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2-Arylhydrazononitriles in heterocyclic synthesis: a novel route to 1,3-diaryl-1,2,4-triazol-5-amines via a Tiemann rearrangement of arylhydrazonoamidoximes
Journal article   Open access  Peer reviewed

2-Arylhydrazononitriles in heterocyclic synthesis: a novel route to 1,3-diaryl-1,2,4-triazol-5-amines via a Tiemann rearrangement of arylhydrazonoamidoximes

Hamad M. Al-Matar, Sayed M. Riyadh and Mohamed H. Elnagdi
ARKIVOC free online journal of organic chemistry, Vol.2007(13), pp.53-62
10/04/2007
DOI: https://doi.org/10.3998/ark.5550190.0008.d08

Abstract

Chemistry Chemistry, Organic Physical Sciences Science & Technology
2-Arylhydrazononitriles react with hydroxylamine hydrochloride in refluxing ethanolic sodium acetate to yield amidoximes that cyclized into 1,2,3-triazol-5-amines or 1,2,4-triazol-5-amines depending on the nature of the substituents on hydrazone linkage. NOE difference experiments could successfully be utilized to distinguish 1,2,3-triazoles from isomeric 1,2,4-triazoles.
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