A one-pot synthesis of pyrido [2, 3-b][1, 4] oxazin-2-ones

…, YD Park, JJ Kim, SG Lee, C Ma, SY Song…

Index: Cho, Su-Dong; Park, Yong-Dae; Kim, Jeum-Jong; Lee, Sang-Gyeong; Ma, Chen; Song, Sang-Yong; Joo, Woo-Hong; Falck; Shiro, Motoo; Shin, Dong-Soo; Yoon, Yong-Jin Journal of Organic Chemistry, 2003 , vol. 68, # 20 p. 7918 - 7920

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Citation Number: 43

Abstract

Pyrido [2, 3-b][1, 4] oxazin-2-ones are conveniently prepared in excellent yields by a one-pot annulation of N-substituted-2-chloroacetamides with 2-halo-3-hydroxypyridines with use of cesium carbonate in refluxing acetonitrile. The key transformation features a Smiles rearrangement of the initial O-alkylation product and subsequent cyclization.