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Heterocyclization reactions of azinoisocyanates. Synthesis of 2H-1,2,4-triazol-3(4H)-one derivatives

✍ Scribed by Kee-Jung Lee; Jin Lyang Kim; Mun Ki Hong; Jung Yong Lee

Book ID: 102342386
Publisher: Journal of Heterocyclic Chemistry
Year: 1999
Tongue: English
Weight: 347 KB
Volume: 36
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570360520

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✦ Synopsis

Abstract

The reaction of 1‐aminoethylidenehydrazones 9 with di‐tert‐butyl dicarbonate and 4‐dimethylaminopyridine led to the corresponding azinoisocyanates 10, which underwent thermal rearrangement under the reaction conditions to give 4‐(tert‐butoxycarbonyl)‐5‐methyl‐2__H__‐1,2,4‐triazol‐3(4__H__)‐ones 14. However, amidrazone 17 gave 2‐(2‐tert‐butoxycarbonyloxy‐2‐phenyl)ethyl‐4‐(tert‐butoxycarbonyl)‐5‐methyl‐2__H__‐1,2,4‐triazol‐3(4__H__)‐one 22 and N‐aziridinyliminocarbamate 18 under the similar conditions.

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