• 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

(杂)芳族C-H键与磺酰叠氮的直接磺酰胺化:一种合成(杂)芳基磺酰胺的新颖高效方法。

Direct sulfonamidation of (hetero)aromatic C-H bonds with sulfonyl azides: a novel and efficient route to -(hetero)aryl sulfonamides.

作者信息

Liu Zhi, Ebadi Abdolghaffar, Toughani Mohsen, Mert Nihat, Vessally Esmail

机构信息

School of Electrical and Automation Engineering, East China Jiaotong University Nanchang 330013 China

Department of Agriculture, Jouybar Branch, Islamic Azad University Jouybar Iran

出版信息

RSC Adv. 2020 Oct 8;10(61):37299-37313. doi: 10.1039/d0ra04255b. eCollection 2020 Oct 7.

DOI:10.1039/d0ra04255b
PMID:35521237
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9057145/
Abstract

-Aryl sulfonamides belong to a highly important class of organosulfur compounds which are found in a number of FDA-approved drugs such as dofetilide, dronedarone, ibutilide, sotalol, sulfadiazine, sulfamethizole, vemurafenib, and many more. There is therefore continuing interest in the development of novel and convenient protocols for the preparation of these pharmaceutically important compounds. Recently, direct sulfonamidation of (hetero)aromatic C-H bonds with easily available sulfonyl azides has emerged as an attractive and powerful strategy to access -(hetero)aryl sulfonamides where non-toxic nitrogen gas forms as the sole by-product. This review highlights recent advances and developments (2012-2020) in this fast growing research area with emphasis on the mechanistic features of the reactions.

摘要

芳基磺酰胺属于一类非常重要的有机硫化合物,在许多美国食品药品监督管理局(FDA)批准的药物中都有发现,如多非利特、决奈达隆、伊布利特、索他洛尔、磺胺嘧啶、磺胺甲噻二唑、维莫非尼等等。因此,人们一直对开发新颖便捷的方法来制备这些具有药物重要性的化合物感兴趣。最近,利用易于获得的磺酰叠氮化物对(杂)芳族C-H键进行直接磺酰胺化反应,已成为一种有吸引力且强大的策略,可用于制备芳基(杂芳基)磺酰胺,该反应以无毒氮气作为唯一副产物生成。本综述重点介绍了这一快速发展的研究领域(2012年至2020年)的最新进展和发展情况,并着重阐述了反应的机理特征。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a88/9057145/b0a2e4b0ca86/d0ra04255b-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a88/9057145/b0a2e4b0ca86/d0ra04255b-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a88/9057145/b0a2e4b0ca86/d0ra04255b-f2.jpg

相似文献

1
Direct sulfonamidation of (hetero)aromatic C-H bonds with sulfonyl azides: a novel and efficient route to -(hetero)aryl sulfonamides.(杂)芳族C-H键与磺酰叠氮的直接磺酰胺化:一种合成(杂)芳基磺酰胺的新颖高效方法。
RSC Adv. 2020 Oct 8;10(61):37299-37313. doi: 10.1039/d0ra04255b. eCollection 2020 Oct 7.
2
Transition-metal-catalyzed C-N bond forming reactions using organic azides as the nitrogen source: a journey for the mild and versatile C-H amination.过渡金属催化的以有机叠氮化物为氮源的 C-N 键形成反应:温和且多功能的 C-H 氨化反应的探索之旅。
Acc Chem Res. 2015 Apr 21;48(4):1040-52. doi: 10.1021/acs.accounts.5b00020. Epub 2015 Mar 30.
3
Cu-Catalyzed Coupling Reactions of Sulfonamides with (Hetero)Aryl Chlorides/Bromides.铜催化的磺酰胺与(杂)芳基氯代物/溴代物的偶联反应。
Angew Chem Int Ed Engl. 2022 Oct 24;61(43):e202210483. doi: 10.1002/anie.202210483. Epub 2022 Sep 21.
4
Direct Amination of Aromatic C-H Bonds with Free Amines.芳基 C-H 键与游离胺的直接胺化反应。
Top Curr Chem (Cham). 2020 Mar 31;378(2):37. doi: 10.1007/s41061-020-0300-1.
5
Photochemical C-H bond coupling for (hetero)aryl C(sp)-C(sp) bond construction.光化学 C-H 键偶联反应在(杂)芳基 C(sp)-C(sp) 键构建中的应用。
Org Biomol Chem. 2019 May 28;17(20):4951-4963. doi: 10.1039/c9ob00244h. Epub 2019 May 8.
6
Mechanism-Guided Development of Transition-Metal-Catalyzed C-N Bond-Forming Reactions Using Dioxazolones as the Versatile Amidating Source.以二恶唑酮为通用酰胺化源的过渡金属催化C-N键形成反应的机理导向开发
Acc Chem Res. 2021 Jun 1;54(11):2683-2700. doi: 10.1021/acs.accounts.1c00198. Epub 2021 May 12.
7
Iridium-catalyzed regioselective C-H sulfonamidation of 1,2,4-thiadiazoles with sulfonyl azides in water.铱催化1,2,4-噻二唑与磺酰叠氮化物在水中的区域选择性C-H磺酰胺化反应
RSC Adv. 2021 Jun 22;11(36):22000-22004. doi: 10.1039/d1ra04450h. eCollection 2021 Jun 21.
8
Old and new antiarrhythmic drugs for converting and maintaining sinus rhythm in atrial fibrillation: comparative efficacy and results of trials.用于房颤转复和维持窦性心律的新旧抗心律失常药物:试验的比较疗效及结果
Am J Cardiol. 2003 Mar 20;91(6A):15D-26D. doi: 10.1016/s0002-9149(02)03375-1.
9
Sulfonyl Azides as Precursors in Ligand-Free Palladium-Catalyzed Synthesis of Sulfonyl Carbamates and Sulfonyl Ureas and Synthesis of Sulfonamides.磺酰叠氮化物作为无配体钯催化合成磺酰氨基甲酸酯和磺酰脲以及合成磺酰胺的前体。
J Org Chem. 2016 Apr 1;81(7):2681-91. doi: 10.1021/acs.joc.5b02755. Epub 2016 Mar 18.
10
2,4-Diamino-1,3,5-triazine-enabled Cu-catalyzed direct sulfonamidation of aromatic C-H bonds.2,4-二氨基-1,3,5-三嗪促进的铜催化芳族C-H键直接磺酰胺化反应。
Org Biomol Chem. 2017 Aug 30;15(34):7212-7217. doi: 10.1039/c7ob01872j.

引用本文的文献

1
Direct selenosulfonylation of unsaturated compounds: a review.不饱和化合物的直接硒磺酰化反应:综述
RSC Adv. 2022 Oct 26;12(47):30564-30576. doi: 10.1039/d2ra04128f. eCollection 2022 Oct 24.
2
Strategies for the direct oxidative esterification of thiols with alcohols.硫醇与醇直接氧化酯化的策略。
RSC Adv. 2022 May 13;12(23):14521-14534. doi: 10.1039/d1ra08058j. eCollection 2022 May 12.
3
Direct halosulfonylation of alkynes: an overview.炔烃的直接卤代磺酰化反应:综述

本文引用的文献

1
A walk around the application of nanocatalysts for cross-dehydrogenative coupling of C-H bonds.纳米催化剂在C-H键交叉脱氢偶联反应中的应用概述
RSC Adv. 2019 Dec 16;9(71):41684-41702. doi: 10.1039/c9ra08752d. eCollection 2019 Dec 13.
2
Arylhydrazines: novel and versatile electrophilic partners in cross-coupling reactions.芳基肼:交叉偶联反应中新型且通用的亲电试剂
RSC Adv. 2018 Oct 1;8(59):33828-33844. doi: 10.1039/c8ra06423g. eCollection 2018 Sep 28.
3
Decarboxylative cross-coupling reactions for P(O)-C bond formation.用于形成P(O)-C键的脱羧交叉偶联反应。
RSC Adv. 2021 Oct 13;11(53):33447-33460. doi: 10.1039/d1ra03443j. eCollection 2021 Oct 8.
4
Alkoxysulfenylation of alkenes: development and recent advances.烯烃的烷氧基硫烯基化反应:发展历程与近期进展
RSC Adv. 2021 Oct 1;11(51):32513-32525. doi: 10.1039/d1ra03980f. eCollection 2021 Sep 27.
5
Direct synthesis of sulfenamides, sulfinamides, and sulfonamides from thiols and amines.由硫醇和胺直接合成亚磺酰胺、亚磺酰亚胺和磺酰胺。
RSC Adv. 2021 Oct 1;11(51):32394-32407. doi: 10.1039/d1ra04368d. eCollection 2021 Sep 27.
6
Recent trends in dehydroxylative trifluoro-methylation, -methoxylation, -methylthiolation, and -methylselenylation of alcohols.醇的脱羟基三氟甲基化、甲氧基化、甲硫基化和甲硒基化的最新趋势
RSC Adv. 2021 Dec 13;11(62):39593-39606. doi: 10.1039/d1ra05018d. eCollection 2021 Dec 6.
7
Recent advances in intermolecular 1,2-difunctionalization of alkenes involving trifluoromethylthiolation.烯烃分子间1,2-双官能团化反应中涉及三氟甲硫基化反应的最新进展。
RSC Adv. 2021 Jul 13;11(40):24474-24486. doi: 10.1039/d1ra02606b.
8
Progress and recent trends in the direct selenocyanation of (hetero)aromatic C-H bonds.(杂)芳族碳氢键直接硒氰化反应的进展与近期趋势
RSC Adv. 2021 Jun 24;11(36):22305-22316. doi: 10.1039/d1ra01035b. eCollection 2021 Jun 21.
9
Hydroxysulfonylation of alkenes: an update.烯烃的羟基磺酰化反应:最新进展
RSC Adv. 2021 Jun 18;11(35):21651-21665. doi: 10.1039/d1ra00513h. eCollection 2021 Jun 15.
10
Palladium-catalyzed bisthiolation of terminal alkynes for the assembly of diverse ()-1,2-bis(arylthio)alkene derivatives.钯催化末端炔烃的双硫醇化反应以合成多种()-1,2-双(芳硫基)烯烃衍生物。
RSC Adv. 2021 Aug 23;11(46):28447-28451. doi: 10.1039/d1ra05773a.
RSC Adv. 2018 Jul 24;8(46):26383-26398. doi: 10.1039/c8ra04557g. eCollection 2018 Jul 19.
4
Recent advances in sulfur-nitrogen bond formation cross-dehydrogenative coupling reactions.硫氮键形成交叉脱氢偶联反应的最新进展。
RSC Adv. 2018 May 21;8(33):18456-18469. doi: 10.1039/c8ra00356d. eCollection 2018 May 17.
5
Cross-dehydrogenative coupling reactions between arenes (C-H) and carboxylic acids (O-H): a straightforward and environmentally benign access to -aryl esters.芳烃(C-H)与羧酸(O-H)之间的交叉脱氢偶联反应:一种直接且环境友好的制备芳基酯的方法。
RSC Adv. 2019 May 31;9(30):17101-17118. doi: 10.1039/c9ra01941c. eCollection 2019 May 29.
6
Recent developments in decarboxylative cross-coupling reactions between carboxylic acids and N-H compounds.羧酸与N-H化合物之间脱羧交叉偶联反应的最新进展。
RSC Adv. 2019 Mar 18;9(16):8964-8976. doi: 10.1039/c9ra00929a. eCollection 2019 Mar 15.
7
Efficient and stable catalysis of hollow CuS nanospheres in the Fenton-like degradation of organic dyes.空心 CuS 纳米球在类 Fenton 降解有机染料中的高效稳定催化作用。
J Hazard Mater. 2020 Sep 5;396:122735. doi: 10.1016/j.jhazmat.2020.122735. Epub 2020 Apr 18.
8
Direct Amination of Aromatic C-H Bonds with Free Amines.芳基 C-H 键与游离胺的直接胺化反应。
Top Curr Chem (Cham). 2020 Mar 31;378(2):37. doi: 10.1007/s41061-020-0300-1.
9
Iridium-catalyzed C-H amidation of s-tetrazines.铱催化的 s-四嗪 C-H 酰胺化反应。
Chem Commun (Camb). 2020 Apr 30;56(34):4692-4695. doi: 10.1039/d0cc01647k. Epub 2020 Mar 25.
10
Copper-mediated tandem ring-opening/cyclization reactions of cyclopropanols with aryldiazonium salts: synthesis of N-arylpyrazoles.
Chem Commun (Camb). 2020 Feb 18;56(14):2202-2205. doi: 10.1039/c9cc09657d. Epub 2020 Jan 24.