A New Route for the Synthesis of (Trichloromethyl)Quinazoline-4(1H)-One and (1,2,3-Triazole)-Quinazoline-4(1H)-One Functionalized Derivatives via Copper-Catalyzed One-Pot Multicomponent Reactions

IF 2 3区 化学 Q2 CHEMISTRY, ORGANIC Journal of Heterocyclic Chemistry Pub Date : 2024-09-27 DOI:10.1002/jhet.4899
Manijeh Nematpour
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Abstract

The synthesis of functionalized (trichloromethyl)quinazoline-4(1H)-one with high yields through a novel three-component intramolecular CH activation reaction from trichloroacetonitrile, benzoyl chlorides, and various primary amines is a remarkable achievement in organic chemistry. This strategy offers a direct and efficient route to access complex molecular structures from readily available starting materials. The use of copper (I) as a catalyst and L-proline as a ligand in tetrahydrofuran at room temperature highlights the importance of transition metal catalysis in enabling selective CH activation processes. Furthermore, the subsequent transformation of the obtained product with phenylacetylene and sodium azide in the presence of a copper catalyst in water solvent at room temperature demonstrates the versatility of this synthetic approach in accessing new (1,2,3-triazole)-quinazoline-4(1H)-one derivative. The combination of available starting materials, catalytic systems, mild reaction conditions, and ease of purification procedures contributes to the attractiveness of this method for the synthesis of diverse (trichloromethyl)quinazoline-4(1H)-one and (1,2,3-triazole)-quinazoline-4(1H)-one derivative.

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铜催化一锅多组分反应合成(三氯甲基)喹唑啉-4(1H)- 1和(1,2,3-三唑)-喹唑啉-4(1H)- 1功能化衍生物的新途径
以三氯乙腈、苯甲酰氯和多种伯胺为原料,通过分子内三组分C - H活化反应,合成功能化(三氯甲基)喹唑啉-4(1H)- 1是有机化学领域的一项重大成就。这种策略提供了一种直接有效的途径,可以从现成的起始材料中获得复杂的分子结构。在室温下,四氢呋喃中使用铜(I)作为催化剂,l -脯氨酸作为配体,突出了过渡金属催化在实现选择性C - H活化过程中的重要性。此外,在室温下,在铜催化剂的存在下,将得到的产物与苯乙炔和叠氮化钠在水溶剂中转化,证明了该合成方法在获得新的(1,2,3-三唑)-喹唑啉-4(1H)- 1衍生物方面的通用性。可用的起始材料、催化体系、温和的反应条件和简单的纯化程序使该方法具有合成多种(三氯甲基)喹唑啉-4(1H)- 1和(1,2,3-三唑)-喹唑啉-4(1H)- 1衍生物的吸引力。
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来源期刊
Journal of Heterocyclic Chemistry
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.
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