Regioselective synthesis of pyrroloquinolines - Approaches to martinelline.

被引：108

作者：

Hadden, M ^{[1
]}

Stevenson, PJ ^{[1
]}

机构：

[1] Queens Univ Belfast, Sch Chem, Belfast BT9 5AG, Antrim, North Ireland

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 06期

关键词：

D O I：

10.1016/S0040-4039(98)02569-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Indium trichloride catalysed Diels-Alder reaction of imines derived from anilines with cyclic enamides regioselectively gave the biologically important pyrroloquinoline nucleus, with a cis ring junction, in moderate yield. Although the euo:endo selectivity was in most cases poor, these isomers are readily separated by flash chromatography. The functionality tolerated at both C2 and C7 should allow further elaboration to Martinelline (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

引用

页码：1215 / 1218

页数：4

共 13 条

[1] THE STEREOCHEMISTRY OF ORGANOMETALLIC COMPOUNDS .60. RHODIUM-CATALYZED REACTIONS OF HYDROGEN AND CARBON-MONOXIDE WITH ALKENYLANILINES
ANASTASIOU, D
CAMPI, EM
CHAOUK, H
FALLON, GD
JACKSON, WR
MCCUBBIN, QJ
TRNACEK, AE
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1994, 47 (06) : 1043 - 1059
[2] Convenient synthesis of pyrano[3,2-c]quinolines and indeno[2,1-c] quinolines by imino Diels-Alder reactions
Babu, G
Perumal, PT
[J]. TETRAHEDRON LETTERS, 1998, 39 (20) : 3225 - 3228
[3] Imino Diels-Alder reactions catalyzed by indium trichloride (InCl3). Facile synthesis of quinoline and phenanthridinone derivatives.
Babu, G
Perumal, PT
[J]. TETRAHEDRON LETTERS, 1997, 38 (28) : 5025 - 5026
[4] THE PREPARATION OF A PYRROLO (3'-2'-3-4)QUINOLONE FROM (2-ETHOXYETHYL)MALONDIANILIDE
GRUNDON, MF
MCCORKINDALE, NJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1957, (AUG): : 3448 - 3450
[5] Gurjar MK, 1997, HETEROCYCLES, V45, P231
[6] HADDEN M, 1998, IN PRESS J CHEM RES
[7] A synthesis of the tricyclic pyrroloquinoline core of martinelline
Ho, TCT
Jones, K
[J]. TETRAHEDRON, 1997, 53 (24) : 8287 - 8294
[8] REACTIONS OF N-ALKYL-N-PHENYL-1H-BENZOTRIAZOLE-1-METHANAMINES WITH N-VINYLAMIDES AND N-VINYLCARBAZOLE - A CONVENIENT SYNTHESIS OF 4-(DIALKYLAMINO)TETRAHYDROQUINOLINES
KATRITZKY, AR
RACHWAL, B
RACHWAL, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (13) : 3993 - 4001
[9] A FACILE SYNTHESIS OF N-ACYL-2-PYRROLINES
KRAUS, GA
NEUENSCHWANDER, K
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (23) : 4791 - 4792
[10] REVERSIBLE INHIBITORS OF THE GASTRIC (H+/K+)-ATPASE .2. 1-ARYLPYRROLO[3,2-C]QUINOLINES - EFFECT OF THE 4-SUBSTITUENT
LEACH, CA
BROWN, TH
IFE, RJ
KEELING, DJ
LAING, SM
PARSONS, ME
PRICE, CA
WIGGALL, KJ
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (10) : 1845 - 1852

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