• 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

LiOBu促进的2'-炔基-联芳基-2-醛-对甲苯磺酰腙的分子内1,3-偶极环加成反应:合成3-取代的1-二苯并[,]吲唑的方法

LiOBu-Promoted Intramolecular 1,3-Dipolar Cycloaddition of the 2'-Alkynyl-biaryl-2-aldehyde -Tosylhydrazones Approach to 3-Substituted 1-Dibenzo[,]indazoles.

作者信息

Lv Jiaying, Hua Ruimao

机构信息

Key Laboratory of Organic Optoelectronics & Molecular Engineering of Ministry of Education, Department of Chemistry, Tsinghua University, Beijing 100084, China.

State Key Laboratory of Chemistry and Utilization of Carbon-Based Energy Resources, College of Chemistry, Xinjiang University, Urumqi 830017, China.

出版信息

Molecules. 2023 Dec 13;28(24):8061. doi: 10.3390/molecules28248061.

DOI:10.3390/molecules28248061
PMID:38138554
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10745680/
Abstract

A two-step, one-pot synthesis of 3-substituted 1-dibenzo[,]indazoles in good to high yields via a LiOBu-promoted intramolecular 1,3-dipolar cyclization of 2'-alkynyl-biaryl-2-aldehyde -tosylhydrazones was developed. The -Ts-hydrazones used were prepared in situ via the reactions of 2'-alkynyl-biaryl-2-aldehydes and TsNHNH-methylbenzenesulfonohydrazide). Two types of signals related to the hydrogen bonds, forming in several products, were observed in the H NMR spectra recorded in DMSO-, assigned to N-H bonds in their dimeric species of product and tautomer.

摘要

通过LiOBu促进的2'-炔基-联芳基-2-醛对甲苯磺酰腙的分子内1,3-偶极环化反应,开发了一种两步一锅法合成3-取代的1-二苯并[,]吲唑的方法,产率良好至高。所用的对甲苯磺酰腙通过2'-炔基-联芳基-2-醛与对甲苯磺酰肼(对甲苯磺酰甲基苯磺酰肼)的反应原位制备。在DMSO-中记录的1H NMR光谱中观察到与几种产物中形成的氢键相关的两种信号,它们归因于产物二聚体及其互变异构体中的N-H键。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/11c3/10745680/afeaca29acc3/molecules-28-08061-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/11c3/10745680/4c6e0dba899d/molecules-28-08061-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/11c3/10745680/df87a0a99f8c/molecules-28-08061-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/11c3/10745680/bdb4cf462783/molecules-28-08061-ch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/11c3/10745680/52514c451bc2/molecules-28-08061-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/11c3/10745680/aa1d4127dee5/molecules-28-08061-ch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/11c3/10745680/94bb111e0c5d/molecules-28-08061-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/11c3/10745680/afeaca29acc3/molecules-28-08061-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/11c3/10745680/4c6e0dba899d/molecules-28-08061-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/11c3/10745680/df87a0a99f8c/molecules-28-08061-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/11c3/10745680/bdb4cf462783/molecules-28-08061-ch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/11c3/10745680/52514c451bc2/molecules-28-08061-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/11c3/10745680/aa1d4127dee5/molecules-28-08061-ch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/11c3/10745680/94bb111e0c5d/molecules-28-08061-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/11c3/10745680/afeaca29acc3/molecules-28-08061-g003.jpg

相似文献

1
LiOBu-Promoted Intramolecular 1,3-Dipolar Cycloaddition of the 2'-Alkynyl-biaryl-2-aldehyde -Tosylhydrazones Approach to 3-Substituted 1-Dibenzo[,]indazoles.LiOBu促进的2'-炔基-联芳基-2-醛-对甲苯磺酰腙的分子内1,3-偶极环加成反应:合成3-取代的1-二苯并[,]吲唑的方法
Molecules. 2023 Dec 13;28(24):8061. doi: 10.3390/molecules28248061.
2
Synthesis of 3-substituted indazoles from arynes and N-tosylhydrazones.芳基炔与 N-对甲苯磺酰腙的 3-取代吲哚合成。
Org Lett. 2011 Jul 1;13(13):3340-3. doi: 10.1021/ol201086g. Epub 2011 Jun 1.
3
Synthesis of 1H-indazoles and 1H-pyrazoles via FeBr3/O2 mediated intramolecular C-H amination.通过 FeBr3/O2 介导的分子内 C-H 胺化反应合成 1H-吲唑和 1H-吡唑。
J Org Chem. 2013 Feb 1;78(3):1317-22. doi: 10.1021/jo3026862. Epub 2013 Jan 18.
4
New synthesis of 1-substituted-1H-indazoles via 1,3-dipolar cycloaddition of in situ generated nitrile imines and benzyne.通过原位生成的腈亚胺和苯炔的 1,3-偶极环加成反应合成 1-取代-1H-吲唑。
Org Lett. 2010 Aug 6;12(15):3368-71. doi: 10.1021/ol101150t.
5
Synthesis of substituted 1H-indazoles from arynes and hydrazones.芳基炔与腙的取代 1H-吲唑合成。
J Org Chem. 2012 Apr 6;77(7):3149-58. doi: 10.1021/jo202598e. Epub 2012 Mar 20.
6
2-Indazole Tautomers Stabilized by Intra- and Intermolecular Hydrogen Bonds.通过分子内和分子间氢键稳定的2-吲唑互变异构体。
J Org Chem. 2019 Jul 19;84(14):9075-9086. doi: 10.1021/acs.joc.9b01021. Epub 2019 Jul 5.
7
DABCO-promoted synthesis of pyrazoles from tosylhydrazones and nitroalkenes.DABCO 促进的对甲苯磺酰腙和硝基烯烃合成吡唑。
Org Biomol Chem. 2013 Oct 7;11(37):6250-4. doi: 10.1039/c3ob41435c.
8
Oxidant-Switched Palladium-Catalyzed Regioselective Mono- versus Bis--Aroylation of 1-Aryl-1-indazoles with Aldehydes via C-H Bond Activation.通过C-H键活化实现的氧化剂切换钯催化的1-芳基-1-吲唑与醛的区域选择性单芳酰化与双芳酰化反应
J Org Chem. 2022 Mar 4;87(5):2668-2685. doi: 10.1021/acs.joc.1c02628. Epub 2022 Feb 4.
9
Tandem Bond-Forming Reactions of 1-Alkynyl Ethers.1-炔基醚的串联键形成反应。
Acc Chem Res. 2016 Jun 21;49(6):1168-81. doi: 10.1021/acs.accounts.6b00107. Epub 2016 May 19.
10
One-pot synthesis of S-alkyl dithiocarbamates via the reaction of N-tosylhydrazones, carbon disulfide and amines.一锅法通过 N-对甲苯磺酰基腙、二硫化碳和胺反应合成 S-烷基二硫代氨基甲酸酯。
Org Biomol Chem. 2013 Sep 14;11(34):5615-20. doi: 10.1039/c3ob40745d.

本文引用的文献

1
Divergent Trideuteromethylthiolation and Aminotrideuteromethylthiolation of Alkenes with -Fluorobenzenesulfonimide and CDSSONa.烯烃与-氟苯磺酰亚胺和CDSSONa的发散性三氘代甲基硫醇化及氨基三氘代甲基硫醇化反应
Org Lett. 2023 Oct 6;25(39):7078-7082. doi: 10.1021/acs.orglett.3c02329. Epub 2023 Sep 21.
2
Copper(I)-Catalyzed Syntheses of Benzo[]fluorenes by the Cascade Reactions of 2-Alkynylbenzaldehyde -Tosylhydrazones and Aromatic Terminal Alkynes.铜(I)催化的 2-炔基苯甲醛-对甲苯磺酰腙和芳基末端炔烃的级联反应合成苯并[ ]芴。
J Org Chem. 2022 Dec 2;87(23):16011-16018. doi: 10.1021/acs.joc.2c02150. Epub 2022 Nov 15.
3
Diazophosphonates: Effective Surrogates for Diazoalkanes in Pyrazole Synthesis.
重氮膦酸酯:在吡唑合成中作为重氮烷烃的有效替代物。
Chemistry. 2021 Oct 1;27(55):13703-13708. doi: 10.1002/chem.202101788. Epub 2021 Sep 8.
4
Recent Advances in Indazole-Containing Derivatives: Synthesis and Biological Perspectives.含吲唑衍生物的最新进展:合成与生物学研究进展。
Molecules. 2018 Oct 26;23(11):2783. doi: 10.3390/molecules23112783.
5
Indazole derivatives and their therapeutic applications: a patent review (2013-2017).吲唑衍生物及其治疗用途:专利审查(2013-2017)。
Expert Opin Ther Pat. 2018 Jun;28(6):441-453. doi: 10.1080/13543776.2018.1472240. Epub 2018 May 11.
6
and Anti-Inflammatory Activity of Indazole and Its Derivatives.吲唑及其衍生物的抗炎活性。
J Clin Diagn Res. 2016 Sep;10(9):FF01-FF06. doi: 10.7860/JCDR/2016/19338.8465. Epub 2016 Sep 1.
7
Diazo Compounds: Versatile Tools for Chemical Biology.重氮化合物:化学生物学的多功能工具
ACS Chem Biol. 2016 Dec 16;11(12):3233-3244. doi: 10.1021/acschembio.6b00810. Epub 2016 Oct 26.
8
1,3-Dipolar Cycloaddition with Diazo Groups: Noncovalent Interactions Overwhelm Strain.1,3-偶极环加成与重氮基团:非共价相互作用压倒应变。
Org Lett. 2016 Sep 16;18(18):4466-4469. doi: 10.1021/acs.orglett.6b01938. Epub 2016 Sep 6.
9
1,3-Dipolar Cycloadditions of Diazo Compounds in the Presence of Azides.叠氮化物存在下重氮化合物的1,3-偶极环加成反应
Org Lett. 2016 Apr 1;18(7):1538-41. doi: 10.1021/acs.orglett.6b00278. Epub 2016 Mar 16.
10
Efficient and Accurate Double-Hybrid-Meta-GGA Density Functionals-Evaluation with the Extended GMTKN30 Database for General Main Group Thermochemistry, Kinetics, and Noncovalent Interactions.高效准确的双杂化-泛函密度泛函——用扩展的 GMTKN30 数据库评估通用主族热化学、动力学和非共价相互作用。
J Chem Theory Comput. 2011 Feb 8;7(2):291-309. doi: 10.1021/ct100466k. Epub 2010 Dec 23.