title: Synthetic studies toward aryl-(4-aryl-4H-[1,2,4]triazole-3-yl)-amine from 1,3-diarylthiourea as urea mimetics.
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.
authors.affiliation: Laboratory for Translational Research, 1 Kendall Square, Building 600 3rd Floor, Harvard Medical School, Cambridge, Massachusetts 02139, USA.
authors.forename: Amarnath
authors.initials: A
authors.lastname: Natarajan
authors.forename: Yuhong
authors.initials: Y
authors.lastname: Guo
authors.forename: Haribabu
authors.initials: H
authors.lastname: Arthanari
authors.forename: Gerhard
authors.initials: G
authors.lastname: Wagner
authors.forename: Jose A
authors.initials: JA
authors.lastname: Halperin
authors.forename: Michael
authors.initials: M
authors.lastname: Chorev
mesh_terms: D009682:Magnetic Resonance Spectroscopy; D018716:Molecular Mimicry; D015394:Molecular Structure; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry*; D014508:Urea / Q000737:chemistry*
chemical_list: D014230:Triazoles; D014508:Urea