Premium
Heterocyclic steroids: Synthesis of androsteno[17,16‐ d ]pyrazoles and androsteno[17,16‐ e ]pyrimidines
Author(s) -
Siddiqui A. U.,
Rao V. U. Maheshwar,
Maimirani M.,
Siddiqui A. H.
Publication year - 1995
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570320159
Subject(s) - chemistry , phenylhydrazine , hydrazine (antidepressant) , dimethylformamide , guanidine , hydrochloride , condensation , urea , medicinal chemistry , organic chemistry , chromatography , solvent , physics , thermodynamics
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.