Transition-Metal-Catalyzed Selective Cyclization Strategy to 2-Substituted Benzofurans and Indoles en Route to the Oxa Analogues of Isocryptolepine

被引：18

作者：

Indu, Satrajit ^{[1
]}

Subramanian, Parthasarathi ^{[1
]}

Kaliappan, Krishna P. ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Bombay 400076, Maharashtra, India

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 2014卷 / 32期

关键词：

Synthetic methods; Cross-coupling; Cyclization; Domino reactions; ALIPHATIC NITRILES SYNTHESIS; ALKYL ARYL KETONES; INDOLOQUINOLINE ALKALOIDS; EFFICIENT SYNTHESIS; O-IODOPHENOLS; PALLADIUM; CRYPTOSANGUINOLENTINE; CRYPTOTACKIEINE; COPPER; FUNCTIONALIZATION;

D O I：

10.1002/ejoc.201402869

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A selective catalytic route to benzofurans and indoles from similar starting materials has been developed. A two-step protocol that involves a transition-metal-catalyzed domino Sonogashira coupling between 2-ethynylanilines and 2-iodophenols followed by selective O- and N-cyclizations afforded 2-(benzofuran-2-yl)anilines and 2-(indol-2-yl)phenols, respectively. The 2-(benzofuran-2-yl) anilines were further utilized in a Lewis acid catalyzed Pictet-Spengler-type cyclization to prepare the oxa analogues of isocryptolepine.

引用

页码：7193 / 7202

页数：10

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