Skeletal Diverse Synthesis of N-Fused Polycyclic Heterocycles via the Sequence of Ugi-Type MCR and Cul-Catalyzed Coupling/Tandem Pictet-Spengler Reaction
Skeletal Diverse Synthesis of N-Fused Polycyclic Heterocycles via the Sequence of Ugi-Type MCR and Cul-Catalyzed Coupling/Tandem Pictet-Spengler Reaction
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DOI：
10.1021/jo202255v
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发表时间：
2012-02-03
影响因子：
3.6
通讯作者：
Chauhan, Prem M. S.
中科院分区：
文献类型：
--
作者：
Tyagi, Vikas;Khan, Shahnawaz;Chauhan, Prem M. S.
N-稠合多环杂环的几种多样性导向合成方法已经被证明，但它们中的大多数都是基于同一库内的点多样性，并且通常涉及耗时的连续多步合成，这也遭受低产率和/或差的前体范围。我们已经开发了一种新的策略，通过Ugi型MCR，然后由CuI催化的偶联反应或串联Pictet-Spengler反应的骨架不同的N-稠合多环化合物的合成。这两步序列提供了八个不同的骨架融合{6-5-5-6}，{5-5-5-6}，{6-5-6-6}，和{5-5-6-6}环系统，在药物化学和化学遗传学中也有应用。
Several diversity-oriented syntheses of N-fused polycyclic heterocycles have been demonstrated but most of them are based on point diversity within the same library and usually involve time-consuming sequential multistep syntheses, which also suffer from low yields and/or poor precursor scopes. We have developed a new strategy for the syntheses of skeletal diverse N-fused polycyclic compounds via an Ugi-type MCR followed by a CuI-catalyzed coupling reaction or tandem Pictet-Spengler reaction. This two-step sequence provides eight distinct skeleton of fused {6-5-5-6}, {5-5-5-6}, {6-5-6-6}, and {5-5-6-6} ring systems that have applications in medicinal chemistry and chemical genetics too.