The synthesis of indolo- and pyrrolo[2,1-a]isoquinolines

被引：27

作者：

de Koning, CB ^{[1
]}

Michael, JP ^{[1
]}

Pathak, R ^{[1
]}

van Otterlo, WAL ^{[1
]}

机构：

[1] Univ Witwatersrand, Inst Mol Sci, Sch Chem, ZA-2050 Johannesburg, South Africa

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 06期

基金：

新加坡国家研究基金会;

关键词：

isoquinolines; potassium t-butoxide;

D O I：

10.1016/j.tetlet.2003.12.020

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of fused isoquinolines from N-benzyl protected indoles and pyrroles is described. For example, treatment of t-butyl-2-(2-formyl-3,4-dihydro-1-naphthalenyl)-3-methyl-1H-indole-l-carboxylate with KOBu' in DMF provided 14-methyl-8-phenylbenzo[h]indolo[2,1-a]isoquinoline in good yield. Analogous N-benzylpyrrole precursors could similarly be cyclized to give pyrrolo[2,1-a]isoquinolines. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：1117 / 1119

页数：3

共 20 条

[1] INDOLO[2,1-A]ISOQUINOLINES - SYNTHESES, STEROID-HORMONE RECEPTOR-BINDING AFFINITIES, AND CYTOSTATIC ACTIVITY [J].

AMBROS, R ;

SCHNEIDER, MR ;

VONANGERER, S .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (01) :153-160

[2]

ANDREAE S, 1991, HOUBENWEYL METHO E A, V7, P571

[3]

Balasubramanian M, 1998, RODDS CHEM, V4, P163

[4] β-Phenylethylamines and the isoquinoline alkaloids [J].

Bentley, KW .

NATURAL PRODUCT REPORTS, 2003, 20 (03) :342-365

[5]

Bringmann G., 1995, ALKALOIDS, V46, P127

[6] Revised structures of N-substituted dibrominated pyrrole derivatives and their polymeric products. Termaleimide models with low optical band gaps [J].

Choi, DS ;

Huang, SL ;

Huang, MS ;

Barnard, TS ;

Adams, RD ;

Seminario, JM ;

Tour, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (08) :2646-2655

[7] A versatile and convenient method for the synthesis of substituted benzo[a]carbazoles and pyrido[2,3-a]carbazoles [J].

de Koning, CB ;

Michael, JP ;

Rousseau, AL .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (11) :1705-1713

[8] The synthesis of naphtho[a]carbazoles and benzo[c]carbazoles [J].

de Koning, CB ;

Michael, JP ;

Nhlapo, JM ;

Pathak, R ;

van Otterlo, WAL .

SYNLETT, 2003, (05) :705-707

[9] Amide rotamers of N-acetyl-1,3-dimethyltetrahydroisoquinolines:: synthesis, variable temperature NMR spectroscopy and molecular modelling [J].

de Koning, CB ;

van Otterlo, WAL ;

Michael, JP .

TETRAHEDRON, 2003, 59 (42) :8337-8345

[10] Synthesis of N-acetyl-1,3-dimethyltetrahydroisoquinolines by intramolecular amidomercuration:: Stereochemical aspects [J].

de Koning, CB ;

Michael, JP ;

van Otterlo, WAL .

SYNLETT, 2002, (12) :2065-2067

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