Organocatalytic Oxidative Annulation of Benzamide Derivatives with Alkynes

被引：106

作者：

Manna, Srimanta ^{[1
,2
]}

Antonchick, Andrey P. ^{[1
,2
]}

机构：

[1] Max Planck Inst Mol Physiol, Abt Chem Biol, D-44227 Dortmund, Germany

[2] Tech Univ Dortmund, Fak Chem, D-44221 Dortmund, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 28期

关键词：

alkynes; annulation; heterocycles; hypervalent iodine; organocatalysis; C-H ACTIVATION; HYPERVALENT IODINE REAGENTS; N BOND FORMATION; ISOQUINOLINE ALKALOIDS; BETA-PHENYLETHYLAMINES; O BOND; COUPLING/CYCLIZATION; FUNCTIONALIZATION; STRATEGY; CYCLOADDITION;

D O I：

10.1002/anie.201404222

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Organocatalytic annulation by functionalization of benzamide derivatives with alkynes has been developed. We report a new approach of cycloaddition under mild reaction conditions using simple catalysts, such as iodobenzene and peracetic acid, as oxidant. Those novel, mild reaction conditions provided a straightforward synthesis of isoquinolones with fast reaction rate. Notable selectivity in annulation of unsymmetrically disubstituted alkynes was demonstrated.

引用

页码：7324 / 7327

页数：4

共 90 条

[51] Metal-Free Cross-Dehydrogenative Coupling of Heterocycles with Aldehydes [J].

Matcha, Kiran ;

Antonchick, Andrey P. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (07) :2082-2086

[52] Recent developments in natural product synthesis using metal-catalysed C-H bond functionalisation [J].

McMurray, Lindsay ;

O'Hara, Fionn ;

Gaunt, Matthew J. .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (04) :1885-1898

[53] α-Functionalization of Carbonyl Compounds Using Hypervalent Iodine Reagents [J].

Merritt, Eleanor A. ;

Olofsson, Berit .

SYNTHESIS-STUTTGART, 2011, (04) :517-538

[54] Synthesis of 1(2H)-isoquinolones by the nickel-catalyzed denitrogenative alkyne insertion of 1,2,3-benzotriazin-4(3H)-ones [J].

Miura, Tomoya ;

Yamauchi, Motoshi ;

Murakami, Masahiro .

ORGANIC LETTERS, 2008, 10 (14) :3085-3088

[55] C-H Activation for the Construction of C-B Bonds [J].

Mkhalid, Ibraheem A. I. ;

Barnard, Jonathan H. ;

Marder, Todd B. ;

Murphy, Jaclyn M. ;

Hartwig, John F. .

CHEMICAL REVIEWS, 2010, 110 (02) :890-931

[56] Rhodium-catalyzed Oxidative Coupling/Cyclization of Benzamides with Alkynes via C-H Bond Cleavage [J].

Mochida, Satoshi ;

Umeda, Nobuyoshi ;

Hirano, Koji ;

Satoh, Tetsuya ;

Miura, Masahiro .

CHEMISTRY LETTERS, 2010, 39 (07) :744-746

[57] Rhodium-Catalyzed Oxidative Coupling/Cyclization of 2-Phenylindoles with Alkynes via C-H and N-H Bond Cleavages with Air as the Oxidant [J].

Morimoto, Keisuke ;

Hirano, Koji ;

Satoh, Tetsuya ;

Miura, Masahiro .

ORGANIC LETTERS, 2010, 12 (09) :2068-2071

[58] Isoquinoline neurotoxins in the brain and Parkinson's disease [J].

Nagatsu, T .

NEUROSCIENCE RESEARCH, 1997, 29 (02) :99-111

[59] Controlling Site Selectivity in Palladium-Catalyzed C-H Bond Functionalization [J].

Neufeldt, Sharon R. ;

Sanford, Melanie S. .

ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (06) :936-946

[60] Hypervalent iodine(III)-induced oxidative [4+2] annulation of o-phenylenediamines and electron-deficient alkynes: direct synthesis of quinoxalines from alkyne substrates under metal-free conditions [J].

Okumura, Sota ;

Takeda, Youhei ;

Kiyokawa, Kensuke ;

Minakata, Satoshi .

CHEMICAL COMMUNICATIONS, 2013, 49 (81) :9266-9268

← 1 2 3 4 5 6 7 8 9 →