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■ A Reinvestigation of the Synthesis of 1,2-Dihydro[1,2]diazepin-3-ones from Pyrones

Norton P. Peet* and Shyam Sunder

*Indianapolis Center, Merrell Dow Research Institute, 9550 Zionsville Road, indianapolis, Indiana 46268-0470, U.S.A.

Abstract

The reactions of 5-acetyl-6-hydroxy-4-(4-methoxyphenyl)-2H-pyran-2-one (5) and 4-(4-methoxyphenyl)-2H-pyran-2,6-dione (4) with hydrazine and phenylhydrazine respectively, gave the respective 1-amino-2-pyridones 8 and 11 rather than diazepinones 6 and 10, as previously reported. In addition. 4-(4-methoxyphenyl)-2-methyl-6-oxo-2H-pyran-3-carboxylic acid (14) gave p-methoxyacetophenone azine (16) upon treatment with hydrazine, rather than pyrazolodiazepinone 15.