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Synthesis of c‐17 trans β‐lactams of the androstane series
Author(s) -
Siddiqui A. U.,
Satyanarayana Y.,
Srinivas M.,
Siddiqui A. H.
Publication year - 1994
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.5570310142
Subject(s) - chemistry , chloroacetyl chloride , ethyl chloroacetate , hydrazide , triethylamine , hydrazine (antidepressant) , ethyl acetoacetate , medicinal chemistry , phenacyl bromide , hydrazone , condensation , organic chemistry , chloride , hydrate , catalysis , chromatography , physics , thermodynamics
3,3′‐Ethylenedioxyandrost‐4‐en‐17β‐ol 1 was converted into the ethyl ester 2 by reaction with potassium metal and ethyl chloroacetate. The ethyl ester 2 on reaction with hydrazine gave the hydrazide 3 . Condensation of 3 with aryl aldehydes gave the Schiff bases 4 . The reaction of Schiff bases 4 with mono‐chloroacetyl chloride in the presence of triethylamine afforded the β‐lactams 5 .