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Paper | Special issue | Vol 47, No. 2, 1998, pp.703-716
Published online, 1st January, 1970
DOI: 10.3987/COM-97-S(N)35
Synthesis of N-Substituted 3-Oxo-17β- carboxamide-4-aza-5α-androstanes and the Tautomerism of 3-Oxo-4-aza-5-androstenes

Peng Xia,* Zheng-yu Yang, Yi Xia, Hao-bing Zhang, Ke-hua Zhang, Xun Sun, Ying Chen, and Yun-qing Zheng

*Department of Organic Chemistry, School of Pharmacy, Shanghai Medical University, 138 Yi Yuan Road Shanghai 200032, China

Abstract

An N-aryl-3-oxo-4-aza-5α-androst-1-ene-17β-carboxamide and three N-aryl or alkyl substituted 17 α-hydroxy-3-oxo-4-aza-5α-androstane-17β-carboxamides were synthesized as antiandrogen candidates from 3-oxoandrost-4-ene-17β-carboxylic acid and androst-4-ene-3,17-dione respectively. The chemo- and stereoselective reduction of 3-oxo-4-aza-5-ene intermediates with formic acid and their tautomerism in a solution of chloroform and methanol were described.