Synthesis of cyclopenta[b]indol-1-ones and carbazol-4-ones from N-(2-halophenyl)-substituted enaminones by intramolecular Heck reaction

被引:42
作者
Sorensen, US [1 ]
Pombo-Villar, E [1 ]
机构
[1] Novartis Pharma AG, Nervous Syst Res, CH-4002 Basel, Switzerland
关键词
D O I
10.1002/hlca.200490020
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient synthetic route towards N-methylated or nonmethylated 3,4-dihydrocyclopent[b]indol-1(2H)-ones (3) and 1,2,3 9-tetrahydrocarbazol-4(4 H)-one (10) was elaborated, based on Pd-catalyzed intramolecular Heck reaction. The chemoselectivity of the cyclization was studied in the case of the bi- and trifunctional substrates 12 and 17, respectively. In the latter case, depending on the catalyst, either the brominated indole 18 or the tetracyclic compound 19 were obtained by single and double Heck reaction, respectively.
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页码:82 / 89
页数:8
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