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 

机构地区：[1]Department of Chemistry,Affiliated Nantong Hospital of Shanghai University(The Sixth People's Hospital of Nantong),Shanghai Engineering Research Center of Organ Repair,Innovative Drug Research Center,School of Medicine,Shanghai University,Shanghai 200444,China [2]State Key Laboratory of Organometallic Chemistry,Shanghai Institute of Organic Chemistry,Chinese Academy of Sciences,Shanghai 200032,China

出　　处：《Chinese Chemical Letters》2024年第4期330-335,共6页中国化学快报（英文版）

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。

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.

关 键 词：ISOCYANIDE Cyanopyrrole INSERTION Allyl compound Bronsted acid catalysis 

分 类 号：O626.13[理学—有机化学]