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Fe 催化的 4-羟基色满-2-酮和吡喃-2-酮的分子内亲核取代/活化芳环开环:通过非对称三芳基甲烷轻松获得 2,3-二取代呋喃并[3,2,-]香豆素和呋喃并[3,2,-]吡喃-4-酮

Fe-Catalyzed Domino Intramolecular Nucleophilic Substitution of 4-Hydroxychromen-2-one and Pyran-2-one/Ring Opening of Activated Arene: An Easy Access to 2,3-Disubstituted Furo[3,2,-]coumarins and Furo[3,2,-]pyran-4-ones via Nonsymmetric Triarylmethanes.

机构信息

Department of Chemistry, University of Minnesota, 207 Pleasant Street SE, Minneapolis, Minnesota 55455, United States.

出版信息

Org Lett. 2020 Mar 6;22(5):1801-1806. doi: 10.1021/acs.orglett.0c00123. Epub 2020 Feb 25.

Abstract

A one-pot synthesis of functionalized 2,3-disubstituted furo[3,2,-]coumarins and furo[3,2,-]pyran-4-ones under hydrated ferric sulfate catalysis was performed. It was revealed that the reaction proceeds with intramolecular cyclofunctionalization of nonsymmetric triarylmethanes via ring opening of 2-methylfuran followed by recyclization, resulting in the selective formation of desired products. The versatility of this method was demonstrated via the succinct synthesis of an anticoagulant agent analogue and 2,3-disubstituted benzofurans.

摘要

在硫酸铁水合物催化下,一锅法合成了功能化的 2,3-二取代呋喃并[3,2,-]色烯和呋喃并[3,2,-]吡喃-4-酮。反应通过非对称三芳基甲烷的分子内环官能化进行,通过 2-甲基呋喃开环,然后再环化,选择性地得到所需产物。该方法通过简洁合成抗凝剂类似物和 2,3-二取代苯并呋喃展示了其多功能性。

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