INVESTIGADORES
BAROLO Silvia Maricel
artículos
Título:
Synthesis of 6-Substituted 2-Pyrrolyl and Indolyl Benzoxazoles by Intramolecular O-Arylation in Photostimulated Reactions
Autor/es:
VICTORIA A. VAILLARD; JAVIER F. GUASTAVINO; MARÍA E. BUDEN; JAVIER I. BARDAGÍ; SILVIA M. BAROLO; ROBERTO A. ROSSI*
Revista:
JOURNAL OF ORGANIC CHEMISTRY
Editorial:
AMER CHEMICAL SOC
Referencias:
Año: 2012 vol. 77 p. 1507 - 1519
ISSN:
0022-3263
Resumen:
The synthesis of a series of 6-substituted 2-pyrrolyl and 2-indolyl benzoxazoles by photostimulated C-Ocyclization of anions from 2-pyrrole carboxamides, 2-indolecarboxamides, or 3-indole carboxamides has been found toproceed in good to excellent yields (41 a 100%) in DMSO andliquid ammonia. The pyrrole and indole carboxamides areobtained in good to very good isolated yields by an amidationreaction of different 2-haloanilines with 2-carboxylic acid ofpyrrole and 2- or 3-carboxylic acid of indole. To explain the regiochemical outcome of these reactions (C-O arylation vs C-Nor C-C arylation), a theoretical analysis was performed using DFT methods and the B3LYP functional.
