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Synthesis of 1‐(2‐hydroxyphenyl)‐2,4‐imidazolidinedione derivatives through cyclic transformations of ethyl 2‐oxo‐3(2 H )‐benzoxazoleacetate derivatives
Author(s) -
Milcent René,
Akhnazarian Anna,
Lensen Nathalie
Publication year - 1996
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.5570330645
Subject(s) - chemistry , ethyl acrylate , benzoxazole , hydrazine (antidepressant) , ammonia , medicinal chemistry , organic chemistry , acrylate , monomer , chromatography , polymer
A series of ethyl 2‐oxo‐3(2 H )‐benzoxazoleacetate derivatives 2 have been synthesized. By reaction with ammonia, primary amines or hydrazine, these compounds 2 were transformed into 1‐(2‐hydroxyphenyl)‐2,4‐imidazolidinedione derivatives 4, 5 and 6 , respectively. Some of these new hydantoins 4 , treated with phosphorus oxychloride, gave 3 H ‐2‐oxoimidazo[2,1‐ b ]benzoxazole derivatives 9 . Ethyl 2‐oxo‐3(2 H )‐benzoxazolepropionate ( 10 ) was prepared by a Michaël reaction of ethyl acrylate with 2‐benzoxazolone ( 1a ). With 10 , no cyclic transformation was observed in the presence of ammonia or alkylamine.