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金属介导的吡咯啉合成。

Metal-mediated synthesis of pyrrolines.

作者信息

Medran Noelia S, La-Venia Agustina, Testero Sebastian A

机构信息

Instituto de Química Rosario - IQUIR (CONICET), Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario Suipacha 531 Rosario S2002LRK Argentina

出版信息

RSC Adv. 2019 Feb 27;9(12):6804-6844. doi: 10.1039/c8ra10247c. eCollection 2019 Feb 22.

DOI:10.1039/c8ra10247c
PMID:35518475
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9061060/
Abstract

The five-membered, nitrogen-containing pyrroline ring is a privileged structure. This ring is present in many bioactive compounds from natural sources. Pyrrolines-the dihydro derivatives of pyrroles-have three structural isomer classes, depending on the location of the double bond: 1-pyrrolines (3,4-dihydro-2-pyrroles), 2-pyrrolines (2,3-dihydro-1-pyrroles) and 3-pyrrolines (2,5-dihydro-1-pyrroles). This review aims to describe the latest advances for the synthesis of pyrrolines by transition metal-catalyzed cyclizations. Only reactions in which the pyrroline ring is formed by metal promotion are described. Transformations of the pyrroline ring in other heterocycles, and the structural manipulations of the pyrroline itself are not discussed. The review is organized into three parts, each covering the metal-mediated synthesis of the three pyrroline isomers. Each part is subdivided according to the metal involved, and concludes with a brief description of notable biological activities within the class.

摘要

五元含氮吡咯啉环是一种优势结构。该环存在于许多天然来源的生物活性化合物中。吡咯啉(吡咯的二氢衍生物)有三类结构异构体,取决于双键的位置:1-吡咯啉(3,4-二氢-2-吡咯)、2-吡咯啉(2,3-二氢-1-吡咯)和3-吡咯啉(2,5-二氢-1-吡咯)。本综述旨在描述过渡金属催化环化合成吡咯啉的最新进展。仅描述通过金属促进形成吡咯啉环的反应。不讨论吡咯啉环在其他杂环中的转化以及吡咯啉本身的结构操作。本综述分为三个部分,每个部分涵盖三种吡咯啉异构体的金属介导合成。每个部分根据所涉及的金属进行细分,并以该类别内显著生物活性的简要描述作为结尾。

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7
Tin(iv) chloride mediated (3 + 2) annulation of -2-aroyl-3-styrylcyclopropane-1,1-dicarboxylates with nitriles: diastereoselective access to 5-vinyl-1-pyrroline derivatives.四氯化锡介导的 -2-芳酰基-3-苯乙烯基环丙烷-1,1-二羧酸酯与腈的(3 + 2)环化反应:非对映选择性合成5-乙烯基-1-吡咯啉衍生物
RSC Adv. 2021 Apr 21;11(25):14980-14985. doi: 10.1039/d1ra01194d.
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Synthesis and Toxicity Evaluation of New Pyrroles Obtained by the Reaction of Activated Alkynes with 1-Methyl-3-(cyanomethyl)benzimidazolium Bromide.新型吡咯的合成及其毒性评价,该吡咯由活性炔与 1-甲基-3-(氰甲基)苯并咪唑溴反应得到。
Molecules. 2021 Oct 25;26(21):6435. doi: 10.3390/molecules26216435.
铑催化的α-亚氨基卡宾与α,β-不饱和酮的环化反应:多取代 2,3-二氢吡咯/吡咯环的构建。
J Org Chem. 2018 Dec 7;83(23):14518-14526. doi: 10.1021/acs.joc.8b01835. Epub 2018 Nov 16.
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3-Aryl-2,5-Dihydropyrroles via Catalytic Carbonyl-Olefin Metathesis.通过催化羰基-烯烃复分解反应合成3-芳基-2,5-二氢吡咯
ACS Catal. 2018 Mar 2;8(3):2006-2011. doi: 10.1021/acscatal.7b03769. Epub 2018 Jan 18.
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Synthesis of 3-(Arylsulfonyl)-3-pyrrolines from Allenyl Sulfonamides by Silver Ion Catalysis.银离子催化烯基砜基磺酰胺合成 3-(芳基磺酰基)-3-吡咯啉。
Org Lett. 2018 Sep 21;20(18):5723-5726. doi: 10.1021/acs.orglett.8b02440. Epub 2018 Sep 4.
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Catalytic Asymmetric [3 + 2] Cycloaddition Reaction between Aurones and Isocyanoacetates: Access to Spiropyrrolines via Silver Catalysis.金酮与异氰基乙酸酯之间的催化不对称[3+2]环加成反应:通过银催化合成螺吡咯啉
J Org Chem. 2018 Sep 21;83(18):10995-11007. doi: 10.1021/acs.joc.8b01622. Epub 2018 Jul 23.
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A Novel Sc(OTf) -Catalyzed (2+2+1)-Cycloannulation/Aza-Friedel-Crafts Alkylation Sequence toward Multicyclic 2-Pyrrolines.一种新型 Sc(OTf) 催化的(2+2+1)-环加成/氮杂-Friedel-Crafts 烷基化序列合成多环 2-吡咯啉。
Chemistry. 2018 Sep 20;24(53):14207-14212. doi: 10.1002/chem.201802478. Epub 2018 Aug 22.
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Regioselective Synthesis of Acylated N-Heterocycles via the Cascade Reactions of Saturated Cyclic Amines with 2-Oxo-2-arylacetic Acids.通过饱和环胺与2-氧代-2-芳基乙酸的串联反应区域选择性合成酰化氮杂环化合物。
J Org Chem. 2018 Jun 15;83(12):6524-6533. doi: 10.1021/acs.joc.8b00805. Epub 2018 May 24.
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Direct Asymmetric Formal [3 + 2] Cycloaddition Reaction of Isocyanoesters with β-Trifluoromethyl β,β-Disubstituted Enones Leading to Optically Active Dihydropyrroles.手性异氰酸酯与β-三氟甲基β,β-二取代烯酮的直接不对称[3 + 2]环加成反应生成手性二氢吡咯。
Org Lett. 2018 May 4;20(9):2716-2719. doi: 10.1021/acs.orglett.8b00925. Epub 2018 Apr 23.
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Copper-Catalyzed Domino Cyclization/Trifluoromethylthiolation of Unactivated Alkenes: Access to SCF-Containing Pyrrolines.铜催化的非活化烯烃的多米诺环化/三氟甲硫基化:含 SCF 的吡咯啉的获得。
Org Lett. 2018 Apr 20;20(8):2261-2264. doi: 10.1021/acs.orglett.8b00614. Epub 2018 Mar 27.