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Synthesis of 2-Imino-1,3,4-thiadiazoles from Hydrazides and Isothiocyanates via Sequential Oxidation and P(NMe2)3-Mediated Annulation Reactions

Zhengyan Huang, Qianqian Zhang, Qiongli Zhao, Wenquan Yu* and Junbiao Chang*

*College of Chemistry, Zhengzhou University, Zhengzhou, Henan 450001, China, Email: wenquan_yuzzu.edu.cn, changjunbiaozzu.edu.cn

Z. Huang, Q. Zhang, Q. Zhao, W. Yu, J. Chang, Org. Lett., 2020, 22, 4378-4382.

DOI: 10.1021/acs.orglett.0c01393 (free Supporting Information)


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Abstract

A simple P(NMe2)3-mediated annulation reaction of N-acyldiazenes with isothiocyanates provides 2-imino-1,3,4-thiadiazoles. N-acyldiazenes can be generated from hydrazides using iodine as oxidant and can be used without purification.

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Key Words

S-Heterocycles, Tris(dimethylamino)phosphine


ID: J54-Y2020