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

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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

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Amines
Urea
Carbodiimides
Thiourea
Dehydration
Substitution reactions
1,2,4-triazole
Direction compound

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthetic studies toward aryl-(4-aryl-4H-[1,2,4]triazole-3-yl)-amine from 1,3-diarylthiourea as urea mimetics. / Natarajan, Amarnath; Guo, Yuhong; Arthanari, Haribabu; Wagner, Gerhard; Halperin, Jose A.; Chorev, Michael.

In: Journal of Organic Chemistry, Vol. 70, No. 16, 05.08.2005, p. 6362-6368.

Research output: Contribution to journalArticle

Natarajan, Amarnath ; Guo, Yuhong ; Arthanari, Haribabu ; Wagner, Gerhard ; Halperin, Jose A. ; Chorev, Michael. / Synthetic studies toward aryl-(4-aryl-4H-[1,2,4]triazole-3-yl)-amine from 1,3-diarylthiourea as urea mimetics. In: Journal of Organic Chemistry. 2005 ; Vol. 70, No. 16. pp. 6362-6368.
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