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Communication | Regular issue | Vol 29, No. 8, 1989, pp.1443-1446
Published online, 1st January, 1970
DOI: 10.3987/COM-89-4996
Reaction of 6-Methyl-2-phenyl-4H-1,3-oxazin-4-one with Oxime Dianions

Yutaka Yamamoto,* Yasuo Morita, Reiko Kikuchi, Emiko Yokoo, Kaori Ohtsuka, and Miwako Katoh

*Faculty of Pharmaceutical Sciences, Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan


6-Methyl-2-phenyl-4H-1,3-oxazin-4-one (1) undergoes novel ring transformation upon treatment with oxime dianions to give isoxazoles (3a-d) and pyridine N-oxides (4c-f). The reaction of 1 with cycloheptanone oxime (2a) or cyclododecanone oxime (2b) in the presence of two equivalents of butyllithium affords isoxazole (3a or 3b). With acetophenone oxime (2c) or acetoxime (2d), pyridine N-oxide (4c or 4d) is formed as a minor product in addition to isoxazole (3c or 3d). Treatment with cyclopentanone oxime (2e) or cyclohexanone oxime (2f) yields pyridine N-oxides (4e or 4f) as a sole product.