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在空气中通过铜催化2-硝基苯甲腈与醇的串联环化反应简便合成喹唑啉-4(3)-酮。

Facile access to quinazolin-4(3)-ones by tandem Cu-catalyzed annulation of 2-nitrobenzonitrile and alcohols under air.

作者信息

Vu Xuan Lam, Van Phuc Ban, Nguyen Minh Hoang, Nguyen Thuy Anh T, Nguyen Thuy Linh, Nguyen Hien, Ngo Quoc Anh, An Nguyen Quang, Hung Tran Quang, Dang Tuan Thanh

机构信息

Faculty of Chemistry, VNU-Hanoi University of Science 19 Le Thanh Tong Hanoi Vietnam

Institute of Chemistry, Vietnamese Academy of Science and Technology (VAST) 18 Hoang Quoc Viet Hanoi Vietnam

出版信息

RSC Adv. 2025 Jul 21;15(32):25965-25970. doi: 10.1039/d5ra01550b.

DOI:10.1039/d5ra01550b
PMID:40697455
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12278901/
Abstract

A convenient Cu-catalyzed synthesis of 2-arylquinazolin-4(3)-one derivatives has been developed from simple starting materials such as 2-nitrobenzonitriles and alcohols under mild conditions. This procedure showed a broad substrate scope and tolerance of functional groups, high yields, and no need to use oxidants or reductants, making synthesis simple, convenient, and sustainable. Our methodology may be utilized for the one-pot synthesis of glycosminine alkaloid.

摘要

已经开发出一种方便的铜催化合成2-芳基喹唑啉-4（3H）-酮衍生物的方法，该方法以2-硝基苯甲腈和醇等简单原料在温和条件下进行。该方法具有广泛的底物范围和对官能团的耐受性，产率高，无需使用氧化剂或还原剂，使得合成简单、方便且可持续。我们的方法可用于糖胺生物碱的一锅法合成。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4dae/12278901/ae2ce61f231d/d5ra01550b-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4dae/12278901/deb591f4187d/d5ra01550b-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4dae/12278901/9c639021f783/d5ra01550b-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4dae/12278901/b0a1f0298c35/d5ra01550b-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4dae/12278901/ae2ce61f231d/d5ra01550b-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4dae/12278901/deb591f4187d/d5ra01550b-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4dae/12278901/9c639021f783/d5ra01550b-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4dae/12278901/b0a1f0298c35/d5ra01550b-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4dae/12278901/ae2ce61f231d/d5ra01550b-s3.jpg

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本文引用的文献

1
Facile Ru-catalysed synthesis of quinazolin-4(3)-ones by tandem cyclization of 2-nitrobenzonitrile and alcohol derivatives under air.
Org Biomol Chem. 2025 Jan 15;23(3):603-607. doi: 10.1039/d4ob01786b.
2
A Phosphine-Free Air-Stable Mn(II)-Catalyst for Sustainable Synthesis of Quinazolin-4(3)-ones, Quinolines, and Quinoxalines in Water.一种无膦且空气稳定的锰（II）催化剂，用于在水中可持续合成喹唑啉-4（3H）-酮、喹啉和喹喔啉。
J Org Chem. 2024 Apr 19;89(8):5250-5265. doi: 10.1021/acs.joc.3c02579. Epub 2024 Mar 30.
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Facile iodine-promoted synthesis of bis(1-imidazo[1,5-]pyridyl)arylmethanes and exploration of applications.碘促进的双（1-咪唑并[1,5-a]吡啶基）芳基甲烷的简便合成及应用探索。
Chem Commun (Camb). 2023 Feb 14;59(14):1947-1950. doi: 10.1039/d2cc05419a.
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Recent advances in the pharmacological diversification of quinazoline/quinazolinone hybrids.喹唑啉/喹唑啉酮杂化物药理学多样化的最新进展
RSC Adv. 2020 Nov 12;10(68):41353-41392. doi: 10.1039/d0ra06642g. eCollection 2020 Nov 11.
5
Cobalt-Catalyzed Tandem Transformation of 2-Aminobenzonitriles to Quinazolinones Using Hydration and Dehydrogenative Coupling Strategy.钴催化 2-氨基苯甲腈到喹唑啉酮的串联转化：水合与脱氢偶联策略。
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Synthesis of Quinazolin-4(3 H)-ones via the Reaction of 2-Halobenzamides with Nitriles.通过2-卤代苯甲酰胺与腈的反应合成喹唑啉-4(3H)-酮
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