Pd-catalyzed ortho-arylation of 3,4-dihydroisoquinolones via C-H bond activation: synthesis of 8-aryl-1,2,3,4-tetrahydroisoquinolines

被引：20

作者：

Kim, Junwon ^{[1
]}

Jo, Mina ^{[1
]}

So, Wonyoung ^{[1
]}

No, Zaesung ^{[1
]}

机构：

[1] Inst Pasteur Korea, Med Chem Grp, Suwon 443270, South Korea

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 11期

关键词：

C-H bond activation; Direct arylation; Dithydroisoquinolones; Tetrahydroisoquinolines; CROSS-COUPLING REACTIONS; INTRAMOLECULAR HECK REACTION; ORGANIC ELECTROPHILES; VASORELAXING ACTIONS; DERIVATIVES; ISOQUINOLINES; APORPHINOIDS; ANTIPLATELET; CYCLIZATION; CYTOTOXICITY;

D O I：

10.1016/j.tetlet.2009.01.010

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient route to synthesize biologically interesting 8-aryl-1,2,3,4-tetrahydroisoquinoline has been developed. It involves the Pd-catalyzed direct arylation of 3,4-dihydroisoquinolones via C-H bond activation with aryl iodides to afford a variety of 8-arylated cross-coupling products. which are subsequently reduced to 8-aryl-1,2,3,4-tetrahydroisoquinolines in good to excellent yields. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：1229 / 1235

页数：7

共 47 条

[1] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].

Alberico, Dino ;

Scott, Mark E. ;

Lautens, Mark .

CHEMICAL REVIEWS, 2007, 107 (01) :174-238

[2] The heck reaction as a sharpening stone of palladium catalysis [J].

Beletskaya, IP ;

Cheprakov, AV .

CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066

[3] Palladium catalysts for the Suzuki cross-coupling reaction: An overview of recent advances [J].

Bellina, F ;

Carpita, A ;

Rossi, R .

SYNTHESIS-STUTTGART, 2004, (15) :2419-2440

[4]

Bringmann G., 2001, PROGR CHEM ORGANIC N, V82

[5] Antiplatelet and vasorelaxing actions of some aporphinoids [J].

Chen, KS ;

Ko, FN ;

Teng, CM ;

Wu, YC .

PLANTA MEDICA, 1996, 62 (02) :133-136

[6] Antiplatelet actions of aporphinoids from formosan plants [J].

Chia, YC ;

Chen, KS ;

Chang, YL ;

Teng, CM ;

Wu, YC .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (23) :3295-3300

[7] The asymmetric intramolecular Heck reaction in natural product total synthesis [J].

Dounay, AB ;

Overman, LE .

CHEMICAL REVIEWS, 2003, 103 (08) :2945-2963

[8] SYNTHESIS OF 8-PHENYL-1,2,3,4-TETRAHYDROISOQUINOLINES [J].

ELLEFSON, CR .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (09) :1533-1536

[9] SYNTHESIS OF 8-ARYLTETRAHYDROISOQUINOLINES AS DOPAMINE ANTAGONISTS AND EVALUATION FOR POTENTIAL NEUROLEPTIC ACTIVITY [J].

ELLEFSON, CR ;

PRODAN, KA ;

BROUGHAM, LR ;

MILLER, A .

JOURNAL OF MEDICINAL CHEMISTRY, 1980, 23 (09) :977-980

[10] The mechanisms of the Stille reaction [J].

Espinet, P ;

Echavarren, AM .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (36) :4704-4734

← 1 2 3 4 5 →