A Multicomponent Coupling Reaction Induced by Insertion of Arynes into the C=O Bond of Formamide

被引：148

作者：

Yoshioka, Eito ^{[1
]}

Kohtani, Shigeru ^{[1
]}

Miyabe, Hideto ^{[1
]}

机构：

[1] Hyogo Univ Hlth Sci, Sch Pharm, Chuo Ku, Kobe, Hyogo 6508530, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 29期

关键词：

2H-chromenes; arynes; coumarins; insertion reaction; synthetic methods; CONCISE TOTAL-SYNTHESIS; DIELS-ALDER REACTIONS; CARBON SIGMA-BONDS; STRAIGHTFORWARD SYNTHESIS; 1,3-DIPOLAR CYCLOADDITION; GENERAL-SYNTHESIS; TERMINAL ALKYNES; BENZYNE; DERIVATIVES; ISOQUINOLINES;

D O I：

10.1002/anie.201102088

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

And aryne makes three: The three-component coupling of arynes, DMF, and active methylenes has provided an efficient method for the synthesis of 2H-chromene and coumarin derivatives (see scheme). The sequential multistep reactions are driven by the release of strain energy in the arynes and intermediates, and this finding was supported by thermodynamics. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：6638 / 6642

页数：5

共 99 条

[11]

Cant A. A., 2009, ANGEW CHEM, V121, P5301

[12] The Benzyne Aza-Claisen Reaction [J].

Cant, Alastair A. ;

Bertrand, Guillaume H. V. ;

Henderson, Jaclyn L. ;

Roberts, Lee ;

Greaney, Michael F. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) :5199-5202

[13] Indolyne and Aryne Distortions and Nucleophilic Regioselectivites [J].

Cheong, Paul H. -Y. ;

Paton, Robert S. ;

Bronner, Sarah M. ;

Im, G-Yoon J. ;

Garg, Neil K. ;

Houk, K. N. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (04) :1267-+

[14] Synthesis, Molecular Modeling, and Selective Inhibitory Activity against Human Monoamine Oxidases of 3-Carboxamido-7-Substituted Coumarins [J].

Chimenti, Franco ;

Secci, Daniela ;

Bolasco, Adriana ;

Chimenti, Paola ;

Bizzarri, Bruna ;

Granese, Arianna ;

Carradori, Simone ;

Yanez, Matilde ;

Orallo, Francisco ;

Ortuso, Francesco ;

Alcaro, Stefano .

JOURNAL OF MEDICINAL CHEMISTRY, 2009, 52 (07) :1935-1942

[15] A novel α,β-unsaturated nitrone-aryne [3+2] cycloaddition and its application in the synthesis of the cortistatin core [J].

Dai, Mingji ;

Wang, Zhang ;

Danishefsky, Samuel J. .

TETRAHEDRON LETTERS, 2008, 49 (47) :6613-6616

[16] Synthesis of dihydronaphthalenes via Aryne Diels-Alder reactions: Scope and diastereoselectivity [J].

Dockendorff, C ;

Sahli, S ;

Olsen, M ;

Milhau, L ;

Lautens, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (43) :15028-15029

[17] Intermolecular C-O Addition of Carboxylic Acids to Arynes [J].

Dubrovskiy, Anton V. ;

Larock, Richard C. .

ORGANIC LETTERS, 2010, 12 (14) :3117-3119

[18] Decoupling deprotonation from metalation:: Thia-Fries rearrangement [J].

Dyke, Alan M. ;

Gill, Duncan M. ;

Harvey, Jeremy N. ;

Hester, Alison J. ;

Lloyd-Jones, Guy C. ;

Munoz, M. Paz ;

Shepperson, Ian R. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (27) :5067-5070

[19] Carbocupration-Functionalization of Arynes: Rapid Access to Variably Ortho-Substituted ((E)-3-Phenylprop-1-enyl)silanes [J].

Ganta, Ashok ;

Snowden, Timothy S. .

ORGANIC LETTERS, 2008, 10 (22) :5103-5106

[20] Palladium-Catalyzed Annulation of Acyloximes with Arynes (or Alkynes) Synthesis of Phenanthridines and Isoquinolines [J].

Gerfaud, Thibaud ;

Neuville, Luc ;

Zhu, Jieping .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (03) :572-577

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