Reactions of Unsaturated 1,3-Oxazines; I. Reaction of 6-Alkoxy-2-aryl-4H-1,3-oxazine-4-one with Hydrazine Derivatives

A. V. Prep'yalov; I. P. Yakovlev; V. E. Zakhs

doi:10.1055/s-1999-3409

Synthesis 1999; 1999(3): 483-486
DOI: 10.1055/s-1999-3409

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Reactions of Unsaturated 1,3-Oxazines; I. Reaction of 6-Alkoxy-2-aryl-4H-1,3-oxazine-4-one with Hydrazine Derivatives

A. V. Prep'yalov^* , I. P. Yakovlev, V. E. Zakhs

^*Eurochim, Lanskoe schosse 22-6-26, St. Petersburg 197343, Russia; Fax +7(8 12)2 46 75 71; E-mail: synthez@mail.wplus.net

Abstract

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6-Alkoxy-2-aryl-4H-1,3-oxazin-4-ones 1a-e react with hydrazine (2a) and phenylhydrazine (2b) with ring opening at the C-2-O followed by recyclization to 1,2,4-triazole-5-acetic acid esters 3a-e, Reactions of the title compounds with unsymmetrical dimethylhydrazine 2c led to formation of 2-substituted 4-hydroxyimidazole-4-carboxylates 5a-c.

1,3-oxazines - hydrazines - imidazoles - 1,2,4-triazoles

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