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由芳基/烷基炔基醛合成氮杂环、氧杂环和硫杂环。

Synthesis of N-, O-, and S-heterocycles from aryl/alkyl alkynyl aldehydes.

作者信息

Doraghi Fatemeh, Mohaghegh Farid, Qareaghaj Omid Hosseinchi, Larijani Bagher, Mahdavi Mohammad

机构信息

Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences Tehran Iran

School of Chemistry, College of Science, University of Tehran Tehran Iran.

出版信息

RSC Adv. 2023 May 9;13(20):13947-13970. doi: 10.1039/d3ra01778h. eCollection 2023 May 2.

DOI:10.1039/d3ra01778h
PMID:37181524
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10167737/
Abstract

In the field of heterocyclic synthesis, alkynyl aldehydes serve as privileged reagents for cyclization reactions with other organic compounds to construct a broad spectrum of N-, O-, and S-heterocycles. Due to the immense application of heterocyclic molecules in pharmaceuticals, natural products, and material chemistry, the synthesis of such scaffolds has received wide attention. The transformations occurred under metal-catalyzed, metal-free-promoted, and visible-light-mediated systems. The present review article highlights the progress made in this field over the past two decades.

摘要

在杂环合成领域,炔基醛作为与其他有机化合物进行环化反应的重要试剂,可构建多种N-、O-和S-杂环。由于杂环分子在药物、天然产物和材料化学中的广泛应用,此类骨架的合成受到了广泛关注。这些转化反应是在金属催化、无金属促进和可见光介导的体系下进行的。本文综述了过去二十年来该领域取得的进展。

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引用本文的文献

1
A domino reaction for the synthesis of pyrrolo[2,1-]isoquinolines from 2-aryl-pyrrolidines and alkynes promoted by a four-component catalytic system under aerobic conditions.在有氧条件下,由四组分催化体系促进的从2-芳基吡咯烷和炔烃合成吡咯并[2,1-]异喹啉的多米诺反应。
RSC Adv. 2023 Dec 6;13(50):35617-35620. doi: 10.1039/d3ra07653a. eCollection 2023 Nov 30.

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Lewis Acid-Promoted Three-Component Cyclization for the Construction of Functionalized Oxazoles.路易斯酸促进的三组分环化反应用于构建官能化恶唑
J Org Chem. 2023 Jan 6;88(1):27-38. doi: 10.1021/acs.joc.2c01432. Epub 2022 Dec 23.
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Rh(II)-Catalyzed C-N Bond Formation Using Enynones and N-H Imines: An Approach to Diarylmethylamines.使用烯炔酮和N-H亚胺的铑(II)催化C-N键形成:一种制备二芳基甲胺的方法。
J Org Chem. 2022 Dec 16;87(24):16424-16435. doi: 10.1021/acs.joc.2c02119. Epub 2022 Dec 5.
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Nitroenediamines (EDAMs), and -methyl-1-(methylthio)-2-nitroethenamine (NMSM) derivatives: scaffolds for heterocycle molecular diversity (update from 2012 to 2021).
硝基乙二胺(EDAMs)以及N-甲基-1-(甲硫基)-2-硝基乙胺(NMSM)衍生物:杂环分子多样性的骨架(2012年至2021年更新)
RSC Adv. 2022 Oct 26;12(47):30436-30456. doi: 10.1039/d2ra05547c. eCollection 2022 Oct 24.
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Synthesis of Diversified Pyrazolo[3,4-]pyridine Frameworks from 5-Aminopyrazoles and Alkynyl Aldehydes via Switchable C≡C Bond Activation Approaches.通过可切换的 C≡C 键活化方法,从 5-氨基吡唑和炔基醛合成多样化的吡唑并[3,4-d]吡啶骨架。
Molecules. 2022 Sep 27;27(19):6381. doi: 10.3390/molecules27196381.
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Design, synthesis, and in silico studies of quinoline-based-benzo[d]imidazole bearing different acetamide derivatives as potent α-glucosidase inhibitors.基于喹啉的苯并[d]咪唑类化合物的设计、合成及不同乙酰苯胺衍生物的计算机模拟研究作为有效的α-葡萄糖苷酶抑制剂。
Sci Rep. 2022 Aug 18;12(1):14019. doi: 10.1038/s41598-022-18455-7.
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Ketone Derivatives of Propargylamines as Synthetic Equivalents of Conjugated 2,4,1-Enynones in the Synthesis of Acetylenic 2-Pyrazolines and Pyrazoles.炔丙胺酮衍生物作为共轭 2,4,1-烯炔酮的合成等价物在乙酰基 2-吡唑啉和吡唑的合成中的应用。
J Org Chem. 2022 May 6;87(9):5916-5924. doi: 10.1021/acs.joc.2c00198. Epub 2022 Apr 8.
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Catalyst- and Additive-Free Approach to Constructing Benzo-oxazine, Benzo-oxazepine, and Benzo-oxazocine: O Atom Transfer and C═O, C-N, and C-O Bond Formation at Room Temperature.无催化剂和添加剂构建苯并恶嗪、苯并恶唑嗪和苯并恶唑啉的方法:室温下的氧原子转移以及C═O、C-N和C-O键的形成
Org Lett. 2021 Nov 5;23(21):8189-8193. doi: 10.1021/acs.orglett.1c02895. Epub 2021 Oct 13.
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Controllable Site-Selective Construction of 2- and 4-Substituted Pyrimido[1,2-]indazole from 3-Aminoindazoles and Ynals.由3-氨基吲唑和炔醛可控地进行位点选择性构建2-和4-取代的嘧啶并[1,2 -]吲唑
J Org Chem. 2021 Jun 16. doi: 10.1021/acs.joc.1c01094.
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Carbene-Catalyzed Atroposelective Annulation and Desymmetrization of Urazoles.卡宾催化的稠环并环化反应和稠氮杂苯的去对称化反应
Org Lett. 2021 May 21;23(10):3991-3996. doi: 10.1021/acs.orglett.1c01191. Epub 2021 May 12.
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Visible Light-Induced Cascade Cyclization of 3-Aminoindazoles, Ynals, and Chalcogens: Access to Chalcogen-Containing Pyrimido[1,2-]-indazoles.可见光诱导的3-氨基吲唑、炔醛和硫族元素的串联环化反应:通向含硫族元素的嘧啶并[1,2 - ]吲唑的方法
Org Lett. 2021 Apr 2;23(7):2754-2759. doi: 10.1021/acs.orglett.1c00664. Epub 2021 Mar 19.