Convergent, regiospecific synthesis of quinolines from o-aminophenylboronates

被引：118

作者：

Horn, Joachim ^{[1
]}

Marsden, Stephen P. ^{[1
]}

Nelson, Adam ^{[1
]}

House, David ^{[2
]}

Weingarten, Gordon G. ^{[2
]}

机构：

[1] Univ Leeds, Sch Chem, Leeds LS2 9JT, W Yorkshire, England

[2] GlaxoSmithKline Inc, Med Res Ctr, Stevenage SG1 2NY, Herts, England

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 18期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1021/ol8016726

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A direct convergent two-component synthesis of quinolines from alpha,beta-unsaturated ketones and o-aminophenylboronic acid derivatives is reported. The reaction is regiocomplementary to the traditional Skraup-Doebner-Von Miller synthesis and proceeds under basic rather than strongly acidic conditions. Quinolines substituted in the benzenoid ring can be accessed by using substituted o-aminophenylboronates prepared by direct palladium-catalyzed borylation of the corresponding o-bromoanilines.

引用

页码：4117 / 4120

页数：4

共 28 条

[1] New vistas in quinoline synthesis [J].

Atechian, Sarkis ;

Nock, Nadine ;

Norcross, Roger D. ;

Ratni, Hassen ;

Thomas, Andrew W. ;

Verron, Julien ;

Masciadri, Raffaello .

TETRAHEDRON, 2007, 63 (13) :2811-2823

[2] Quinoline synthesis:: scope and regiochemistry of photocyclisation of substituted benzylidenecyclopentanone O-alkyl and O-acetyloximes [J].

Austin, Mark ;

Egan, Oliver J. ;

Tully, Raymond ;

Pratt, Albert C. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (23) :3778-3786

[3]

Balasubramanian M., 1996, COMPREHENSIVE HETERO, V5, P245, DOI 10.1016/B978-008096518-5.00109

[4] Palladium-catalyzed borylation of ortho-substituted phenyl halides and application to the one-pot synthesis of 2,2′-disubstituted biphenyls [J].

Baudoin, O ;

Guénard, D ;

Guéritte, F .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (26) :9268-9271

[5] The Suzuki-Miyaura cross coupling reactions on solid support.: Link to solution phase directed ortho metalation.: The Leznoff acetal linker approach to biaryl and heterobiaryl aldehydes [J].

Chamoin, S ;

Houldsworth, S ;

Kruse, CG ;

Bakker, WI ;

Snieckus, V .

TETRAHEDRON LETTERS, 1998, 39 (24) :4179-4182

[6] NUCLEOPHILIC-ADDITION OF LITHIO DERIVATIVES TO 1-SUBSTITUTED BENZO[C]NAPHTHYRIDINES (2,9-DIAZAPHENANTHRENES) [J].

COCHENNEC, C ;

ROCCA, P ;

MARSAIS, F ;

GODARD, A ;

QUEGUINER, G .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (08) :979-984

[7] On the mechanism of the Skraup-Doebner-Von Miller quinoline synthesis [J].

Denmark, SE ;

Venkatraman, S .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (04) :1668-1676

[8]

Doebner O., 1881, Ber. Dtsch. Chem. Ges, V14, P2812, DOI [10.1002/cber.188101402258, DOI 10.1002/CBER.188101402258]

[9] Novel and convenient synthesis of substituted quinolines by copper- or palladium-catalyzed cyclodehydration of 1-(2-aminoaryl)-2-yn-1-ols [J].

Gabriele, Bartolo ;

Mancuso, Raffaella ;

Salerno, Giuseppe ;

Ruffolo, Giuseppe ;

Plastina, Pierluigi .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (18) :6873-6877

[10] An expeditious synthesis of 6-aminophenanthridines [J].

Gug, F ;

Blondel, M ;

Desban, N ;

Bouaziz, S ;

Vierfond, JM ;

Galons, H .

TETRAHEDRON LETTERS, 2005, 46 (21) :3725-3727

← 1 2 3 →