• 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

电化学和机械化学策略作为合成具有生物学相关性的3-硝基咪唑并[1,2 -]吡啶的双重合成方法

Electro- and Mechanochemical Strategy as a Dual Synthetic Approach for Biologically Relevant 3-Nitro-imidazo-[1,2-]pyridines.

作者信息

Mukherjee Debojyoti, Karmakar Indrajit, Brahmachari Goutam

机构信息

Laboratory of Natural Products & Organic Synthesis, Department of Chemistry, Visva-Bharati (a Central University), Santiniketan, West Bengal 731 235, India.

出版信息

J Org Chem. 2024 Sep 6;89(17):12071-12084. doi: 10.1021/acs.joc.4c00881. Epub 2024 Aug 15.

DOI:10.1021/acs.joc.4c00881
PMID:39145592
Abstract

We herein disclose a dual synthetic approach involving electrochemical and mechanochemical strategies for diversely functionalized 3-nitro-2-aryl-immidazo[1,2-]pyridines. Both methods offer a practical and straightforward alternative route for accessing this important class of biologically promising nitrogen-containing heterocycles. Significant advantages of the newly developed methods include mild and energy-efficient reaction conditions, avoidance of transition metal catalysts, external heating and additional oxidants, shorter reaction times, good to excellent yields, broad substrate scope, gram-scale applicability, operational simplicity, and eco-friendliness. Furthermore, a synthetic application was extended by successfully reducing synthesized 3-nitro-2-aryl-immidazo[1,2-]pyridines to their corresponding amino derivatives.

摘要

我们在此公开了一种涉及电化学和机械化学策略的双重合成方法,用于制备功能多样的3-硝基-2-芳基咪唑并[1,2 - ]吡啶。这两种方法都为获取这类具有重要生物学前景的含氮杂环化合物提供了实用且直接的替代途径。新开发方法的显著优点包括温和且节能的反应条件、无需过渡金属催化剂、外部加热和额外氧化剂、反应时间短、产率良好至优异、底物范围广、克级规模适用性、操作简便以及环境友好性。此外,通过成功地将合成的3-硝基-2-芳基咪唑并[1,2 - ]吡啶还原为相应的氨基衍生物,扩展了其合成应用。

相似文献

1
Electro- and Mechanochemical Strategy as a Dual Synthetic Approach for Biologically Relevant 3-Nitro-imidazo-[1,2-]pyridines.电化学和机械化学策略作为合成具有生物学相关性的3-硝基咪唑并[1,2 -]吡啶的双重合成方法
J Org Chem. 2024 Sep 6;89(17):12071-12084. doi: 10.1021/acs.joc.4c00881. Epub 2024 Aug 15.
2
Mechanochemical Solvent-Free One-Pot Synthesis of Poly-Functionalized 5-(Arylselanyl)-1H-1,2,3-triazoles Through a Copper(I)-Catalyzed Click Reaction.通过铜(I)催化的点击反应实现多官能化5-(芳基硒基)-1H-1,2,3-三唑的机械化学无溶剂一锅法合成。
Chemistry. 2023 Nov 13;29(63):e202302539. doi: 10.1002/chem.202302539. Epub 2023 Sep 28.
3
C-Alkylation of Imidazo[1,2-a]pyridines via Three-Component Aza-Friedel-Crafts Reaction Catalyzed by Y(OTf).通过Y(OTf)催化的三组分氮杂傅克反应实现咪唑并[1,2-a]吡啶的C-烷基化反应
Molecules. 2024 Jul 24;29(15):3463. doi: 10.3390/molecules29153463.
4
Electrochemical Regioselective C()-H Selenylation and Sulfenylation of Substituted 2-Amino-1,4-naphthoquinones.取代的2-氨基-1,4-萘醌的电化学区域选择性C()-H硒化和硫醚化反应
J Org Chem. 2023 Jan 20;88(2):1049-1060. doi: 10.1021/acs.joc.2c02486. Epub 2023 Jan 4.
5
A practical and efficient approach to imidazo[1,2-]pyridine-fused isoquinolines through the post-GBB transformation strategy.一种通过后GBB转化策略合成咪唑并[1,2 - ]吡啶稠合异喹啉的实用且高效的方法。
Beilstein J Org Chem. 2017 May 4;13:817-824. doi: 10.3762/bjoc.13.82. eCollection 2017.
6
Visible-Light-Induced Dehydrogenative Imidoylation of Imidazo[1,2-]pyridines with α-Amino Acid Derivatives and α-Amino Ketones.可见光诱导的咪唑并[1,2-]吡啶与α-氨基酸衍生物和α-氨基酮的脱氢亚胺化反应。
J Org Chem. 2020 Dec 4;85(23):15062-15071. doi: 10.1021/acs.joc.0c01940. Epub 2020 Nov 2.
7
Metal- and Solvent-Free Approach to Diversely Substituted Picolinates via Domino Reaction of Cyclic Sulfamidate Imines with β,γ-Unsaturated α-Ketocarbonyls.通过环状磺酰胺亚胺与β,γ-不饱和α-酮羰基的多米诺反应,实现了金属和溶剂免费的方法来多样化取代的吡啶酸盐。
J Org Chem. 2017 Oct 20;82(20):10928-10938. doi: 10.1021/acs.joc.7b01792. Epub 2017 Oct 2.
8
1,1,1,3,3,3-Hexafluoro-2-Propanol-Promoted Friedel-Crafts Reaction: Metal-Free Synthesis of C3-Difluoromethyl Carbinol-Containing Imidazo[1,2-]pyridines at Room Temperature.1,1,1,3,3,3-六氟-2-丙醇促进的傅克反应:室温下无金属合成含C3-二氟甲基甲醇的咪唑并[1,2 -]吡啶
Molecules. 2023 Nov 10;28(22):7522. doi: 10.3390/molecules28227522.
9
Alumina-Supported Gold Nanoparticles as a Bifunctional Catalyst for the Synthesis of 2-Amino-3-arylimidazo[1,2-]pyridines.氧化铝负载的金纳米颗粒作为合成2-氨基-3-芳基咪唑并[1,2 - ]吡啶的双功能催化剂
ACS Omega. 2018 Dec 20;3(12):17947-17956. doi: 10.1021/acsomega.8b03047. eCollection 2018 Dec 31.
10
Metal-free synthesis of imidazo[1,5-a]pyridines via elemental sulfur mediated sequential dual oxidative Csp-H amination.无金属条件下通过元素硫介导的顺序双氧化 Csp-H 氨化反应合成咪唑并[1,5-a]吡啶。
Org Biomol Chem. 2018 Aug 8;16(31):5570-5574. doi: 10.1039/c8ob01391h.