title: Synthesis of 6-substituted 2-pyrrolyl and indolyl benzoxazoles by intramolecular O-arylation in photostimulated reactions.
abstract: 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.
authors.affiliation: INFIQC, Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, X5000HUA Córdoba, Argentina.
authors.forename: Victoria A
authors.initials: VA
authors.lastname: Vaillard
authors.forename: Javier F
authors.initials: JF
authors.lastname: Guastavino
authors.forename: María E
authors.initials: ME
authors.lastname: Budén
authors.forename: Javier I
authors.initials: JI
authors.lastname: Bardagí
authors.forename: Silvia M
authors.initials: SM
authors.lastname: Barolo
authors.forename: Roberto A
authors.initials: RA
authors.lastname: Rossi
mesh_terms: D001583:Benzoxazoles / Q000138:chemical synthesis* / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic / Q000379:methods*; D004579:Electron Transport; D007211:Indoles / Q000737:chemistry*; D055668:Photochemical Processes; D011758:Pyrroles / Q000737:chemistry*
chemical_list: D001583:Benzoxazoles; D007211:Indoles; D011758:Pyrroles