Expeditious Microwave-Assisted Synthesis of 1,3-Benzoxazoles Incorporating Substituted Thiazolidinone Moieties
Abstract
The rapid synthesis of 3-[4-(1,3-benzoxazol-2-yl)phenyl]-2-aryl-1,3-thiazolidin-4-one 4(a-h) was achieved through microwave-assisted methods. This involved the reaction of Schiff bases derived from 2-(4-amino phenyl) benzoxazole 3(a-h) with ethanol, SHCH2COOH (thioglycolic acid) (1 mol, 0.92 mL), and ZnCl2 (5 mol%) under microwave irradiation (400W, 146°C) for 3-4 minutes, resulting in excellent yields. Compound precursors 3(a-h) were prepared from aromatic aldehydes and 2-(4-amino phenyl) benzoxazole in ethanol, followed by microwave irradiation for 1-2 minutes, with reaction progress monitored via TLC. The expeditious reaction time is a notable advantage of this protocol. Comprehensive structural elucidation of the synthesized compounds involved elemental analysis, IR, NMR, 13C NMR, and Mass spectroscopy. These newly synthesized compounds, 4(a-h), were subjected to in vitro antimicrobial screening against Staphylococcus aureus, Escherichia coli, and antifungal screening against Aspergillus Niger. The zone of inhibition in millimeters was measured using the cup plate method. Several compounds within the series exhibited substantial activity when compared to the standard drugs streptomycin and Fluconazole.
Keywords:
Thiazolidinone, Microwave, Thioglycollic acid, ZnCl2DOI
https://doi.org/10.25004/IJPSDR.2023.150609References
Baswat AR, Rathod SR, Rathod SD. Ionic liquid [Et3NH][HSO4] promoted One-pot Synthesis of 1, 3-Benzoxazoles with Substituted Thiazolidinone Moiety. Bull Env Pharmacol Life Sci. 2022; 1364-1368.
Metzger JV. The Chemistry of Heterocyclic Compounds, Thiazole and Its Derivatives. John Wiley & Sons. 2009.
Singh SP, Parmar SS, Raman K, Stenberg VI. Chemistry and biological activity of thiazolidinones. Chem Rev. 1981; 81: 175.
Patel D, Kumari P, Patel N. Synthesis and characterization of some new thiazolidinones containing coumarin moiety and their antimicrobial study. Arch Appl Sci Res. 2010; 2: 68.
Mistry KM, Desai R. Synthesis of Novel Heterocyclic 4-Thiazolidinone Derivatives and their Antibacterial Activity. Eur J Chem. 2004; 1: 189-193.
Desai KG, Desai KR. A facile microwave enhanced synthesis of sulfur-containing 5-membered heterocycles derived from 2-mercaptobenzothiazole over ZnCl2/DMF and antimicrobial activity evaluation. J Sulfur Chem. 2006; 27: 315-328.
Seelam N, Shrivastava SP. Synthesis and in vitro study of [1,3,4] thiazol-2l-3,3a,5,6-tetrahydro-2H-pyrazolo[3,4-d]thiazoles as antimicrobial agents. J Saudi Chem Soc. 2016; 20(1): 33-39.
Jayalakshmi PM, Sheeba Jasmin TS, Manu Jose. Microwave Assisted Synthesis and Antibacterial Evaluation of 1, 3, 4-Thiadiazole Derivatives. Int J Pharm Sci Drug Res. 2021; 14(10).
Chawla P, Singh R, Saraf SK. Syntheses and evaluation of 2, 5-disubstituted 4-thiazolidinone analogues as antimicrobial agents. Med Chem Res. 2012; 21:2064.
Jain AK, Vaidya A, Ravichandran V, Kashaw SK, Agrawal RK. Recent developments and biological activities of thiazolidinone derivatives: a review. Bioorg Med Chem. 2012; 20:3378.
Vazzana I, Terranova E, Mattioli F, Sparatore F. Aromatic Schiff Bases and 2,3-Disubstituted-1,3-thiazolidin-4-one Derivatives as Anti-Inflammatory Agents. ARKIVOC. 2004; 5: 364-374.
Saini N, Sharma A, Thakur VK, Makatsoris C, Dandia A, Bhagat M, Tonk RK, Sharma PC. Microwave assisted green synthesis of thiazolidin-4-one derivatives: A perspective on potent antiviral and antimicrobial activities. Curr Res Green Sustainable Chem. 2020; 3: 100021.
Rao A, Balzarini J, Carbone A, Chimirri A, De Clercq E, Luca DD, Monforte AM, Monforte P, Pannecouque C, Farmaco M. Synthesis and anti-HIV studies of 2- and 3-adamantyl-substituted thiazolidin-4-ones.Farmaco. 2004; 59: 33.
Babaoglu K, Page MA, Jones VC, McNeil MR, Dong C, Naismith JH, Lee RE. Novel inhibitors of an emerging target in Mycobacterium tuberculosis; substituted thiazolidinones as inhibitors of dTDP-rhamnose synthesis. Bioorg Med Chem Lett. 2003; 13: 3227.
Hafez HN, Abdel-Rahman BA, Gazzar E. Synthesis and antitumor activity of substituted triazolo[4,3-a]pyrimidin-6-sulfonamide with an incorporated thiazolidinone moiety. Bioorg Med Chem Lett. 2009; 19: 4143-4147.
Published
Abstract Display: 350 
PDF Downloads: 355 
