Tetrahedron letters

Novel synthesis of pyridazino [4, 5-b][1, 4] oxazin-3, 8-diones

…, JJ Kim, WH Joo, M Shiro, JR Falck, DS Shin, YJ Yoon

Index: Cho, Su-Dong; Song, Sang-Yong; Park, Yong-Dae; Kim, Jeum-Jong; Joo, Woo-Hong; Shiro, Motoo; Falck; Shin, Dong-Soo; Yoon, Yong-Jin Tetrahedron Letters, 2003 , vol. 44, # 50 p. 8995 - 8998

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Citation Number: 19

Abstract

A novel and effective synthesis of pyridazino [4, 5-b][1, 4] oxazin-3, 8-diones via Smiles rearrangement is presented. Treatment of N-substituted 2-chloro (or hydroxy) acetamide, 2- tetrahydropyranyl-4-chloro-5-hydroxy (or chloro) pyridazin-3-one and cesium carbonate in refluxing acetonitrile was afforded the corresponding pyridazino [4, 5-b][1, 4] oxazin-3, 8- diones in excellent yield.