1-azatriene cyclisation as a route to annelated pyrido[4,3-b]indoles

被引：43

作者：

Gilchrist, TL ^{[1
]}

Kemmitt, PD ^{[1
]}

Germain, AL ^{[1
]}

机构：

[1] GLAXO GRP RES LTD,RES & DEV,GREENFORD UB6 0HE,MIDDX,ENGLAND

来源：

TETRAHEDRON | 1997年 / 53卷 / 12期

基金：

英国工程与自然科学研究理事会;

关键词：

ELECTROCYCLIC RING-CLOSURE; HETEROCYCLES; CYCLIZATION; INDOLES; SYSTEM;

D O I：

10.1016/S0040-4020(97)00117-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Derivatives of indole-3-carbaldehyde oxime have been prepared that bear a carbon-carbon double bond at C-2 and a five- or six-membered ring linking the alpha-carbon artom of the vinyl group and the indole nitrogen atom. Compound 9, with a five-membered ring linking the two atoms, failed to undergo a cyclisation reaction on heating. However the oximes 16 and 22, with a six-memberd ring linking the two atoms. cyclised in boiling toluene. The cyclisation led to the formation of the pyrido-indoles 17 and 18, respectively. (C) 1997 Elsevier Science Ltd.

引用

页码：4447 / 4456

页数：10

共 19 条

[1] EFFICIENT SYNTHESIS OF 2-CHLOROINDOLE, 2-BROMOINDOLE, AND 2-IODOINDOLE [J].

BERGMAN, J ;

VENEMALM, L .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (08) :2495-2497

[2] A DIECKMANN/RING EXPANSION APPROACH TO TETRAHYDROPYRIDO[1,2-A]INDOLES AND TETRAHYDROAZEPINO[1,2-A]INDOLES [J].

BIT, RA ;

DAVIS, PD ;

HILL, CH ;

KEECH, E ;

VESEY, DR .

TETRAHEDRON, 1991, 47 (26) :4645-4664

[3] TOTAL SYNTHESIS OF GROSSULARINES-1 AND-2 [J].

CHOSHI, T ;

YAMADA, S ;

SUGINO, E ;

KUWADA, T ;

HIBINO, S .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (18) :5899-5904

[4] 2-(QUINUCLIDIN-3-YL)PYRIDO[4,3-B]INDOL-1-ONES AND ISOQUINOLIN-1-ONES - POTENT CONFORMATIONALLY RESTRICTED 5-HT(3) RECEPTOR ANTAGONISTS [J].

CLARK, RD ;

MILLER, AB ;

BERGER, J ;

REPKE, DB ;

WEINHARDT, KK ;

KOWALCZYK, BA ;

EGLEN, RM ;

BONHAUS, DW ;

LEE, CH ;

MICHEL, AD ;

SMITH, WL ;

WONG, EHF .

JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (18) :2645-2657

[5]

GERMAIN AL, 1994, HETEROCYCLES, V37, P697

[6] PREPARATION OF 1-SUBSTITUTED-3,4-DIHYDRONAPHTHALENE-2-CARBOXALDEHYDE N,N-DIMETHYLHYDRAZONES BY PALLADIUM(0) COUPLING, AND THEIR ELECTROCYCLIC RING-CLOSURE [J].

GILCHRIST, TL ;

HEALY, MAM .

TETRAHEDRON, 1993, 49 (12) :2543-2556

[7] FORMATION OF A 12-AZASTEROID BY 1-AZATRIENE CYCLIZATION [J].

GILCHRIST, TL ;

HEALY, MAM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (07) :749-750

[8] 5H-2-PYRINDINES FROM 2-BROMOCYCLOPENTENE-1-CARBOXALDEHYDE [J].

GILCHRIST, TL ;

KEMMITT, PD ;

GERMAIN, AL .

TETRAHEDRON, 1995, 51 (33) :9119-9126

[9] THE SYNTHESIS OF FUSED RING NITROGEN-HETEROCYCLES VIA REGIOSPECIFIC INTRAMOLECULAR HECK REACTIONS [J].

GRIGG, R ;

SRIDHARAN, V ;

STEVENSON, P ;

SUKIRTHALINGAM, S ;

WORAKUN, T .

TETRAHEDRON, 1990, 46 (11) :4003-4018

[10] THE SYNTHESIS OF BRIDGED-RING CARBOCYCLES AND HETEROCYCLES VIA PALLADIUM CATALYZED REGIOSPECIFIC CYCLIZATION REACTIONS [J].

GRIGG, R ;

SANTHAKUMAR, V ;

SRIDHARAN, V ;

STEVENSON, P ;

TEASDALE, A ;

THORNTONPETT, M ;

WORAKUN, T .

TETRAHEDRON, 1991, 47 (46) :9703-9720

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