对醌胺与2-硝基苯并呋喃的去芳构化[3+2]环加成反应  

Dearomative [3+2] Cycloaddition of para-Quinamines and 2-Nitrobenzofurans

作　　者：曾海鹰 王浩宇[1] 葛真真 赵建强 陈明丰 周鸣强[1,3] 袁伟成 ZENG Haiying;WANG Haoyu;GE Zhenzhen;ZHAO Jianqiang;CHEN Mingfeng;ZHOU Mingqiang;YUAN Weicheng(National Engineering Research Center of Chiral Drugs,Chengdu Institute of Organic Chemistry,Chinese Academy of Sciences,Chengdu 610041,China;Research Center for Chiral Drug Innovation,Institute for Advanced Study,Chengdu University,Chengdu 610106,China;University of Chinese Academy of Sciences,Beijing 100049,China;Zhejiang Nexchem Pharmaceutical Co.,Ltd.,Jinhua 321016,China)

机构地区：[1]中国科学院,成都有机化学研究所,手性药物国家工程研究中心,四川成都610041 [2]成都大学高等研究院,手性药物创新研究中心,四川成都610106 [3]中国科学院大学,北京100049 [4]浙江耐司康药业有限公司,浙江金华321016

出　　处：《合成化学》2023年第7期539-544,共6页Chinese Journal of Synthetic Chemistry

基　　金：国家自然科学基金资助项目(22171029,21901024,21871252,21801024,21801026)。

摘　　要：苯并呋喃并[3,2-b]吡咯骨架作为一类重要的结构骨架广泛存在于各类药物和生物活性分子中,具有潜在的应用价值。本文以对醌胺和2-硝基苯并呋喃为原料,在无机碱K_(2)CO_(3)的作用下发生去芳构化[3+2]环加成反应,合成了10个结构新颖的含苯并呋喃并[3,2-b]吡咯骨架的化合物3a~3j,收率为64%~94%,dr>19∶1,并对这些化合物进行了^(1)H NMR、^(13)C NMR、m.p.和HR-MS(ESI-TOF)表征。Benzofuran[3,2-b]pyrrole skeleton as an important structural framework,is widely found in number of pharmaceuticals and bioactive molecules,possessing potential applications.In this paper,the dearomative[3+2]cycloaddition of para-quinamines and 2-nitrobenzofurans with K_(2)CO_(3)as the base was developed.A series of structurally novel polycyclic compounds 3a~3j containing benzofuran[3,2-b]pyrrole skeleton could be smoothly obtained in 64%~94%yields with>19∶1 dr.These compounds were characterized by ^(1)H NMR,^(13)C NMR,m.p.and HR-MS(ESI-TOF).

关 键 词：对醌胺 2-硝基苯并呋喃 去芳构化 合成 [3+2]环加成 去对称化 多环化合物 

分 类 号：O621.3[理学—有机化学]