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Extended Multicomponent Reactions with Indole Aldehydes: Access to Unprecedented Polyheterocyclic Scaffolds, Ligands of the Aryl Hydrocarbon Receptor
Angewandte Chemie International Edition ( IF 16.6 ) Pub Date : 2020-10-13 , DOI: 10.1002/anie.202011253
Ouldouz Ghashghaei 1 , Marina Pedrola 1 , Francesca Seghetti 1 , Victor V. Martin 1 , Ricardo Zavarce 1 , Michal Babiak 2 , Jiri Novacek 2 , Frederick Hartung 3 , Katharina M. Rolfes 3 , Thomas Haarmann‐Stemmann 3 , Rodolfo Lavilla 1
Affiliation  

The participation of reactants undergoing a polarity inversion along a multicomponent reaction allows the continuation of the transformation with productive domino processes. Thus, indole aldehydes in Groebke–Blackburn–Bienaymé reactions lead to an initial adduct which spontaneously triggers a series of events leading to the discovery of novel reaction pathways together with direct access to a variety of linked, fused, and bridged polyheterocyclic scaffolds. Indole 3‐ and 4‐carbaldehydes with suitable isocyanides and aminoazines afford fused adducts through oxidative Pictet–Spengler processes, whereas indole 2‐carbaldehyde yields linked indolocarbazoles under mild conditions, and a bridged macrocycle at high temperature. These novel structures are potent activators of the human aryl hydrocarbon receptor signaling pathway.

中文翻译:

与吲哚醛的扩展多组分反应:前所未有的多杂环支架,芳烃受体的配体的获得

沿着多组分反应经历极性反转的反应物的参与允许通过生产性多米诺过程的转化继续进行。因此,Groebke–Blackburn–Bienaymé反应中的吲哚醛会导致初始加合物,该加合物自发触发一系列事件,从而导致发现新的反应途径,并直接进入各种连接的,稠合的和桥连的多杂环骨架。吲哚3-和4-甲醛与合适的异氰酸酯和氨基嗪通过氧化Pictet-Spengler过程提供稠合的加合物,而吲哚2-甲醛在温和条件下与吲哚并咔唑连接,在高温下桥接大环。这些新颖的结构是人类芳烃受体信号通路的有效激活剂。
更新日期:2020-10-13
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