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■ Formation of Xanthone Oxime and Related Compounds Using a Combination of tert-Butyl Nitrite and Potassium Hexamethyldisilazide

Yusuke Iwama, Takahiro Noro, Kentaro Okano, Hidetsura Cho,* and Hidetoshi Tokuyama*

*Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, Aramaki, Aoba-ku, Sendai 980-8578, Japan

Abstract

Synthesis of xanthone oxime and related compounds via nitrosation of the dibenzylic position using a combination of tert-butyl nitrite and potassium hexamethyldisilazide is described. The reaction conditions are effective for the synthesis of xanthone oxime as well as thioxanthone, acridone, and anthrone oximes, which have been difficult to synthesize from the corresponding ketones by conventional dehydrative condensation with hydroxylamine.