N-（吡啶-2-基）酰胺导向、铜介导的芳烃C - H键氰化反应：合成3-（吡啶-2-基）喹唑啉-2,4(1H,3H)-二酮的新方法

IF 2 3区化学 Q2 CHEMISTRY, ORGANIC

Journal of Heterocyclic Chemistry Pub Date : 2025-06-01 DOI:10.1002/jhet.4953

Ali Nasirpour, Zarrin Ghasemi, Seyed Abolfazl Hosseini-Yazdi, Michal Dusek, Monika Kucerakova

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引用次数: 0

摘要

在此，我们报道了N-（吡啶-2-基）酰胺作为铜介导芳酰胺与KOCN偶联的导向基团的效率，得到3-（吡啶-2-基）喹唑啉-2,4(1H,3H)-二酮衍生物。这些产物是通过原位生成的2-芳基异氰酸酯中间体的分子内环化得到的。我们还鉴定了一种双共络合物，推测它是参与邻位C - H活化反应的物质。

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N-(Pyridin-2-yl)Amide-Directed, Copper-Mediated Cyanatation of Arene CH Bonds: A New Approach for the Synthesis of 3-(Pyridin-2-yl)Quinazoline-2,4(1H,3H)-Diones

Herein, we report the efficiency of N-(pyridine-2-yl)-amide as a directing group for copper-mediated coupling of arylamide with KOCN to give 3-(pyridin-2-yl)quinazoline-2,4(1H,3H)-dione derivatives. These products were obtained through an intramolecular cyclization of in situ-generated 2-arylisocyanate intermediates. We also identified a bicopperic complex speculated to be a species involved in ortho CH activation reactions.

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来源期刊

Journal of Heterocyclic Chemistry 化学-有机化学

CiteScore

5.20

自引率

4.20%

发文量

177

审稿时长

3.9 months

期刊介绍： The Journal of Heterocyclic Chemistry is interested in publishing research on all aspects of heterocyclic chemistry, especially development and application of efficient synthetic methodologies and strategies for the synthesis of various heterocyclic compounds. In addition, Journal of Heterocyclic Chemistry promotes research in other areas that contribute to heterocyclic synthesis/application, such as synthesis design, reaction techniques, flow chemistry and continuous processing, multiphase catalysis, green chemistry, catalyst immobilization and recycling.