Imidazodipyridines via DMAP Catalyzed Domino N−H Carbonylation and 6π‐Electrocyclization: Synthetic Scope and Application,Advanced Synthesis & Catalysis

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Imidazodipyridines via DMAP Catalyzed Domino N−H Carbonylation and 6π‐Electrocyclization: Synthetic Scope and Application
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2020-06-22 , DOI: 10.1002/adsc.202000553
Kena Zhang ₁ , Abderrahman El Bouakher ₁ , Hélène Lévaique ₂ , Jérome Bignon ₂ , Pascal Retailleau ₃ , Mouad Alami ₁ , Abdallah Hamze ₁

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In this work, we report a domino reaction for access to highly functionalized imidazo[1,2‐a :5,4‐b′ ]dipyridines simply by stirring Boc₂O in the presence of DMAP as a catalyst with readily prepared 3‐amino‐2‐(vinyl)imidazo[1,2‐a ]pyridine. This methodology enables the synthesis of highly functionalized imidazodipyridines. The process proved to be compatible with a wide variety of substrates. The synthetic potential of this method was illustrated by performing a Suzuki‐Miyaura coupling on 4‐phenylimidazo‐dipyridin‐2‐ol derivatives. Screening of the biological activity of the newly generated compounds led to the identification of a new hit. Compound 7 l exhibits good antiproliferative activity in the submicromolar range against the human colon cancer cell line.

中文翻译：

通过DMAP催化的咪唑二吡啶类化合物的Domino NH羰基化和6π电环化：合成范围和应用

在这项工作中，我们报告了通过在DMAP作为催化剂存在下，将Boc ₂ O与易于制备的3-氨基一起搅拌，简单地搅拌Boc ₂ O即可获得高度官能化的咪唑并[1,2- a：5,4- b' ]二吡啶的多米诺反应-2-（乙烯基）咪唑并[1,2- a ]吡啶。该方法使得能够合成高度官能化的咪唑并二吡啶。事实证明，该工艺可与多种基材兼容。该方法的合成潜力通过对4-苯基咪唑基-联吡啶-2-醇衍生物进行Suzuki-Miyaura偶联来说明。筛选新产生的化合物的生物活性导致鉴定出新的命中。化合物7 l 在亚微摩尔范围内对人结肠癌细胞系具有良好的抗增殖活性。

更新日期：2020-08-04

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