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羰基化合物到酰胺键形成的历程。

Carbonyl Compounds' Journey to Amide Bond Formation.

机构信息

Instituto de Química (INQUI), Universidade Federal de Mato Grosso do Sul, 79074-460, Campo Grande, Mato Grosso do Sul, Brazil.

Crop Protection Chemicals Division, CSIR-Indian Institute of Chemical Technology, Uppal Road, Tarnaka, Hyderabad, 500007, India.

出版信息

Chem Asian J. 2019 Feb 1;14(3):344-388. doi: 10.1002/asia.201801560. Epub 2019 Jan 9.

DOI:10.1002/asia.201801560
PMID:30623602
Abstract

The formation of amide bonds is one of the most stimulating emerging areas in organic and medicinal chemistry. Amides are recognized as central building blocks in a plethora of interesting pharmaceuticals, proteins, peptides, polymers, natural products, functional materials, and biologically relevant carbocyclic or heterocyclic molecules, and they are also found in a variety of industrial fields. Therefore, a review of recent developments and challenges in the formation of amide bonds from carbonyl compounds is particularly important. Herein, we have scrutinized a range of metal-catalyzed and metal-free approaches for the synthesis of amides from aldehydes, ketones, and oximes. In addition, this Minireview highlights relevant mechanistic studies, as well as the potential applications of these methods in the synthesis of candidate drug molecules. We hope that the data compiled herein will encourage further progress in this notable area of chemistry research.

摘要

酰胺键的形成是有机和药物化学中最具活力的新兴领域之一。酰胺被认为是许多有趣的药物、蛋白质、肽、聚合物、天然产物、功能材料以及与生物相关的碳环或杂环分子的核心构建块,它们也存在于各种工业领域中。因此,综述羰基化合物形成酰胺键的最新发展和挑战尤为重要。在此,我们仔细研究了一系列用于从醛、酮和肟合成酰胺的金属催化和无金属方法。此外,本综述还强调了相关的机理研究,以及这些方法在候选药物分子合成中的潜在应用。我们希望本文中汇编的数据将鼓励这一重要化学研究领域的进一步发展。

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1
Carbonyl Compounds' Journey to Amide Bond Formation.羰基化合物到酰胺键形成的历程。
Chem Asian J. 2019 Feb 1;14(3):344-388. doi: 10.1002/asia.201801560. Epub 2019 Jan 9.
2
Metal-catalysed approaches to amide bond formation.金属催化的酰胺键形成方法。
Chem Soc Rev. 2011 Jul;40(7):3405-15. doi: 10.1039/c0cs00196a. Epub 2011 Mar 17.
3
Catalytic synthesis of amides via aldoximes rearrangement.通过醛肟重排催化合成酰胺。
Chem Commun (Camb). 2015 Feb 14;51(13):2495-505. doi: 10.1039/c4cc08684h.
4
Recent Advances in the Metal-Catalyzed Activation of Amide Bonds.金属催化酰胺键的活化研究进展。
Chem Asian J. 2019 Jan 4;14(1):76-93. doi: 10.1002/asia.201801317. Epub 2018 Dec 6.
5
Metal-catalyzed alpha-arylation of carbonyl and related molecules: novel trends in C-C bond formation by C-H bond functionalization.金属催化的羰基和相关分子的α-芳基化:C-H 键功能化构建 C-C 键的新趋势
Angew Chem Int Ed Engl. 2010;49(4):676-707. doi: 10.1002/anie.200903424.
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Metal-organic cooperative catalysis in C-H and C-C bond activation and its concurrent recovery.金属有机协同催化在C-H和C-C键活化及其同步回收中的应用
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7
Twisted Amides: From Obscurity to Broadly Useful Transition-Metal-Catalyzed Reactions by N-C Amide Bond Activation.扭曲酰胺:通过N-C酰胺键活化从鲜为人知到广泛应用于过渡金属催化反应
Chemistry. 2017 May 29;23(30):7157-7173. doi: 10.1002/chem.201605012. Epub 2017 Feb 20.
8
One-Pot Amide Bond Formation from Aldehydes and Amines via a Photoorganocatalytic Activation of Aldehydes.一锅法醛和胺通过醛的光有机催化活化形成酰胺键。
J Org Chem. 2016 Aug 19;81(16):7023-8. doi: 10.1021/acs.joc.6b00488. Epub 2016 Jun 3.
9
Recent developments in functionalization of acyclic α-keto amides.环状α-酮酰胺的功能化的最新进展。
Org Biomol Chem. 2018 Oct 10;16(39):7068-7083. doi: 10.1039/c8ob01423j.
10
Rethinking amide bond synthesis.重新思考酰胺键的合成。
Nature. 2011 Dec 21;480(7378):471-9. doi: 10.1038/nature10702.

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