Journal
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE
Volume 82, Issue 8, Pages 1314-1321Publisher
NATL RESEARCH COUNCIL CANADA
DOI: 10.1139/V04-100
Keywords
benzoxazinones; naphthoxazinones; organometallic reagents; amide preparation; aminoalkylphenols.
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A facile and simple method for the preparation of 3,4-dialkyl-3,4-dihydro-2H-1,3-benzoxazin-2-ones or naphthoxazin-2-ones in high yields from aminoalkylphenols and aminoalkylnaphthols is described. The reactions of the products obtained with organolithium and Grignard reagents were studied, and a method for the preparation of N-[1-(2-hydroxyphenyl)alkyl]-N-alkylamides, which are of pharmaceutical interest, from benzoxazinones was developed. A possible reaction mechanism is also proposed. The relative configuration of chiral products was determined from conformational analysis of H-1 NMR spectra.
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