Synthesis of pyrrolo-isoquinolines related to the lamellarins using silver-catalyzed Cycloisomerization/Dipolar cycloaddition

被引：157

作者：

Su, Shun

Porco, John A., Jr. ^{[1
]}

机构：

[1] Boston Univ, Dept Chem, Boston, MA 02215 USA

[2] Boston Univ, Ctr Chem Methodol & Lib Dev, Boston, MA 02215 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2007年 / 129卷 / 25期

关键词：

D O I：

10.1021/ja072737v

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Synthesis of pyrrolo-isoquinolines related to the lamellarin alkaloids employing silver-catalyzed cycloisomerization-dipolar cycloaddition of alkynyl N-benzylidene glycinates is described. Mechanistic studies revealed Ag(I)-catalyzed cycloisomerization to an azomethine ylide as a key step for formation of angular pyrrolo-isoquinolines.

引用

收藏

页码：7744 / +

页数：3

相关论文

共 31 条

[1] Direct Mannich and nitro-Mannich reactions with non-activated imines:: AgOTf-catalyzed addition of pronucleophiles to ortho-alkynylaryl aldimines leading to 1,2-dihydroisoquinolines [J].

Asao, N ;

Yudha, S ;

Nogami, T ;

Yamamoto, Y .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (34) :5526-5528

[2] An environmentally friendly synthetic method of 1,2-dihydroisoquinoline frameworks via three-component reaction with o-alkynylbenzaldehydes, primary amines, and pronucleophiles [J].

Asao, Naoki ;

Iso, Kentaro ;

Yudha S., Salprima .

ORGANIC LETTERS, 2006, 8 (18) :4149-4151

[3] Mycobacterium tuberculosis DNA gyrase:: Interaction with quinolones and correlation with antimycobacterial drug activity [J].

Aubry, A ;

Pan, XS ;

Fisher, LM ;

Jarlier, V ;

Cambau, E .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 2004, 48 (04) :1281-1288

[4] Benzoindolizine derivatives of N-acylphenothiazine.: Synthesis and characterization [J].

Bâcu, E ;

Samson-Belei, D ;

Nowogrocki, G ;

Couture, A ;

Grandclaudon, P .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (13) :2377-2382

[5]

Bailly Christian, 2004, Current Medicinal Chemistry - Anti-Cancer Agents, V4, P363, DOI 10.2174/1568011043352939

[6] Convergent total synthesis of lamellarin K [J].

Banwell, M ;

Flynn, B ;

Hockless, D .

CHEMICAL COMMUNICATIONS, 1997, (23) :2259-2260

[7] Discovery of chemical reactions through multidimensional screening [J].

Beeler, Aaron B. ;

Su, Shun ;

Singleton, Chris A. ;

Porco, John A., Jr. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (05) :1413-1419

[8] Intramolecular dipolar cycloaddition reactions of azomethine ylides [J].

Coldham, I ;

Hufton, R .

CHEMICAL REVIEWS, 2005, 105 (07) :2765-2809

[9]

CUADRO AM, 1989, HETEROCYCLES, V29, P57

[10] Synthesis of 3,4-disubstituted isoquinolines via palladium-catalyzed cross-coupling of 2-(1-alkynyl)benzaldimines and organic halides [J].

Dai, GX ;

Larock, RC .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (03) :920-928

← 1 2 3 4 →