Synthesis of substituted carbazoles and β-carbolines by cyclization of diketoindole derivatives

被引：49

作者：

Duval, E

Cuny, GD

机构：

[1] Brigham & Womens Hosp, Lab Drug Discovery Neurodegenerat, Cambridge, MA 02139 USA

[2] Harvard Univ, Sch Med, Cambridge, MA 02139 USA

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 28期

关键词：

carbazole; beta-carbol.ne; indole; Friedel-Crafts; cyclization;

D O I：

10.1016/j.tetlet.2004.05.053

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new route to substituted beta-carbolines and carbazoles is described. Diketoindole intermediates, prepared by Friedel-Crafts acylations of 3-substituted indoles, have been converted to 3-hydroxyearbazoles and beta-carbolines in good yields, 51-96% and 82-97%, respectively. This method also allows for the formation of 4-substituted beta-carbolines. The application of this methodology to the synthesis of the natural products hyellazole and 6-chlorohyellazole is also described. (C) 2004 Elsevier Ltd. All rights reserved.

引用

收藏

页码：5411 / 5413

页数：3

相关论文

共 34 条

[1]

Abbiati G, 2001, SYNTHESIS-STUTTGART, P2477

[2] SYNTHESIS OF THE CARBAZOLE ALKALOIDS HYELLAZOLE AND 6-CHLOROHYELLAZOLE AND RELATED DERIVATIVES [J].

BECCALLI, EM ;

MARCHESINI, A ;

PILATI, T .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (05) :579-587

[3]

CARDELLINA JH, 1979, TETRAHEDRON LETT, V20, P4915

[4] Total syntheses of carazostatin, hyellazole, and carbazoquinocins B-F [J].

Choshi, T ;

Sada, T ;

Fujimoto, H ;

Nagayama, C ;

Sugino, E ;

Hibino, S .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (08) :2535-2543

[5] Total syntheses of carazostatin and hyellazole by allene-mediated electrocyclic reaction [J].

Choshi, T ;

Sada, T ;

Fujimoto, H ;

Nagayama, C ;

Sugino, E ;

Hibino, S .

TETRAHEDRON LETTERS, 1996, 37 (15) :2593-2596

[6] THE PICTET-SPENGLER CONDENSATION - A NEW DIRECTION FOR AN OLD REACTION [J].

COX, ED ;

COOK, JM .

CHEMICAL REVIEWS, 1995, 95 (06) :1797-1842

[7] AN ANNULATION METHOD FOR THE SYNTHESIS OF HIGHLY SUBSTITUTED POLYCYCLIC AROMATIC AND HETEROAROMATIC-COMPOUNDS [J].

DANHEISER, RL ;

BRISBOIS, RG ;

KOWALCZYK, JJ ;

MILLER, RF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (08) :3093-3100

[8] Indole inhibitors of human nonpancreatic secretory phospholipase A(2) .1. Indole-3-acetamides [J].

Dillard, RD ;

Bach, NJ ;

Draheim, SE ;

Berry, DR ;

Carlson, DG ;

Chirgadze, NY ;

Clawson, DK ;

Hartley, LW ;

Johnson, LM ;

Jones, ND ;

McKinney, ER ;

Mihelich, ED ;

Olkowski, JL ;

Schevitz, RW ;

Smith, AC ;

Snyder, DW ;

Sommers, CD ;

Wery, JP .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (26) :5119-5136

[9] STRUCTURE DETERMINATION OF LAVENDAMYCIN - A NEW ANTI-TUMOR ANTIBIOTIC FROM STREPTOMYCES-LAVENDULAE [J].

DOYLE, TW ;

BALITZ, DM ;

GRULICH, RE ;

NETTLETON, DE ;

GOULD, SJ ;

TANN, CH ;

MOEWS, AE .

TETRAHEDRON LETTERS, 1981, 22 (46) :4595-4598

[10]

DULENKO VI, 1985, CHEM HETEROCYCL COMP, P302

← 1 2 3 4 →