Synthesis of Substituted Quinolines by the Electrophilic Cyclization of N-(2-Alkynyl)anilines.

Synthesis of Substituted Quinolines by the Electrophilic Cyclization of N-(2-Alkynyl)anilines.
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DOI:
10.1016/j.tet.2009.12.012
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发表时间:
2010-02-06
期刊:
影响因子:
2.1
通讯作者:
Larock RC
Larock RC
中科院分区:
化学3区
文献类型:
--
作者:
Zhang X;Yao T;Campo MA;Larock RC

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用ICl、I2、Br2、PhSeBr和p-O2NC6H4SCl对N-(2-炔基)苯胺进行6-内切亲电环化反应,可以在温和的反应条件下合成多种取代喹啉。在各种官能团的存在下,该反应以中等到较高的产率提供了含3-卤素、硒和含硫的喹啉。用Hg(OTf)2催化这些炔基苯胺的闭环反应,合成了3位含一个氢的类似喹啉。
A wide variety of substituted quinolines are readily synthesized under mild reaction conditions by the 6-endo-dig electrophilic cyclization of N-(2-alkynyl)anilines by ICl, I2, Br2, PhSeBr and p-O2NC6H4SCl. The reaction affords 3-halogen-, selenium- and sulfur-containing quinolines in moderate to good yields in the presence of various functional groups. Analogous quinolines bearing a hydrogen in the 3-position have been synthesized by the Hg(OTf)2-catalyzed ring closure of these same alkynylanilines.
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