有机铜介导的用于合成稠合杂环的双组分2'-取代串联反应
ORGANOCOPPER-MEDIATED TWO-COMPONENT 2'-SUBSTITUTION CASCADE TOWARDS -FUSED HETEROCYCLES.
作者信息
Chernyak D, Gevorgyan V
机构信息
University of Illinois at Chicago, 845 West Taylor St., Chicago 60607, Illinois, USA.
出版信息
Chem Heterocycl Compd (N Y). 2012 Mar 1;47(12):1516-1526. doi: 10.1007/s10593-012-0942-1.
Abstract
Organocuprates efficiently undergo reaction with heterocyclic propargyl mesylates at low temperature to produce N-fused heterocycles. The copper reagent plays a "double duty" in this cascade transformation, which proceeds through an S2'-substitution followed by a consequent cycloisomerization step.
摘要
有机铜酸盐在低温下能与杂环炔丙基甲磺酸酯高效反应，生成氮稠合杂环。在这种串联转化中，铜试剂发挥了“双重作用”，该反应通过S2'-取代，随后是环异构化步骤进行。
相似文献
1
ORGANOCOPPER-MEDIATED TWO-COMPONENT 2'-SUBSTITUTION CASCADE TOWARDS -FUSED HETEROCYCLES.有机铜介导的用于合成稠合杂环的双组分2'-取代串联反应
Chem Heterocycl Compd (N Y). 2012 Mar 1;47(12):1516-1526. doi: 10.1007/s10593-012-0942-1.
2
Low temperature organocopper-mediated two-component cross coupling/cycloisomerization approach toward N-fused heterocycles.低温有机铜介导的合成氮稠合杂环的双组分交叉偶联/环异构化方法。
Org Lett. 2008 Jun 5;10(11):2307-10. doi: 10.1021/ol8008705. Epub 2008 May 8.
3
Re-Orienting Coupling of Organocuprates with Propargyl Electrophiles from S2' to S2 with Stereocontrol.通过立体控制将有机铜酸盐与炔丙基亲电试剂的偶联从S2'重新定向到S2。
Chem Sci. 2016;7(8):4985-4989. doi: 10.1039/C6SC01086E. Epub 2016 May 10.
4
Synthesis of 2-(Di/tri/tetraazolyl)-2 H-azirine-2-carboxylates by Halogen Substitution: Evidence for an S2'-S2' Cascade Mechanism.通过卤素取代合成2-(二/三/四唑基)-2H-氮丙啶-2-羧酸酯：S2'-S2'级联机制的证据
J Org Chem. 2018 Nov 2;83(21):13473-13480. doi: 10.1021/acs.joc.8b02295. Epub 2018 Oct 18.
5
Stereoselective synthesis of 3,6-disubstituted-3,6-dihydropyridin-2-ones as potential diketopiperazine mimetics using organocopper-mediated anti-SN2' reactions and their use in the preparation of low-molecule CXCR4 antagonists.利用有机铜介导的反-SN2'反应立体选择性合成3,6-二取代-3,6-二氢吡啶-2-酮作为潜在的二酮哌嗪模拟物及其在制备小分子CXCR4拮抗剂中的应用
J Org Chem. 2006 May 12;71(10):3942-51. doi: 10.1021/jo060390t.
6
Synthesis of multi-substituted allenes from organoalane reagents and propargyl esters by using a nickel catalyst.使用镍催化剂由有机铝试剂和炔丙基酯合成多取代丙二烯。
Org Biomol Chem. 2018 Jul 4;16(26):4797-4806. doi: 10.1039/c8ob00781k.
7
The role of allyl ammonium salts in palladium-catalyzed cascade reactions towards the synthesis of spiro-fused heterocycles.烯丙基铵盐在钯催化的级联反应中合成螺稠合杂环的作用。
Nat Commun. 2020 Oct 23;11(1):5383. doi: 10.1038/s41467-020-19110-3.
8
Theoretical investigation of Banert cascade reaction.巴纳特级联反应的理论研究
R Soc Open Sci. 2018 Apr 4;5(4):171075. doi: 10.1098/rsos.171075. eCollection 2018 Apr.
9
Multisubstituted N-fused heterocycles via transition metal-catalyzed cycloisomerization protocols.通过过渡金属催化的环异构化反应制备多取代N-稠合杂环化合物。
Tetrahedron. 2008 Jul 14;64(29):6876-6883. doi: 10.1016/j.tet.2008.04.023.
10
Facile access to 2-acyloxy-, aryloxy- and alkenyloxy-2H-azirines via an S2'-S2' cascade in 2-halo-2H-azirines.通过 2-卤代-2H-氮丙啶中的 S2′-S2′级联反应，轻松获得 2-酰氧基、芳氧基和烯氧基-2H-氮丙啶。
Org Biomol Chem. 2018 May 2;16(17):3248-3257. doi: 10.1039/c8ob00553b.
引用本文的文献
1
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.
2
Investigation of the Pyridinium Ylide--Alkyne Cycloaddition as a Fluorogenic Coupling Reaction.作为一种荧光偶联反应的吡啶叶立德-炔环加成反应的研究。
Molecules. 2016 Mar 10;21(3):332. doi: 10.3390/molecules21030332.
本文引用的文献
1
Essential role of mitochondria in apoptosis of cancer cells induced by the marine alkaloid Lamellarin D.海洋生物碱拉米林 D 诱导癌细胞凋亡中线粒体的重要作用。
Mol Cancer Ther. 2009 Dec;8(12):3307-17. doi: 10.1158/1535-7163.MCT-09-0639.
2
Lamellarin D bioconjugates I: Synthesis and cellular internalization of PEG-derivatives.片螺素D生物共轭物I：聚乙二醇衍生物的合成与细胞内化
Bioconjug Chem. 2009 Jun;20(6):1100-11. doi: 10.1021/bc800503k.
3
Low temperature organocopper-mediated two-component cross coupling/cycloisomerization approach toward N-fused heterocycles.低温有机铜介导的合成氮稠合杂环的双组分交叉偶联/环异构化方法。
Org Lett. 2008 Jun 5;10(11):2307-10. doi: 10.1021/ol8008705. Epub 2008 May 8.
4
Metal-catalyzed 1,2-shift of diverse migrating groups in allenyl systems as a new paradigm toward densely functionalized heterocycles.金属催化的烯丙基体系中各种迁移基团的1,2-迁移：一种构建高度官能化杂环的新范式
J Am Chem Soc. 2008 Jan 30;130(4):1440-52. doi: 10.1021/ja0773507. Epub 2008 Jan 4.
5
Electronic effects in the pt-catalyzed cycloisomerization of propargylic esters: synthesis of 2,3-disubstituted indolizines as a mechanistic probe.铂催化的炔丙基酯环异构化反应中的电子效应：作为机理探针的2,3-二取代中氮茚的合成
Org Lett. 2007 Oct 25;9(22):4547-50. doi: 10.1021/ol701973s. Epub 2007 Sep 11.
6
Highly efficient synthesis of functionalized indolizines and indolizinones by copper-catalyzed cycloisomerizations of propargylic pyridines.通过铜催化的炔丙基吡啶环异构化高效合成官能化中氮茚和中氮茚酮。
J Org Chem. 2007 Sep 28;72(20):7783-6. doi: 10.1021/jo070983j. Epub 2007 Aug 25.
7
Mechanistically diverse copper-, silver-, and gold-catalyzed acyloxy and phosphatyloxy migrations: efficient synthesis of heterocycles via cascade migration/cycloisomerization approach.机理多样的铜、银和金催化的酰氧基和磷酰氧基迁移：通过级联迁移/环异构化方法高效合成杂环化合物
J Am Chem Soc. 2007 Aug 15;129(32):9868-78. doi: 10.1021/ja072446m. Epub 2007 Jul 21.
8
Base- and ligand-free room-temperature synthesis of N-fused heteroaromatic compounds via the transition metal-catalyzed cycloisomerization protocol.通过过渡金属催化的环异构化协议在无碱和无配体条件下室温合成氮稠合杂芳族化合物。
Org Lett. 2007 Aug 16;9(17):3433-6. doi: 10.1021/ol701464j. Epub 2007 Jul 17.
9
Direct transition metal-catalyzed functionalization of heteroaromatic compounds.直接过渡金属催化的杂芳族化合物官能化
Chem Soc Rev. 2007 Jul;36(7):1173-93. doi: 10.1039/b606984n. Epub 2007 Mar 5.
10
Direct palladium-catalyzed alkynylation of N-fused heterocycles.钯直接催化的氮稠杂环炔基化反应。
J Am Chem Soc. 2007 Jun 27;129(25):7742-3. doi: 10.1021/ja072718l. Epub 2007 Jun 1.
Zotero 插件