SIOC English
有机化学
高级检索

有机化学 ›› 2026, Vol. 46 ›› Issue (10): 4087-4097.DOI: 10.6023/cjoc202602009 上一篇    下一篇

研究论文

1-甲基-2-苯基-2,3-二氢喹唑啉-4(1H)-酮及其衍生物的合成

唐旭†, 刘庆玉†, 虞莹, 何振语, 陈书友*(), 李世清*(), 孔翔飞*()   

  1. 桂林理工大学化学与生物工程学院 广西桂林 541004
  • 收稿日期:2026-04-08 修回日期:2026-05-21 发布日期:2026-06-10
  • 作者简介:

    †共同第一作者.

  • 基金资助:
    国家自然科学基金(22261014)

Synthesis of 1-Methyl-2-phenyl-2,3-dihydroquinazoline-4(1H)-one and Its Derivatives

Xu Tang†, Qingyu Liu†, Ying Yu, Zhenyu He, Shuyou Chen*(), Shiqing Li*(), Xiangfei Kong*()   

  1. College of Chemistry and Bioengineering, Guilin University of Technology, Guilin, Guangxi 541004

RichHTML

2

PDF

81

补充材料

1

N1-取代的喹唑啉酮类生物碱在药物研发领域具有重要的研究价值, 开发了一种高效合成1-甲基-2-苯基-2,3-二氢喹唑啉-4(1H)-酮及其衍生物的方法, 即采用邻甲氨基苯甲酰胺和苯甲醛衍生物为原料, 消旋磷酸为催化剂, 4Å型分子筛为吸水剂, 在120 ℃时反应24 h. 反应最终以57%~97%的产率得到26个目标产物, 其结构经1H NMR、13C NMR、HRMS及X射线单晶衍射谱表征. 此外, 当使用手性磷酸催化剂时, 实现了手性目标产物的合成. 总之, 该方法原料易得、经济高效且官能团耐受性良好, 为合成N1-取代的喹唑啉酮类生物碱提供了一种实用且高效的策略.

关键词: 喹唑啉酮, 消旋磷酸, 手性磷酸

N1-Substituted quinazolinone alkaloids hold significant research value in drug discovery. An efficient approach for the synthesis of 1-methyl-2-phenyl-2,3-dihydroquinazolin-4(1H)-one and its derivatives was developed. Using o-methylamino-benzamide and benzaldehyde derivatives as starting materials, racemic phosphoric acid as the catalyst, and 4 Å molecular sieves as a desiccant, the reaction proceeded at 120 ℃ for 24 h. Twenty-six target products were prepared with yields ranging from 57% to 98%. The structures of all compounds were characterized by 1H NMR, 13C NMR, HRMS and single crystal X-ray diffraction analysis. Moreover, the synthesis of chiral target products was achieved when using chiral phosphoric acid as the catalyst. In summary, this method features readily accessible starting materials, cost-effectiveness, high efficiency, and good functional-group tolerance, offering a practical and efficient strategy for synthesizing N1-substituted quinazolinone alkaloids.

Key words: quinazolinone, racemic phosphoric acid, chiral phosphoric acid