Three-Component Coupling Sequence for the Regiospecific Synthesis of Substituted Pyridines

被引：92

作者：

Chen, Ming Z. ^{[2
]}

Micalizio, Glenn C. ^{[1
]}

机构：

[1] Scripps Res Inst, Dept Chem, Jupiter, FL 33458 USA

[2] Scripps Res Inst, Kellogg Sch Sci & Technol, Jupiter, FL 33458 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 02期

基金：

美国国家卫生研究院;

关键词：

DERIVATIVES; IMINES;

D O I：

10.1021/ja2105703

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A de novo synthesis of substituted pyridines is described that proceeds through nucleophilic addition of a dithiane anion to an alpha,beta-unsaturated carbonyl followed by metallacycle-mediated union of the resulting allylic alcohol with preformed trimethylsilane-imines (generated in situ by the low-temperature reaction of lithium hexamethyldisilazide with an aldehyde) and Ag(I)- or Hg(II)-mediated ring closure. The process is useful for the convergent assembly of di- through penta-substituted pyridines with complete regiochemical control.

引用

页码：1352 / 1356

页数：5

共 17 条

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

BOGER, DL .

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

[2] Preparation of Stereodefined Homoallylic Amines from the Reductive Cross-Coupling of Allylic Alcohols with Imines [J].

Chen, Ming Z. ;

McLaughlin, Martin ;

Takahashi, Masayuki ;

Tarselli, Michael A. ;

Yang, Dexi ;

Umemura, Shuhei ;

Micalizio, Glenn C. .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (23) :8048-8059

[3] Synthesis of dihydropyridines and pyridines from Imines and alkynes via C-H activation [J].

Colby, Denise A. ;

Bergman, Robert G. ;

Ellman, Jonathan A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (11) :3645-3651

[4] Heteroaromatic Synthesis via Olefin Cross-Metathesis: Entry to Polysubstituted Pyridines [J].

Donohoe, Timothy J. ;

Basutto, Jose A. ;

Bower, John F. ;

Rathi, Akshat .

ORGANIC LETTERS, 2011, 13 (05) :1036-1039

[5] Synthesis of substituted pyridines and pyridazines via ring closing metathesis [J].

Donohoe, Timothy J. ;

Fishlock, Lisa P. ;

Basutto, Jose A. ;

Bower, John F. ;

Procopiou, Panayiotis A. ;

Thompson, Amber L. .

CHEMICAL COMMUNICATIONS, 2009, (21) :3008-3010

[6] De novo synthesis of substituted pyridines [J].

Henry, GD .

TETRAHEDRON, 2004, 60 (29) :6043-6061

[7]

Li J. J., 2005, NAME REACTIONS HETER, P558

[8] A simple, modular synthesis of substituted pyridines [J].

Liu, Songbai ;

Liebeskind, Lanny S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (22) :6918-+

[9] One-pot synthesis of highly functionalized pyridines via a rhodium carbenoid induced ring expansion of isoxazoles [J].

Manning, James R. ;

Davies, Huw M. L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (27) :8602-+

[10] Synthesis of substituted pyridine derivatives via the ruthenium-catalyzed cycloisomerization of 3-azadienynes [J].

Movassaghi, M ;

Hill, MD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (14) :4592-4593

← 1 2 →