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■ Reaction of Lactim Ethers with Carboethoxymethylpiperidines. A Synthesis of 1,9-Diazateroid

Takao Yamazaki,* Hiroki Takahata, Minoru Ishikura, and Masanori Nagata

*Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University, 2630 Sugitani, Toyama, Toyama 930-0194, Japan

Abstract

Imine-enamine tautomerization was observed in methyl valelo-lactim (2) and methyl caprolactim (3), whereas rarely in methyl butyrolactim (1) on NMR. The evidence for the tautomerization was elucidated also by the chemical behaviors of the lactim ethers towards cyclic β-aminoesters such as, 2-carboethoxymethyl piperidine derivatives, which often gave two kinds of products probably resulted from both the imine and the enamine forms. This was applied to a synthesis of the 1,9-diazasteroid.