(Z)-Stereoselective Synthesis of Mono- and Bis-heterocyclic Benzimidazol-2-ones via Cascade Processes Coupled with the Ugi Multicomponent Reaction.
(Z)-Stereoselective Synthesis of Mono- and Bis-heterocyclic Benzimidazol-2-ones via Cascade Processes Coupled with the Ugi Multicomponent Reaction.
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DOI：
10.1021/acs.joc.5b00955
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发表时间：
2015-08
期刊：
影响因子：
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通讯作者：
Zhigang Xu;Guillermo Martinez-Ariza;A. Cappelli;S. Roberts;C. Hulme
中科院分区：
文献类型：
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作者：
Zhigang Xu;Guillermo Martinez-Ariza;A. Cappelli;S. Roberts;C. Hulme
本文报道了几种新的级联反应，其使得能够获得各种独特的单杂环和双杂环支架。级联事件的顺序通过Ugi加合物的酸处理介导，所述Ugi加合物提供1，5-苯并二氮杂卓，其随后经历优雅的重排以提供（E）-苯并咪唑酮，其通过酸促进的互变异构转化为它们相应的（Z）-异构体。此外，通过类似的多米诺骨牌样过程也可以获得与（Z）-苯并咪唑-2-酮连接的各种杂环，这表明了获得显著新的支架多样性的一般策略，每个支架包含四个潜在的多样化点。五种支架的最终结构已经通过X射线晶体学明确证明。
Several novel cascade reactions are herein reported that enable access to a variety of unique mono- and bis-heterocyclic scaffolds. The sequence of cascade events are mediated through acid treatment of an Ugi adduct that affords 1,5-benzodiazepines which subsequently undergo an elegant rearrangement to deliver (E)-benzimidazolones, which through acid-promoted tautomerization convert to their corresponding (Z)-isomers. Moreover, a variety of heterocycles tethered to (Z)-benzimidazole-2-ones are also accessible through similar domino-like processes, demonstrating a general strategy to access significantly new scaffold diversity, each containing four points of potential diversification. Final structures of five scaffolds have been definitively proven by X-ray crystallography.