Work

Synthetic Studies toward Aryl-(4-aryl-4H-[1,2,4]triazole-3-yl)-amine from 1,3-Diarylthiourea as Urea Mimetics

Year: 2005

Type: article

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.

Source: The Journal of Organic Chemistry

DOI: 10.1021/jo0508189

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

Institution: Harvard University

Language: English

Topic: Structural and Chemical Analysis of Organic and Inorganic Compounds

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: National Cancer Institute

Awards: G10709470, G3041574123, Inhibition of Translation Initiation in Cancer Therapy