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斯特凡诺·马尔卡奇尼：异腈化学的先驱。

Stefano Marcaccini: a pioneer in isocyanide chemistry.

作者信息

Neo Ana G, Ramiro José Luis, García-Valverde María, Díaz Jesús, Marcos Carlos F

机构信息

Laboratory of Bioorganic Chemistry & Membrane Biophysics (L.O.B.O.), Universidad de Extremadura, 10003, Cáceres, Spain.

Departamento de Química, Facultad de Ciencias, Universidad de Burgos, 09001, Burgos, Spain.

出版信息

Mol Divers. 2024 Feb;28(1):335-418. doi: 10.1007/s11030-023-10641-7. Epub 2023 Apr 12.

DOI:10.1007/s11030-023-10641-7
PMID:37043161
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10876884/
Abstract

Stefano Marcaccini was one of the pioneers in the use of isocyanide-based multicomponent reactions in organic synthesis. Throughout his career at the University of Florence he explored many different faces of isocyanide chemistry, especially those geared towards the synthesis of biologically relevant heterocycles. His work inspired many researchers who contributed to other important developments in the field of multicomponent reactions and created a school of synthetic chemists that continues today. In this manuscript we intend to review the articles on isocyanide multicomponent reactions published by Dr. Marcaccini and analyse their influence on the following works by other researchers. With this, we hope to highlight the immense contribution of Stefano Marcaccini to the development of isocyanide chemistry and modern organic synthesis as well as the influence of his research on future generations. We believe that this review will not only be a well-deserved tribute to the figure of Stefano Marcaccini, but will also serve as a useful inspiration for chemists working in this field.

摘要

斯特凡诺·马尔卡奇尼是在有机合成中使用基于异腈的多组分反应的先驱之一。在他于佛罗伦萨大学的整个职业生涯中，他探索了异腈化学的许多不同方面，尤其是那些致力于合成具有生物学相关性的杂环的方面。他的工作激励了许多研究人员，他们为多组分反应领域的其他重要发展做出了贡献，并创建了一个至今仍在延续的合成化学家学派。在本手稿中，我们打算回顾马尔卡奇尼博士发表的关于异腈多组分反应的文章，并分析它们对其他研究人员后续工作的影响。借此，我们希望突出斯特凡诺·马尔卡奇尼对异腈化学和现代有机合成发展的巨大贡献以及他的研究对后代的影响。我们相信，这篇综述不仅将是对斯特凡诺·马尔卡奇尼的当之无愧的致敬，也将为该领域的化学家提供有益的灵感。

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J Org Chem. 2022 Jun 17;87(12):7778-7785. doi: 10.1021/acs.joc.2c00387. Epub 2022 Jun 6.
4
Synthesis of Chromeno[3,4-]piperazines by an Enol-Ugi/Reduction/Cyclization Sequence.通过烯醇-乌吉/还原/环化序列合成色烯并[3,4-]哌嗪。
Molecules. 2021 Feb 27;26(5):1287. doi: 10.3390/molecules26051287.
5
Uncatalyzed diastereoselective synthesis of alkyliminofurochromone-derived benzylmalononitriles via a three-component cascade reaction: competition between Diels-Alder cycloaddition and Michael addition.无催化立体选择性合成烷基亚氨基呋罗chromone 衍生的苄基丙二腈的三组分级联反应：Diels-Alder 环加成和迈克尔加成的竞争。
Org Biomol Chem. 2021 Mar 21;19(11):2517-2525. doi: 10.1039/d0ob02540b. Epub 2021 Mar 5.
6
Radical Borylative Cyclization of Isocyanoarenes with N-Heterocyclic Carbene Borane: Synthesis of Borylated Aza-arenes.异腈芳烃与氮杂环卡宾硼烷的自由基硼化环化反应：硼化氮杂芳烃的合成
Org Lett. 2021 Mar 5;23(5):1891-1897. doi: 10.1021/acs.orglett.1c00309. Epub 2021 Feb 16.
7
Keto-Enol Tautomerism in Passerini and Ugi Adducts.酮-烯醇互变异构在 Passerini 和 Ugi 加合物中的作用。
Molecules. 2021 Feb 9;26(4):919. doi: 10.3390/molecules26040919.
8
4CzIPN-Bu-Catalyzed Proton-Coupled Electron Transfer for Photosynthesis of Phosphorylated -Heteroaromatics.4CzIPN-Bu 催化的磷酸化 - 杂芳烃的光合质子耦合电子转移。
J Am Chem Soc. 2021 Jan 20;143(2):964-972. doi: 10.1021/jacs.0c11138. Epub 2020 Dec 29.
9
One-Pot Synthesis of Enantiopure Pyrrolopiperazines.一锅法合成手性吡咯哌嗪。
J Org Chem. 2020 Nov 6;85(21):14240-14245. doi: 10.1021/acs.joc.0c02103. Epub 2020 Oct 14.
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Electrochemical Oxidative Carbon-Atom Difunctionalization: Towards Multisubstituted Imino Sulfide Ethers.电化学氧化碳-原子双官能化：迈向多取代亚氨基硫醚醚类化合物
Angew Chem Int Ed Engl. 2021 Jan 18;60(3):1573-1577. doi: 10.1002/anie.202011329. Epub 2020 Nov 12.