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 pharmaceutica interest, from benzoxazinones was developed. A opssible reaction mechanism is also proposed. The relative configuration of chiral products was determined from conformational analysis of 1H-NMR spectra.

A facile synthesis of 3,4-dialkyl-3,4-dihydro-2H-1,3-benzoxazin-2-ones and naphthoxazin-2-ones and their reactions with organolithium and grignard reagents - preparation of N-[1-(2'-hydroxyphenyl)alkyl]amides

CIMARELLI, Cristina;PALMIERI, Gianni;
2004-01-01

Abstract

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 pharmaceutica interest, from benzoxazinones was developed. A opssible reaction mechanism is also proposed. The relative configuration of chiral products was determined from conformational analysis of 1H-NMR spectra.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11581/112732
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