• 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

一锅法在水中由乙基芳烃合成咪唑和噻唑。

One-Pot NBS-Promoted Synthesis of Imidazoles and Thiazoles from Ethylarenes in Water.

机构信息

School of Pharmacy, China Pharmaceutical University, Nanjing 210009, Jiangsu, China.

State Key Laboratory of Drug Research and CAS Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, Shanghai, China.

出版信息

Molecules. 2019 Mar 4;24(5):893. doi: 10.3390/molecules24050893.

DOI:10.3390/molecules24050893
PMID:30836604
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6429224/
Abstract

A facile and eco-friendly method has been developed for the synthesis of imidazoles and thiazoles from ethylarenes in water. The reaction proceeds via in situ formation of α-bromoketone using NBS as a bromine source as well as an oxidant, followed by trapping with suitable nucleophiles to provide the corresponding products in good yields under metal-free conditions.

摘要

一种简便、环保的方法已经被开发出来,用于在水中从芳基乙烷合成咪唑和噻唑。该反应通过使用 NBS 作为溴源和氧化剂原位形成α-溴代酮,然后用合适的亲核试剂捕获,在无金属条件下以良好的收率得到相应的产物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0cd2/6429224/93087b98c504/molecules-24-00893-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0cd2/6429224/af67901ff634/molecules-24-00893-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0cd2/6429224/7808c0d8b224/molecules-24-00893-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0cd2/6429224/b7eac0419414/molecules-24-00893-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0cd2/6429224/f561ab232c87/molecules-24-00893-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0cd2/6429224/d0977949cc26/molecules-24-00893-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0cd2/6429224/93087b98c504/molecules-24-00893-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0cd2/6429224/af67901ff634/molecules-24-00893-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0cd2/6429224/7808c0d8b224/molecules-24-00893-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0cd2/6429224/b7eac0419414/molecules-24-00893-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0cd2/6429224/f561ab232c87/molecules-24-00893-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0cd2/6429224/d0977949cc26/molecules-24-00893-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0cd2/6429224/93087b98c504/molecules-24-00893-sch004.jpg

相似文献

1
One-Pot NBS-Promoted Synthesis of Imidazoles and Thiazoles from Ethylarenes in Water.一锅法在水中由乙基芳烃合成咪唑和噻唑。
Molecules. 2019 Mar 4;24(5):893. doi: 10.3390/molecules24050893.
2
N-Bromosuccinimide promoted and base switchable one pot synthesis of α-imido and α-amino ketones from styrenes.N-溴代琥珀酰亚胺促进的、碱可切换的从苯乙烯一锅法合成α-亚氨基酮和α-氨基酮。
Org Biomol Chem. 2016 Jan 21;14(3):858-61. doi: 10.1039/c5ob02034d. Epub 2015 Dec 10.
3
One-pot synthesis of 2'-aminobenzothiazolo-arylmethyl-2-naphthols catalyzed by NBS under solvent-free conditions.在无溶剂条件下,NBS催化一锅法合成2'-氨基苯并噻唑-芳基甲基-2-萘酚。
ScientificWorldJournal. 2013 May 30;2013:702929. doi: 10.1155/2013/702929. Print 2013.
4
N-bromosuccinimide/1,8-diazabicyclo[5.4.1]undec-7-ene combination: β-amination of chalcones via a tandem bromoamination/debromination sequence.N-溴代丁二酰亚胺/1,8-二氮杂双环[5.4.1]十一碳-7-烯组合:通过串联溴化胺/脱溴化序列实现查耳酮的β-胺化。
Org Lett. 2013 Feb 15;15(4):852-5. doi: 10.1021/ol303539u. Epub 2013 Jan 31.
5
Ultrasound-promoted a green protocol for the synthesis of 2,4-diarylthiazoles under ambient temperature in [bmim]BF(4).超声促进的在室温下于[bmim]BF(4)中合成2,4-二芳基噻唑的绿色方法。
Ultrason Sonochem. 2009 Aug;16(6):711-7. doi: 10.1016/j.ultsonch.2009.04.001. Epub 2009 Apr 12.
6
Direct Transformation of Ethylarenes into Primary Aromatic Amides with N-Bromosuccinimide and I2-Aqueous NH3.N-溴代丁二酰亚胺和 I2- 水合氨将乙苯直接转化为伯芳酰胺。
Org Lett. 2016 Feb 19;18(4):784-7. doi: 10.1021/acs.orglett.6b00048. Epub 2016 Jan 27.
7
A facile solid-phase synthesis of 1,2,4,5-tetrasubstituted imidazoles using sodium benzenesulfinate as a traceless linker.一种使用苯亚磺酸钠作为无痕连接基的1,2,4,5-四取代咪唑的简便固相合成方法。
J Comb Chem. 2005 Sep-Oct;7(5):644-7. doi: 10.1021/cc049818x.
8
Bromonium ion-promoted glycosidic bond formation and simultaneous bromination of an activated aryl aglycon.溴鎓离子促进的糖苷键形成及活化芳基苷元的同步溴化反应。
Carbohydr Res. 2002 Jan 7;337(1):31-6. doi: 10.1016/s0008-6215(01)00276-2.
9
A versatile and one-pot strategy to synthesize α-amino ketones from benzylic secondary alcohols using N-bromosuccinimide.一种使用 N-溴代丁二酰亚胺从苄基仲醇合成 α-氨基酮的多功能一锅合成策略。
Org Lett. 2015 Feb 6;17(3):406-9. doi: 10.1021/ol503683q. Epub 2015 Jan 29.
10
N-Bromosuccinimide as an oxidant for the transition-metal-free synthesis of 2-aminobenzoxazoles from benzoxazoles and secondary amines.N-溴代琥珀酰亚胺作为一种氧化剂,用于在无过渡金属条件下由苯并恶唑和仲胺合成2-氨基苯并恶唑。
Org Biomol Chem. 2014 May 21;12(19):3108-13. doi: 10.1039/c4ob00386a.

本文引用的文献

1
Catalyst free, C-3 functionalization of imidazo[1,2-a]pyridines to rapidly access new chemical space for drug discovery efforts.无催化剂、C-3 位官能化的咪唑并[1,2-a]吡啶,为药物研发工作迅速开辟新的化学空间。
Chem Commun (Camb). 2018 Nov 15;54(92):12954-12957. doi: 10.1039/c8cc07063f.
2
Copper-catalyzed C-N bond formation with imidazo[1,2-a]pyridines.铜催化的咪唑并[1,2-a]吡啶 C-N 键形成反应。
Org Biomol Chem. 2018 Sep 19;16(36):6655-6658. doi: 10.1039/c8ob01853g.
3
Palladium-catalyzed oxidative C-H/C-H cross-coupling of imidazopyridines with azoles.
钯催化的咪唑并吡啶与唑类的氧化 C-H/C-H 交叉偶联反应。
Org Biomol Chem. 2018 Aug 22;16(33):6039-6046. doi: 10.1039/c8ob01263f.
4
Digitization of multistep organic synthesis in reactionware for on-demand pharmaceuticals.反应器皿中多步骤有机合成的数字化,用于按需药物。
Science. 2018 Jan 19;359(6373):314-319. doi: 10.1126/science.aao3466.
5
Iodine-Mediated Difunctionalization of Imidazopyridines with Sodium Sulfinates: Synthesis of Sulfones and Sulfides.碘介导的亚磺酸钠与咪唑并吡啶的双官能化反应:砜和硫醚的合成。
J Org Chem. 2018 Jan 5;83(1):338-349. doi: 10.1021/acs.joc.7b02734. Epub 2017 Dec 27.
6
Imidazo[1,2-α]pyridines possess adenosine A receptor affinity for the potential treatment of cognition in neurological disorders.咪唑并[1,2-α]吡啶对腺苷A受体具有亲和力,具有治疗神经疾病认知功能障碍的潜力。
Bioorg Med Chem Lett. 2017 Sep 1;27(17):3963-3967. doi: 10.1016/j.bmcl.2017.07.071. Epub 2017 Jul 29.
7
Direct Transformation of Ethylarenes into Primary Aromatic Amides with N-Bromosuccinimide and I2-Aqueous NH3.N-溴代丁二酰亚胺和 I2- 水合氨将乙苯直接转化为伯芳酰胺。
Org Lett. 2016 Feb 19;18(4):784-7. doi: 10.1021/acs.orglett.6b00048. Epub 2016 Jan 27.
8
General Method for the Preparation of Electron-Deficient Imidazo[1,2-a]pyridines and Related Heterocycles.缺电子咪唑并[1,2 - a]吡啶及相关杂环化合物的通用制备方法。
Org Lett. 2015 Dec 18;17(24):6002-5. doi: 10.1021/acs.orglett.5b02966. Epub 2015 Nov 24.
9
Green and Efficient: Iron-Catalyzed Selective Oxidation of Olefins to Carbonyls with O2.绿色高效:铁催化氧气选择性氧化烯烃为羰基化合物。
J Am Chem Soc. 2015 Jul 1;137(25):8206-18. doi: 10.1021/jacs.5b03956. Epub 2015 Jun 16.
10
Synthesis of novel azole-fused quinazolines via one-pot, sequential Ullmann-type coupling and intramolecular dehydrogenative C-N bonding.通过一锅法、连续的乌尔曼型偶联和分子内脱氢C-N键合合成新型唑并喹唑啉类化合物。
Org Biomol Chem. 2015 Mar 14;13(10):2947-50. doi: 10.1039/c4ob02375g.