Tandem Silver-Catalyzed Cyclization/Nucleophilic Functionalization of 2-Alkynylindole-3-carbaldehyde Oximes to Afford New 2,4-Disubstituted γ-Carbolines

被引：12

作者：

Rodrigues, Nuno ^{[1
]}

Boiaryna, Liliana ^{[1
]}

Vercouillie, Johnny ^{[2
]}

Guilloteau, Denis ^{[2
]}

Suzenet, Franck ^{[1
]}

Buron, Frederic ^{[1
]}

Routier, Sylvain ^{[1
]}

机构：

[1] Univ Orleans, CNRS UMR 7311, ICOA, F-45067 Orleans, France

[2] Univ Francois Rabelais Tours, CHRU Tours, UMR Inserm U930, Tours, France

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 2016卷 / 29期

关键词：

Fused-ring systems; Nitrogen heterocycles; Alkynes; Cyclization; Silver; N-OXIDES; TERMINAL ACETYLENES; KINASE INHIBITORS; CYTOTOXIC AGENTS; BETA-CARBOLINES; 2-ALKYNYLBENZALDOXIME; IMINOANNULATION; 1-AROXYISOQUINOLINES; CYCLIZATION; CHLORIDE;

D O I：

10.1002/ejoc.201600904

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Highly substituted pyrido[4,3-b]indole derivatives were synthesized through a straightforward one-pot silver-catalyzed process involving 2-alkynylindole-3-carbaldehyde oximes. The tandem cyclization/nucleophilic addition sequence was optimized and applied to a wide range of nucleophiles, which reacted regioselectively at the pyrido[4,3-b]indole C4 position. The scope and limitations of the methodology were evaluated and the final compounds were obtained in fair to very good yields. This versatile method proved to be compatible with various chemical functionalities or (hetero)cycles.

引用

页码：5024 / 5036

页数：13

共 13 条

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