Synthesis of novel carbo-and heteropolycycles. 12. A new versatile synthesis of oxazoles by intramolecular aza-Wittig reaction

…, S Yanagida, T Ozaki, S Hagiwara…

Index: Takeuchi, Hisato; Yanagida, Shun-ichi; Ozaki, Tooru; Hagiwara, Satoshi; Eguchi, Shoji Journal of Organic Chemistry, 1989 , vol. 54, # 2 p. 431 - 434

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Citation Number: 118

Abstract

A new synthesis of oxazoles by an intramolecular aza-Wittig reaction is described. Readily available a-azido ketones 2 were converted to (Z)-P-(acyloxy) vinyl azides 3 by selective enol acylation. These vinyl azides 3 reacted with triethyl phosphite to afford the corresponding oxazole derivatives 5 via the Staudinger reaction, followed by an intramolecular aza-Wittig reaction. In particular, this oxazole synthesis was useful for ...