2-碘代烯炔酰胺的合成及其与乙烯酮的区域选择性[2+2]环加成反应。
Synthesis of 2-iodoynamides and regioselective [2+2] cycloadditions with ketene.
作者信息
Wang Yu-Pu, Danheiser Rick L
机构信息
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA.
出版信息
Tetrahedron Lett. 2011 Apr 27;52(17):2111-2114. doi: 10.1016/j.tetlet.2010.11.002.
Abstract
The first synthesis of 2-iodoynamides is described as well as the first [2+2] cycloadditions of ketene with iodo alkynes.
摘要
首次描述了2-碘代烯炔酰胺的合成以及乙烯酮与碘代炔烃的首次[2+2]环加成反应。
相似文献
1
Synthesis of 2-iodoynamides and regioselective [2+2] cycloadditions with ketene.2-碘代烯炔酰胺的合成及其与乙烯酮的区域选择性[2+2]环加成反应。
Tetrahedron Lett. 2011 Apr 27;52(17):2111-2114. doi: 10.1016/j.tetlet.2010.11.002.
2
Lewis Acid-Promoted [2 + 2] Cycloadditions of Allenes and Ketenes: Versatile Methods for Natural Product Synthesis.路易斯酸促进的丙二烯与乙烯酮的[2 + 2]环加成反应：天然产物合成的通用方法
Acc Chem Res. 2023 Aug 15;56(16):2253-2264. doi: 10.1021/acs.accounts.3c00334. Epub 2023 Aug 4.
3
Anti-Carboalumination of Alkynes Using Aluminum Trihalide and Silyl Ketene Imines: Stereo- and Regioselective Synthesis of Alkenylaluminum Compounds Bearing a Cyano Group.三卤化铝和硅烯酮亚胺对炔烃的反碳化作用：带有氰基的烯基铝化合物的立体和区域选择性合成。
Org Lett. 2018 Jun 15;20(12):3651-3655. doi: 10.1021/acs.orglett.8b01371. Epub 2018 May 30.
4
Modular mesoionics: understanding and controlling regioselectivity in 1,3-dipolar cycloadditions of Münchnone derivatives.模块化介离子：理解和控制 Münchnone 衍生物 1,3-偶极环加成反应的区域选择性。
J Am Chem Soc. 2013 Nov 20;135(46):17349-58. doi: 10.1021/ja406833q. Epub 2013 Nov 7.
5
Regioselective Synthesis of 2,4,5-Trisubstituted Oxazoles and Ketene Aminals via Hydroamidation and Iodo-Imidation of Ynamides.通过炔酰胺的氨氢化和碘代亚胺化反应的区域选择性合成 2,4,5-三取代恶唑和烯酮亚胺。
J Org Chem. 2017 Oct 6;82(19):10583-10594. doi: 10.1021/acs.joc.7b02124. Epub 2017 Sep 25.
6
Lewis acid-promoted ketene-alkene [2 + 2] cycloadditions.路易斯酸促进的烯酮-烯烃 [2 + 2] 环加成反应。
J Am Chem Soc. 2013 Feb 6;135(5):1673-6. doi: 10.1021/ja3103007. Epub 2013 Jan 28.
7
Gold(I)-catalyzed regioselective cyclizations of silyl ketene amides and carbamates with alkynes.金（I）催化的甲硅烷基烯酮酰胺和氨基甲酸酯与炔烃的区域选择性环化反应。
J Org Chem. 2007 Aug 3;72(16):6287-9. doi: 10.1021/jo071014r. Epub 2007 Jul 11.
8
DFT study on the mechanisms and diastereoselectivities of Lewis acid-promoted ketene-alkene [2 + 2] cycloadditions: what is the role of Lewis acid in the ketene and C = X (X = O, CH₂, and NH) [2 + 2] cycloaddition reactions?路易斯酸促进的乙烯酮-烯烃[2+2]环加成反应的机理及非对映选择性的密度泛函理论研究：路易斯酸在乙烯酮与C=X（X=O、CH₂和NH）[2+2]环加成反应中起什么作用？
J Phys Chem A. 2014 Jun 19;118(24):4288-300. doi: 10.1021/jp500358m. Epub 2014 Jun 6.
9
Tandem azidination- and hydroazidination-Huisgen [3 + 2] cycloadditions of ynamides. Synthesis of chiral amide-substituted triazoles.烯炔酰胺的串联叠氮化和氢叠氮化-Huisgen [3 + 2]环加成反应。手性酰胺取代三唑的合成。
Org Biomol Chem. 2006 Jul 21;4(14):2679-82. doi: 10.1039/b606680a. Epub 2006 Jun 16.
10
Regioselective synthesis of pyrazole triflones based on triflyl alkyne cycloadditions.基于三氟甲磺酸炔环加成反应的吡唑三氟酮的区域选择性合成。
Org Lett. 2012 Oct 19;14(20):5330-3. doi: 10.1021/ol3025154. Epub 2012 Oct 4.
引用本文的文献
1
Alkynyl Radicals, Myths and Realities.炔基自由基：神话与现实
JACS Au. 2025 Feb 6;5(2):448-465. doi: 10.1021/jacsau.4c01040. eCollection 2025 Feb 24.
2
1,3-Butadiynamides the Ethynylogous Ynamides: Synthesis, Properties and Applications in Heterocyclic Chemistry.1,3-丁二炔酰胺：乙炔基取代的炔酰胺、合成、性质及在杂环化学中的应用。
Molecules. 2023 Jun 5;28(11):4564. doi: 10.3390/molecules28114564.
3
Reactant-induced photoactivation of in situ generated organogold intermediates leading to alkynylated indoles via Csp-Csp cross-coupling.反应物诱导原位生成的有机金中间体发生光活化，通过Csp-Csp交叉偶联生成炔基化吲哚。
Nat Commun. 2022 Apr 28;13(1):2295. doi: 10.1038/s41467-022-29982-2.
4
S3S63 Terminal Ynamides: Synthesis, Coupling Reactions and Additions to Common Electrophiles.S3S63 末端烯炔酰胺：合成、偶联反应及与常见亲电试剂的加成反应
Tetrahedron Lett. 2015 May 6;56(19):2377-2392. doi: 10.1016/j.tetlet.2015.03.111.
5
Ynamides in ring forming transformations.酰胺在成环转化中的应用。
Acc Chem Res. 2014 Feb 18;47(2):560-78. doi: 10.1021/ar400193g. Epub 2013 Oct 28.
6
Benzannulation via the reaction of ynamides and vinylketenes. application to the synthesis of highly substituted indoles.通过炔酰胺和乙烯基酮的反应进行苯并环化。在高取代吲哚合成中的应用。
J Org Chem. 2013 Sep 20;78(18):9396-414. doi: 10.1021/jo401635c. Epub 2013 Sep 3.
7
Introducing a new class of N-phosphoryl ynamides via Cu(I)-catalyzed amidations of alkynyl bromides.通过铜（I）催化的炔基溴代酰胺化反应，引入一类新型 N-膦酰基炔酰胺。
Org Lett. 2011 Sep 16;13(18):4862-5. doi: 10.1021/ol201947b. Epub 2011 Aug 17.
8
N-allyl-N-sulfonyl ynamides as synthetic precursors to amidines and vinylogous amidines. An unexpected N-to-C 1,3-sulfonyl shift in nitrile synthesis.N-烯丙基-N-磺酰基炔酰胺作为脒和亚胺甲酰胺的合成前体。腈合成中意想不到的 N 到 C 1,3-磺酰基迁移。
J Org Chem. 2011 Jun 17;76(12):5092-103. doi: 10.1021/jo200780x. Epub 2011 May 24.
本文引用的文献
1
N-Functionalized 1-Alkynylamides: New Building Blocks for Transition Metal Mediated Inter- and Intramolecular [2+2+1] Cycloadditions.N-官能化的1-炔基酰胺：过渡金属介导的分子间和分子内[2+2+1]环加成反应的新型构建模块。
Angew Chem Int Ed Engl. 1998 Mar 2;37(4):489-492. doi: 10.1002/(SICI)1521-3773(19980302)37:4<489::AID-ANIE489>3.0.CO;2-N.
2
[2+2] Cycloaddition of ketenes with ynamides. A general method for the synthesis of 3-aminocyclobutenone derivatives.烯酮与烯炔酰胺的[2+2]环加成反应。一种合成3-氨基环丁烯酮衍生物的通用方法。
Tetrahedron. 2006 Apr 17;62(16):3815-3822. doi: 10.1016/j.tet.2005.11.088.
3
4
Ynamides: a modern functional group for the new millennium.ynamides：新千年的现代官能团。
Chem Rev. 2010 Sep 8;110(9):5064-106. doi: 10.1021/cr100003s.
5
Ynamides: versatile tools in organic synthesis.酰亚胺：有机合成中的多功能工具。
Angew Chem Int Ed Engl. 2010 Apr 6;49(16):2840-59. doi: 10.1002/anie.200905817.
6
Nickel-catalyzed [3 + 2 + 2] cycloaddition of ethyl cyclopropylideneacetate and heteroatom-substituted alkynes: application to selective three-component reaction with 1,3-diynes.镍催化的乙基环丙叉基乙酸酯与杂原子取代炔烃的[3 + 2 + 2]环加成反应：在与 1,3-二炔的选择性三组分反应中的应用。
J Org Chem. 2010 Jan 15;75(2):480-3. doi: 10.1021/jo902251m.
7
Methoden der Organischen Chemie (Houben-Weyl).《有机化学方法》（胡本-魏尔）
Science. 1964 May 8;144(3619):702-3. doi: 10.1126/science.144.3619.702-b.
8
Copper(II)-catalyzed amidations of alkynyl bromides as a general synthesis of ynamides and Z-enamides. An intramolecular amidation for the synthesis of macrocyclic ynamides.铜（II）催化的炔基溴酰胺化反应作为烯炔酰胺和Z-烯酰胺的通用合成方法。用于合成大环烯炔酰胺的分子内酰胺化反应。
J Org Chem. 2006 May 26;71(11):4170-7. doi: 10.1021/jo060230h.
9
Enantioselective synthesis of axially chiral anilides through rhodium-catalyzed [2+2+2] cycloaddition of 1,6-diynes with trimethylsilylynamides.通过铑催化的1,6-二炔与三甲基甲硅烷基酰胺的[2+2+2]环加成反应对轴向手性酰胺进行对映选择性合成。
J Am Chem Soc. 2006 Apr 12;128(14):4586-7. doi: 10.1021/ja060348f.
10
Copper sulfate-pentahydrate-1,10-phenanthroline catalyzed amidations of alkynyl bromides. Synthesis of heteroaromatic amine substituted ynamides.五水硫酸铜-1,10-菲啰啉催化的炔基溴酰胺化反应。杂芳胺取代的烯炔酰胺的合成。
Org Lett. 2004 Apr 1;6(7):1151-4. doi: 10.1021/ol049827e.
Zotero 插件