• 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

分子碘介导的含杂原子的烯基或炔基体系的连接环化反应。

Molecular iodine-mediated cyclization of tethered heteroatom-containing alkenyl or alkynyl systems.

机构信息

Department of Chemistry, College of Science, Engineering and Technology, University of South Africa, P.O. Box 392, Pretoria 0003, South Africa.

出版信息

Molecules. 2009 Nov 25;14(12):4814-37. doi: 10.3390/molecules14124814.

DOI:10.3390/molecules14124814
PMID:20032861
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6255281/
Abstract

Molecular iodine has established itself as a readily available and easy-to-handle electrophilic and oxidizing reagent used in various organic transformations. In this review attention is focused on the use of molecular iodine in promoting cyclization (iodocyclization and cyclodehydroiodination) of tethered heteroatom-containing alkenyl or alkynyl systems.

摘要

分子碘已被确立为一种易得且易于处理的亲电试剂和氧化剂,用于各种有机转化。在这篇综述中,重点关注了分子碘在促进含杂原子的烯基或炔基连接体系的环化(碘环化和环脱氢碘化)反应中的应用。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/327a17053b3e/molecules-14-04814-sch035.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/f2d12be38fc1/molecules-14-04814-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/eb7d9ec37327/molecules-14-04814-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/810c69d3d649/molecules-14-04814-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/a0c36e6307bf/molecules-14-04814-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/54996111a9fd/molecules-14-04814-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/12fd3dc65601/molecules-14-04814-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/3dfd66288ea6/molecules-14-04814-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/f44798d9fe37/molecules-14-04814-sch006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/79b80aec85da/molecules-14-04814-sch007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/1ae32c0b83b4/molecules-14-04814-sch008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/6c847686746e/molecules-14-04814-sch009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/63d705d918b7/molecules-14-04814-sch010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/c66d4942aae3/molecules-14-04814-sch011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/2f42187a6712/molecules-14-04814-sch012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/abe6012d808f/molecules-14-04814-sch013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/2e0f1a813a71/molecules-14-04814-sch014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/48e293ccb488/molecules-14-04814-sch015.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/b9c42701db2d/molecules-14-04814-sch016.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/18eb11a31042/molecules-14-04814-sch017.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/a538e140e78c/molecules-14-04814-sch018.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/9b75b79149b5/molecules-14-04814-sch019.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/2177f88b03a2/molecules-14-04814-sch020.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/f8ba4e33cda9/molecules-14-04814-sch021.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/0cc71bd94ce1/molecules-14-04814-sch022.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/a66bd1a4883f/molecules-14-04814-sch023.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/4f9ef58ca9cd/molecules-14-04814-sch024.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/259e38dfe88e/molecules-14-04814-sch025.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/b823e1f53fba/molecules-14-04814-sch026.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/ddaf88aa6fc7/molecules-14-04814-sch027.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/e21fd06f929c/molecules-14-04814-sch028.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/80d62e719ce7/molecules-14-04814-sch029.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/678792c6a801/molecules-14-04814-sch030.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/92a07a8e17fd/molecules-14-04814-sch031.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/fcfd6c6d9c3e/molecules-14-04814-sch032.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/d698d00d8768/molecules-14-04814-sch033.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/82639a1844c9/molecules-14-04814-sch034.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/327a17053b3e/molecules-14-04814-sch035.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/f2d12be38fc1/molecules-14-04814-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/eb7d9ec37327/molecules-14-04814-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/810c69d3d649/molecules-14-04814-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/a0c36e6307bf/molecules-14-04814-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/54996111a9fd/molecules-14-04814-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/12fd3dc65601/molecules-14-04814-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/3dfd66288ea6/molecules-14-04814-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/f44798d9fe37/molecules-14-04814-sch006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/79b80aec85da/molecules-14-04814-sch007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/1ae32c0b83b4/molecules-14-04814-sch008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/6c847686746e/molecules-14-04814-sch009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/63d705d918b7/molecules-14-04814-sch010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/c66d4942aae3/molecules-14-04814-sch011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/2f42187a6712/molecules-14-04814-sch012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/abe6012d808f/molecules-14-04814-sch013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/2e0f1a813a71/molecules-14-04814-sch014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/48e293ccb488/molecules-14-04814-sch015.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/b9c42701db2d/molecules-14-04814-sch016.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/18eb11a31042/molecules-14-04814-sch017.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/a538e140e78c/molecules-14-04814-sch018.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/9b75b79149b5/molecules-14-04814-sch019.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/2177f88b03a2/molecules-14-04814-sch020.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/f8ba4e33cda9/molecules-14-04814-sch021.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/0cc71bd94ce1/molecules-14-04814-sch022.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/a66bd1a4883f/molecules-14-04814-sch023.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/4f9ef58ca9cd/molecules-14-04814-sch024.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/259e38dfe88e/molecules-14-04814-sch025.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/b823e1f53fba/molecules-14-04814-sch026.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/ddaf88aa6fc7/molecules-14-04814-sch027.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/e21fd06f929c/molecules-14-04814-sch028.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/80d62e719ce7/molecules-14-04814-sch029.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/678792c6a801/molecules-14-04814-sch030.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/92a07a8e17fd/molecules-14-04814-sch031.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/fcfd6c6d9c3e/molecules-14-04814-sch032.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/d698d00d8768/molecules-14-04814-sch033.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/82639a1844c9/molecules-14-04814-sch034.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0af7/6255281/327a17053b3e/molecules-14-04814-sch035.jpg

相似文献

1
Molecular iodine-mediated cyclization of tethered heteroatom-containing alkenyl or alkynyl systems.分子碘介导的含杂原子的烯基或炔基体系的连接环化反应。
Molecules. 2009 Nov 25;14(12):4814-37. doi: 10.3390/molecules14124814.
2
Iodine-mediated solvent-controlled selective electrophilic cyclization and oxidative esterification of o-alkynyl aldehydes: an easy access to pyranoquinolines, pyranoquinolinones, and isocumarins.碘介导的溶剂控制选择性亲电环化和邻炔基醛的氧化酯化反应:一种易于获得吡喃并喹啉、吡喃并喹啉酮和异香豆素的方法。
J Org Chem. 2010 Nov 19;75(22):7691-703. doi: 10.1021/jo101526b. Epub 2010 Oct 29.
3
A simple and mild synthesis of 1H-isochromenes and (Z)-1-alkylidene-1,3-dihydroisobenzofurans by the iodocyclization of 2-(1-alkynyl)benzylic alcohols.2-(1-炔基)苄基醇的碘环化反应合成 1H-异色烯和(Z)-1-亚烷基-1,3-二氢异苯并呋喃
J Org Chem. 2010 Feb 5;75(3):897-901. doi: 10.1021/jo902333y.
4
Synthesis of dibenzocyclohepten-5-ones by electrophilic iodocyclization of 1-([1,1'-biphenyl]-2-yl)alkynones.通过 1-([1,1'-联苯]-2-基)炔酮的亲电碘环化合成二苯并环庚烯-5-酮。
J Org Chem. 2014 Apr 18;79(8):3452-64. doi: 10.1021/jo5001803. Epub 2014 Mar 31.
5
Dearomative Iodocyclization of -(-Alkynyl)aryl Isoindole.邻炔基芳基异吲哚的去芳构化碘环化反应。
J Org Chem. 2022 Jun 3;87(11):7531-7535. doi: 10.1021/acs.joc.2c00424. Epub 2022 May 19.
6
Iodine-mediated electrophilic cyclization of 2-alkynyl-1-methylene azide aromatics leading to highly substituted isoquinolines and its application to the synthesis of norchelerythrine.碘介导的2-炔基-1-亚甲基叠氮芳烃的亲电环化反应合成高度取代异喹啉及其在去甲白屈菜红碱合成中的应用
J Am Chem Soc. 2008 Nov 19;130(46):15720-5. doi: 10.1021/ja805326f. Epub 2008 Oct 23.
7
Synthesis of tetrahydrofurans by cyclization of homoallylic alcohols with iodine/iodine(III).通过偕丙醇与碘/三碘化物的环化反应合成四氢呋喃。
J Org Chem. 2011 Mar 4;76(5):1499-502. doi: 10.1021/jo102413u. Epub 2011 Jan 18.
8
Synthesis of 1,3,4-trisubstituted isoquinolines by iodine-mediated electrophilic cyclization of 2-alkynyl benzyl azides.通过碘介导的2-炔基苄基叠氮化物的亲电环化反应合成1,3,4-三取代异喹啉。
Angew Chem Int Ed Engl. 2007;46(25):4764-6. doi: 10.1002/anie.200701392.
9
Synthesis of substituted 3-iodocoumarins and 3-iodobutenolides via electrophilic iodocyclization of ethoxyalkyne diols.取代 3-碘香豆素和 3-碘丁烯内酯的合成通过乙氧基炔二醇的亲电碘环化。
J Org Chem. 2013 Jun 21;78(12):5878-88. doi: 10.1021/jo400499r. Epub 2013 Jun 3.
10
Synthesis of pyrazoles via electrophilic cyclization.通过亲电环化合成吡唑。
J Org Chem. 2011 Aug 19;76(16):6726-42. doi: 10.1021/jo201119e. Epub 2011 Jul 20.

引用本文的文献

1
Recent Advances in Iodine-Mediated Radical Reactions.碘介导自由基反应的最新进展
Adv Synth Catal. 2025 Apr 1;367(7). doi: 10.1002/adsc.202401486. Epub 2025 Feb 11.
2
Recent progress in transition-metal-free functionalization of allenamides.联烯酰胺无过渡金属官能团化的最新进展
RSC Adv. 2020 Oct 6;10(60):36818-36827. doi: 10.1039/d0ra07119f. eCollection 2020 Oct 1.
3
Iodine-catalyzed efficient synthesis of xanthene/thioxanthene-indole derivatives under mild conditions.碘催化在温和条件下高效合成呫吨/噻吨-吲哚衍生物。

本文引用的文献

1
Highly substituted indole library synthesis by palladium-catalyzed coupling reactions in solution and on a solid support.通过溶液中和固体载体上的钯催化偶联反应合成高度取代的吲哚文库。
J Comb Chem. 2009 Sep-Oct;11(5):875-9. doi: 10.1021/cc900057n.
2
Design, synthesis and evaluation of tetrahydropyran based COX-1/-2 inhibitors.基于四氢吡喃的COX-1/-2抑制剂的设计、合成与评价
Eur J Med Chem. 2009 Mar;44(3):1278-87. doi: 10.1016/j.ejmech.2008.08.008. Epub 2008 Sep 3.
3
Iodocarbocyclization reaction of beta-ketoesters and alkynes.β-酮酯与炔烃的碘代碳环化反应
RSC Adv. 2020 Jul 2;10(42):25165-25169. doi: 10.1039/d0ra05217e. eCollection 2020 Jun 29.
4
Halogen-Induced Controllable Cyclizations as Diverse Heterocycle Synthetic Strategy.卤素诱导的可控环化反应作为一种多样化杂环合成策略。
Molecules. 2020 Dec 18;25(24):6007. doi: 10.3390/molecules25246007.
5
Preparation and Utility of -Alkynyl Azoles in Synthesis.- 炔基唑的合成制备及应用。
Molecules. 2019 Jan 24;24(3):422. doi: 10.3390/molecules24030422.
6
Recent advances in the synthesis of thiophene derivatives by cyclization of functionalized alkynes.通过官能化炔烃环化合成噻吩衍生物的最新进展。
Molecules. 2014 Sep 29;19(10):15687-719. doi: 10.3390/molecules191015687.
7
Molecular iodine--an expedient reagent for oxidative aromatization reactions of alpha,beta-unsaturated cyclic compounds.分子碘--一种用于α,β-不饱和环状化合物氧化芳构化反应的简便试剂。
Molecules. 2009 Dec 16;14(12):5308-22. doi: 10.3390/molecules14125308.
Org Lett. 2007 Jul 19;9(15):2823-6. doi: 10.1021/ol0710459. Epub 2007 Jun 22.
4
Synthesis, characterization, and estrogen receptor binding affinity of flavone-, indole-, and furan-estradiol conjugates.黄酮、吲哚和呋喃雌二醇缀合物的合成、表征及雌激素受体结合亲和力
Bioorg Med Chem Lett. 2007 Jun 1;17(11):3212-6. doi: 10.1016/j.bmcl.2007.03.016. Epub 2007 Mar 12.
5
Synthesis of 2-azaindolizines by using an iodine-mediated oxidative desulfurization promoted cyclization of N-2-pyridylmethyl thioamides and an investigation of their photophysical properties.通过碘介导的氧化脱硫促进N-2-吡啶基甲基硫代酰胺环化反应合成2-氮杂吲哚嗪及其光物理性质研究
Org Lett. 2006 Nov 23;8(24):5621-4. doi: 10.1021/ol0623623.
6
Selective endo and exo iodocyclizations in the synthesis of quinolines and indoles.喹啉和吲哚合成中的选择性内式和外式碘环化反应。
Org Lett. 2006 Jan 19;8(2):243-6. doi: 10.1021/ol052518j.
7
Iodo- and bromo-enolcyclization of 2-(2-propenyl)cyclohexanediones and 2-(2-propenyl)cyclohexenone derivatives using iodine in methanol and pyridinium hydrobromide perbromide in dichloromethane.在甲醇中使用碘以及在二氯甲烷中使用氢溴酸吡啶鎓全溴化物对2-(2-丙烯基)环己二酮和2-(2-丙烯基)环己烯酮衍生物进行碘代和溴代烯醇环化反应。
Org Biomol Chem. 2005 Jul 7;3(13):2469-75. doi: 10.1039/b505491e. Epub 2005 May 31.
8
5-Endo-dig electrophilic cyclization of 1,4-disubstituted but-3-yn-1-ones: regiocontrolled synthesis of 2,5-disubstituted 3-bromo- and 3-iodofurans.1,4-二取代丁-3-炔-1-酮的5-内-亲电环化反应:2,5-二取代3-溴呋喃和3-碘呋喃的区域选择性合成
Org Lett. 2005 Apr 28;7(9):1769-72. doi: 10.1021/ol050372i.
9
Regio- and stereoselective synthesis of isoindolin-1-ones via electrophilic cyclization.通过亲电环化反应实现异吲哚啉-1-酮的区域和立体选择性合成。
J Org Chem. 2005 Feb 18;70(4):1432-7. doi: 10.1021/jo048007c.
10
Synthesis of 3-iodoindoles by electrophilic cyclization of N,N-dialkyl-2-(1-alkynyl)anilines.通过N,N-二烷基-2-(1-炔基)苯胺的亲电环化合成3-碘吲哚。
Org Lett. 2004 Mar 18;6(6):1037-40. doi: 10.1021/ol0498996.