烯丙基-Ugi 产物的区域和化学选择性环化反应合成 3-吡咯啉骨架。
Regio- and chemo-selective cyclization of allenic-Ugi products for the synthesis of 3-pyrroline skeletons.
机构信息
Peptide Chemistry Research Center, K. N. Toosi University of Technology, P. O. Box 15875-4416, Tehran, Iran.
出版信息
Org Biomol Chem. 2019 Oct 21;17(39):8858-8870. doi: 10.1039/c9ob01963d. Epub 2019 Sep 26.
PMID:31556430
Abstract
A highly efficient and stable novel class of allenic-Ugi products through a Crabbé homologation reaction is successfully demonstrated. Then, a regio- and chemo-selective cyclization of allenic-Ugi derivatives in a 5-exo-dig fashion to access 3-pyrroline skeletons is developed. Also, computational studies were performed and explained to provide insights into the reaction mechanism. This approach displays high bond-forming efficiency and atom economy with high yields.
摘要
通过 Crabbé 同系化反应，成功地展示了一类高效且稳定的新型烯丙基-Ugi 产物。然后，发展了烯丙基-Ugi 衍生物的区域和化学选择性 5-exo- 环化反应，以获得 3-吡咯啉骨架。此外，还进行了计算研究并加以解释，以深入了解反应机理。该方法具有高产率、高键形成效率和原子经济性。
相似文献
1
Regio- and chemo-selective cyclization of allenic-Ugi products for the synthesis of 3-pyrroline skeletons.烯丙基-Ugi 产物的区域和化学选择性环化反应合成 3-吡咯啉骨架。
Org Biomol Chem. 2019 Oct 21;17(39):8858-8870. doi: 10.1039/c9ob01963d. Epub 2019 Sep 26.
2
Synthesis of Pyrrolidin-5-one-2-carboxamides through Cyclization of -Substituted-2-alleneamides.通过α-取代-2-丙二烯酰胺的环化反应合成吡咯烷-5-酮-2-甲酰胺
J Org Chem. 2022 Jun 17;87(12):7778-7785. doi: 10.1021/acs.joc.2c00387. Epub 2022 Jun 6.
3
Base mediated 7-exo-dig intramolecular cyclization of Ugi-propargyl precursors: a highly efficient and regioselective synthetic approach toward diverse 1,4-benzoxazepine-5(2H)-ones.碱介导的Ugi-炔丙基前体的7-外向-双分子内环化反应：一种高效且区域选择性地合成多种1,4-苯并恶唑嗪-5(2H)-酮的方法。
Org Biomol Chem. 2014 Aug 7;12(29):5346-50. doi: 10.1039/c4ob00793j.
4
A versatile synthesis of β-lactam-fused oxacycles through the palladium-catalyzed chemo-, regio-, and diastereoselective cyclization of allenic diols.通过钯催化的丙二烯二醇的化学、区域和非对映选择性环化反应，实现β-内酰胺稠合氧杂环的通用合成。
Chemistry. 2015 Jan 26;21(5):2200-13. doi: 10.1002/chem.201405181. Epub 2014 Dec 2.
5
Catalyst-Controlled Structural Divergence: Selective Intramolecular 7-endo-dig and 6-exo-dig Post-Ugi Cyclization for the Synthesis of Benzoxazepinones and Benzoxazinones.催化剂控制的结构发散：选择性的分子内 7-endo-dig 和 6-exo-dig 后-Ugi 环化反应合成苯并恶嗪酮和苯并恶嗪酮。
J Org Chem. 2018 Jan 5;83(1):57-68. doi: 10.1021/acs.joc.7b02123. Epub 2017 Dec 11.
6
Intramolecular 6-- Post-Ugi Cyclization of N-Substituted 2-Alkynamides: Direct Access to Functionalized Morpholinone Glycoconjugates.N-取代 2-炔酰胺的分子内 6-后-Ugi 环化：功能化吗啉酮糖缀合物的直接途径。
Org Lett. 2020 Dec 4;22(23):9258-9262. doi: 10.1021/acs.orglett.0c03486. Epub 2020 Nov 17.
7
Iron(III)-Catalyzed Domino Claisen Rearrangement/Regio- and Chemoselective Aerobic Dehydrogenative Cyclization of β-Naphthyl-Substituted-Allenylmethyl Ether.铁(III)催化的串联 Claisen 重排/β-萘基取代烯丙基甲基醚的区域和化学选择性有氧脱氢环化反应。
Org Lett. 2019 Feb 15;21(4):955-959. doi: 10.1021/acs.orglett.8b03941. Epub 2019 Jan 25.
8
Intramolecular Gold-Catalyzed and NaH-Supported Cyclization Reactions of N-Propargyl Indole Derivatives with Pyrazole and Pyrrole Rings: Synthesis of Pyrazolodiazepinoindole, Pyrazolopyrazinoindole, and Pyrrolopyrazinoindole.N-炔丙基吲哚衍生物与吡唑和吡咯环的分子内金催化及NaH促进的环化反应：吡唑并二氮杂卓吲哚、吡唑并吡嗪吲哚和吡咯并吡嗪吲哚的合成
J Org Chem. 2015 Dec 18;80(24):12552-61. doi: 10.1021/acs.joc.5b02419. Epub 2015 Dec 8.
9
A Gold-Catalyzed Domino Cyclization Enabling Rapid Construction of Diverse Polyheterocyclic Frameworks.金催化的多米诺环化反应实现了多样的多杂环骨架的快速构建。
Angew Chem Int Ed Engl. 2018 Jan 2;57(1):272-276. doi: 10.1002/anie.201710592. Epub 2017 Dec 7.
10
A convenient method to construct (Z)-oxazines via 6-exo-dig iodocyclization and synthesis of indolin-3-one.通过 6-endo-碘环化和吲哚啉-3-酮合成构建（Z）-恶嗪的简便方法。
Org Biomol Chem. 2013 Oct 14;11(38):6520-5. doi: 10.1039/c3ob41272e. Epub 2013 Aug 21.
引用本文的文献
1
Copper (triazole-5-yl)methanamine complexes onto MCM-41: the synthesis of pyridine-containing pseudopeptides through the 6--dig cyclization of 1,5-enynes.铜（三唑 - 5 - 基）甲胺配合物负载于MCM - 41上：通过1,5 - 烯炔的6 - 外向环化反应合成含吡啶的拟肽。
RSC Adv. 2020 Mar 12;10(18):10577-10583. doi: 10.1039/c9ra10885h. eCollection 2020 Mar 11.
Zotero 插件