• 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

有氧条件下吡啶并三唑与末端炔烃的铜催化环化反应:吲哚嗪的高效合成

Cu-Catalyzed Transannulation Reaction of Pyridotriazoles with Terminal Alkynes under Aerobic Conditions: Efficient Synthesis of Indolizines.

作者信息

Helan V, Gulevich A V, Gevorgyan V

机构信息

Department of Chemistry, University of Illinois at Chicago, 845 W Taylor St., Room 4500, Chicago, Illinois 60607, USA.

出版信息

Chem Sci. 2015 Mar;6(3):1928-1931. doi: 10.1039/C4SC03358B.

DOI:10.1039/C4SC03358B
PMID:25705369
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4332698/
Abstract

The Cu(I)-catalyzed denitrogenative transannulation reaction of pyridotriazoles with terminal alkynes en route to indolizines was developed. Compared to the previously reported Rh-catalyzed transannulation reaction, this Cu-catalyzed method features aerobic conditions and much broader scope of pyridotriazoles and alkynes.

摘要

开发了一种通过吡啶并三唑与末端炔烃的铜(I)催化脱氮环化反应合成中氮茚的方法。与先前报道的铑催化环化反应相比,这种铜催化方法具有需氧条件以及更广泛的吡啶并三唑和炔烃范围。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7d64/5810241/bc06d7427e81/c4sc03358b-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7d64/5810241/74fba9aa622e/c4sc03358b-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7d64/5810241/f53e06d0d2ac/c4sc03358b-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7d64/5810241/bc06d7427e81/c4sc03358b-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7d64/5810241/74fba9aa622e/c4sc03358b-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7d64/5810241/f53e06d0d2ac/c4sc03358b-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7d64/5810241/bc06d7427e81/c4sc03358b-s3.jpg

相似文献

1
Cu-Catalyzed Transannulation Reaction of Pyridotriazoles with Terminal Alkynes under Aerobic Conditions: Efficient Synthesis of Indolizines.有氧条件下吡啶并三唑与末端炔烃的铜催化环化反应:吲哚嗪的高效合成
Chem Sci. 2015 Mar;6(3):1928-1931. doi: 10.1039/C4SC03358B.
2
Cu-catalyzed transannulation reaction of pyridotriazoles: general access to fused polycyclic indolizines.铜催化的吡啶并三唑的环化反应:通向稠合多环中氮茚的通用方法。
Chem Commun (Camb). 2015 Dec 14;51(96):17166-9. doi: 10.1039/c5cc07598j.
3
Enantioselective Nickel-Catalyzed Denitrogenative Transannulation En Route to N-N Atropisomers.对映选择性镍催化脱氮环化反应通向N-N位阻异构体
Angew Chem Int Ed Engl. 2024 Jun 21;63(26):e202400441. doi: 10.1002/anie.202400441. Epub 2024 May 24.
4
Indium-Catalyzed Denitrogenative Transannulation of Pyridotriazoles: Synthesis of Pyrido[1,2- a]indoles.铟催化的吡啶并三唑脱氮环化反应:吡啶并[1,2-a]吲哚的合成
Org Lett. 2019 Apr 5;21(7):2043-2047. doi: 10.1021/acs.orglett.9b00180. Epub 2019 Mar 12.
5
Lewis Acid-Catalyzed Denitrogenative Transannulation of Pyridotriazoles with Nitriles: Synthesis of Imidazopyridines.Lewis 酸催化的吡啶并三唑与腈的脱氮交叉环化反应:咪唑并吡啶的合成。
J Org Chem. 2016 Oct 7;81(19):9461-9469. doi: 10.1021/acs.joc.6b01742. Epub 2016 Sep 29.
6
Copper-Catalyzed Denitrogenative Transannulation Reaction of Pyridotriazoles: Synthesis of Imidazo[1,5-a]pyridines with Amines and Amino Acids.铜催化吡啶三唑的脱氮环化反应:胺和氨基酸参与的咪唑并[1,5-a]吡啶的合成
Org Lett. 2016 Feb 5;18(3):464-7. doi: 10.1021/acs.orglett.5b03509. Epub 2016 Jan 14.
7
Co-Catalyzed Transannulation of Pyridotriazoles with Isothiocyanates and Xanthate Esters.偕二氮杂茂与异硫氰酸酯和黄原酸酯的共催化转环反应。
Org Lett. 2020 Nov 6;22(21):8500-8504. doi: 10.1021/acs.orglett.0c03099. Epub 2020 Oct 12.
8
Rh-catalyzed transannulation of pyridotriazoles with alkynes and nitriles.铑催化吡啶并三唑与炔烃和腈的环化反应。
Angew Chem Int Ed Engl. 2007;46(25):4757-9. doi: 10.1002/anie.200700804.
9
Regioselective Synthesis of 3-Substituted Isocoumarin-1-imines via Palladium-Catalyzed Denitrogenative Transannulation of 1,2,3-Benzotriazin-4(3H)-ones and Terminal Alkynes.通过钯催化的1,2,3-苯并三嗪-4(3H)-酮与末端炔烃的脱氮跨环化反应区域选择性合成3-取代异香豆素-1-亚胺
Chem Asian J. 2023 Nov 2;18(21):e202300726. doi: 10.1002/asia.202300726. Epub 2023 Sep 25.
10
One-Pot Synthesis of Indolizines via Sequential Rhodium-Catalyzed [2 + 1]-Cyclopropanation, Palladium-Catalyzed Ring Expansion, and Oxidation Reactions from Pyridotriazoles and 1,3-Dienes.通过铑催化的[2 + 1]-环丙烷化、钯催化的环扩张和氧化反应,从吡啶并三唑和 1,3-二烯一锅合成吲哚嗪。
Org Lett. 2017 Oct 20;19(20):5677-5680. doi: 10.1021/acs.orglett.7b02826. Epub 2017 Oct 9.

引用本文的文献

1
Research on transition metals for the multicomponent synthesis of benzo-fused γ-lactams.用于苯并稠合γ-内酰胺多组分合成的过渡金属研究。
RSC Adv. 2025 Jan 23;15(4):2334-2346. doi: 10.1039/d4ra08798d.
2
Metal-Free Synthesis of Functionalized Indolizines via a Cascade Michael/S2/Aromatization Reaction of 2-Alkylazaarene Derivatives with Bromonitroolefins.通过2-烷基氮杂芳烃衍生物与溴代硝基烯烃的串联迈克尔/S2/芳构化反应实现官能化中氮茚的无金属合成。
ACS Omega. 2024 Dec 9;9(50):49980-49985. doi: 10.1021/acsomega.4c09295. eCollection 2024 Dec 17.
3
Based on magnetically recoverable catalysts: a green strategy to sulfonamides.

本文引用的文献

1
Synthesis and preliminary in vitro activity of mono- and bis-1-1,2,3-triazole-tethered β-lactam-isatin conjugates against the human protozoal pathogen .单-和双-1,2,3-三唑连接的β-内酰胺-异吲哚酮缀合物对人类原生动物病原体的合成及初步体外活性
Med Chem Res. 2014;23(8):3671-3680. doi: 10.1007/s00044-014-0956-6. Epub 2014 Feb 22.
2
Rhodium-catalyzed NH insertion of pyridyl carbenes derived from pyridotriazoles: a general and efficient approach to 2-picolylamines and imidazo[1,5-a]pyridines.铑催化吡啶并三唑衍生的吡啶基卡宾的氮插入反应:一种合成2-吡啶甲胺和咪唑并[1,5-a]吡啶的通用高效方法。
Angew Chem Int Ed Engl. 2014 Dec 15;53(51):14191-5. doi: 10.1002/anie.201408335. Epub 2014 Oct 21.
3
基于磁性可回收催化剂:合成磺胺类药物的绿色策略
Mol Divers. 2024 Nov 4. doi: 10.1007/s11030-024-11030-4.
4
Advances in Selected Heterocyclization Methods.特定杂环化方法的进展
Synlett. 2023 Aug;34(13):1554-1562. doi: 10.1055/s-0042-1751429. Epub 2023 Mar 10.
5
Recent Advances in Catalytic Alkyne Transformation via Copper Carbene Intermediates.铜卡宾中间体介导的炔烃转化的最新进展。
Molecules. 2022 May 11;27(10):3088. doi: 10.3390/molecules27103088.
6
Ru(ii)-catalyzed C6-selective C-H acylmethylation of pyridones using sulfoxonium ylides as carbene precursors.以锍叶立德作为卡宾前体,钌(II)催化吡啶酮的C6选择性C-H酰基甲基化反应。
RSC Adv. 2020 Feb 11;10(11):6351-6355. doi: 10.1039/c9ra10749e. eCollection 2020 Feb 7.
7
A new cross-conjugated mesomeric betaine.一种新型交叉共轭的介离子甜菜碱。
RSC Adv. 2021 Jul 21;11(41):25296-25304. doi: 10.1039/d1ra03981d. eCollection 2021 Jul 19.
8
Aziridinium Ylides: Underutilized Intermediates for Complex Amine Synthesis.氮杂环丙烷叶立德:用于复杂胺合成的未充分利用的中间体。
Trends Chem. 2020 Oct;2(10):874-887. doi: 10.1016/j.trechm.2020.08.003. Epub 2020 Sep 2.
9
Co-Catalyzed Transannulation of Pyridotriazoles with Isothiocyanates and Xanthate Esters.偕二氮杂茂与异硫氰酸酯和黄原酸酯的共催化转环反应。
Org Lett. 2020 Nov 6;22(21):8500-8504. doi: 10.1021/acs.orglett.0c03099. Epub 2020 Oct 12.
10
Denitrogenative Transformations of Pyridotriazoles and Related Compounds: Synthesis of -Containing Heterocyclic Compounds and Beyond.吡啶并三唑及相关化合物的脱氮转化:含氮杂环化合物及其他化合物的合成
J Org Chem. 2020 Sep 4;85(17):11030-11046. doi: 10.1021/acs.joc.0c01652. Epub 2020 Aug 21.
Synthesis of phenanthrenes through copper-catalyzed cross-coupling of N-tosylhydrazones with terminal alkynes.
通过 N-对甲苯磺酰腙与末端炔烃的铜催化交叉偶联合成菲。
J Org Chem. 2014 Sep 19;79(18):8689-99. doi: 10.1021/jo501489c. Epub 2014 Sep 3.
4
Silver-catalyzed cyclization of 2-pyridyl alkynyl carbinols with isocyanides: divergent synthesis of indolizines and pyrroles.银催化2-吡啶基炔丙醇与异腈的环化反应:中氮茚和吡咯的发散性合成
Chem Commun (Camb). 2014 Oct 14;50(80):11837-9. doi: 10.1039/c4cc04905e.
5
Formal [3+2] cycloaddition of 1-cyanocyclopropane 1-ester with pyridine, quinoline or isoquinoline: a general and efficient strategy for construction of cyanoindolizine skeletons.1-氰基环丙烷-1-酯与吡啶、喹啉或异喹啉的形式[3+2]环加成反应:构建氰基中氮茚骨架的通用高效策略。
Chem Commun (Camb). 2014 Aug 21;50(65):9068-71. doi: 10.1039/c4cc03267e.
6
Cerium(III)-catalyzed cascade cyclization: an efficient approach to functionalized pyrrolo[1,2-a]quinolines.铈(III)催化的串联环化反应:一种合成官能化吡咯并[1,2 - a]喹啉的有效方法。
Org Biomol Chem. 2014 Jul 21;12(27):4837-40. doi: 10.1039/c4ob00708e.
7
Reactions of metallocarbenes derived from N-sulfonyl-1,2,3-triazoles.N-磺酰基-1,2,3-三唑衍生的金属卡宾的反应。
Chem Soc Rev. 2014 Aug 7;43(15):5151-62. doi: 10.1039/c4cs00072b.
8
A reagent-free oxidative cyclization approach to indolizine derivatives from α-picoline derivatives and nitroolefins.一种从α-甲基吡啶衍生物和硝基烯烃出发制备中氮茚衍生物的无试剂氧化环化方法。
Chem Asian J. 2014 Aug;9(8):2068-71. doi: 10.1002/asia.201402096. Epub 2014 Apr 29.
9
Copper(II)-catalyzed carbon-carbon triple bond cleavage of internal alkynes for the synthesis of annulated indolizines.铜(II)催化的内炔烃碳-碳三键断裂反应在稠合吲哚嗪合成中的应用。
J Org Chem. 2014 May 2;79(9):3992-8. doi: 10.1021/jo500456d. Epub 2014 Apr 21.
10
Efficient synthesis strategies by application of transition metal-catalyzed carbene/nitrene insertions into C-H bonds.通过应用过渡金属催化的卡宾/氮宾插入 C-H 键的高效合成策略。
Nat Prod Rep. 2014 Apr;31(4):449-55. doi: 10.1039/c3np70084d. Epub 2014 Mar 4.