A Novel Synthesis of 3-Aryl-5-tert-butyl-4-oxazolin -2-ones

A Novel Synthesis of 3-Aryl-5-tert-butyl-4-oxazolin -2-ones

An efficient synthetic method for 3-aryl-5-butyl-4-oxazolin-2-ones (6) is described. The reaction of ethyl N-arylcarbamates (10) with 1-bromo-3, 3-dimethyl-2-butanone (9a) or 1-bromo-3-ethyl-3-methyl-2-pentanone (9b) using 2.2 eq of lithium bis(trimethylsilyl)amide afforded 6 in good yields. The rea...

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Veröffentlicht in:Chemical & pharmaceutical bulletin 1996/04/15, Vol.44(4), pp.699-702
Hauptverfasser: KUDO, Noriaki, TANIGUCHI, Misa, SATO, Kazuo
Format: Artikel
Sprache:eng
Schlagworte:
a-oxazolin-2one
Chemistry
cyclization
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Organic chemistry
Preparations and properties
α-bromoketone
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Zusammenfassung:An efficient synthetic method for 3-aryl-5-butyl-4-oxazolin-2-ones (6) is described. The reaction of ethyl N-arylcarbamates (10) with 1-bromo-3, 3-dimethyl-2-butanone (9a) or 1-bromo-3-ethyl-3-methyl-2-pentanone (9b) using 2.2 eq of lithium bis(trimethylsilyl)amide afforded 6 in good yields. The reaction mechanisms are discussed.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.44.699