Synthesis of substituted isoquinolines utilizing palladium-catalyzed α-arylation of ketones

被引：50

作者：

Donohoe, Timothy J. ^{[1
]}

Pilgrim, Ben S. ^{[1
]}

Jones, Geraint R. ^{[1
]}

Bassuto, Jose A. ^{[1
]}

机构：

[1] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England

来源：

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA | 2012年 / 109卷 / 29期

关键词：

alpha arylation; heterocycle; isoquinoline-N-oxide; one-pot; MEDIATED ELECTROPHILIC CYCLIZATION; AIR-STABLE CATALYSTS; ONE-POT SYNTHESIS; N-OXIDES; BENZODIAZEPINE-RECEPTORS; COUPLING REACTIONS; INTERNAL ALKYNES; ARYL HALIDES; INDOLES; COMPLEXES;

D O I：

10.1073/pnas.1206532109

中图分类号：

O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];

学科分类号：

07 ; 0710 ; 09 ;

摘要：

The utilization of sequential palladium-catalyzed alpha-arylation and cyclization reactions provides a general approach to an array of isoquinolines and their corresponding N-oxides. This methodology allows the convergent combination of readily available precursors in a regioselective manner and in excellent overall yields. This powerful route to polysubstituted isoquinolines, which is not limited to electron rich moieties, also allows rapid access to analogues of biologically active compounds.

引用

页码：11605 / 11608

页数：4

共 57 条

[1] SYNTHESIS AND RESOLUTION OF 1-(2-DIPHENYLPHOSPHINO-1-NAPHTHYL)ISOQUINOLINE - A P-N CHELATING LIGAND FOR ASYMMETRIC CATALYSIS [J].

ALCOCK, NW ;

BROWN, JM ;

HULMES, DI .

TETRAHEDRON-ASYMMETRY, 1993, 4 (04) :743-756

[2] The azaallylic anion as a synthon for Pd-catalyzed synthesis of heterocycles:: Domino two- and three-component synthesis of indoles [J].

Barluenga, Jose ;

Jimenez-Aquino, Agustin ;

Valdes, Carlos ;

Aznar, Fernando .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (09) :1529-1532

[3] Modular Synthesis of Indoles from Imines and o-Dihaloarenes or o-Chlorosulfonates by a Pd-Catalyzed Cascade Process [J].

Barluenga, Jose ;

Jimenez-Aquino, Agustin ;

Aznar, Fernando ;

Valdes, Carlos .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (11) :4031-4041

[4] Transition Metal-Catalyzed Direct Arylation of Substrates with Activated sp3-Hybridized C-H Bonds and Some of Their Synthetic Equivalents with Aryl Halides and Pseudohalides [J].

Bellina, Fabio ;

Rossi, Renzo .

CHEMICAL REVIEWS, 2010, 110 (02) :1082-1146

[5]

Bentley K.W., 1998, ISOQUINOLINE ALKALOI

[6] β-Phenylethylamines and the isoquinoline alkaloids [J].

Bentley, Kenneth W. .

NATURAL PRODUCT REPORTS, 2006, 23 (03) :444-463

[7]

Bischler A., 1893, CHEM BER, V26, P1903

[8] 1,1'-BIS[(ALKYL/ARYL)PHOSPHINO]FERROCENES - SYNTHESIS AND METAL-COMPLEX FORMATION - CRYSTAL-STRUCTURE OF 3 METAL-COMPLEXES OF FE(ETA-5-C5H4PPH2)2- [J].

BUTLER, IR ;

CULLEN, WR ;

KIM, TJ ;

RETTIG, SJ ;

TROTTER, J .

ORGANOMETALLICS, 1985, 4 (06) :972-980

[9] Palladium-Catalyzed Direct Arylation of Azine and Azole N-Oxides: Reaction Development, Scope and Applications in Synthesis [J].

Campeau, Louis-Charles ;

Stuart, David R. ;

Leclerc, Jean-Philippe ;

Bertrand-Laperle, Megan ;

Villemure, Elisia ;

Sun, Ho-Yan ;

Lasserre, Sandrine ;

Guimond, Nicolas ;

Lecavallier, Melanie ;

Fagnou, Keith .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (09) :3291-3306

[10] Synthesis of 3,4-Dihydroisoquinolines by a C(sp3)-H Activation/Electrocyclization Strategy: Total Synthesis of Coralydine [J].

Chaumontet, Manon ;

Piccardi, Riccardo ;

Baudoin, Olivier .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (01) :179-182

← 1 2 3 4 5 6 →