Synthesis of Highly Substituted Quinolines via a Tandem Ynamide Benzannulation/Iodocyclization Strategy.
Synthesis of Highly Substituted Quinolines via a Tandem Ynamide Benzannulation/Iodocyclization Strategy.
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DOI：
10.1021/acs.joc.5b01648
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发表时间：
2010-08
期刊：
影响因子：
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通讯作者：
Thomas P. Willumstad;Paul D. Boudreau;R. Danheiser
中科院分区：
文献类型：
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作者：
Thomas P. Willumstad;Paul D. Boudreau;R. Danheiser
描述了一种两阶段的“串联策略”，用于区域控制合成非常高度取代的喹啉。基于环丁烯酮或重氮酮与N-炔丙基取代的苯胺的反应的苯甲酰化通过几个周环反应的级联进行，以生成多取代的苯胺衍生物。在串联策略的第二阶段中，酚类苯并环化产物的三氟甲磺酸酯衍生物在暴露于碘时经历Larock环化以形成产物，所述产物通过诸如钯催化偶联的方法进一步加工以产生可以在双环系统的每个位置处被取代的喹啉。
A two-stage "tandem strategy" for the regiocontrolled synthesis of very highly substituted quinolines is described. Benzannulation based on the reaction of cyclobutenones or diazo ketones with N-propargyl-substituted ynamides proceeds via a cascade of several pericyclic reactions to generate multiply substituted aniline derivatives. In the second stage of the tandem strategy, triflate derivatives of the phenolic benzannulation products undergo Larock cyclization upon exposure to iodine to form products that are further elaborated by methods such as palladium-catalyzed coupling to generate quinolines that can be substituted at every position of the bicyclic system.