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A Safe Synthesis of 1,5-Disubstituted 3-Amino-1H-1,2,4-triazoles from 1,3,4-Oxadiazolium Hexafluorophosphates

Brian Wong, Andreas Stumpf, Diane Carrera, Chunang Gu, Haiming Zhang*

*Small Molecule Process Chemistry, Genentech, Inc., 1 DNA Way, South San Francisco, CA 94080, USA, Email: zhang.haiminggene.com

B. Wong, A. Stumpf. D. Carrera, C. Gu, H. Zhang, Synthesis, 2013, 45, 1083-1093.

DOI: 10.1055/s-0032-1316877 (free Supporting Information)


Abstract

Hexafluorophosphoric acid promotes the formation of 1,3,4-oxadiazolium hexafluorophosphate salts from N′-acyl-N-aroyl-N-arylhydrazides or N′-acyl-N-acyl-N-arylhydrazides under mild conditions. A subsequent reaction with cyanamide in propan-2-ol in the presence of triethylamine generates 1,5-disubstituted 3-amino-1H-1,2,4-triazoles in good yields.

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Key Words

heterocycles, substituent effects, rearrangement, hydrazides, aminotriazoles, oxazoles, 1,2,4-triazoles


ID: J66-Y2013