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不对称比格利希反应的最新进展:综述。

Current progress in asymmetric Biginelli reaction: an update.

机构信息

Department of Chemistry, Alzahra University, Tehran, Iran.

Department of Chemistry, Razi University, Kermanshah, 67149, Iran.

出版信息

Mol Divers. 2018 Aug;22(3):751-767. doi: 10.1007/s11030-018-9841-4. Epub 2018 Jun 23.

DOI:10.1007/s11030-018-9841-4
PMID:29936682
Abstract

The Biginelli reaction, involving a three-component reaction of an aromatic aldehyde, urea and ethyl acetoacetate, has emerged as an extremely useful synthetic tool to organic chemists for the synthesis of 3,4-dihydropyrimidine-2-(1H)-ones and related heterocyclic compounds. In the past decades, the asymmetric variants of this reaction have been at the forefront of investigations in several research groups. In 2013, we highlighted the developments occurred in the asymmetric version of the Biginelli reaction. This review article focuses on the recent developments of asymmetric Biginelli reaction covers the literature going back to 2012.

摘要

Biginelli 反应是一种三组分反应,涉及芳香醛、尿素和乙酰乙酸乙酯,它已成为有机化学家合成 3,4-二氢嘧啶-2(1H)-酮和相关杂环化合物的极其有用的合成工具。在过去的几十年中,该反应的不对称变体一直是几个研究小组研究的前沿。2013 年,我们重点介绍了不对称 Biginelli 反应的发展。本文综述了不对称 Biginelli 反应的最新进展,涵盖了 2012 年以来的文献。

相似文献

1
Current progress in asymmetric Biginelli reaction: an update.不对称比格利希反应的最新进展:综述。
Mol Divers. 2018 Aug;22(3):751-767. doi: 10.1007/s11030-018-9841-4. Epub 2018 Jun 23.
2
Recent progress in asymmetric Biginelli reaction.不对称比格涅利反应的最新进展。
Mol Divers. 2013 May;17(2):389-407. doi: 10.1007/s11030-013-9439-9. Epub 2013 Apr 16.
3
High Glass Transition Temperature Renewable Polymers via Biginelli Multicomponent Polymerization.通过Biginelli多组分聚合制备高玻璃化转变温度的可再生聚合物
Macromol Rapid Commun. 2016 Apr;37(7):643-9. doi: 10.1002/marc.201500717. Epub 2016 Jan 22.
4
Recent advances in the Biginelli dihydropyrimidine synthesis. New tricks from an old dog.Biginelli二氢嘧啶合成反应的最新进展。老方法的新技巧。
Acc Chem Res. 2000 Dec;33(12):879-88. doi: 10.1021/ar000048h.
5
An enantioselective biginelli reaction catalyzed by a simple chiral secondary amine and achiral brønsted acid by a dual-activation route.一种通过双活化途径由简单手性仲胺和非手性布朗斯特酸催化的对映选择性贝纳利反应。
Chemistry. 2008;14(10):3177-81. doi: 10.1002/chem.200701581.
6
Modification of Starch via the Biginelli Multicomponent Reaction.通过比格利尼多组分反应对淀粉进行修饰。
Macromol Rapid Commun. 2020 Jan;41(1):e1900375. doi: 10.1002/marc.201900375. Epub 2019 Sep 13.
7
Brønsted-acid-catalyzed asymmetric multicomponent reactions for the facile synthesis of highly enantioenriched structurally diverse nitrogenous heterocycles.布朗斯特酸催化的不对称多组分反应,用于方便地合成高对映选择性的结构多样的含氮杂环。
Acc Chem Res. 2011 Nov 15;44(11):1156-71. doi: 10.1021/ar2000343. Epub 2011 Jul 29.
8
Biginelli reaction catalyzed by copper nanoparticles.铜纳米粒子催化的 Biginelli 反应。
PLoS One. 2012;7(8):e43078. doi: 10.1371/journal.pone.0043078. Epub 2012 Aug 17.
9
Unexpected three-component domino synthesis of pyridin-2-ones catalyzed by promiscuous acylase in non-aqueous solvent.非水溶剂中通过混杂脂肪酶催化的吡啶-2-酮的非预期三组分多米诺合成。
Biochimie. 2013 Jul;95(7):1462-5. doi: 10.1016/j.biochi.2013.03.012. Epub 2013 Apr 6.
10
Biologically active dihydropyrimidones of the Biginelli-type--a literature survey.贝纳利型生物活性二氢嘧啶酮——文献综述
Eur J Med Chem. 2000 Dec;35(12):1043-52. doi: 10.1016/s0223-5234(00)01189-2.

引用本文的文献

1
Diverse Methods with Stereoselective Induction in the Asymmetric Biginelli Reaction.不对称Biginelli反应中具有立体选择性诱导的多种方法。
Molecules. 2024 Aug 15;29(16):3864. doi: 10.3390/molecules29163864.
2
Precision in stereochemistry: the integral role of catalytic asymmetric Biginelli reaction in crafting enantiomerically pure dihydropyrimidinones.立体化学中的精准性:催化不对称Biginelli反应在制备对映体纯二氢嘧啶酮中的不可或缺作用。
Mol Divers. 2024 Dec;28(6):4441-4466. doi: 10.1007/s11030-024-10827-7. Epub 2024 Mar 27.
3
Synthesis of 3,4-Dihydropyrimidin(thio)one Containing Scaffold: Biginelli-like Reactions.

本文引用的文献

1
3,4-Dihydropyrimidinone-coumarin analogues as a new class of selective agent against S. aureus: Synthesis, biological evaluation and molecular modelling study.3,4-二氢嘧啶酮-香豆素类似物作为一类新型抗金黄色葡萄球菌的选择性药物:合成、生物学评价及分子模拟研究
Bioorg Med Chem. 2017 Feb 15;25(4):1413-1422. doi: 10.1016/j.bmc.2017.01.001. Epub 2017 Jan 5.
2
Towards Enzyme-like, Sustainable Catalysis: Switchable, Highly Efficient Asymmetric Synthesis of Enantiopure Biginelli Dihydropyrimidinones or Hexahydropyrimidinones.迈向类酶可持续催化:对映体纯的 3,4-二氢嘧啶-2(1H)-酮或六氢嘧啶-2-酮的可切换、高效不对称合成
Chemistry. 2016 Nov 21;22(48):17182-17186. doi: 10.1002/chem.201604433. Epub 2016 Oct 18.
3
含3,4-二氢嘧啶(硫)酮骨架的合成:类Biginelli反应
Pharmaceuticals (Basel). 2022 Jul 30;15(8):948. doi: 10.3390/ph15080948.
4
Synthesis and Characterization of Dihydrouracil Analogs Utilizing Biginelli Hybrids.二氢尿嘧啶类似物的利用Biginelli 杂环的合成与表征。
Molecules. 2022 May 4;27(9):2939. doi: 10.3390/molecules27092939.
5
Overview on magnetically recyclable ferrite nanoparticles: synthesis and their applications in coupling and multicomponent reactions.磁性可回收铁氧体纳米颗粒综述:合成及其在偶联和多组分反应中的应用
RSC Adv. 2021 Sep 1;11(47):29333-29353. doi: 10.1039/d1ra03874e.
6
Biginelli Reaction Mediated Synthesis of Antimicrobial Pyrimidine Derivatives and Their Therapeutic Properties.Biginelli 反应介导的抗微生物嘧啶衍生物的合成及其治疗性质。
Molecules. 2021 Oct 4;26(19):6022. doi: 10.3390/molecules26196022.
Computational Catalysis Using the Artificial Force Induced Reaction Method.
使用人工力诱导反应方法的计算催化。
Acc Chem Res. 2016 Apr 19;49(4):763-73. doi: 10.1021/acs.accounts.6b00023. Epub 2016 Mar 29.
4
Organocatalysis by Networks of Cooperative Hydrogen Bonds: Enantioselective Direct Mannich Addition to Preformed Arylideneureas.氢键网络的有机催化:预形成的芳基亚氨基脲的对映选择性直接曼尼希加成。
Angew Chem Int Ed Engl. 2016 Mar 18;55(13):4312-6. doi: 10.1002/anie.201511555. Epub 2016 Feb 25.
5
Organocatalytic Asymmetric Biginelli-like Reaction Involving Isatin.涉及异吲哚酮的有机催化不对称类Biginelli反应
J Org Chem. 2016 Mar 4;81(5):1877-84. doi: 10.1021/acs.joc.5b02680. Epub 2016 Feb 12.
6
A highly enantioselective Biginelli reaction using self-assembled methanoproline-thiourea organocatalysts: asymmetric synthesis of 6-isopropyl-3,4-dihydropyrimidines.使用自组装的甲氨基脯氨酸-硫脲有机催化剂的高度对映选择性Biginelli反应:6-异丙基-3,4-二氢嘧啶的不对称合成
Chem Commun (Camb). 2016 Jan 4;52(1):80-3. doi: 10.1039/c5cc07880f.
7
Computational studies on the regioselectivity of metal-catalyzed synthesis of 1,2,3 triazoles via click reaction: a review.通过点击反应金属催化合成1,2,3-三唑区域选择性的计算研究:综述
J Mol Model. 2015 Oct;21(10):264. doi: 10.1007/s00894-015-2810-2. Epub 2015 Sep 18.
8
A mini-review on Biginelli adducts with notable pharmacological properties.关于具有显著药理学性质的 Biginelli 加合物的小型综述。
J Adv Res. 2015 May;6(3):363-73. doi: 10.1016/j.jare.2014.10.006. Epub 2014 Nov 1.
9
Microwave-assisted synthesis and biological evaluation of dihydropyrimidinone derivatives as anti-inflammatory, antibacterial, and antifungal agents.作为抗炎、抗菌和抗真菌剂的二氢嘧啶酮衍生物的微波辅助合成及生物学评价
Int J Med Chem. 2013;2013:197612. doi: 10.1155/2013/197612. Epub 2013 Apr 15.
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Earthworm is a versatile and sustainable biocatalyst for organic synthesis.蚯蚓是一种用于有机合成的多功能且可持续的生物催化剂。
PLoS One. 2014 Aug 22;9(8):e105284. doi: 10.1371/journal.pone.0105284. eCollection 2014.