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