New rearrangement of 4-isoxazoline system: conversion of ketones into alpha,beta-unsaturated amides.
A new rearrangement pattern of the 4-isoxazoline system is reported. The reaction, starting from 3,3-disubstituted derivatives and leading to alpha,beta-unsaturated amides, proceeds through the quaternarization of the nitrogen atom and involves the heterolytic cleavage of C(3)-N bond, assisted by the formation of a relatively stable intermediate. The overall process represents a useful conversion of ketones into alpha,beta-unsaturated amides.
Chiacchio
Ugo
U
Dipartimento di Scienze Chimiche, Università di Catania, Viale Andrea Doria 6, 95125 Catania, Italy. uchiacchio@dipchi.unict.it
Rescifina
Antonio
A
Chiacchio
Maria Assunta
MA
Romeo
Giovanni
G
Romeo
Roberto
R