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锆催化利用邻苯二酚、醛和醋酸铵反应一锅法合成苯并恶唑。

Zirconium-catalyzed one-pot synthesis of benzoxazoles using reaction of catechols, aldehydes and ammonium acetate.

作者信息

Mohammadi Masoumeh, Aboonajmi Jasem, Panahi Farhad, Sasanipour Maryam, Sharghi Hashem

机构信息

Department of Chemistry, College of Sciences, Shiraz University, Shiraz, Fars, 71454, Iran.

出版信息

Sci Rep. 2024 Oct 29;14(1):25973. doi: 10.1038/s41598-024-76839-3.

DOI:10.1038/s41598-024-76839-3
PMID:39472665
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11522672/
Abstract

In this study, an efficient method for the synthesis of benzoxazoles by coupling catechols, aldehydes and ammonium acetate using ZrCl as catalyst in ethanol is reported. A wide range of benzoxazoles (59 examples) are smoothly produced in high yields (up to 97%). Other advantages of the method include large-scale synthesis and the use of oxygen as an oxidant. The mild reaction conditions allowed late-stage functionalization, facilitating access to several derivatives with biologically relevant structures such as β-lactam and quinoline heterocycles.

摘要

本研究报道了一种在乙醇中以ZrCl为催化剂,通过邻苯二酚、醛和醋酸铵偶联合成苯并恶唑的有效方法。多种苯并恶唑(59个实例)能以高产率(高达97%)顺利生成。该方法的其他优点包括大规模合成以及使用氧气作为氧化剂。温和的反应条件允许进行后期官能化,便于获得几种具有生物学相关结构的衍生物,如β-内酰胺和喹啉杂环。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9c20/11522672/7cbb00594741/41598_2024_76839_Fig13_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9c20/11522672/126bb30990ce/41598_2024_76839_Fig8_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9c20/11522672/967c7456409b/41598_2024_76839_Fig9_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9c20/11522672/ce4eeb14a1b7/41598_2024_76839_Fig10_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9c20/11522672/b2ed829750f9/41598_2024_76839_Fig11_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9c20/11522672/f65f61ab84b6/41598_2024_76839_Fig12_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9c20/11522672/7cbb00594741/41598_2024_76839_Fig13_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9c20/11522672/126bb30990ce/41598_2024_76839_Fig8_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9c20/11522672/967c7456409b/41598_2024_76839_Fig9_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9c20/11522672/ce4eeb14a1b7/41598_2024_76839_Fig10_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9c20/11522672/b2ed829750f9/41598_2024_76839_Fig11_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9c20/11522672/f65f61ab84b6/41598_2024_76839_Fig12_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9c20/11522672/7cbb00594741/41598_2024_76839_Fig13_HTML.jpg

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本文引用的文献

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Int J Mol Sci. 2023 Jun 28;24(13):10807. doi: 10.3390/ijms241310807.
2
Trends and Opportunities in Organic Synthesis: Global State of Research Metrics and Advances in Precision, Efficiency, and Green Chemistry.有机合成的趋势与机遇:研究指标的全球状况及精准度、效率和绿色化学方面的进展。
J Org Chem. 2023 Apr 7;88(7):4031-4035. doi: 10.1021/acs.joc.2c03057.
3
DTPA-Bound Planar Catechin with Potent Antioxidant Activity Triggered by Fe Coordination.
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Antioxidants (Basel). 2023 Jan 18;12(2):225. doi: 10.3390/antiox12020225.
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Design and synthesis of functionalized 4-aryl-Catechol derivatives as new antiinflammtory agents with in vivo efficacy.设计和合成功能化 4-芳基儿茶酚衍生物作为具有体内疗效的新型抗炎剂。
Eur J Med Chem. 2022 Dec 5;243:114788. doi: 10.1016/j.ejmech.2022.114788. Epub 2022 Sep 27.
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Zirconium-Based Catalysts in Organic Synthesis.有机合成中的锆基催化剂
Top Curr Chem (Cham). 2022 Aug 11;380(5):41. doi: 10.1007/s41061-022-00396-4.
6
Iodine-catalyzed synthesis of benzoxazoles using catechols, ammonium acetate, and alkenes/alkynes/ketones C-C and C-O bond cleavage.碘催化利用邻苯二酚、醋酸铵和烯烃/炔烃/酮类进行苯并恶唑的合成及碳-碳和碳-氧键断裂。
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