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Communication | Regular issue | Vol 24, No. 5, 1986, pp.1247-1250
Published online, 1st January, 1970
DOI: 10.3987/R-1986-05-1247
Metallo-ketene-S,N-acetals. New Synthesis of Azacycloalka[3,2-c]pyridin-2-ones

Hiroki Takahata, Toshiaki Suzuki, and Takao Yamazaki*

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

Abstract

S-Lithio-ketene-S,N-actals (3 and 4), generated from N-methylthiolactams (1 and 2) with n-buthyllithium (n-BuLi), react with aryl isocyanates (5) to give 3-(N-arylcarbamoyl)thiolactams (6 and 7), which are transformed into azacycloalka[3,2-c]pyridine-2-ones (12 and 13), respectively, using sulfide extrusion of thioiminium salts (8 and 9) with malononitrile followed by cyclization.