Electron Transfer Mediated Synthesis of Phenanthridines by Intramolecular Arylation of Anions from N-(o-Halobenzyl)arylamines. Regiochemical and Mechanistic Analysis

. M. E. BUDÉN, V. B. DORN, M.GAMBA, A. B. PIERINI, R. A. ROSSI,

JOURNAL OF ORGANIC CHEMISTRY

AMER CHEMICAL SOC

Año: 2009

0022-3263

The synthesis of a series of substituted phenanthridines by the photostimulated SRN1 substitution reaction using the anion of ortho-haloarylbenzylanilines as starting substrate was performed. The ortho-arylbenzyl lanilines were obtain by nucleophilic substitution using o-halobenzylchloride with different anilines with good to very good isolated yields (69-85%). Through an intramolecular C-C bond formation of ortho-haloarylbenzyl lanilines by the SRN1 mechanism phenanthridines were achieved. These reactions proceed in synthetically very good to excellent yields (79-95%). Reactions of diverse set of ortho-haloarylbenzyl lanilines were studied. In order to explain the regiochemistry of these reactions a theoretical analysis was made with DFT methods (B3LYP/6-31+G* and B3LYP/LANL2DZ).