Yang Ren-Yin, Sun Jing, Sun Qiu, Yan Chao-Guo
College of Chemistry & Chemical Engineering , Yangzhou University , Yangzhou 225002 , China.
J Org Chem. 2018 Jun 1;83(11):5909-5919. doi: 10.1021/acs.joc.8b00196. Epub 2018 May 14.
A HOTf catalyzed three-component reaction of indoles, acetophenones, and ( E)-3-phenacylideneoxindolinones resulted in the unexpected polysubstituted 3-(9 H-carbazol-2-yl)indolin-2-ones in good yields. A similar reaction with various cyclic ketones afforded the corresponding carbocyclic fused 3-(9 H-carbazol-2-yl)indolin-2-ones. On the other hand, ( E)-3-arylideneoxindolinones in the three-component reaction gave the expected spiro[tetrahydrocarbazole-3,3'-oxindoles] through a domino alkenylation/Diels-Alder reaction. The unusual different reactivity of ( E)-3-phenacylideneoxindolinones and ( E)-3-arylideneoxindolinones in the three-component reactions was believed to involve the different reaction paths caused by the existence of the carbonyl group.
一种由HOTf催化的吲哚、苯乙酮和（E）-3-苯亚甲基氧化吲哚酮的三组分反应，以良好的产率意外地得到了多取代的3-（9H-咔唑-2-基）吲哚-2-酮。与各种环状酮的类似反应得到了相应的碳环稠合的3-（9H-咔唑-2-基）吲哚-2-酮。另一方面，三组分反应中的（E）-3-亚芳基氧化吲哚酮通过多米诺烯基化/狄尔斯-阿尔德反应得到了预期的螺[四氢咔唑-3,3'-氧化吲哚]。（E）-3-苯亚甲基氧化吲哚酮和（E）-3-亚芳基氧化吲哚酮在三组分反应中不同寻常的不同反应活性被认为涉及由羰基的存在引起的不同反应路径。
