Tetrabutylammonium pyridin-2-olate:: A new reagent for the efficient synthesis of N-aryl pyridin-2-ones

被引：10

作者：

Zhang, Huiping ^{[1
]}

Chen, Bang-Chi ^{[1
]}

Wang, Bei ^{[1
]}

Chao, Sam T. ^{[1
]}

Zhao, Rulin ^{[1
]}

Lim, Ngiapkie ^{[1
]}

Balasubramanian, Balu ^{[1
]}

机构：

[1] Bristol Myers Squibb Res & Dev, Discovery Chem, Princeton, NJ 08543 USA

来源：

SYNTHESIS-STUTTGART | 2008年 / 10期

关键词：

preparation; tetrabutylammomum pyridin-2-olate; aryl iodides; CuI-catalyzed coupling reaction; N-aryl pyridin-2-ones;

D O I：

10.1055/s-2008-1072569

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new reagent, tetrabutylammonium pyridin-2-olate, was prepared and its application to the efficient synthesis of N-aryl pyridine-2-ones was demonstrated using CuI-catalyzed coupling reactions with aryl iodides. This coupling reaction is mild, high-yielding, and remarkably chemoselective (N- vs. O-arylation). It is also compatible with substrates containing labile functional groups.

引用

页码：1523 / 1526

页数：4

共 34 条

[1] Polyquinanes by [4+4] cycloaddition-transannular cyclization [J].

Ader, TA ;

Champey, CA ;

Kuznetsova, LV ;

Li, T ;

Lim, YH ;

Rucando, D ;

Sieburth, SM .

ORGANIC LETTERS, 2001, 3 (14) :2165-2167

[2]

AGEJASCHICHARRO J, 2003, Patent No. 2003053948

[3] Cu-catalyzed N- and O-arylation of 2-, 3-, and 4-hydroxypyridines and hydroxyquinolines [J].

Altman, Ryan A. ;

Buchwald, Stephen L. .

ORGANIC LETTERS, 2007, 9 (04) :643-646

[4] Enantioselective photochemical reactions of 2-pyridones in solution [J].

Bach, T ;

Bergmann, H ;

Harms, K .

ORGANIC LETTERS, 2001, 3 (04) :601-603

[5]

Boehringer M, 2007, WO, Patent No. [2007054453, 2007, 2007054453]

[6]

Boga C, 2001, EUR J ORG CHEM, V2001, P1175

[7] Palladium-mediated three-component synthesis of furo[2,3-b]pyridones by one-pot coupling of 3-lodopyridones, alkynes, and organic halides [J].

Bossharth, E ;

Desbordes, P ;

Monteiro, N ;

Balme, G .

ORGANIC LETTERS, 2003, 5 (14) :2441-2444

[8]

Corte JR, 2006, US, Patent No. 2006074103

[9] Highly efficient and mild copper-catalyzed N- and C-arylations with aryl bromides and iodides [J].

Cristau, HJ ;

Cellier, PP ;

Spindler, JF ;

Taillefer, M .

CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (22) :5607-5622

[10] A versatile copper-catalyzed coupling reaction of pyridin-2(1H)-ones with aryl halides [J].

Filipski, Kevin J. ;

Kohrt, Jeffrey T. ;

Casimiro-Garcia, Agustin ;

Van Huis, Chad A. ;

Dudley, Danette A. ;

Cody, Wayne L. ;

Bigge, Christopher F. ;

Desiraju, Shrilakshmi ;

Sun, Shaoyi ;

Maiti, Samarendra N. ;

Jaber, Mohamad R. ;

Edmunds, Jeremy J. .

TETRAHEDRON LETTERS, 2006, 47 (44) :7677-7680

← 1 2 3 4 →