• 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

通过连续的[3,3]-重排/环化反应,由N-苯氧基酰胺和炔基苯并碘恶唑酮无金属直接构建2-(恶唑-5-基)苯酚

Metal-Free Direct Construction of 2-(Oxazol-5-yl)phenols from N-Phenoxyamides and Alkynylbenziodoxolones via Sequential [3,3]-Rearrangement/Cyclization.

作者信息

Li Ming, Wang Jia-Hui, Li Wei, Wen Li-Rong

机构信息

State Key Laboratory Base of Eco-Chemical Engineering, College of Chemistry and Molecular Engineering , Qingdao University of Science & Technology , Qingdao , 266042 , China.

出版信息

Org Lett. 2018 Dec 7;20(23):7694-7698. doi: 10.1021/acs.orglett.8b03427. Epub 2018 Nov 29.

DOI:10.1021/acs.orglett.8b03427
PMID:30489085
Abstract

A mild and straightforward synthetic protocol for the construction of 2-(oxazol-5-yl)phenol derivatives promoted by KCO from N-phenoxyamides and alkynylbenziodoxolones at room temperature has been developed. Importantly, this protocol involves a tandem sequence that includes [3,3]-rearrangement/alkylidene carbene insertion/Michael addition/cyclization. The metal-free conditions, broad substrate scope, and simple execution make this novel protocol very attractive.

摘要

已开发出一种温和且直接的合成方案,用于在室温下由碳酸钾促进从N-苯氧基酰胺和炔基苯并碘恶唑酮构建2-(恶唑-5-基)苯酚衍生物。重要的是,该方案涉及一个串联序列,包括[3,3]-重排/亚烷基卡宾插入/迈克尔加成/环化。无金属条件、广泛的底物范围和简单的操作使这个新方案非常有吸引力。

相似文献

1
Metal-Free Direct Construction of 2-(Oxazol-5-yl)phenols from N-Phenoxyamides and Alkynylbenziodoxolones via Sequential [3,3]-Rearrangement/Cyclization.通过连续的[3,3]-重排/环化反应,由N-苯氧基酰胺和炔基苯并碘恶唑酮无金属直接构建2-(恶唑-5-基)苯酚
Org Lett. 2018 Dec 7;20(23):7694-7698. doi: 10.1021/acs.orglett.8b03427. Epub 2018 Nov 29.
2
PIFA-Mediated Tandem Hofmann-Type Rearrangement and Cyclization Reaction of α-Acyl-β-aminoacrylamides: Access to Polysubstituted Oxazol-2(3)-ones.PIFA介导的α-酰基-β-氨基丙烯酰胺的串联霍夫曼型重排和环化反应:通向多取代恶唑-2(3)-酮的方法
J Org Chem. 2021 Dec 17;86(24):17944-17954. doi: 10.1021/acs.joc.1c02276. Epub 2021 Dec 6.
3
Yb(OTf)3-Mediated Access to Furans from β-Ketothioamides via Eschenmoser Sulfide Contraction Reaction.Yb(OTf)₃介导的β-酮硫代酰胺通过埃申莫瑟硫化物缩合反应制备呋喃。
J Org Chem. 2015 Dec 18;80(24):11999-2005. doi: 10.1021/acs.joc.5b01924. Epub 2015 Nov 18.
4
Mild Base-Promoted Tandem Nucleophilic Substitution/Decarboxylation/Hydroamination: Access to 3-Sulfonylindoles and 2-Methyleneindophenols.温和碱促进的串联亲核取代/脱羧/氢胺化反应:通向3-磺酰基吲哚和2-亚甲基吲哚酚的方法。
Org Lett. 2021 Dec 3;23(23):9157-9162. doi: 10.1021/acs.orglett.1c03472. Epub 2021 Nov 12.
5
N-Phenoxyamides as Multitasking Reagents: Base-Controlled Selective Construction of Benzofurans or Dihydrobenzofuro[2,3- d]oxazoles.
J Org Chem. 2019 Jul 5;84(13):8523-8530. doi: 10.1021/acs.joc.9b00858. Epub 2019 Jun 24.
6
Construction of divergent fused heterocycles via an acid-promoted intramolecular ipso-Friedel-Crafts alkylation of phenol derivatives.通过酸促进的酚衍生物的分子内 ipso-Friedel-Crafts 烷基化反应构建发散的融合杂环。
J Org Chem. 2014 May 2;79(9):3866-75. doi: 10.1021/jo500308y. Epub 2014 Apr 22.
7
One Base for Two Shots: Metal-Free Substituent-Controlled Synthesis of Two Kinds of Oxadiazine Derivatives from Alkynylbenziodoxolones and Amidoximes.一箭双雕:基于无金属取代基控制从炔基苯并碘杂环戊二酮和偕胺肟合成两种恶二嗪衍生物
J Org Chem. 2019 Jun 7;84(11):6904-6915. doi: 10.1021/acs.joc.9b00659. Epub 2019 May 23.
8
Sequential O-H/C-H bond insertion of phenols initiated by the gold(I)-catalyzed cyclization of 1-bromo-1,5-enynes.金(I)催化 1-溴-1,5-炔烃环化引发的酚的顺序 O-H/C-H 键插入。
Org Lett. 2015 Apr 17;17(8):1982-5. doi: 10.1021/acs.orglett.5b00738. Epub 2015 Mar 31.
9
A simple, tandem approach to the construction of pyridine derivatives under metal-free conditions: a one-step synthesis of the monoterpene natural product, (-)-actinidine.一种在无金属条件下构建吡啶衍生物的简单串联方法:一步合成单萜天然产物(-)-actinidine。
Chem Commun (Camb). 2019 Mar 18;55(22):3270-3273. doi: 10.1039/c9cc01097a. Epub 2019 Feb 27.
10
Tandem [4 + 1 + 1] annulation and metal-free aerobic oxidative aromatization: straightforward synthesis of highly substituted phenols from one aldehyde and two ketones.串联[4+1+1]环化和无金属有氧氧化芳构化:由一种醛和两种酮直接合成高取代酚。
Chem Commun (Camb). 2010 Dec 21;46(47):9061-3. doi: 10.1039/c0cc02313b. Epub 2010 Oct 25.

引用本文的文献

1
Aryl-, Akynyl-, and Alkenylbenziodoxoles: Synthesis and Synthetic Applications.芳基、炔基和烯基苯并[1,3]间二氧杂环戊烯:合成与合成应用。
Molecules. 2023 Feb 24;28(5):2136. doi: 10.3390/molecules28052136.
2
Recent progress in alkynylation with hypervalent iodine reagents.高价碘试剂参与的炔烃化反应研究进展。
Chem Commun (Camb). 2023 Feb 7;59(12):1589-1604. doi: 10.1039/d2cc06168f.