N-alkylation of 17-azasteroids.
N-Alkylation of 17-azasteroid lactams (16-oxo-17-azaandrost-5-en-3 beta-ol acetate 3 and its D-homo analog 4) was studied. It has been found that both lactams are readily alkylated with iodomethane or iodoethane. In contrast to this there was no reaction with 2-iodo-6-methylheptane due to the steric hindrance. 1,4-Addition of lactam to the conjugated systems was also studied. The addition to acrylonitrile proved to be easy compared to crotononitrile. However the efficient addition to the latter compound was also attained by using potassium t-butoxide as a base in t-butanol.
Morzycki
J W
JW
Institute of Chemistry, University of Warsaw, Bialystok, Poland.
Lotowski
Z
Z
D000181:Acrylonitrile; D000478:Alkylation; D000737:Androstenols / Q000737:chemistry*; D001378:Azasteroids / Q000737:chemistry*; D006847:Hydrocarbons, Iodinated; D007202:Indicators and Reagents; D009570:Nitriles
C086454:16-oxo-17-azaandrost-5-en-3-ol acetate; D000737:Androstenols; D001378:Azasteroids; D006847:Hydrocarbons, Iodinated; D007202:Indicators and Reagents; D009570:Nitriles; C031103:crotononitrile; C015660:allyl cyanide; C014055:methyl iodide; D000181:Acrylonitrile