Electron-Transfer-Mediated Synthesis of Phenanthridines by Intramolecular Arylation of Anions from N-(ortho-Halobenzyl) arylamines: Regiochemical and …

…, M Gamba, AB Pierini, RA Rossi

Index: Buden, Maria E.; Dorn, Viviana B.; Gamba, Martina; Pierini, Adriana B.; Rossi, Roberto A. Journal of Organic Chemistry, 2010 , vol. 75, # 7 p. 2206 - 2218

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Citation Number: 52

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 ...