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

被引：79

作者：

Buden, Maria E. ^{[1
]}

Dorn, Viviana B. ^{[1
]}

Garnba, Martina ^{[1
]}

Pierini, Adriana B. ^{[1
]}

Rossi, Roberto A. ^{[1
]}

机构：

[1] Univ Nacl Cordoba, Fac Ciencias Quim, Dept Quim Organ, INFIQC, RA-5000 Cordoba, Argentina

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 07期

关键词：

CONDENSED POLYNUCLEAR COMPOUNDS; ARYL HALIDES; CYCLIZATION; ALKALOIDS; ENERGY; DERIVATIVES; CONSTRUCTION; ROUTES; IONS;

D O I：

10.1021/jo9025918

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 tri-spheridine, a natural product, in very good yield. In order to explain the regiochemical outcome or these reactions, a theoretical analysis was performed with DFT methods and the B3LYP functional.

引用

页码：2206 / 2218

页数：13

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