356531-16-3Relevant academic research and scientific papers
Synthesis of N-methyl-5,6-dihydrobenzo[c]phenanthridine and its sp3 C(6)-H bond functionalization via oxidative cross-dehydrogenative coupling reactions
Romo-Pérez, Adriana,Miranda, Luis D.,García, Abraham
, p. 6669 - 6673 (2015)
An expeditious route involving a Pd-catalyzed intramolecular biaryl-coupling for the synthesis of the N-methyl-5,6-dihydrobenzo[c]phenanthridine scaffold has been developed. For the first time, we herein report the sp3 C(6)-H functionalization
Electron-transfer-mediated synthesis of phenanthridines by intramolecular arylation of anions from n-(ortho-Halobenzyl)arylamines: regiochemical and mechanistic analysis
Buden, Maria E.,Dorn, Viviana B.,Gamba, Martina,Pierini, Adriana B.,Rossi, Roberto A.
supporting information; experimental part, p. 2206 - 2218 (2010/06/17)
The synthesis of a series of substituted phenanthridines by photostimulated C-C cyclization of anions from N-(orrAo-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 N-(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.
