Paper
Electron-transfer-mediated synthesis of phenanthridines by intramolecular arylation of anions from N-(ortho-halobenzyl)arylamines: regiochemical and mechanistic analysis.
Published Mar 8, 2010 · M. E. Budén, Viviana Dorn, Martina Gamba
The Journal of organic chemistry
62
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0
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Abstract
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 ortho-halobenzylchlorides with different arylamines. The reaction of the anions of a diverse set of N-(ortho-halobenzyl)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.
This study demonstrates a very efficient method for synthesizing phenanthridines and trispheridine in good to excellent yields using N-(ortho-halobenzyl)arylamines, with potential applications in organic synthesis.
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