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■ 1,3-Dipolar Cycloadditoin Reaction of 2-[(Trimethylsilylmethylamino)(methylthio)]methylene-1,3-indandione: Synthetic Equivalent of Cyclic Dicarbonyl Alkylidene-azomethine Ylide as a Novel 1,3-Dipolar Reagent

Yoshinori Tominaga, Satoshi Takada, and Shinya Kohra

*Faculty of Pharmaceutical Sciences, Nagasaki University, 1-14, Bunkyo-machi, Nagasaki 852-8521, Japan

Abstract

2-[(Trimethylsilylmethylamino)(methylthio)]methylene-1,3-indandione (1), readily prepared by reaction of the corresponding 2-bis(methylthio)methylene-1,3-indandione (7) with trimethylsilylmethylamine (8), was found to be a synthetic equivalent of carbonyl alkylidene-azomethine ylide. Reaction of 1 with reactive hetero-dipolarophiles such as aldehydes and ketones and reactive alkenes in the presence of cesium fluoride gave 1,3-dipolar cycloadducts, 2-(1,3-dioxoindan-2-ylidene)-1,3-oxazolidines (5a-i) and 2-(1,3-dioxoindan-2-ylidene)pyrrolidines (6a-c).