CuI-Zn (OAc)2催化1,3-二酮/β-酮酯选择性C - _ - C键裂解生成喹唑啉-4(3H)-：微波辐射下快速、无溶剂合成策略

IF 2.9 3区化学 Q2 CHEMISTRY, ORGANIC Journal of Heterocyclic Chemistry Pub Date : 2024-10-30 DOI:10.1002/jhet.4929

Nazia Kausar, Mohd Afzal, Abdullah Alarifi, Abdulla Al Masum

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引用次数: 0

摘要

在微波辐射下，CuI-Zn (OAc)2催化1,3-二酮（包括环和非环）和β-酮酯的C - _ - C键选择性断裂，实现了一种新的、快速的、无溶剂的合成喹唑啉-4(3H)- 1的策略。与通常应用的合成策略不同的是，蒽酰胺（2-氨基苯酰胺）与各种醛或苄基醇进行环化-氧化顺序，这里，在CuI-Zn(OAc)2催化剂的存在下，蒽酰胺与β-酮酯/1,3-二酮化合物在无溶剂温和条件下通过罕见的C -羟基- C键裂解形成喹唑啉-4(3H)- 1支架，收率高。此外，该方法还显示出克级反应的能力。

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CuI–Zn(OAc)2 Catalyzed Selective CC Bond Cleavage of 1,3-Diketones/β-Ketoester for the Formation of Quinazolin-4(3H)-Ones: A Fast, Solvent-Free, Synthetic Strategy Under Microwave Irradiation

CuI–Zn(OAc)₂ catalyzed a new, fast, solvent-free strategy for the synthesis of quinazolin-4(3H)-ones via selective scission of CC bond of the 1,3-diketone (both cyclic and acyclic) and β-ketoester was achieved under microwave irradiation. In contrast to the frequently applied synthetic strategy that involves cyclization-oxidation sequence of anthranilamides (2-aminobenzamides) with various aldehydes or benzyl alcohols, here, anthranilamide reacts with β-ketoester/1,3-diketo compounds in presence of CuI-Zn(OAc)₂ catalyst to form quinazolin-4(3H)-ones scaffold through an uncommon CC bond cleavage under solvent-free mild conditions with excellent yields. Besides, this method displays its capacity for gram-scale 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.