Heterocyclic steroids: Synthesis of androsteno[17,16-d]pyrazoles and androsteno[17,16-e]pyrimidines

The Vilsmeier-Haack reaction of 3β-acetoxyandost-5-en-17-one ( 1 ) with phosporous oxychloride and dimethylformamide gave 3β-acetoxy-17-chloro-16-formylandrosta-5,16-diene ( 2 ). Reaction of 2 with hydrazine and phenylhydrazine provided substituted 5-androsteno[17,16-d]pyrazoles 3 and 4 respectively. Similarly, condensation of 2 with urea and guanidine hydrochloride revealed the formation of the corresponding substituted pyrimidines 5 and 6 respectively.