Advances in Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones

Abstract

2,3-Dihydroquinazolin-4(1H)-one compounds are an important class of nitrogen-containing fused heterocycles, which possess a wide range of pharmacological and biological activities and have important applications in the fields of synthesis and research & development of drugs. Therefore, its synthetic methods have also attracted considerable attention. In this paper, the main advances in the synthesis of 2,3-dihydroquinazolin-4(1H)-ones and their proposed reaction mechanisms from the raw materials such as o-aminobenzamides, isatoic anhydrides, o-nitrobenzamides, o-azidobenzamide, o-bromobenzamide, o-bromobenzonitrile, o-aminobenzoic acids, o-aminobenzonitrile, o-amino-N-(propa-1,2-dienyl)benzamides, and N-alkyl anilines were introduced and reviewed, respectively. Finally, the synthesis of these compounds was summarized and the prospect of their development was prospected. Keywords 2,3-dihydroquinazolin-4(1H)-one; o-aminobenzamides; isatoic anhydrides; N-alkyl anilines; C-H activation & functionalization; palladium catalysis 2,3-二氢喹唑啉-4(1H)-酮是一类重要的含氮稠杂环 化合物, 具有抗癌 [1～3] 、抗肿瘤 [4～6] 、治疗高血压 [7～9] 、 抗炎 [10～12] 、抗菌 [13～15] 、利尿 [9,16,17] 、抗病毒 [18] 、抗痉 挛 [19] 、抑制疟原虫增殖 [20] 、驱虫 [21] 、镇痛 [12] 等作用以 及抑制组织蛋白酶 B&H [22] 、胆碱酯酶 [23,24] 、凝血因子 Xa [25] 、肌苷 5'-一磷酸脱氢酶 [26] 、蛋白激酶 C-θ [27] 、瞬 时受体电位通道 M2 [28] 等广泛的药理及生物活性; 此外, 该类化合物也很容易被氧化成其喹唑啉-4(3H)-酮类似 物, 后者通常作为重要模块用于构建天然产物 [29～31] 及 药物分子 [32～34]. 由于 2,3-二氢喹啉-4(1H)-酮类化合物具有广泛且重 要的生物活性及应用价值, 其合成方法也自然引起了人 们的极大兴趣和关注.根据国内外的研究动态, 对其主 要合成方法进行了总结.

Synthesis and Biological Activities of Novel N-(2-(5-(3-Bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl)-1,3,4-oxadiazol-2-yl)-4-chloro-6-methylphenyl) Amides

“…结果表明该系列化合物具有一定的杀虫活性, 对油 菜菌核病菌的抑菌效果较为明显, 部分化合物优于对照 药 triadimefon 和 chlorantraniliprole, 为后续此类型化合 物的深入研究提供了参考信息. 4)按照文献 [4,23,24] 合成. 白色固体, 产率 70%.…”

“…Keywords N-pyridylpyrazole derivatives; 1,3,4-oxadiazole; synthesis; insecticidal activity; fungicidal activity 在长期的生产实践过程中, 农药的使用在解决粮食 问题上发挥着至关重要的作用, 尤其是化学农药, 在农 业病虫草害综合防治中具有廉价、使用方便以及效果显 著等优点, 因而备受瞩目 [1～3] . 但近年来, 随着人们对 环境保护认识的日益加深, 一些传统农药由于高毒、生 态污染及易产生抗性等问题而陆续遭到禁用, 因此具有 高效、低毒和对环境友好等特点的新型绿色农药的研发 是新农药创制的必然趋势 [4,5] .…”

Engineering the heterogeneous photocatalytic activity of crystalline decatungstate-based coordination polymers

“…A common strategy to obtain ordered crystalline materials containing specific transition metal-based structures is to construct frameworks based on coordination bonds between metal ions and organic linkers. 18–20 A variety of crystalline coordination polymers featuring transition metal coordinated DT units have been reported as potential photocatalysts in recent studies. They exhibit distinct structures and DT coordination modes, which lead to different catalytic performances.…”

Studies on the Synthesis and Biological Activities of Novel Dihydroquinazolinone-Containing Caffeine Derivatives

“…7 进而与中间体 2a～2i 在氩气 氛围中及化学计量的三氟甲磺酸存在下, 以水/乙醇 (V∶V＝3∶1)为溶剂、 75 ℃下反应 1～5 h, 可以 44%～ 55%的产率得到目标化合物 Ia～Ii. 值得注意的是, 与 以往文献中选择单一溶剂和催化量的强酸的反应条件 合成二氢喹唑啉酮类结构相比 [26] , 本工作选用化学计 量的强酸以及水/乙醇混合溶剂体系, 不仅使缩合反应 顺利发生, 更提高了转化率. 以中间体 7 与中间体 4a～ 4d 在同样的条件下反应即可顺利获得目标产物 Ij～Im.…”