Palladium(II)/Copper Halide/Solvent Combination for Selective Intramolecular Domino Reactions of Indolecarboxylic Acid Allylamides: An Unprecedented Arylation/Esterification Sequence

被引：57

作者：

Broggini, Gianluigi ^{[1
]}

Barbera, Vincenzina ^{[2
]}

Beccalli, Egle M. ^{[3
]}

Borsini, Elena ^{[3
]}

Galli, Simona ^{[1
]}

Lanza, Giuseppe ^{[2
]}

Zecchi, Gaetano ^{[1
]}

机构：

[1] Univ Insubria, Dipartimento Sci Chim & Ambientali, I-22100 Como, Italy

[2] Univ Catania, Dipartimento Sci Farmaco, I-95125 Catania, Italy

[3] Univ Milan, DISMAB, Sez Chim Organ A Marchesini, I-20133 Milan, Italy

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2012年 / 354卷 / 01期

关键词：

copper; domino reactions; homogeneous catalysis; palladium; N BOND FORMATION; C-H ACTIVATION; ELECTROPHILIC SUBSTITUTION; CATALYZED CYCLIZATION; INDOLE-DERIVATIVES; PALLADIUM; ALKENES; DIAMINATION; FUNCTIONALIZATION; OXIDATION;

D O I：

10.1002/adsc.201100614

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Intramolecular oxidative palladium-catalyzed reactions of indolylallylamides in the presence of the couple bis(acetonitrile) palladium dichloride and copper(II) halide are described. Starting from 2- and 3-indolylallylamides and involving in both cases the C-3 position of the indole nucleus, variously substituted beta-carbolinones were obtained by arylation/halogenation, arylation/esterification or arylation/carboalkoxylation processes. On the other hand, an unusual aminohalogenation/halogenation sequence performed on 2-indolylallylamides gave rise to pyrazino[1,2-a]indole products. The carboesterification process is the result of an unknown path that involves the DMF or DMA used as solvent. The outcome of the reactions of the 3-indolylallylamides arises from a totally selective 1,2-migration of the acyl group on the supposed spiro intermediates formed from the nucleophilic attack of the C-3 indole position.

引用

页码：159 / 170

页数：12

共 111 条

[1] Pd-catalyzed cyclization of 1-allyl-2-indolecarboxamides by intramolecular amidation of unactivated ethylenic bond [J].