Tetrahedron

Reaction of 1-substituted 3, 5-diamino-1, 2, 4-triazoles with β-keto esters: synthesis and new rearrangement of mesoionic 3-amino-2H-[1, 2, 4] triazolo-[4, 3-a] …

VM Chernyshev, AV Astakhov, ZA Starikova

Index: Chernyshev, Victor M.; Astakhov, Alexander V.; Starikova, Zoya A. Tetrahedron, 2010 , vol. 66, # 18 p. 3301 - 3313

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Citation Number: 16

Abstract

Reaction of 3, 5-diamino-1-R-1, 2, 4-triazoles (R= Ph, Bn) with β-keto esters results in the reversible formation of N-(5-amino-1-R-1, 2, 4-triazol-3-yl)-substituted enaminoesters (8). Subsequent transformations depended on the reaction conditions. Compounds 8 undergo intermolecular reactions of condensation and amidation in the absence of solvent. However, in the presence of acetic acid they form 3-amino-5-oxo-2-R-2, 5-dihydro-[1, 2, 4] triazolo [4 ...