New rearrangement of 4-isoxazoline system: conversion of ketones into alpha,beta-unsaturated amides |
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Authors: | Chiacchio Ugo Rescifina Antonio Chiacchio Maria Assunta Romeo Giovanni Romeo Roberto |
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Affiliation: | Dipartimento di Scienze Chimiche, Università di Catania, Viale Andrea Doria 6, 95125 Catania, Italy. uchiacchio@dipchi.unict.it |
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Abstract: | 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. |
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