Au. Siddiqui et al., HETEROCYCLIC STEROIDS - SYNTHESIS OF ANDROSTENO[17,16-D]PYRAZOLES ANDANDROSTENO[17,16-E]PYRIMIDINES, Journal of heterocyclic chemistry, 32(1), 1995, pp. 353-354
The Vilsmeier-Haack reaction of 3beta-acetoxyandost-5-en-17-one (1) wi
th phosporous oxychloride and dimethylformamide gave 3beta-acetoxy-17-
chloro-16-formylandrosta-5, 16-diene (2). Reaction of 2 with hydrazine
and phenylhydrazine provided substituted 5-androsteno[17,16-d]pyrazol
es 3 and 4 respectively. Similarly, condensation of 2 with urea and gu
anidine hydrochloride revealed the formation of the corresponding subs
tituted pyrimidines 5 and 6 respectively.