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

Anna L. Samsonenko; Anastasia S. Kostyuchenko; Tatyana Y. Zheleznova; Evgenii B. Uliankin; Sergei A. Chernenko; Vladislav Y. Shuvalov; Anton L. Shatsauskas; Alexander S. Fisyuk

doi:10.1055/a-2579-4076

Synlett, Table of Contents

Synlett 2025; 36(12): 1765-1769
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

Anna L. Samsonenko

^aLaboratory of New Organic Materials, Omsk State Technical University, Mira Ave. 11, 644050 Omsk, Russian Federation

^bDepartment of Organic Chemistry, Omsk F. M. Dostoevsky State University, Mira Ave. 55A, Omsk 644077, Russian Federation
Anastasia S. Kostyuchenko

^aLaboratory of New Organic Materials, Omsk State Technical University, Mira Ave. 11, 644050 Omsk, Russian Federation

^bDepartment of Organic Chemistry, Omsk F. M. Dostoevsky State University, Mira Ave. 55A, Omsk 644077, Russian Federation
Tatyana Y. Zheleznova

^aLaboratory of New Organic Materials, Omsk State Technical University, Mira Ave. 11, 644050 Omsk, Russian Federation

^bDepartment of Organic Chemistry, Omsk F. M. Dostoevsky State University, Mira Ave. 55A, Omsk 644077, Russian Federation
Evgenii B. Uliankin

^aLaboratory of New Organic Materials, Omsk State Technical University, Mira Ave. 11, 644050 Omsk, Russian Federation

^bDepartment of Organic Chemistry, Omsk F. M. Dostoevsky State University, Mira Ave. 55A, Omsk 644077, Russian Federation
Sergei A. Chernenko

^aLaboratory of New Organic Materials, Omsk State Technical University, Mira Ave. 11, 644050 Omsk, Russian Federation

^bDepartment of Organic Chemistry, Omsk F. M. Dostoevsky State University, Mira Ave. 55A, Omsk 644077, Russian Federation
Vladislav Y. Shuvalov

^bDepartment of Organic Chemistry, Omsk F. M. Dostoevsky State University, Mira Ave. 55A, Omsk 644077, Russian Federation
Anton L. Shatsauskas

^bDepartment of Organic Chemistry, Omsk F. M. Dostoevsky State University, Mira Ave. 55A, Omsk 644077, Russian Federation
Alexander S. Fisyuk ∗

^aLaboratory of New Organic Materials, Omsk State Technical University, Mira Ave. 11, 644050 Omsk, Russian Federation

^bDepartment of Organic Chemistry, Omsk F. M. Dostoevsky State University, Mira Ave. 55A, Omsk 644077, Russian Federation

Abstract

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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

Full Text

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