Synthesis of 6-Substituted 2-Pyrrolyl and Indolyl Benzoxazoles by Intramolecular O-Arylation in Photostimulated Reactions

• DOI: 10.1021/jo202386b
• Publication Date: 2011-12-22T19:23:46Z
• Authors: Victoria A. Vaillard; Javier F. Guastavino; María E. Budén; Javier I. Bardagí; Silvia M. Barolo; Roberto A. Rossi
• Keywords: Pyrrole

The synthesis of a series 6-substituted 2-pyrrolyl and 2-indolyl benzoxazoles by photostimulated C–O cyclization anions from 2-pyrrole carboxamides, 2-indole or 3-indole carboxamides has been found to proceed in good excellent yields (41–100%) DMSO liquid ammonia. pyrrole indole are obtained very isolated an amidation reaction different 2-haloanilines with 2-carboxylic acid 2- 3-carboxylic indole. To explain the regiochemical outcome these reactions (C–O arylation vs C–N C–C arylation), theoretical analysis was performed using DFT methods B3LYP functional.