Solvent Free Microwave Accelerated Synthesis of Heterocyclic Thiazolidin-4-ones as Antimicrobial and Antifungal Agents

Abstract

A simple and efficient method has been developed for conversion of arenecarbaldehyde-3-methylquinoxalin-2-ylhydrazones to 3-(2-methylquinoxalin-3-yl)-2-(substitutedphenyl)thiazolidin-4-ones in good yields using microwave irradiation technique on silica as solid support under solvent free conditions. The synthesized compounds were characterized by elemental microanalysis, infrared spectroscopy, 1 H NMR, and mass spectroscopy. All the synthesized thiazolidinones were investigated for their antimicrobial and antifungal activities. The results of the biological activities revealed that the compounds 3b, 3d, 3f and 3h exhibited excellent antibacterial activities while 3d and 3h exhibited good antifungal activity.

Emerging green synthetic routes for thiazole and its derivatives: Current perspectives

“…T A B L E 1 Outline for microwave-assisted synthesis of thiazole derivatives. --3-5 min 82-94 [41] -PEG-400 and water 80 28-34 min 84-89 [42] -Water 130 15 min 52-89 [43] ---0.5-2.91 min 70-80 [44] Chitosan-MgO nanocomposite Dioxane -30-40 min 80-96 [45] SiO 2 /active carbon Diethyl ether -5 min 73-98 [46] -Water 90 6-9 min 80-89 [47] -Water 110 7-10 min 89-92 [48] -Water 110 7 min 89 [49] -Dry toluene 110 12 min 16-64 [50] Silica gel --3-5 min 70-88 [51] -Ethanol 60-120 2-10 min 64-76 [52] -DMF 40 2 h 55-92 [53] --150 4-8 min 22-86 [54] Acetic acid --3 min 92 [55] -Toluene -6-8 min 64-82 [56] Zeolite 5A --0.5-1 min 89-96 [57] Montmorillonite K-10 clay -130 2-5 min 89-96 [58] Montmorillonite K-10 clay --3 min 85-92 [58] Montmorillonite K-10 clay --2.5-6 min 60-75 [59] Montmorillonite K-10 clay --3-5 min 54-74 [59] -Ethanol -3.5 min 82 [60] --200 10 min 98 [61] K 2 CO 3 DMF 130 10 min 61-90 [62] GAA Ethanol 120 2-4 min 88-95 [63] AcOH Ethanol 87 4-6 min 82-92 [64] -PEG-400 -5 min 96-97 [65] Abbreviations: AcOH, acetic acid; DMF, dimethylformamide; GAA, glacial acetic acid; PEG-400, polyethylene glycol-400.…”

“…Sekhar et al [ 51 ] described a solvent‐free synthesis of 3‐(2‐methylquinoxalin‐3‐yl)‐2‐(aryl)thiazolidin‐4‐one derivatives from heterocyclic hydrazone and thioglycolic acid by using silica gel as a solid reaction medium (60–120 mesh size) under microwave irradiation at 540 W for 3–5 min to afford excellent yield (70%–88%). However, if the power is increased thioglycolic acid starts evaporating and poor yield is obtained (Scheme 11).…”

Microwave assisted green synthesis of thiazolidin-4-one derivatives: A perspective on potent antiviral and antimicrobial activities

“…All the synthesized analogues were characterized by infrared spectroscopy, elemental microanalysis, 1 H NMR, and mass spectroscopy. The consequences of the biological activities discovered that the analogues 12 , 13 , 14 and 15 (structures are displayed in figure 5 ) (zone of inhibition = 10-30mm)demonstratedexceptional antibacterial activities while 13 and 15 (zone of inhibition = 15-30mm) revealedvirtuous antifungal activity [ 24 ].…”

Synthesis of Triazoloquinoxalines as Antitubercular Agents

“…[23][24][25][26][27][28] In view of our initial successes on the utilization of hypervalent iodine reagents for the synthesis of various heterocyclic compounds under solvent-free conditions, 29,30 and because of the biological significance of 1,2,4-triazole derivatives, we decided to develop an efficient and environmentally benign synthesis of 1,2,4-triazoles that proceeds under solvent-free conditions. Herein, we report our results on oxidative transformation of arenecarbaldehyde 3-methylquinoxalin-2-yl-hydrazones to 1-aryl-4-methyl-1,2,4-triazolo [4,3-a]quinoxalines (Scheme 1) with iodobenzene diacetate that leads to the expeditious formation of 1-aryl-4-methyl-1,2,4-triazolo [4,3-a]quinoxalines in fairly good yields.…”