Novel applications of hypervalent iodine:: PIFA mediated synthesis of benzo[c]phenanthiridines and benzo[c]phenanthridinones

被引：73

作者：

Moreno, I ^{[1
]}

Tellitu, I ^{[1
]}

Etayo, J ^{[1
]}

SanMartín, R ^{[1
]}

Domínguez, E ^{[1
]}

机构：

[1] Univ Basque Country, Fac Ciencias, Dept Quim Organ 2, E-48080 Bilbao, Spain

来源：

TETRAHEDRON | 2001年 / 57卷 / 25期

关键词：

hypervalent iodine; PIFA; biaryl coupling; benzo[c]phenanthridines; benzo[c]phenanthridinones;

D O I：

10.1016/S0040-4020(01)00459-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A short and efficient access to benzo[c]phenanthridines and phenanthridinones is achieved by the action of phenyliodine(m)-bis(trifluoroacetate) (PIFA) on properly substituted benzylnaphthylamines and naphthylbenzamides, respectively. This reagent promotes a non-phenolic oxidative biaryl coupling process, the key step of the synthesis. A study of the electronic and steric requirements of the substrates is carried out since, in some cases, dimerization processes prevail over intramolecular cyclization. A mechanistic proposal is also included. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：5403 / 5411

页数：9

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