info:eu-repo/semantics/article
Synthesis of 6-substituted 2-pyrrolyl and indolyl benzoxazoles by intramolecular O-arylation in photostimulated reactions
Fecha
2012-02Registro en:
Vaillard, Victoria Anahi; Guastavino, Javier Fernando; Buden, Maria Eugenia; Bardagi, Javier Ivan; Barolo, Silvia Maricel; et al.; Synthesis of 6-substituted 2-pyrrolyl and indolyl benzoxazoles by intramolecular O-arylation in photostimulated reactions; American Chemical Society; Journal of Organic Chemistry; 77; 3; 2-2012; 1507-1519
0022-3263
1520-6904
CONICET Digital
CONICET
Autor
Vaillard, Victoria Anahi
Guastavino, Javier Fernando
Buden, Maria Eugenia
Bardagi, Javier Ivan
Barolo, Silvia Maricel
Rossi, Roberto Arturo
Resumen
The synthesis of a series of 6-substituted 2-pyrrolyl and 2-indolyl benzoxazoles by photostimulated C-O cyclization of anions from 2-pyrrole carboxamides, 2-indole carboxamides, or 3-indole carboxamides has been found to proceed in good to excellent yields (41-100%) in DMSO and liquid ammonia. The pyrrole and indole carboxamides are obtained in good to very good isolated yields by an amidation reaction of different 2-haloanilines with 2-carboxylic acid of pyrrole and 2- or 3-carboxylic acid of indole. To explain the regiochemical outcome of these reactions (C-O arylation vs C-N or C-C arylation), a theoretical analysis was performed using DFT methods and the B3LYP functional.