• 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

Castagnoli-Cushman衍生的α-和β-杂环氯乙烯的模块化合成及无过渡金属的炔基化/烯基化反应

Modular synthesis and transition metal-free alkynylation/alkenylation of Castagnoli-Cushman-derived ,- and ,-heterocyclic vinyl chlorides.

作者信息

Beng Timothy K, Farah Abdikani Omar, Shearer Victoria

机构信息

Department of Chemistry, Central Washington University Ellensburg WA 98926 USA

出版信息

RSC Adv. 2020 Oct 7;10(61):37153-37160. doi: 10.1039/d0ra06619b.

DOI:10.1039/d0ra06619b
PMID:35521247
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9057152/
Abstract

A modular and functional group-tolerant protocol for the transition metal-free coupling of novel ,- and ,-heterocyclic vinyl chlorides with terminal acetylenes and styrenes has been developed, leading to the epimerization-free synthesis of fully carbofunctionalized dihydro-1,4-oxazines/thiazines. Bicyclic morpholines have also been prepared through the interrogation of newly synthesized cross-conjugated dienes in Diels-Alder reactions. The use of environmentally benign reaction media endows the current strategy with a practical advantage.

摘要

已开发出一种模块化且官能团耐受性好的方案,用于新型α-和β-杂环氯乙烯与末端乙炔和苯乙烯的无过渡金属偶联,从而实现全碳官能化二氢-1,4-恶嗪/噻嗪的无差向异构化合成。还通过在狄尔斯-阿尔德反应中研究新合成的交叉共轭二烯制备了双环吗啉。使用环境友好的反应介质赋予了当前策略实际优势。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/829c/9057152/00fb969c6416/d0ra06619b-s6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/829c/9057152/4d73b36e64be/d0ra06619b-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/829c/9057152/0588031c84d8/d0ra06619b-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/829c/9057152/3f5062950630/d0ra06619b-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/829c/9057152/9f4dd0ac8483/d0ra06619b-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/829c/9057152/fd8897c51f2b/d0ra06619b-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/829c/9057152/e6fab2437fe7/d0ra06619b-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/829c/9057152/d404248b6779/d0ra06619b-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/829c/9057152/dedb7127da49/d0ra06619b-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/829c/9057152/00fb969c6416/d0ra06619b-s6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/829c/9057152/4d73b36e64be/d0ra06619b-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/829c/9057152/0588031c84d8/d0ra06619b-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/829c/9057152/3f5062950630/d0ra06619b-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/829c/9057152/9f4dd0ac8483/d0ra06619b-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/829c/9057152/fd8897c51f2b/d0ra06619b-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/829c/9057152/e6fab2437fe7/d0ra06619b-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/829c/9057152/d404248b6779/d0ra06619b-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/829c/9057152/dedb7127da49/d0ra06619b-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/829c/9057152/00fb969c6416/d0ra06619b-s6.jpg

相似文献

1
Modular synthesis and transition metal-free alkynylation/alkenylation of Castagnoli-Cushman-derived ,- and ,-heterocyclic vinyl chlorides.Castagnoli-Cushman衍生的α-和β-杂环氯乙烯的模块化合成及无过渡金属的炔基化/烯基化反应
RSC Adv. 2020 Oct 7;10(61):37153-37160. doi: 10.1039/d0ra06619b.
2
Employing Arynes in Diels-Alder Reactions and Transition-Metal-Free Multicomponent Coupling and Arylation Reactions.芳炔在 Diels-Alder 反应和过渡金属自由的多组分偶联和芳基化反应中的应用。
Acc Chem Res. 2016 Sep 20;49(9):1658-70. doi: 10.1021/acs.accounts.6b00188. Epub 2016 Aug 25.
3
Intermolecular Diels-Alder Cycloaddition/Cross-Coupling Sequences of 2-Bromo-1,3-butadienes.2-溴-1,3-丁二烯的分子间 Diels-Alder 环加成/交叉偶联序列。
Org Lett. 2020 Feb 7;22(3):1022-1027. doi: 10.1021/acs.orglett.9b04567. Epub 2020 Jan 28.
4
Highly substituted tetrahydropyrones from hetero-Diels-Alder reactions of 2-alkenals with stereochemical induction from chiral dienes.通过2-烯醛与手性二烯的立体化学诱导进行杂环狄尔斯-阿尔德反应得到的高度取代的四氢吡喃。
J Org Chem. 2005 Apr 1;70(7):2820-3. doi: 10.1021/jo0488311.
5
One-step route to tricyclic fused 1,2,3,4-tetrahydroisoquinoline systems via the Castagnoli-Cushman protocol.通过卡斯塔尼奥利-库什曼反应一步合成三环稠合的1,2,3,4-四氢异喹啉体系。
Beilstein J Org Chem. 2020 Jun 24;16:1456-1464. doi: 10.3762/bjoc.16.121. eCollection 2020.
6
New Heterocyclic Product Space for the Castagnoli-Cushman Three-Component Reaction.用于 Castagnoli-Cushman 三组分反应的新杂环产物空间。
Org Lett. 2015 Aug 7;17(15):3930-3. doi: 10.1021/acs.orglett.5b02014. Epub 2015 Jul 30.
7
Synthesis of polycyclic structures by the Diels-Alder reaction of inner-outer-ring 1,3-bis(trimethylsilyloxy)dienes.通过内-外环1,3-双(三甲基硅氧基)二烯的狄尔斯-阿尔德反应合成多环结构。
J Org Chem. 2001 Feb 23;66(4):1395-402. doi: 10.1021/jo0015319.
8
Transition-Metal-Free Cross-Coupling of Benzothiophenes and Styrenes in a Stereoselective Synthesis of Substituted (E,Z)-1,3-Dienes.苯并噻吩与苯乙烯的无过渡金属交叉偶联用于立体选择性合成取代的(E,Z)-1,3-二烯
Angew Chem Int Ed Engl. 2019 Jun 24;58(26):8779-8783. doi: 10.1002/anie.201902903. Epub 2019 Jun 7.
9
Reaction of Aldehydes/Ketones with Electron-Deficient 1,3,5-Triazines Leading to Functionalized Pyrimidines as Diels-Alder/Retro-Diels-Alder Reaction Products: Reaction Development and Mechanistic Studies.醛/酮与缺电子 1,3,5-三嗪反应生成功能化嘧啶作为 Diels-Alder/Retro-Diels-Alder 反应产物:反应开发和机理研究。
J Org Chem. 2017 Mar 3;82(5):2336-2344. doi: 10.1021/acs.joc.6b02570. Epub 2017 Feb 10.
10
Catalytic enantioselective aza-Diels-alder reactions of imines--an approach to optically active nonproteinogenic alpha-amino acids.亚胺的催化对映选择性氮杂狄尔斯-阿尔德反应——一种合成光学活性非蛋白质ogenicα-氨基酸的方法。
Chemistry. 2000 Jul 3;6(13):2435-48. doi: 10.1002/1521-3765(20000703)6:13<2435::aid-chem2435>3.0.co;2-z.

引用本文的文献

1
The Castagnoli-Cushman Reaction.卡斯达格利-库什曼反应。
Molecules. 2023 Mar 15;28(6):2654. doi: 10.3390/molecules28062654.
2
Serendipitous synthesis of cross-conjugated dienes by cascade deconstructive esterification of thiomorpholinone-tethered alkenoic acids.通过硫代吗啉酮连接的链烯酸的级联解构酯化反应意外合成交叉共轭二烯。
RSC Adv. 2023 Jan 23;13(5):3181-3185. doi: 10.1039/d2ra07916j. eCollection 2023 Jan 18.

本文引用的文献

1
Transition metal-free domino acyl substitution/Michael addition of alkenyl Grignard reagents to lactam esters: synthesis of lactam-bearing homoallylic ketones.无过渡金属催化的多米诺酰基取代/烯基格氏试剂对内酰胺酯的迈克尔加成反应:含内酰胺的高烯丙基酮的合成
RSC Adv. 2020 Jun 11;10(38):22454-22459. doi: 10.1039/d0ra03885g. eCollection 2020 Jun 10.
2
Base-Controlled Heck, Suzuki, and Sonogashira Reactions Catalyzed by Ligand-Free Platinum or Palladium Single Atom and Sub-Nanometer Clusters.无配体铂或钯单原子及亚纳米团簇催化的碱控Heck、Suzuki和Sonogashira反应
J Am Chem Soc. 2019 Feb 6;141(5):1928-1940. doi: 10.1021/jacs.8b07884. Epub 2019 Jan 28.
3
Well-Defined Alkyne Metathesis Catalysts: Developments and Recent Applications.
定义明确的炔烃复分解催化剂:发展与近期应用。
Chemistry. 2019 Mar 1;25(13):3190-3208. doi: 10.1002/chem.201804511. Epub 2018 Dec 14.
4
Kinetic Strategies for the Formation of Graphyne Nanowires via Sonogashira Coupling on Ag(111).通过在Ag(111)上进行Sonogashira偶联形成石墨炔纳米线的动力学策略。
J Am Chem Soc. 2018 Oct 17;140(41):13421-13428. doi: 10.1021/jacs.8b08477. Epub 2018 Oct 4.
5
Lewis Acid Induced Toggle from Ir(II) to Ir(IV) Pathways in Photocatalytic Reactions: Synthesis of Thiomorpholines and Thiazepanes from Aldehydes and SLAP Reagents.光催化反应中Lewis酸诱导的从Ir(II)到Ir(IV)途径的转变:由醛和SLAP试剂合成硫代吗啉和硫氮杂环庚烷
ACS Cent Sci. 2017 Jan 25;3(1):66-72. doi: 10.1021/acscentsci.6b00334. Epub 2016 Dec 29.
6
Expedient and modular access to 2-azabicyclic architectures by iron-catalyzed dehydrative coupling of alcohol-bearing allylic lactams.通过铁催化含醇烯丙基内酰胺的脱水偶联实现对2-氮杂双环结构的便捷模块化合成。
Org Biomol Chem. 2017 Feb 1;15(5):1217-1221. doi: 10.1039/c6ob02652d.
7
Modular access to vicinally functionalized allylic (thio)morpholinonates and piperidinonates by substrate-controlled annulation of 1,3-azadienes with hexacyclic anhydrides.通过1,3-氮杂二烯与六元环酐的底物控制环化反应模块化合成邻位官能化烯丙基(硫代)吗啉酮和哌啶酮。
Org Biomol Chem. 2016 Sep 21;14(37):8864-8872. doi: 10.1039/c6ob01526c.
8
DDQ-Mediated Three-Component Dioxygenation of Alkenes.DDQ 介导的烯烃的三组分双氧化反应。
J Org Chem. 2016 Oct 7;81(19):9350-9355. doi: 10.1021/acs.joc.6b01988. Epub 2016 Sep 22.
9
Orthogonal ring-closing alkyne and olefin metathesis for the synthesis of small GTPase-targeting bicyclic peptides.用于合成靶向小GTP酶的双环肽的正交闭环炔烃和烯烃复分解反应
Nat Commun. 2016 Apr 14;7:11300. doi: 10.1038/ncomms11300.
10
Dienamine Activation of Diazoenals: Application to the Direct Synthesis of Functionalized 1,4-Oxazines.二氮烯醛的二胺激活:在功能化 1,4-噁嗪的直接合成中的应用。
Angew Chem Int Ed Engl. 2016 Jun 27;55(27):7831-5. doi: 10.1002/anie.201600878. Epub 2016 Mar 7.