Microwave-assisted direct biaryl coupling: first application to the synthesis of aporphines

被引：27

作者：

Chaudhary, Sandeep

Pecic, Stevan

LeGendre, Onica

Harding, Wayne W. ^{[1
]}

机构：

[1] NYU, Dept Chem, Hunter Coll, New York, NY 10065 USA

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 20期

基金：

美国国家卫生研究院;

关键词：

H BOND ACTIVATION; DIRECT ARYLATION; (+/-)-NANTENINE DERIVATIVES; ORGANIC-SYNTHESIS; DRUG DISCOVERY; HETEROCYCLES; ALKALOIDS; CATALYSIS; IMPACT; ARYL;

D O I：

10.1016/j.tetlet.2009.03.029

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have investigated the use of microwaves in a direct biaryl Coupling reaction for the synthesis of analogs of the aporphine alkaloid nantenine. Our Study shows that the aporphine core may be rapidly accessed from benzyl-tetrahydroisoquinoline substrates with this method. This is the first report of a microwave-assisted direct biaryl coupling reaction in the synthesis of aporphine molecules. (C) 2009 Elsevier Ltd. All rights reserved.

引用

收藏

页码：2437 / 2439

页数：3

相关论文

共 29 条

[21] Rh(I)-catalyzed arylation of heterocycles via C-H bond activation: expanded scope through mechanistic insight [J].

Lewis, Jared C. ;

Berman, Ashley M. ;

Bergman, Robert G. ;

Ellman, Jonathan A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (08) :2493-2500

[22] Microwave-promoted rhodium-catalyzed arylation of heterocycles through C-H bond activation [J].

Lewis, JC ;

Wu, JY ;

Bergman, RG ;

Ellman, JA .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (10) :1589-1591

[23] Efficient palladium(II) catalysis under air.: Base-free oxidative heck reactions at room temperature or with microwave heating [J].

Lindh, Jonas ;

Enquist, Per-Anders ;

Pilotti, Ake ;

Nilsson, Peter ;

Larhed, Mats .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (21) :7957-7962

[24] The impact of microwave-assisted organic synthesis in drug discovery [J].

Mavandadi, F ;

Pilotti, Å .

DRUG DISCOVERY TODAY, 2006, 11 (3-4) :165-174

[25] Pharmacological effects of (+)-nantenine, an alkaloid isolated from Platycapnos spicata, in several rat isolated tissues [J].

Orallo, F .

PLANTA MEDICA, 2003, 69 (02) :135-142

[26] Alkaloids of Hernandia voyronii: Chloroquine-potentiating activity and structure elucidation of herveline D [J].

Rasoanaivo, P ;

Ratsimamanga-Urverg, S ;

Rafatro, H ;

Ramanitrahasimbola, D ;

Palazzino, G ;

Galeffi, C ;

Nicoletti, M .

PLANTA MEDICA, 1998, 64 (01) :58-62

[27]

Stevigny C., 2005, Current Medicinal Chemistry - Anti-Cancer Agents, V5, P173, DOI 10.2174/1568011053174864

[28] Microwave-assisted Negishi and Kumada cross-coupling reactions of aryl chlorides [J].

Walla, P ;

Kappe, CO .

CHEMICAL COMMUNICATIONS, 2004, (05) :564-565

[29] Advances in development of dopaminergic aporphinoids [J].

Zhang, Ao ;

Zhang, Yi ;

Branfman, Alan R. ;

Baldessarini, Ross J. ;

Neumeyer, John L. .

JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (02) :171-181