Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, PR China.
J Org Chem. 2011 Nov 4;76(21):8690-7. doi: 10.1021/jo2012187. Epub 2011 Oct 10.
A variety of 2-aryl-3-arylamino-2-alkenenitriles were converted to N-arylindole-3-carbonitriles in a one-pot manner through NBS- or NCS-mediated halogenation followed by Zn(OAc)(2)-catalyzed intramolecular cyclization. It is postulated that the process involves the formation of arylnitrenium ion intermediates, which undergo the electrophilic aromatic substitution to give the cyclized N-arylindole product.
多种 2-芳基-3-芳基氨基-2-烯腈可通过 NBS 或 NCS 介导的卤化作用转化为 N-芳基吲哚-3-氰基化合物，然后通过 Zn(OAc)(2)催化的分子内环化作用一步合成。该过程涉及芳基氮翁离子中间体的形成，这些中间体经历亲电芳香取代反应，生成环状的 N-芳基吲哚产物。
