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A facile synthesis of 3-Substituted 5-Oxo-1,2,4-thiadiazoles from amidoximes

✍ Scribed by Yasuhisa Kohara; Keiji Kubo; Eiko Imamiya; Takehiko Naka

Publisher
Journal of Heterocyclic Chemistry
Year
2000
Tongue
English
Weight
288 KB
Volume
37
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

The reaction of amidoximes 1 with 1,1′‐thiocarbonyldiimidazole (TCDI) followed by treatment with silica gel or boron trifluoride diethyl etherate (BF~3~·OEt~2~) provided 3‐substituted 4,5‐dihydro‐5‐oxo‐1,2,4‐thiadiazoles 2 in moderate yields. The Lewis acids are considered to promote the rearrangement of the thioxocarbamate intermediates 5 to the thiol carbarn ate intermediates 7, which cyclize to afford 4,5‐dihydro‐5‐oxo‐1,2,4‐thiadiazoles 2.

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