A Convenient, Rapid Microwave-Assisted Synthesis of 2-Substituted Phenyl-2,3-Dihydrobenzo[B][1,4]Thiazepine-3-Carboxamide Derivatives and Its Antimicrobial Activity

Abstract

Using an environmentally benign procedure under microwave irradiation, a variety of 4-methyl-N-(4-(2-oxo-2H-chromen-3-yl)thiazol-2-yl)-2-substituted phenyl-2,3-dihydrobenzo [b][1,4]thiazepine-3-carboxamide compounds were synthesized from 2-arylidene-3-oxo-N-(4-(2-oxo-2H-chromen-3-yl)thiazol-2-yl)butanamide. Structures of these compounds were confirmed by IR, NMR (¹H & ¹³C), and mass spectral analyses. Also, a considerable increase in the reaction rate has been observed with better yield in the microwave technique. The newly synthesized compounds were evaluated for antimicrobial activity against a variety of bacterial strains, and some of these compounds have shown significant antibacterial and antifungal activities.

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GRAPHICAL ABSTRACT

Keywords:

• 3-(2-Amino-1,3-thiazol-4-yl)-2H-chromen-2-one
• antimicrobial activities
• 2,3-dihydro[b][1,4]benzothiazepines
• microwave irradiation
• 3-oxo-N-[4-(2-oxo-2H-chromen-3-yl)thiazol-2-yl]butanamide

Acknowledgments

One of the authors (JPR) is thankful to Mr. Priyakant R. Raval, Cyanamid India Ltd., Atul (Gujarat), Charutar Vidya Mandal's SICART, Vallabh Vidyanagar, Dist. Anand, Gujarat, India, for providing spectral and analytical data of the compounds 4a–j and 6a–j. The authors are also thankful to the Head of the Bioscience Department of VNSGU, Surat, for biological screening.