1,2,3,9-Tetrahydro-4H-carbazol-4-one and 8,9-Dihydropyrido-[1,2-a]indol-6(7H)-one from 1H-Indole-2-butanoic Acid

被引：33

作者：

Bunce, Richard A. ^{[1
]}

Nammalwar, Baskar ^{[1
]}

机构：

[1] Oklahoma State Univ, Dept Chem, Stillwater, OK 74078 USA

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 2009年 / 46卷 / 02期

关键词：

PALLADIUM-CATALYZED SYNTHESIS; SEROTONIN-3 RECEPTOR ANTAGONISTS; EFFICIENT SYNTHESIS; ORGANIC-SYNTHESIS; INDOLES; ENAMINONES; ESTERS; 1,2-DIHYDRO-4(3H)-CARBAZOLONES; DERIVATIVES; REACTIVITY;

D O I：

10.1002/jhet.22

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Efficient syntheses of the title ring systems have been developed from 1H-indole-2-butanoic acid, which was easily prepared from 2-fluoro-1-nitrobenzene in four steps. Heating 1H-indole-2-butanoic acid in toluene containing p-toluenesulfonic acid at 110 degrees C furnished 1,2,3,9-tetrahydro-4H-carbazol-4-one in 88% yield. Heating this same acid in toluene with no added acid gave 8,9-dihydropyrido[1,2-a]-indol-6(7H)-one in 90% yield. The tetrahydro-4H-carbazol-4-one was also prepared directly in 92% yield from methyl 6-(2-nitrophenyl)-5-oxohexanoate by a tandem reduction-cycloaromatization-acylation reaction with iron in concentrated hydrochloric acid at 110 degrees C. Application of this approach to the closure of five- and seven-membered rings was also successful.

引用

页码：172 / 177

页数：6

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