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Divergent Reactions of 2‐Aminophenol with α‐Bromoacetate : Asymmetric Synthesis of Two Regioisomeric 1, 4‐Benzoxazinones
Author(s) -
Kim Seo Yun,
Han Gun Hee,
Hong Su Kyung,
Park Jieun,
Park Yong Sun
Publication year - 2021
Publication title -
bulletin of the korean chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.237
H-Index - 59
ISSN - 1229-5949
DOI - 10.1002/bkcs.12165
Subject(s) - chemistry , reactivity (psychology) , alkyl , nucleophilic substitution , alkylation , substitution reaction , ethyl bromoacetate , organic chemistry , stereochemistry , medicinal chemistry , catalysis , medicine , alternative medicine , pathology
2‐Aminophenol displays a diverse pattern of reactivity in the substitution reaction of α‐bromoacetate. The substitution under neutral or basic conditions results in the formation of 1,4‐benzoxazinones, whereas Lewis acid‐promoted substitution leads to Friedel–Crafts alkylation of 2‐aminophenol. Asymmetric synthesis of two regioisomeric 1,4‐benzoxazinones is accomplished from the nucleophilic substitution of highly diastereoenriched α‐aryl‐α‐bromoacetates with N ‐alkyl‐2‐aminophenols under varied reaction conditions.