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Synlett 2025; 36(12): 1765-1769
DOI: 10.1055/a-2579-4076
DOI: 10.1055/a-2579-4076
letter
Divergent Approach to the Synthesis of 2-Aryl-5-(thiophen-2-yl)-1,3,4-oxadiazoles and -1,3,4-thiadiazoles
Authors
This work was supported by the Russian Science Foundation (Grant No. 20-73-10043).
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 - heterocyclesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2579-4076.
- Supporting Information (PDF)
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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