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通过香豆素甲醛的三组分膦酰化反应合成6-色烯并[4,3 -]喹啉-7-基膦酸酯及其抗菌和光物理性质

Synthesis of 6-Chromeno[4,3-]quinolin-7-ylphosphonates through Three Component Phosphonylation of Coumarin Carbaldehyde and Their Antimicrobial and Photophysical Properties.

作者信息

Ghashghaee Mojtaba, Kaboudin Babak, Kazemi Foad, Hassan Maryam, Fukaya Haruhiko, Yanai Hikaru

机构信息

Department of Chemistry, Institute for Advanced Studies in Basic Sciences (IASBS), Gava Zang, Zanjan 45137-66731, Iran.

Zanjan Pharmaceutical Biotechnology Research Center, Zanjan University of Medical Sciences, Zanjan 45139-56184, Iran.

出版信息

J Org Chem. 2024 Jun 7;89(11):7662-7670. doi: 10.1021/acs.joc.4c00340. Epub 2024 May 29.

DOI:10.1021/acs.joc.4c00340
PMID:38809577
Abstract

Organophosphorylated coumarin derivatives were synthesized by a three-component reaction of 4-chloro-3-formylcoumarin, aromatic amines, and dialkyl phosphite in the presence of ZnCl. This process includes the formation of C(sp)-P and C(sp)-N bonds in one pot. The modular scope of the reaction allowed rapid access to a variety of 6-chromeno[4,3-]quinolin-7-ylphosphonate derivatives in good yields. Furthermore, photophysical studies of the products revealed their stimulating fluorescence properties.

摘要

通过4-氯-3-甲酰基香豆素、芳香胺和亚磷酸二烷基酯在ZnCl存在下的三组分反应合成了有机磷酰化香豆素衍生物。该过程包括在一锅法中形成C(sp)-P键和C(sp)-N键。反应的模块化范围使得能够以良好的产率快速获得各种6-色烯并[4,3-]喹啉-7-基膦酸酯衍生物。此外,对产物的光物理研究揭示了它们具有激发荧光特性。

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