Synthesis of c‐17  trans  β‐lactams of the androstane series | Zendy

Siddiqui A. U. | Zendy; Satyanarayana Y. | Zendy; Srinivas M. | Zendy; Siddiqui A. H. | Zendy

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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 .

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