Synthetic studies toward aryl-(4-aryl-4H-[1,2,4]triazole-3-yl)-amine from 1,3-diarylthiourea as urea mimetics

Amarnath Natarajan, Yuhong Guo, Haribabu Arthanari, Gerhard Wagner, Jose A. Halperin, Michael Chorev

Research output: Contribution to journalArticle

36 Scopus citations

Abstract

A thiophile-promoted synthesis of disubstituted 4H-[1,2,4]triazole-3-yl- amines as urea mimetics from the corresponding 1,3-disubstituted thioureas has been studied, and the scope and limitations of this reaction are presented. The reaction proceeds through the formation of a carbodiimide, followed by a sequential addition-dehydration with acyl hydrazides. 1,3-Branched dialkylthioureas result in the formation of the corresponding ureas. The electronic and steric effects of the substitution on the phenyl rings of the 1,3-diarylthioureas play an important role in the formation of the intermediary carbodiimde and the direction of the subsequent ring closure of the N-acyl hydrazide adduct.

Original languageEnglish (US)
Pages (from-to)6362-6368
Number of pages7
JournalJournal of Organic Chemistry
Volume70
Issue number16
DOIs
StatePublished - Aug 5 2005

ASJC Scopus subject areas

  • Organic Chemistry

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