Synthesis of β- and γ-carbolines by the palladium-catalyzed iminoannulation of internal alkynes

被引：117

作者：

Zhang, HM ^{[1
]}

Larock, RC ^{[1
]}

机构：

[1] Iowa State Univ, Dept Chem, Ames, IA 50011 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 20期

关键词：

D O I：

10.1021/ol010124w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A variety of substituted beta- and gamma -carbolines have been prepared in good to excellent yields by the annulation of internal acetylenes by the tert-butylimines of N-substituted 3-iodoindole-2-carboxaldehydes and 2-haloindole-3-carboxaldehydes, respectively, in the presence of a palladium catalyst.

引用

收藏

页码：3083 / 3086

页数：4

相关论文

共 31 条

[1]

Baker B. J., 1996, Alkaloids: Chemical and Biological Perspectives, V10, P357

[2] Lewis acid-directed cyclocondensation of piperidone enol ethers with 2-methoxy-4-(N-phenylsulfonyl)-1,4-benzoquinoneimine:: A new regioselective synthesis of oxygenated carbolines [J].

Engler, TA ;

Wanner, J .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (08) :2444-2457

[3]

Gribble G.W., 1990, ALKALOIDS, V39

[4] THE 1ST SYNTHESIS OF MUTAGENIC TRP-P-1 VIA THE ELECTROCYCLIC REACTION OF 1-AZAHEXA-1,3,5-TRIENE SYSTEM [J].

HIBINO, S ;

SUGINO, E ;

OGURA, N ;

SHINTANI, Y ;

SATO, K .

HETEROCYCLES, 1990, 30 (01) :271-273

[5] SYNTHESIS OF BIOACTIVE NITROGEN-HETEROCYCLES FROM MARINE ORGANISMS [J].

HINO, T ;

NAKAGAWA, M .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1994, 31 (03) :625-630

[6] Novel synthetic strategy of carbolines via palladium-catalyzed amination and arylation reaction [J].

Iwaki, T ;

Yasuhara, A ;

Sakamoto, T .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (11) :1505-1510

[7]

Larock R. C, 1999, PERSPECTIVES ORGANOP, P111

[8] Palladium-catalyzed annulation [J].

Larock, RC .

PURE AND APPLIED CHEMISTRY, 1999, 71 (08) :1435-1442

[9] Synthesis of polycyclic aromatic hydrocarbons by the Pd-catalyzed annulation of alkynes [J].

Larock, RC ;

Doty, MJ ;

Tian, QP ;

Zenner, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (22) :7536-7537

[10] SYNTHESIS OF AROMATIC HETEROCYCLES VIA PALLADIUM-CATALYZED ANNULATION OF INTERNAL ALKYNES [J].

LAROCK, RC ;

YUM, EK ;

DOTY, MJ ;

SHAM, KKC .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (11) :3270-3271

← 1 2 3 4 →