• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利：CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法，用中文像聊天一样搜索，搜遍4000万医学文献。AI智能推荐，让科研检索更轻松。

立即免费搜索

文件翻译

保留排版，准确专业，支持PDF/Word/PPT等文件格式，支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述，25分钟生成高质量综述，智能提取关键信息，辅助科研写作。

立即免费体验

通过异腈的TMSCl活化合成多种氮杂环的无过渡金属和无氧化剂方法。

Transition-metal and oxidant-free approach for the synthesis of diverse N-heterocycles by TMSCl activation of isocyanides.

作者信息

Luo Liangliang, Li Hongyan, Liu Jinxin, Zhou Yuan, Dong Lin, Xiao You-Cai, Chen Fen-Er

机构信息

Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University Chengdu 610041 China

Engineering Center of Catalysis and Synthesis for Chiral Molecules, Department of Chemistry, Fudan University Shanghai 200433 China

出版信息

RSC Adv. 2020 Aug 7;10(49):29257-29262. doi: 10.1039/d0ra04636a. eCollection 2020 Aug 5.

DOI:10.1039/d0ra04636a
PMID:35521093
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9055958/
Abstract

A highly efficient TMSCl-mediated addition of N-nucleophiles to isocyanides has been achieved. This transition-metal and oxidant-free strategy has been applied to the construction of various N-heterocyles such as quinazolinone, benzimidazole and benzothiazole derivatives by the use of distinct amino-based binucleophiles. The notable feature of this protocol includes its mild reaction condition, broad functional group tolerance and excellent yield.

摘要

实现了一种高效的TMSCl介导的N-亲核试剂与异腈的加成反应。这种无过渡金属和氧化剂的策略已被应用于通过使用不同的氨基双亲核试剂构建各种N-杂环，如喹唑啉酮、苯并咪唑和苯并噻唑衍生物。该方法的显著特点包括反应条件温和、官能团耐受性广和产率优异。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1645/9055958/aabae020d381/d0ra04636a-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1645/9055958/b54ed1b390c5/d0ra04636a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1645/9055958/2e864f949dcd/d0ra04636a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1645/9055958/c62e690242bb/d0ra04636a-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1645/9055958/aabae020d381/d0ra04636a-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1645/9055958/b54ed1b390c5/d0ra04636a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1645/9055958/2e864f949dcd/d0ra04636a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1645/9055958/c62e690242bb/d0ra04636a-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1645/9055958/aabae020d381/d0ra04636a-s4.jpg

相似文献

1
Transition-metal and oxidant-free approach for the synthesis of diverse N-heterocycles by TMSCl activation of isocyanides.通过异腈的TMSCl活化合成多种氮杂环的无过渡金属和无氧化剂方法。
RSC Adv. 2020 Aug 7;10(49):29257-29262. doi: 10.1039/d0ra04636a. eCollection 2020 Aug 5.
2
Iodine-mediated electrochemical C(sp)-H cyclization: the synthesis of quinazolinone-fused N-heterocycles.碘介导的电化学 C(sp 3 )-H 环化反应：喹唑啉酮并 N-杂环的合成。
Chem Commun (Camb). 2022 Jan 4;58(3):411-414. doi: 10.1039/d1cc05865g.
3
TMSCl-Catalyzed Electrophilic Thiocyano Oxyfunctionalization of Alkenes Using N-Thiocyano-dibenzenesulfonimide.使用N-硫氰基-二苯磺酰亚胺通过TMSCl催化的烯烃亲电硫氰基氧官能团化反应
Org Lett. 2019 Jul 5;21(13):5106-5110. doi: 10.1021/acs.orglett.9b01706. Epub 2019 Jun 20.
4
Metal-free oxidative isocyanides insertion with aromatic aldehydes to aroylated N-heterocycles.无金属氧化异腈与芳香醛插入反应合成芳酰化氮杂环化合物
RSC Adv. 2018 Jan 15;8(6):3036-3040. doi: 10.1039/c7ra12755c. eCollection 2018 Jan 12.
5
An Efficient Synthesis of Benzimidazole and Benzothiazole Derivatives Using a Nickel(II) Metal-Organic Framework.使用镍（II）金属有机框架高效合成苯并咪唑和苯并噻唑衍生物
Curr Org Synth. 2020;17(2):109-116. doi: 10.2174/1570179417666200117110758.
6
Non-metal-mediated -oxyl radical (TEMPO)-induced acceptorless dehydrogenation of N-heterocycles electrocatalysis.非金属介导的氮杂环的2,2,6,6-四甲基哌啶-1-氧自由基（TEMPO）诱导的无受体脱氢反应——电催化
RSC Adv. 2022 Feb 16;12(9):5483-5488. doi: 10.1039/d1ra08919f. eCollection 2022 Feb 10.
7
Isocyanides in the synthesis of nitrogen heterocycles.异氰化物在杂环氮化合物合成中的应用。
Angew Chem Int Ed Engl. 2010 Nov 22;49(48):9094-124. doi: 10.1002/anie.201000723.
8
In Situ Activation of Disulfides for Multicomponent Reactions with Isocyanides and a Broad Range of Nucleophiles.用于与异腈和多种亲核试剂进行多组分反应的二硫化物的原位活化
Org Lett. 2019 Mar 1;21(5):1484-1487. doi: 10.1021/acs.orglett.9b00275. Epub 2019 Feb 11.
9
Transition Metal-Catalyzed Tandem Reactions of Ynamides for Divergent N-Heterocycle Synthesis.用于多样化氮杂环合成的烯酰胺的过渡金属催化串联反应
Acc Chem Res. 2020 Sep 15;53(9):2003-2019. doi: 10.1021/acs.accounts.0c00417. Epub 2020 Sep 1.
10
Transition Metal-Participated Synthesis and Utilization of N-containing Heterocycles: Exploring for Nitrogen Sources.过渡金属参与的含氮杂环的合成与利用：探寻氮源
Chem Rec. 2016 Jun;16(3):1701-14. doi: 10.1002/tcr.201600020. Epub 2016 May 27.

引用本文的文献

1
Crafting mono- and novel bis-methylated pyrroloquinoxaline derivatives from a shared precursor and its application in the total synthesis of marinoquinoline A.由共同前体合成单甲基化和新型双甲基化吡咯并喹喔啉衍生物及其在马里诺喹啉A全合成中的应用。
RSC Adv. 2023 Oct 10;13(42):29561-29567. doi: 10.1039/d3ra05952a. eCollection 2023 Oct 4.

本文引用的文献

1
Base Metal Catalyzed Isocyanide Insertions.贱金属催化的异腈插入反应。
Angew Chem Int Ed Engl. 2020 Jan 7;59(2):540-558. doi: 10.1002/anie.201905838. Epub 2019 Oct 4.
2
Cobalt-Catalyzed Aerobic Oxidative Cyclization of 2-Aminophenols with Isonitriles: 2-Aminophenol Enabled O Activation by Cobalt(II).钴催化 2-氨基苯酚与异腈的有氧氧化环化反应：钴(II)促进 2-氨基苯酚的 O 活化。
Org Lett. 2019 Jun 21;21(12):4510-4514. doi: 10.1021/acs.orglett.9b01384. Epub 2019 Jun 3.
3
I/TBHP-Mediated Oxidative Coupling of Amino-Based Bisnucleophiles and Isocyanides: Access to 2-Aminobenzoxazinones, 2-Aminobenzoxazines, and 2-Aminoquinazolines under Metal-Free Conditions.
无金属条件下 I/TBHP 介导的基于氨基酸的双亲核试剂与异氰化物的氧化偶联反应：制备 2-氨基苯并恶嗪酮、2-氨基苯并恶嗪和 2-氨基喹唑啉
J Org Chem. 2018 Nov 2;83(21):13491-13497. doi: 10.1021/acs.joc.8b02395. Epub 2018 Oct 19.
4
First-Row Transition-Metal-Catalyzed Carbonylative Transformations of Carbon Electrophiles.第一过渡金属催化的碳亲电试剂羰基化转化反应。
Chem Rev. 2019 Feb 27;119(4):2090-2127. doi: 10.1021/acs.chemrev.8b00068. Epub 2018 May 3.
5
Organic synthesis provides opportunities to transform drug discovery.有机合成提供了转化药物发现的机会。
Nat Chem. 2018 Apr;10(4):383-394. doi: 10.1038/s41557-018-0021-z. Epub 2018 Mar 22.
6
Oxalic/malonic acids as carbon building blocks for benzazole, quinazoline and quinazolinone synthesis.草酸/丙二酸作为苯并唑、喹唑啉和喹唑啉酮合成的碳砌块。
Org Biomol Chem. 2018 Feb 21;16(8):1337-1342. doi: 10.1039/c7ob03064a.
7
Silver Nitrate-Catalyzed Isocyanide Insertion/Lactamization Sequence to Imidazolones and Quinazolin-4-ones: Development and Application in Natural Product Synthesis.硝酸银催化的异氰化物插入/内酰胺化序列合成咪唑酮和喹唑啉-4-酮：在天然产物合成中的发展和应用。
Org Lett. 2017 Sep 15;19(18):4872-4875. doi: 10.1021/acs.orglett.7b02334. Epub 2017 Aug 25.
8
Dual Activation of Nucleophiles and Electrophiles by N-Heterocyclic Carbene Organocatalysis: Chemoselective N-Imination of Indoles with Isocyanides.N-杂环卡宾有机催化的亲核试剂和亲电试剂的双重活化：异氰与吲哚的选择性 N-亚胺化反应。
Org Lett. 2017 Jun 16;19(12):3259-3262. doi: 10.1021/acs.orglett.7b01377. Epub 2017 Jun 5.
9
Organocatalytic activation of isocyanides: N-heterocyclic carbene-catalyzed enaminone synthesis from ketones.异腈的有机催化活化：N-杂环卡宾催化由酮合成烯胺酮
Chem Sci. 2017 Mar 1;8(3):2401-2406. doi: 10.1039/c6sc05266e. Epub 2016 Dec 20.
10
To each his own: isonitriles for all flavors. Functionalized isocyanides as valuable tools in organic synthesis.各有所好：异腈适用于各种口味。官能化异腈是有机合成中的有价值工具。
Chem Soc Rev. 2017 Mar 6;46(5):1295-1357. doi: 10.1039/c6cs00444j.