Citation: Yaping Zhang, Wei Zhou, Mingchun Gao, Tianqi Liu, Bingxin Liu, Chang-Hua Ding, Bin Xu. Oxidative cyclization of allyl compounds and isocyanide: A facile entry to polysubstituted 2-cyanopyrroles[J]. Chinese Chemical Letters, ;2024, 35(4): 108836. doi: 10.1016/j.cclet.2023.108836 shu

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

Yaping Zhang ^a ,
Wei Zhou ^a ,
Mingchun Gao ^a ,
Tianqi Liu ^a ,
Bingxin Liu ^a ,
Chang-Hua Ding ^{a, *,} ,
Bin Xu ^{a, b, *,}

a.
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
b.
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

dingchanghua@shu.edu.cn

xubin@shu.edu.cn

Received Date: 27 April 2023
Revised Date: 3 July 2023
Accepted Date: 24 July 2023
Available Online: 26 July 2023

Figures(7)

A facile TfOH-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.
- Isocyanide,
- Cyanopyrrole,
- Insertion,
- Allyl compound,
- Bronsted acid catalysis
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