Premium
Ring closure of 1‐[4‐(imidazol‐1‐yl)phenyl]‐3‐phenyl‐2‐propen‐1‐one derivatives to potential biologically active compounds
Author(s) -
Coudert P.,
Couquelet J.,
Tronche P.,
Leal F.
Publication year - 1993
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.5570300444
Subject(s) - chemistry , acetic acid , medicinal chemistry , pyridazine , hydrazine (antidepressant) , dehydrogenation , organic chemistry , cyanohydrin , nitrone , catalysis , cycloaddition , chromatography
1‐[4‐(Imidazol‐1‐yl)phenyl]‐3‐phenyl‐2‐propen‐1‐one 1 reacted with acetone cyanohydrin, ethyl phenylacetate and cyanoacetamide to give the adducts 2, 8 and 10 respectively. Action of hydrazine hydrate on both the γ‐ketonitrile 2 and the corresponding γ‐ketoacid 4 led to pyridazine derivatives 3 and 5 . 4,5‐Dihydropyridazinone 5 was dehydrogenated by the action of bromine in acetic acid to give pyridazinone 6 . Cyclization of acid 8 in acetic medium resulted in α‐pyrone 9 . Cyanopentanamide 10 was converted with hydrochloric acid into δ‐ketoacid 13 which led to α‐pyrone 14 via an intramolecular dehydration. Refluxing 10 in the presence of acetic acid and ammonium acetate gave 3,4‐dihydropyridone 11 which was dehydrogenated to produce pyridone 12 .