Divergent Approach to the Synthesis of 2-Aryl-5-(thiophen-2-yl)-1,3,4-oxadiazoles and -1,3,4-thiadiazoles

Abstract

The reaction of 2-(chloromethyl)-1,3,4-thiadiazoles and -1,3,4-oxadiazoles with thioacetic acid in the presence of DIPEA led to the formation of S-[(1,3,4-thiadiazol-2-yl)methyl]- and [(1,3,4-oxadiazol-2-yl)methyl]ethanethioate. A series of 2-thienyl-substituted 1,3,4-oxadiazoles and 1,3,4-thiadiazoles were obtained by the reaction of 3-chloroacrylaldehydes with (1,3,4-thiadiazol-2-yl)- and (1,3,4-oxadiazol-2-yl)methanethiols formed in situ from S-[(1,3,4-thia(oxa)diazol-2-yl)methyl]ethanethioate in methanol in the presence of K₂CO₃. The photophysical properties of the synthesized compounds were studied.

Key words

3-chloroacrylaldehydes - 1,3,4-oxadiazoles - 1,3,4-thiadiazoles - divergent synthesis - heterocycles

Publication History

Received: 01 March 2025

Accepted after revision: 09 April 2025

Accepted Manuscript online:
09 April 2025

Article published online:
28 May 2025

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