One-pot synthesis of 1,3,4-thiadiazoles using Vilsmeier reagent as a versatile cyclodehydration agent

A simple and efficient synthetic method for the one-pot synthesis of 1,3,4-thiadiazoles utilizing Vilsmeier reagent was developed. In this method carboxylic acids and hydrazine were converted to 1,3,4-thiadiazoles in the presence of Vilsmeier reagent and Lawesson's reagent. The influence of the...

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Bibliographic Details
Published in:Tetrahedron 2017-04, Vol.73 (14), p.1867-1872
Main Author: Zarei, Maaroof
Format: Article
Language:English
Subjects:
1,3,4-Thiadiazoles
Acylhydrazine
Diacylhydrazine
Lawesson's reagent
Vilsmeier reagent
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Summary:A simple and efficient synthetic method for the one-pot synthesis of 1,3,4-thiadiazoles utilizing Vilsmeier reagent was developed. In this method carboxylic acids and hydrazine were converted to 1,3,4-thiadiazoles in the presence of Vilsmeier reagent and Lawesson's reagent. The influence of the thionation reagent, solvent, temperature and time, in this reaction was discussed. The developed methodology for 1,3,4-thiadiazole synthesis has the advantage of simplicity, ambient reaction conditions, easy purification and good to excellent yield of products. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2017.02.042