hz, 4H), 7.62 (d, J = 8.5 Hz, 4H), 6.87 (s, 2H), 3.30 (s, 3H), 1.98 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 176.6, 144.5, 133.0, 132.9, 132.5, 123.4, 114.6, 113.7, 52.7, 21.1; MS (70 eV) m/z 480 (M+), 404, 325, 196, 89; Anal. Calcd for C20H16Br2O4: C, 50.03; H, 3.36. Found: C, 50.16; H, 3.27.

2 -Methoxy- 2 -methyl- 4 , 6 -bis ( ( Z ) - 3 - nitrobenzylidene)-1,3-dioxan-5-one (3c). Mp: > 250 ˚C; IR (KBr) ν 2920, 1701, 1615, 1528, 1345 cm-1; 1H NMR (500 MHz, DMSO-d6) δ 8.71 (s, 2H), 8.26 (d, J = 8.0 Hz, 2H), 8.21 (d, J = 8.0 Hz, 2H), 7.74 (dd, J = 8.0, 8.0 Hz, 2H), 7.07 (s, 2H), 3.35 (s, 3H), 2.05 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 176.4, 148.6, 145.3, 137.2, 134.6, 130.9, 125.2, 124.2, 114.0, 113.7, 52.9, 21.0; MS (70 eV) m/z 412 (M+), 381, 337, 163, 129; Anal. Calcd for C20H16N2O8: C, 58.26; H, 3.91; N, 6.79. Found: C, 58.33; H, 3.79; N, 6.90.

4,4’-((1Z,1’Z)-(2-Methoxy-2-methyl-5-oxo-1,3-dioxane-4,6-diylidene)bis(methanylylidene))dibenzonitrile (3d). Mp: 248-249 ˚C; IR (KBr) ν 3053, 2228, 1603, 1279 cm-1; 1H NMR (500 MHz, DMSO-d6) δ 8.02 (d, J = 8.0 Hz, 4H), 7.90 (d, J = 8.0 Hz, 4H), 6.97 (s, 2H), 3.34 (s, 3H), 2.03 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 176.6, 145.6, 137.6, 133.2, 131.7, 119.3, 114.1, 113.9, 111.7, 52.9, 20.9; MS (70 eV) m/z 372 (M+), 341, 297, 173, 143; Anal. Calcd for C22H16N2O4: C, 70.96; H, 4.33; N, 7.52. Found: C, 70.77; H, 4.60; N, 7.59.

4,6-Bis((Z)-2,4-dichlorobenzylidene)-2-methoxy-2-methyl-1,3-dioxan-5-one (3e). Mp: 195-196 ˚C; IR (KBr) ν 1739, 1577, 1466, 1281, 826 cm-1; 1H NMR (500 MHz, DMSO-d6) δ 8.12 (d, J = 8.0 Hz, 2H), 7.73 (s, 2H), 7.51 (d, J = 8.0 Hz, 2H), 7.08 (s, 2H), 3.32 (s, 3H), 1.96 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 176.2, 145.0, 135.3, 134.9, 132.3, 129.9, 129.3, 128.3, 113.9, 109.2, 52.8, 20.7; MS (70 eV) m/z 460 (M+), 427, 349, 186, 123; Anal. Calcd for C20H14Cl4O2: C, 52.21; H, 3.07. Found: C, 52.16; H, 3.28.

4,6-Bis((Z)-4-chlorobenzylidene)-2-ethoxy-2-methyl-1,3-dioxan-5-one (3h). Mp: 176-177 ˚C; IR (KBr) ν 2965, 1595, 1485, 802 cm-1; 1H NMR (500 MHz, DMSO-d6) δ 7.85 (d, J = 8.5 Hz, 4H), 7.50 (d, J = 8.5 Hz, 4H), 6.87 (s, 2H), 3.61 (q, J = 7.0 Hz, 2H), 2.0 (s, 3H), 1.03 (t, J = 7.0 Hz, 3H); 13C NMR (125 MHz, DMSO-d6) δ 176.6, 144.4, 134.3, 132.6, 132.0, 129.3, 114.0, 113.2, 60.9, 21.7, 15.1; MS (70 eV) m/z 404 (M+), 334, 281, 181, 152; Anal. Calcd for C21H18Cl2O4: C, 62.24; H, 4.48. Found: C, 62.03; H, 4.59.

4,6-Bis((Z)-4-bromobenzylidene)-2-ethoxy-2-methyl-1,3-dioxan-5-one (3i). Mp: 234-235 ˚C; IR (KBr) ν 2923, 1597, 1481, 1283, 812 cm-1; 1H NMR (500 MHz, DMSO-d6) δ 7.79 (d, J = 8.5 Hz, 4H), 7.64 (d, J = 8.5 Hz, 4H), 6.85 (s, 2H), 3.60 (q, J = 7.0 Hz, 2H), 1.99 (s, 3H), 1.02 (t, J = 7.0 Hz, 3H); 13C NMR (125 MHz, DMSO-d6) δ 176.6, 144.5, 132.9, 132.3, 123.1, 114.1, 113.2, 112.9, 61.0, 21.6, 15.1; MS (70 eV) m/z 494 (M+), 424, 269, 198, 149; Anal. Calcd for C21H18Br2O4: C, 51.04; H, 3.67. Found: C, 50.92; H, 3.77.

4,6-Bis((Z)-2,4-dichlorobenzylidene)-2-ethoxy-2-methyl-1,3-dioxan-5-one (3j). Mp: 205-206 ˚C; IR (KBr) ν 2923, 1577, 1464, 1126 cm-1; 1H NMR (500 MHz, DMSO-d6) δ 8.11 (d, J = 8.5 Hz, 2H), 7.70 (s, 2H), 7.50 (d, J = 8.5 Hz, 2H), 7.06 (s, 2H), 3.61 (q, J = 7.0 Hz, 2H), 1.96 (s, 3H), 1.04 (t, J = 7.0 Hz, 3H); 13C NMR (125 MHz, DMSO-d6) δ 176.4, 145.2, 135.3, 134.8, 132.3, 129.9, 129.4, 128.4, 113.6, 108.9, 61.3, 21.5, 15.3; MS (70 eV) m/z 474 (M+), 404, 217, 186, 123; Anal. Calcd for C21H16Cl4O4: C, 53.20; H, 3.40. Found: C, 53.36; H, 3.38.

4,6-Bis((Z)-4-(dimethylamino)benzylidene)-2-ethoxy-2-methyl-1,3-dioxan-5-one (3l). Mp: 230-231 ˚C; IR (KBr) ν 1591, 1527, 1127 cm-1; 1H NMR (500 MHz, DMSO-d6) δ 7.69 (d, J = 9.0 Hz, 4H), 6.76 (d, J = 9.0 Hz, 4H), 6.75 (s, 2H), 3.58 (q, J = 7.0 Hz, 2H), 2.98 (s, 12H), 1.94 (s, 3H), 1.02 (t, J = 7.0 Hz, 3H); 13C NMR (125 MHz, DMSO-d6) δ 175.7, 151.0, 141.9, 132.6, 121.0, 116.1, 112.5, 112.3, 60.2, 40.1, 22.1, 15.3; MS (70 eV) m/z 422 (M+), 306, 266, 205, 161; Anal. Calcd for C25H30N2O4: C, 71.07; H, 7.16; N, 6.63. Found: C, 71.15; H, 7.27; N, 6.52.

4,6-Bis((Z)-4-chlorobenzylidene)-2-methoxy-1,3-dioxan-5-one (3m). Mp: 155-156 ˚C; IR (KBr) ν 2934, 1606, 1578, 1464, 825 cm-1; 1H NMR (500 MHz, DMSO-d6) δ 7.87 (d, J = 8.5 Hz, 4H), 7.50 (d, J = 8.5 Hz, 4H), 6.93 (s, 2H), 6.55 (s, 1H), 3.43 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 176.4, 144.1, 134.5, 132.7, 131.8, 129.3, 114.9, 107.2, 54.3; MS (70 eV) m/z 376 (M+), 315, 281, 225, 152; Anal. Calcd for C19H14Cl2O4: C, 60.50; H, 3.74. Found: C, 60.66; H, 3.85.

4,6-Bis((Z)-2,4-dichlorobenzylidene)-2-methoxy-1,3-dioxan-5-one (3n). Mp: 186-187 ˚C; IR (KBr) ν 2897, 1577, 1464, 1268, 824 cm-1; 1H NMR (500 MHz, DMSO-d6) δ 8.12 (d, J = 8.5 Hz, 2H), 7.72 (s, 2H), 7.52 (d, J = 8.5 Hz, 2H), 7.11 (s, 2H), 6.58 (s, 1H), 3.43 (s, 3H); 13C NMR (125 MHz, DMSO-d6) δ 176.2, 144.9, 135.3, 135.0, 132.3, 129.9, 129.3, 128.3, 109.9, 107.3, 54.5; MS (70 eV) m/z 446 (M+), 409, 349, 186, 123; Anal. Calcd for C19H12Cl4O4: C, 51.16; H, 2.71. Found: C, 51.27; H, 2.86.

Acknowledgment

The Research Council at CCERCI (Grant # 96-112) is acknowledged for financial support of this work.

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Received: 2018-10-28
Accepted: 2019-02-26
Published Online: 2019-05-31

© 2019 M. Javad Poursharifi et al., published by De Gruyter

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

Articles in the same Issue

  1. Research Article
  2. Magnesium porphyrazine with peripheral methyl (3,5-dibromophenylmethyl)amino groups – synthesis and optical properties
  3. Synthesis and fungicidal activity of novel imidazo[4, 5-b]pyridine derivatives
  4. Synthesis of indazolo[5,4-b][1,6]naphthyridine and indazolo[6,7-b][1,6]naphthyridine derivatives
  5. Zinc Chloride Catalyzed Amino Claisen Rearrangement of 1-N-Allylindolines: An Expedient Protocol for the Synthesis of Functionalized 7-Allylindolines
  6. Synthesis and Biological Evaluation of (E)-N’-Benzylidene-7-methyl-2-propyl-1H-benzo[d] imidazole-5-carbohydrazides as Antioxidant, Anti-inflammatory and Analgesic agents
  7. Efficient synthesis, reactions and spectral characterization of pyrazolo[4’,3’:4,5]thieno[3,2-d] pyrimidines and related heterocycles
  8. Asymmetric Mannich Reaction: Synthesis of Novel Chiral 5-(substituted aryl)-1,3,4-Thiadiazole Derivatives with Anti-Plant-Virus Potency
  9. Synthesis and antitubercular activity of new N-[5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl]-(nitroheteroaryl)carboxamides
  10. Remarkable electronic effect on the total stereoselectivity of the cycloaddition reaction of arylnitrile oxides with pyrrol-2-one derivatives
  11. Preliminary Communications
  12. Crystal structure and molecular docking studies of new pyrazole-4-carboxamides
  13. Research Article
  14. Synthesis of polycyclic phosphonates via an intramolecular Diels-Alder reaction of 2-benzoylbenzalaldehyde and alkenyl phosphites
  15. Asymmetric total synthesis of filamentous fungi related resorcylic acid lactones 7-epi-zeaenol and zeaenol
  16. The first in situ synthesis of 1,3-dioxan-5-one derivatives and their direct use in Claisen-Schmidt reactions
  17. Synthesis and fungicidal activities of perfluoropropan-2-yl-based novel quinoline derivatives
  18. Combined XRD-paramagnetic 13C NMR spectroscopy of 1,2,3-triazoles for revealing copper traces in a Huisgen click-chemistry cycloaddition. A model case
  19. Cytotoxic and antimicrobial activities of some novel heterocycles employing 6-(1,3-diphenyl-1H-pyrazol-4-yl)-4-oxo-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile
  20. Substrate-controlled Diastereoselective Michael Addition of Alkylidene Malonates by Grignard Reagents
  21. Synthesis of 1,2,3 triazole-linked benzimidazole through a copper-catalyzed click reaction
  22. Synthesis and spectral characteristics of N-(1-([1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-ylamino)-2,2,2-trichloroethyl)carboxamides
  23. Facile One-pot Protocol of Derivatization Nitropyridines: Access to 3-Acetamidopyridin-2-yl 4-methylbenzenesulfonate Derivatives
  24. Naphthalene substituted benzo[c]coumarins: Synthesis, characterization and evaluation of antibacterial activity and cytotoxicity
  25. A Green Synthesis and Antibacterial Activity of N-Arylsulfonylhydrazone Compounds
  26. Preliminary Communications
  27. Facile Synthesis of Spiro[cyclohexane-1,3’-indoline]-2,2’-diones
  28. Research Article
  29. Synthesis and AChE inhibitory activity of N-glycosyl benzofuran derivatives
  30. [DMImd-DMP]: A highly efficient and reusable catalyst for the synthesis of 4H-benzo[b]pyran derivatives
https://doi.org/10.1515/hc-2019-0013
Keywords for this article
1,3-dioxan-5-one; trioses; Claisen-Schmidt reaction; dihydroxyacetone; one-pot reactions
Creative Commons
BY 4.0

Articles in the same Issue

  1. Research Article
  2. Magnesium porphyrazine with peripheral methyl (3,5-dibromophenylmethyl)amino groups – synthesis and optical properties
  3. Synthesis and fungicidal activity of novel imidazo[4, 5-b]pyridine derivatives
  4. Synthesis of indazolo[5,4-b][1,6]naphthyridine and indazolo[6,7-b][1,6]naphthyridine derivatives
  5. Zinc Chloride Catalyzed Amino Claisen Rearrangement of 1-N-Allylindolines: An Expedient Protocol for the Synthesis of Functionalized 7-Allylindolines
  6. Synthesis and Biological Evaluation of (E)-N’-Benzylidene-7-methyl-2-propyl-1H-benzo[d] imidazole-5-carbohydrazides as Antioxidant, Anti-inflammatory and Analgesic agents
  7. Efficient synthesis, reactions and spectral characterization of pyrazolo[4’,3’:4,5]thieno[3,2-d] pyrimidines and related heterocycles
  8. Asymmetric Mannich Reaction: Synthesis of Novel Chiral 5-(substituted aryl)-1,3,4-Thiadiazole Derivatives with Anti-Plant-Virus Potency
  9. Synthesis and antitubercular activity of new N-[5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl]-(nitroheteroaryl)carboxamides
  10. Remarkable electronic effect on the total stereoselectivity of the cycloaddition reaction of arylnitrile oxides with pyrrol-2-one derivatives
  11. Preliminary Communications
  12. Crystal structure and molecular docking studies of new pyrazole-4-carboxamides
  13. Research Article
  14. Synthesis of polycyclic phosphonates via an intramolecular Diels-Alder reaction of 2-benzoylbenzalaldehyde and alkenyl phosphites
  15. Asymmetric total synthesis of filamentous fungi related resorcylic acid lactones 7-epi-zeaenol and zeaenol
  16. The first in situ synthesis of 1,3-dioxan-5-one derivatives and their direct use in Claisen-Schmidt reactions
  17. Synthesis and fungicidal activities of perfluoropropan-2-yl-based novel quinoline derivatives
  18. Combined XRD-paramagnetic 13C NMR spectroscopy of 1,2,3-triazoles for revealing copper traces in a Huisgen click-chemistry cycloaddition. A model case
  19. Cytotoxic and antimicrobial activities of some novel heterocycles employing 6-(1,3-diphenyl-1H-pyrazol-4-yl)-4-oxo-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile
  20. Substrate-controlled Diastereoselective Michael Addition of Alkylidene Malonates by Grignard Reagents
  21. Synthesis of 1,2,3 triazole-linked benzimidazole through a copper-catalyzed click reaction
  22. Synthesis and spectral characteristics of N-(1-([1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-ylamino)-2,2,2-trichloroethyl)carboxamides
  23. Facile One-pot Protocol of Derivatization Nitropyridines: Access to 3-Acetamidopyridin-2-yl 4-methylbenzenesulfonate Derivatives
  24. Naphthalene substituted benzo[c]coumarins: Synthesis, characterization and evaluation of antibacterial activity and cytotoxicity
  25. A Green Synthesis and Antibacterial Activity of N-Arylsulfonylhydrazone Compounds
  26. Preliminary Communications
  27. Facile Synthesis of Spiro[cyclohexane-1,3’-indoline]-2,2’-diones
  28. Research Article
  29. Synthesis and AChE inhibitory activity of N-glycosyl benzofuran derivatives
  30. [DMImd-DMP]: A highly efficient and reusable catalyst for the synthesis of 4H-benzo[b]pyran derivatives
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