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

Yaping Zhang ¹Wei Zhou ¹Mingchun Gao ¹Tianqi Liu ¹Bingxin Liu ¹Chang-Hua Ding ¹Bin Xu²

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作者信息

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

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 function-alized 2-cyanopyrroles are constructed efficiently through a new formal[3+2]mode,demonstrating di-verse 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,re-spectively.This protocol features broad substrate scope,operational simplicity and good functional group tolerance.

Key words

Isocyanide/Cyanopyrrole/Insertion/Allyl compound/Bronsted acid catalysis

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基金项目

国家自然科学基金(22171178)

国家自然科学基金(21871174)

国家自然科学基金(22071143)

上海市教委科研创新计划(2019-01-07-00-09-E00008)

出版年

2024

中国化学快报(英文版)

中国化学会

中国化学快报(英文版)

CSTPCD

影响因子：0.771

ISSN：1001-8417

参考文献量2

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