INVESTIGADORES
DORN Viviana
artículos
Título:
Electron-Transfer-Mediated Synthesis of Phenanthridines by Intramolecular Arylation of Anions from N-(ortho-Halobenzyl)arylamines: Regiochemical and Mechanistic Analysis
Autor/es:
BUDÉN, M.E.; DORN, V. B.; GAMBA, M; PIERINI, A. B.; ROSSI, R.A.
Revista:
JOURNAL OF ORGANIC CHEMISTRY
Editorial:
AMER CHEMICAL SOC
Referencias:
Lugar: New York; Año: 2010 vol. 75 p. 2206 - 2218
ISSN:
0022-3263
Resumen:
The synthesis of a series of substituted phenanthridines by photostimulated C-C cyclization of
anions from N-(ortho-halobenzyl)arylamines has been found to proceed in very good to excellent
yields (79-95%) in liquid ammonia and in DMSO. The N-(ortho-halobenzyl)arylamines are
obtained in good to very good isolated yields (44-85%) by nucleophilic substitution of orthohalobenzylchlorides
with different arylamines. The reaction of the anions of a diverse set ofN-(orthohalobenzyl)
arylamines was studied, and the methodology was extended to the synthesis of trispheridine,
a natural product, in very good yield. In order to explain the regiochemical outcome of
these reactions, a theoretical analysis was performed with DFT methods and the B3LYP functional.