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

Article abstract of DOI:10.1016/0040-4020(82)85031-X

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.