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Rearrangement reactions of phenyl chloroformate derivatives of 2‐Hydroxyaminoacetanilides to hydantoins, ureas and hydantoie acid derivatives
Author(s) -
Hell Stanley C.,
Conklin George,
Mccaully Ronald J.
Publication year - 1976
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.5570130109
Subject(s) - chemistry , ethyl chloroformate , chloroformate , organic chemistry , medicinal chemistry
Alkaline treatment of 2′‐benzoyl‐2‐( N ‐carbophenoxy‐ N ‐hydroxyamino)‐4′‐chloroacetanilide ( 10 ) and its corresponding acetate 6 afforded respectively 5‐(2‐benzoyl‐4‐chlorophenyl)‐3‐hydroxy‐hydantoic acid ( 12 ) and 6‐chloro‐4‐phenylquinazolone ( 13 ). A study of the course of the reaction was carried out with the corresponding compounds that are devoid of the 2‐benzoyl group. An elucidation of the rearrangement is based on the isolation and independent synthesis of the heterocyclic intermediates.