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DOI: https://doi.org/10.6023/cjoc202602009

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研究

  • 唐旭 ,
  • 刘庆玉 ,
  • 虞莹 ,
  • 何振语 ,
  • 陈书友 ,
  • 李世清 ,
  • 孔翔飞
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  • 桂林理工大学化学与生物工程学院 桂林 541004

收稿日期: 2026-04-08

  修回日期: 2026-05-21

  网络出版日期: 2026-06-11

基金资助

国家自然科学基金地区科学基金项目（22261014）.

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Synthesis of 1-methyl-2-phenyl-2,3-dihydroquinazoline-4(1H)-one and its derivative

  • Tang Xu ,
  • Liu Qingyu ,
  • Yu Ying ,
  • He Zhenyu ,
  • Chen Shuyou ,
  • Li Shiqing ,
  • Kong Xiangfei
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  • College of Chemistry and Bioengineering, Guilin University of Technology, Guilin 541004, Guangxi, China

Received date: 2026-04-08

  Revised date: 2026-05-21

  Online published: 2026-06-11

Supported by

National Science Foundation of China (Grant Nos. 22261014)

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摘要

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,因此,本文提出一种高效合成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,使用消旋磷酸为催化剂,4Å型分子筛为吸水剂,在120 ℃时反应24 h。最终以57% - 98%的产率合成26个目标产物,其分子结构与核磁共振氢谱和碳谱、高分辨质谱、X射线单晶衍射谱的表征结果吻合;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

本文引用格式

唐旭 , 刘庆玉 , 虞莹 , 何振语 , 陈书友 , 李世清 , 孔翔飞 . 1-甲基-2-苯基-2,3-二氢喹唑啉-4(1H)-酮及其衍生物的合成研究[J]. 有机化学, 0 : 602009 -602009 . DOI: 10.6023/cjoc202602009

Abstract

N1-Substituted quinazolinone alkaloids hold significant research value in drug discovery; however, synthetic methods for such alkaloids have rarely been reported. Herein, we present an efficient approach for the synthesis of 1-methyl-2-phenyl-2,3-dihydroquinazolin-4(1H)-one and its derivatives. Using o-methylaminobenzamide 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 °C for 24 h. The final yield of the 26 target products ranged of 57% - 98%. The structures of all compounds were fully characterized by ¹H NMR, ¹³C NMR and high resolution mass spectrum. The structure of the template product was characterized by X-ray single-crystal diffraction. 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

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