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使用多种催化剂的克劳森-卡斯吡咯合成法：从传统方法到更绿色方法的转变

Clauson-Kaas pyrrole synthesis using diverse catalysts: a transition from conventional to greener approach.

作者信息

Singh Dileep Kumar, Kumar Rajesh

机构信息

Department of Chemistry, Bipin Bihari College, Affiliated to Bundelkhand University, Jhansi-284001, Uttar Pradesh, India.

P.G. Department of Chemistry, R. D. S. College, B. R. A. Bihar University, Muzaffarpur-842002, Bihar, India.

出版信息

Beilstein J Org Chem. 2023 Jun 27;19:928-955. doi: 10.3762/bjoc.19.71. eCollection 2023.

DOI:10.3762/bjoc.19.71
PMID:37404802
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10315892/
Abstract

Pyrrole is an important aromatic heterocyclic scaffold found in many natural products and predominantly used in pharmaceuticals. Continuous efforts are being made to design and synthesize various pyrrole derivatives using different synthetic procedures. Among them, the Clauson-Kaas reaction is a very old and well-known method for synthesizing a large number of N-substituted pyrroles. In recent years, due to global warming and environmental concern, research laboratories and pharmaceutical industries around the world are searching for more environmentally friendly reaction conditions for synthesizing compounds. As a result, this review describes the use of various eco-friendly greener protocols to synthesize N-substituted pyrroles. This synthesis involves the reaction of various aliphatic/aromatic primary amines, and sulfonyl primary amines with 2,5-dimethoxytetrahydrofuran in the presence of numerous acid catalysts and transition metal catalysts. The goal of this review is to summarize the synthesis of various N-substituted pyrrole derivatives using a modified Clauson-Kaas reaction under diverse conventional and greener reaction conditions.

摘要

吡咯是一种重要的芳香杂环骨架，存在于许多天然产物中，主要用于制药领域。人们一直在不断努力，使用不同的合成方法来设计和合成各种吡咯衍生物。其中，克劳森 - 卡斯反应是一种非常古老且著名的合成大量N - 取代吡咯的方法。近年来，由于全球变暖和环境问题，世界各地的研究实验室和制药行业都在寻找更环保的反应条件来合成化合物。因此，本综述描述了使用各种环保的绿色方法合成N - 取代吡咯。这种合成涉及各种脂肪族/芳香族伯胺以及磺酰基伯胺与2,5 - 二甲氧基四氢呋喃在多种酸催化剂和过渡金属催化剂存在下的反应。本综述的目的是总结在不同的传统和绿色反应条件下，使用改进的克劳森 - 卡斯反应合成各种N - 取代吡咯衍生物的方法。

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ACS Infect Dis. 2022 Apr 8;8(4):757-767. doi: 10.1021/acsinfecdis.1c00450. Epub 2022 Mar 3.
4
Pyrrole as an Important Scaffold of Anticancer Drugs: Recent Advances.吡咯作为抗癌药物的重要支架：最新进展。
J Pharm Pharm Sci. 2022;25:24-40. doi: 10.18433/jpps32417.
5
Recent advances in the biosynthesis strategies of nitrogen heterocyclic natural products.氮杂环天然产物生物合成策略的最新进展。
Nat Prod Rep. 2022 Jan 26;39(1):139-162. doi: 10.1039/d1np00017a.
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Total Synthesis and Antimalarial Activity of 2-(-Hydroxybenzyl)-prodigiosins, Isoheptylprodigiosin, and Geometric Isomers of Tambjamine MYP1 Isolated from Marine Bacteria.2-(-羟苄基)普洛托品、异庚基普洛托品和海洋细菌分离的 Tambjamine MYP1 的几何异构体的全合成及抗疟活性。
J Med Chem. 2021 Jun 24;64(12):8739-8754. doi: 10.1021/acs.jmedchem.1c00748. Epub 2021 Jun 10.
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Potent Antimalarials with Development Potential Identified by Structure-Guided Computational Optimization of a Pyrrole-Based Dihydroorotate Dehydrogenase Inhibitor Series.通过基于吡咯的二氢乳清酸脱氢酶抑制剂系列的结构导向计算优化，鉴定出具有发展潜力的有效抗疟药物。
J Med Chem. 2021 May 13;64(9):6085-6136. doi: 10.1021/acs.jmedchem.1c00173. Epub 2021 Apr 20.
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Pyrrole-2,5-dione analogs as a promising antioxidant agents: microwave-assisted synthesis, bio-evaluation, SAR analysis and DFT studies/interpretation.吡咯-2,5-二酮类似物作为一种有前途的抗氧化剂：微波辅助合成、生物评价、SAR 分析和 DFT 研究/解释。
Bioorg Chem. 2021 Jan;106:104465. doi: 10.1016/j.bioorg.2020.104465. Epub 2020 Nov 9.
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Cascade Synthesis of Pyrroles from Nitroarenes with Benign Reductants Using a Heterogeneous Cobalt Catalyst.使用多相钴催化剂，以良性还原剂从硝基芳烃级联合成吡咯。
Angew Chem Int Ed Engl. 2020 Oct 12;59(42):18679-18685. doi: 10.1002/anie.202007613. Epub 2020 Aug 31.
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A Review on Recent Advances in Nitrogen-Containing Molecules and Their Biological Applications.关于含氮分子及其生物应用的最新进展综述。
Molecules. 2020 Apr 20;25(8):1909. doi: 10.3390/molecules25081909.