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三氟甲磺酸钪介导的香豆素稠合呋喃的一锅法合成:一种依赖硫醇的反应,用于简便合成2-苯基-4H-呋喃并[3,2-]色烯-4-酮。

Sc(OTf)-Mediated One-Pot Synthesis of Coumarin-Fused Furans: A Thiol-Dependent Reaction for the Easy Access of 2-Phenyl-4H-furo[3,2-]chromen-4-ones.

作者信息

Jana Asim, Ali Danish, Bhaumick Prabhas, Choudhury Lokman H

机构信息

Department of Chemistry, Indian Institute of Technology Patna, Bihta, Patna 801106, India.

出版信息

J Org Chem. 2022 Jun 17;87(12):7763-7777. doi: 10.1021/acs.joc.2c00353. Epub 2022 Jun 1.

Abstract

Herein, we report a simple and efficient method for the preparation of novel thioether-linked coumarin-fused furans from the one-pot three-component reaction of arylglyoxal, 4-hydroxycoumarin, and various aromatic thiols in the presence of Sc(OTf) as a catalyst. This methodology is also applicable to cyclic 1,3-dicarbonyls such as cyclohexane-1,3-dione and dimedone. Depending upon the thiols, this methodology can either give a three-component thioether-linked coumarin-fused furan () or a two-component furocoumarin product (). Wide substrate scope, good to excellent yields, and products having more than one pharmaceutically important motif are the salient features of this methodology.

摘要

在此,我们报道了一种简单高效的方法,用于在三氟甲磺酸钪作为催化剂存在下,通过芳基乙二醛、4-羟基香豆素和各种芳香硫醇的一锅三组分反应制备新型硫醚连接的香豆素稠合呋喃。该方法也适用于环状1,3-二羰基化合物,如环己烷-1,3-二酮和达米酮。根据硫醇的不同,该方法可以得到三组分硫醚连接的香豆素稠合呋喃()或二组分呋喃香豆素产物()。底物范围广、产率良好至优异以及产物具有不止一个药学上重要的基序是该方法的显著特点。

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