文献类型：期刊文献

英文题名：Substrate-Controlled Diversity-Oriented Synthesis of Novel Polycyclic Frameworks via [4+2] and [3+2] Annulations of Ninhydrin-Derived MBH Adducts with 3,4-Dihydroisoquinolines

作者：Wang, Kaikai[1];Zhou, Wenwen[1];Jia, Jun[2];Ye, Junwei[1];Yuan, Mengxin[1];Yang, Jie[3];Qi, Yonghua[1];Chen, Rongxiang[1]

通讯作者：Chen, RX[1];Yang, J[2]

机构：[1]Xinxiang Univ, Sch Pharm, Xinxiang 453000, Peoples R China;[2]Jilin Prov Prod Qual Supervis & Inspect Inst, Changchun 130012, Peoples R China;[3]Xinxiang Univ, Sch Chem & Mat Engn, Xinxiang 453000, 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;[2]corresponding author), Xinxiang Univ, Sch Chem & Mat Engn, Xinxiang 453000, Peoples R China.|[11071]新乡学院;

年份：2023

卷号：28

期号：19

外文期刊名：MOLECULES

收录：;Scopus(收录号：2-s2.0-85173993098);WOS:【SCI-EXPANDED(收录号:WOS:001085016400001)】；

基金：

1. The authors are grateful for the financial support from the National Natural Science Foundation of China (21801214, K.W.), the Program for Youth Backbone Teacher Training in University of Henan Province (2021GGJS163, K.W.), the Higher Education Institution Key Research Project Plan of Henan Province (23A150044, K.W.), Science and Technology Research Program of Henan Province (202102210232, J.Y.), and the Henan Province professional degree graduate excellent teaching case project (YJS2023AL094, Y.Q.).

语种：英文

外文关键词：substrate-controlled; ninhydrin-derived MBH adducts; 3,4-dihydroisoquinolines; cycloaddition; polycyclic frameworks; Diels-Alder reaction; [3+2] cycloaddition

摘要：Substrate-controlled diversity-oriented synthesis of polycyclic frameworks via [4 + 2] and [3 + 2] annulations between ninhydrin-derived Morita-Baylis-Hillman (MBH) adducts and 3,4-dihydroisoquinolines under similar reaction conditions have been developed. The reaction provides diversity-oriented synthesis of a series of novel and structurally complex spiro multi heterocyclic skeletons in good yields (up to 87% and 90%, respectively) with excellent diastereoselectivities (up to >25:1 dr). In particular, the switchable [4 + 2] and [3 + 2] annulation reactions are controlled by tuning the hydroxyl protecting group on the ninhydrin-derived MBH adduct to deliver structural diverse spiro[indene-2,2 '-[1,3]oxazino[2,3-a]isoquinoline] and spiro[indene-2,1 '-pyrrolo[2,1-a]isoquinoline], respectively. Furthermore, the relative configuration and chemical structure of two kinds of cycloadducts were confirmed through X-ray diffraction analysis.