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Report | Regular issue | Vol 20, No. 5, 1983, pp.857-861
Published online, 1st January, 1970
DOI: 10.3987/R-1983-05-0857
Synthesis of 13-Aza-16-oxa, 13-Aza-16-thia- and 13,16-Diazasteroidal Compounds through Cyclization of N-Acyliminium ion Intermediates

Shinzo Kano and Yoko Yuasa

*School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan

Abstract

5,5-Dimethyl-2,4-oxazolidinedione, 2,4-thiazolidinedione and 5,5-dimethylhydantoin were coupled with 2-(3,4-dihydro-1-naphthyl)ethyl alcohol by an application of Mitsunobu’s method to give the corresponding N-substituted products (5)-(7), respectively. Reduction of 5-7 with diisobutylaluminium hydride, followed by cyclization of the reduction products with formic acid yielded the 13-aza-16-oxa- (11), 13-aza-16-thia- (12) and 13,16-diaza-1,3,5 (10), 9(11)-estratetraen-17-one (13), respectively.