文献类型：期刊文献

英文题名：Dearomative [4+2] cycloaddition of 3-nitroindoles with ortho-amino Morita-Baylis-Hillman carbonates to forge indole-fused quinolines

作者：Wang, Kai-Kai[1];Li, Yan-Li[2];Li, Lan-Xin[1];Yao, Wei-Wei[1];Li, Ya-Fei[1];Wang, Wen-Fei[1];Chen, Rongxiang[1];Hu, Yi-Fan[1];Sun, Aili[1]

通讯作者：Chen, RX[1];Sun, AL[1]

机构：[1]Xinxiang Univ, Sch Pharm, Xinxiang 453000, Peoples R China;[2]Xinxiang Univ, Med Coll, Xinxiang, Peoples R China

第一机构：新乡学院

通讯机构：[1]corresponding author), Xinxiang Univ, Sch Pharm, Xinxiang 453000, Peoples R China.|[11071]新乡学院;

年份：2024

外文期刊名：JOURNAL OF HETEROCYCLIC CHEMISTRY

收录：;WOS:【SCI-EXPANDED(收录号:WOS:001143877800001)】；

基金：We are grateful for the financial support from the National Natural Science Foundation of China (21801214), the Program for Youth Backbone Teacher Training in University of Henan Province (2021GGJS163), and the Higher Education Institution Key Research Project Plan of Henan Province (23A150044, 24A150033, and 24B150031).

语种：英文

摘要：A dearomative [4 + 2] cycloaddition of 3-nitroindoles ortho-amino Morita-Baylis-Hillman carbonates was established under mild conditions. This method provides an efficient and practical approach for delivering tetrahydro-5H-indolo[2,3-b]quinolines containing three contiguous stereocenters, two tertiary and one quaternary, in high yield (up to 95%) with excellent diastereoselectivity (all cases >25:1 dr). The potential synthetic applications of this strategy were also highlighted by the scale-up experiment and further synthetic transformation. Moreover, the structure and relative configuration of the cycloadduct was unequivocally confirmed by single-crystal X-ray diffraction.