Synthesis of 3-[4-(1-Benzofuran-2-yl)-1,3-thiazol-2-yl]-2-(4-aryl)-1,3-thiazolidin-4-one Derivatives as Biological Agents

Abstract

A protocol for the synthesis of 3-[4-(1-benzofuran-2-yl)-1,3-thiazol-2-yl]-2-(4-aryl)-1,3-thiazolidin-4-one derivatives (5a–e) has been developed from 1-(1-benzofuran-2-yl)-2-bromoethanone (2),which served as a key intermediate for the synthesis of the title compounds. The reaction of compound 2 with thiourea furnished 4-(1-benzofuran-2-yl)-1,3-thiazol-2-amine 3, which upon further reaction with various aromatic aldehydes, gave Schiff bases 4a–e. These Schiff bases, when treated with thioacetic acid in the presence of catalytic amount of anhydrous ZnCl₂, yielded thiazolidinone derivatives 5a–e. All the newly synthesized compounds have been characterized by analytical and spectral data and screened for their antimicrobial and analgesic activity.

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Keywords:

• Analgesic and antimicrobial activity
• anhydrous ZnCl₂
• 1-(1-benzofuran-2-yl)-2-bromoethanone
• Schiff base
• thiazolidinone ring
• thioacetic acid.

Acknowledgments

The authors thank the Indian Institute of Science, Bangalore, India, and Karnataka University, Dharwad, India, for providing spectral data. One of the authors (B.K.V.) thanks Kuvempu University for awarding a Research Fellowship.