铜催化[5 + 1]环化溶剂控制选择性合成喹唑啉酮和2-芳基喹唑啉酮

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron Pub Date : 2025-07-24 DOI:10.1016/j.tet.2025.134858

Min Wang, Kexin Li, Jiaao Xue, Kewei Hu, Duoluo Guo, Qun Cai

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引用次数: 0

摘要

建立了铜催化环化反应选择性合成喹唑啉酮类和2-芳基喹唑啉酮类化合物的方法。在Cu/DMSO体系中，邻氨基苯甲酰胺作为史无前例的C1源参与了[5 + 1]环化，通过双C-N键裂解形成2-芳基喹唑啉酮。同时调整溶剂为MeOH，可获得高收率的喹唑啉酮。此外，克级组装和后期转化的喹唑啉类化合物证明了该方法的重要合成应用。

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Solvent-controlled selective synthesis of quinazolinones and 2-arylquinazolinones via copper-catalyzed [5 + 1] annulation

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Solvent-controlled selective synthesis of quinazolinones and 2-arylquinazolinones via copper-catalyzed [5 + 1] annulation

A copper-catalyzed cyclization for the selective synthesis of quinazolinones and 2-arylquinazolinones depending on solvent control has been established. o-Aminobenzamide is employed as an unprecedented C1 source involving in the [5 + 1] annulation to form 2-arylquinazolinones via double C–N bonds cleavage in Cu/DMSO system. While adjusting the solvent to MeOH achieves quinazolinones in high yields. Furthermore, the gram-scalable assembly and late-stage transformations of quinazolines demonstrate significant synthetic applications of this method.

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来源期刊

Tetrahedron 化学-有机化学

CiteScore

3.90

自引率

4.80%

发文量

439

审稿时长

34 days

期刊介绍： Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry. Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters. Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.