A simple, modular synthesis of substituted pyridines

被引：290

作者：

Liu, Songbai ^{[1
]}

Liebeskind, Lanny S. ^{[1
]}

机构：

[1] Emory Univ, Dept Chem, Atlanta, GA 30322 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 22期

关键词：

D O I：

10.1021/ja8013743

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A simple, modular method to prepare highly substituted pyridines is disclosed. The method employs a cascade reaction comprising (1) a novel N-iminative, Cu-catalyzed cross-coupling of alkenylboronic acids at the N-O bond of alpha,beta-unsaturated ketoxime O-pentafluorobenzoates, (2) electrocyclization of the resulting 3-azatriene, and (3) air oxidation affording highly substituted pyridines in moderate to excellent isolated yields (43-91%). Starting materials are readily available, and functional group tolerance is very good.

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页码：6918 / +

页数：3

相关论文

共 28 条

[1]

[Anonymous], SYNTHESIS

[2]

Bagley MC, 2001, SYNLETT, P1149

[3] DIELS-ALDER REACTIONS OF HETEROCYCLIC AZADIENES - SCOPE AND APPLICATIONS [J].

BOGER, DL .

CHEMICAL REVIEWS, 1986, 86 (05) :781-793

[4] Novel N-(2-benzo[b]thienyl)iminophosphoranes and their use in the synthesis of benzo[b]thieno[2,3-b]pyridines [J].

Bonini, C ;

D'Auria, M ;

Funicello, M ;

Romaniello, G .

TETRAHEDRON, 2002, 58 (18) :3507-3512

[5]

Ciufolini MA, 1998, SYNLETT, P105

[6] The fascinating construction of pyridine ring systems by transition metal-catalysed [2+2+2] cycloaddition reactions [J].

Heller, Barbara ;

Hapke, Marko .

CHEMICAL SOCIETY REVIEWS, 2007, 36 (07) :1085-1094

[7] A NEW PYRIDINE SYNTHESIS [J].

KELLY, TR ;

LIU, HT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (17) :4998-4999

[8] Discovery of 4-amino-5-(3-bromophenyl)-7-(6-morpholino-pyridin-3-yl)pyrido[2,3-d]pyrimidine, an orally active, non-nucleoside adenosine kinase inhibitor [J].

Lee, CH ;

Jiang, MQ ;

Cowart, M ;

Gfesser, G ;

Perner, R ;

Kim, KH ;

Gu, YG ;

Williams, M ;

Jarvis, MF ;

Kowaluk, EA ;

Stewart, AO ;

Bhagwat, SS .

JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (13) :2133-2138

[9] N-substituted imines by the copper-catalyzed N-imination of boronic acids and organostannanes with O-acyl ketoximes [J].

Liu, Songbai ;

Yu, Ying ;

Liebeskind, Lanny S. .

ORGANIC LETTERS, 2007, 9 (10) :1947-1950

[10] A new total synthesis of the zinc matrixmetalloproteinase inhibitor ageladine a featuring a biogenetically patterned 6π-2-azatriene electrocyclization [J].

Meketa, Matthew L. ;

Weinreb, Steven M. .

ORGANIC LETTERS, 2007, 9 (05) :853-855