Synthesis of 4-hydroxy-5-methyl-2-[2-(4-oxo-4H-chromen-3-yl)ethenyl]-6H-1,3-oxazin-6-ones and their reaction with hydrazine

Abstract

4-Hydroxy-6H-1,3-oxazin-6-ones containing a 3-vinylchromone fragment in the 2-position were synthesized. The direction of their reactions with hydrazine hydrate was found to depend on the solvent nature. The reaction in protic solvents (methanol, acetic acid) resulted in recyclization of both oxazine ring to 1,2,4-triazole and pyranone ring to pyrazole. Aprotic acetonitrile favored attack of hydrazine exclusively on the oxazine ring, while the 3-vinylchromone fragment remained intact.