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A new route to 2‐styrylbenzimidazoles
Author(s) -
Balazs Marjorie K.,
Furst Arthur
Publication year - 1970
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.5570070624
Subject(s) - chemistry , oxazolone , phenylpyruvic acid , hydrolysis , ring (chemistry) , stereochemistry , medicinal chemistry , organic chemistry , amino acid , biochemistry , phenylalanine
Abstract An attempt was made to prepare 2‐benzylquinoxalin‐3‐one by hydrolyzing the azlactone, 2‐phenyl‐4‐benzylidene‐5‐oxazolone to β‐phenylpyruvic acid and then treating this in situ with o ‐phenylenediamine (OPDA). The initial hydrolysis apparantly proceeded only as far as opening the azlactone ring forming 2‐benzamidocinnamic acid which condensed with OPDA to form a substituted styrylbenzimidazole.