A Novel Synthesis of 4H-1, 4-Benzoxazines

A Novel Synthesis of 4H-1, 4-Benzoxazines

The reaction of methyl 2-chloro-5-ethoxycarbonylamino-4-fluorobenzoate (4a) and 1-bromo-3, 3-dimethyl-2-butanone (2) in the presence of 2.2 eq of lithium bis(trimethylsilyl)amide afforded the 4H-1, 4-benzoxazine (6a) in good yield instead of the expected 4-oxazolin-2-one (5a). The generality of the...

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Veröffentlicht in:Chemical & pharmaceutical bulletin 1996/09/15, Vol.44(9), pp.1663-1668
Hauptverfasser: KUDO, Noriaki, FURUTA, Satoru, SATO, Kazuo
Format: Artikel
Sprache:eng
Schlagworte:
4-oxazolin-2-one
4H-1, 4-benzoxazine
Chemistry
electron-withdrawing group
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
intramolecular cyclization
Organic chemistry
Preparations and properties
α-bromoketone
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Beschreibung
Zusammenfassung:The reaction of methyl 2-chloro-5-ethoxycarbonylamino-4-fluorobenzoate (4a) and 1-bromo-3, 3-dimethyl-2-butanone (2) in the presence of 2.2 eq of lithium bis(trimethylsilyl)amide afforded the 4H-1, 4-benzoxazine (6a) in good yield instead of the expected 4-oxazolin-2-one (5a). The generality of the reaction and the mechanism are discussed.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.44.1663