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1-羟基吖啶酮的一锅法合成:β-喹醇与 -甲氧基羰基芳基异氰酸酯。

One-Pot Synthesis of 1-Hydroxyacridones from -Quinols and -Methoxycarbonylaryl Isocyanates.

机构信息

Department of Chemistry, Hunter College, 695 Park Avenue, New York, New York 10065, United States.

Ph.D. Program in Chemistry, The Graduate Center of the City University of New York, New York, New York 10016, United States.

出版信息

J Org Chem. 2020 Mar 20;85(6):4515-4524. doi: 10.1021/acs.joc.9b03307. Epub 2020 Feb 27.

DOI:10.1021/acs.joc.9b03307
PMID:32070098
Abstract

A variety of substituted acridones were synthesized via a one-pot, metal-free cascade reaction. In this event, the DBU-mediated addition between quinols and -methoxycarbonylaryl isocyanates formed a bicyclic oxazolidinone, followed by a sequence of intramolecular condensation, tautomerization, and decarboxylation, which led to the formation of acridones. The acridones showed mild activity against the human cytomegalovirus.

摘要

通过一锅、无金属级联反应,合成了多种取代的吖啶酮。在这个反应中,DBU 介导的醌和 -甲氧羰基芳基异氰酸酯之间的加成反应形成了二环恶唑烷酮,然后经过一系列的分子内缩合、互变异构和脱羧反应,生成了吖啶酮。吖啶酮对人巨细胞病毒表现出温和的活性。

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