Oxidative cyclization of allyl compounds and isocyanide: A facile entry to polysubstituted 2-cyanopyrroles

作     者：Yaping Zhang Wei Zhou Mingchun Gao Tianqi Liu Bingxin Liu Chang-Hua Ding Bin Xu Yaping Zhang;Wei Zhou;Mingchun Gao;Tianqi Liu;Bingxin Liu;Chang-Hua Ding;Bin Xu

作者机构：Department of ChemistryAffiliated Nantong Hospital of Shanghai University(The Sixth People's Hospital of Nantong)Shanghai Engineering Research Center of Organ RepairInnovative Drug Research CenterSchool of MedicineShanghai UniversityShanghai 200444China State Key Laboratory of Organometallic ChemistryShanghai Institute of Organic ChemistryChinese Academy of SciencesShanghai 200032China 

出 版 物：《Chinese Chemical Letters》 (中国化学快报（英文版）)

年 卷 期：2024年第35卷第4期

页      面：330-335页

核心收录：

学科分类：081704[工学-应用化学] 07[理学] 08[工学] 0817[工学-化学工程与技术] 070303[理学-有机化学] 0703[理学-化学] 

基　　金：the National Natural Science Foundation of China(Nos.22171178, 21871174, 22071143) Innovation Program of Shanghai Municipal Education Commission (No.2019–01–07–00–09-E00008) for financial support 

主　　题：Isocyanide Cyanopyrrole Insertion Allyl compound Bronsted acid catalysis 

摘      要：A facile Tf OH-catalyzed oxidative cyclization of allyl compounds and isocyanide has been developed with the assistance of DDQ, where isocyanide is used as the crucial N and CN sources. Highly functionalized 2-cyanopyrroles are constructed efficiently through a new formal [3 + 2] mode, demonstrating diverse reactivity and synthetic utility in organic chemistry. 2-Cyanopyrrole is converted into a nucleobase analogue of Remdesivir and 5H-pyrrolo[2,1-a]isoindole through a three-step or a two-step sequence, respectively. This protocol features broad substrate scope, operational simplicity and good functional group tolerance.