Efficient Synthesis of (2Z,5Z)-3-Benzyl/alkyl-5-(2-oxo-5-aryl-3 (2H)-furanylidene)-2-(phenylimino)-1,3-thiazolidin-4-ones via a One-Pot Three-Component Reaction

Abstract

A simple and efficient strategy for the chemoselective synthesis of (2Z,5Z)-3-benzyl/alkyl-5-(2-oxo-5-arylfuran-3(2H)-ylidene)-2-(phenylimino)thiazolidin-4-one derivatives is developed via a sequential three-component reaction of readily available phenacyl bromides, pyridine and methyl 2-(3-benzyl/alkyl-4-oxo-2-(phenylimino)thiazolidin-5-ylidene)acetates in acetonitrile at room temperature. The advantages of this one-pot sequential Michael addition/1,2-H shift/elimination of pyridine/intramolecular cyclization are highlighted by its low energy requirements (short reaction times at room temperature), excellent yields, the absence of a metal catalyst, and mild conditions. The product structures are characterized by spectroscopic techniques and single-crystal X-ray analysis.

Key words

phenacyl bromide - pyridine - thiazolidinone - Michael addition - intramolecular cyclization - chemoselective reaction

Publication History

Received: 23 September 2023

Accepted after revision: 22 January 2024

Article published online:
13 February 2024

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