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Paper | Special issue | Vol 37, No. 1, 1994, pp.523-528
Published online, 1st January, 1970
DOI: 10.3987/COM-93-S46
Oxidation of Dioxopyprroline with m-Chloroperbenzoic Acid: Selective Formation of 2,3-Dioxo-1,4-oxazine

Takehiro Sano,* Kazuko Amano, Masaharu Seki, Hiroyuki Hirota, Jun Toda, Fumiyuki Kiuchi, and Yoshisuke Tsuda

*Showa College of Pharmaceutical Sciences, 3-3165, Higashi-tamagawagakuen, Machida, Tokyo 194-8543, Japan

Abstract

Treatment of 4-ethoxycarbonyl-5-phenyl-1H-pyrrole-2,3-diones (1a-1e) and 4-benzoyl-1,5-diphenyl-1H-pyrrole-2,3-dione (1f) with m -chloroperbenzoic acid caused Baeyer-Villiger oxidation to give 2,3-dioxo-1,4-oxazines (2a-2f) in moderate yields, respectively. This conversion of the 1H-pyrrole-2,3-dione into the 2,3-dioxo-1,4-oxazine provides the first synthesis of monocyclic 2,3-dioxo-1,4-oxazine ring system.