- Metal-Free Solvent Promoted Oxidation of Benzylic Secondary Amines to Nitrones with H2O2
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An environmentally benign protocol for the generation of nitrones from benzylic secondary amines via catalyst-free oxidation of secondary amines using H2O2 in MeOH or CH3CN is described. This methodology provides a selective access to a variety of C-aryl nitrones in yields of 60 to 93%. Several studies have been performed to shed light on the reaction mechanism and the role of the solvent.
- Adrio, Javier,Amarante, Giovanni Wilson,Granato, álisson Silva
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p. 13817 - 13823
(2021/10/01)
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- REACTION DES NITRONES AVEC LES CHLORURES D'ACIDES: ACTION DE CHLORURES D'ARYL-SULFONYLES ET DU CHLORURE DE BENZOYLE SUR DES N-OXY (ARYL-1 DIHYDRO-3,4 ISOQUINOLEINES). FORMATION D'UNE ISOQUINOLEINE, D'UN ISOCARBOSTYRYLE OU D'UNE INDOLINE SELON LES CONDITIONS
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Toluene-p-sulphonyl chloride, p-nitrobenzoyl chloride, and benzoyl chloride react with 1-aryl 3,4-isoquinoline N-oxide depending on the acidity of the medium, the nature of the substituent at C-1, and the nature of the acid chloride, to give an isoquinoline, an isocarbostyril (resulting from the migration of the phenyl substituent at C-1), an indoline (resulting from migration of the phenyl moiety incorporated in the heterocycle), or the formation of an O-acyl hydroxamic acid.The maximum selectivity is obtained in an heterogeneous medium and is governed by the intermediate formation of an hydroxylated pseudo-base.
- Cherest, M.,Lusinchi, X.
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p. 3471 - 3478
(2007/10/02)
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