Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (4): 1668-1676.DOI: 10.6023/cjoc202601030 Previous Articles     Next Articles

ARTICLES

叔丁基过氧化氢促进喹喔啉酮、N-芳基甘氨酸和多聚甲醛的三组分反应: 高效合成四氢咪唑并[1,5-a]喹喔啉酮

李婷a, 欧阳文韬a, 易荣楠b,*(), 唐欲才c, 杨梓d,*(), 吴超a,*(), 何卫民a,*()   

  1. a 南华大学化学化工学院 湖南衡阳 421001
    b 湖南警察学院 食药环及毒品检验技术湖南省普通高等学校重点实验室 食药环及毒品检验技术湖南省普通高等学校重点实验室 长沙 410138
    c 湖南文理学院化学与材料工程学院 湖南常德 415000
    d 长沙医学院 功能核酸基础与临床湖南省普通高校重点实验室 功能核酸基础与临床湖南省普通高校重点实验室 长沙 410219
  • 收稿日期:2026-01-20 修回日期:2026-03-31 发布日期:2026-04-13
  • 通讯作者: 易荣楠, 杨梓, 吴超, 何卫民
  • 基金资助:
    湖南省自然科学基金(2026JJ90135); 湖南省教育厅科学研究(25A0703); 长沙市自然科学基金(104872)

t-Butyl Hydroperoxide-Promoted Three-Component Reaction of Quinoxalin-2(1H)-ones, N-Phenylglycines and Paraformaldehyde: an Efficient Approach to Tetrahydroimidazo-[1,5-a]quinoxalin-4(5H)-ones

Ting Lia, Wentao Ouyanga, Rongnan Yib,*(), Yucai Tangc, Zi Yangd,*(), Chao Wua,*(), Weimin Hea,*()   

  1. a School of Chemistry and Chemical Engineering, University of South China, Hengyang, Hunan 421001
    b Key Laboratory of Food & Environment & Drug Monitoring and Testing of Universities in Hunan Province, Hunan Police Academy, Changsha 410138
    c College of Chemistry and Materials Engineering, Hunan University of Arts and Science, Changde, Hunan 415000
    d Hunan Provincial University Key Laboratory of the Fundamental and Clinical Research on Functional Nucleic Acid, Changsha Medical University, Changsha 410219
  • Received:2026-01-20 Revised:2026-03-31 Published:2026-04-13
  • Contact: Rongnan Yi, Zi Yang, Chao Wu, Weimin He
  • Supported by:
    Hunan Provincial Natural Science Foundation(2026JJ90135); Scientific Research Fund of Hunan Provincial Education Department(25A0703); Changsha Natural Science Foundation(104872)

C3-Functionalized quinoxalin-2(1H)-ones generally exhibit promising biological activities and pharmacological values. Currently, a series of C3-functionalized quinoxalin-2(1H)-ones bearing alkyl, aryl, amino, fluoroalkyl, acyl, and phosphoryl groups have been synthesized through the C3—H functionalization strategy. However, reports on the construction of fused-heterocycles incorporating a quinoxalinone skeleton via a cascade cyclization reaction initiated by C3—H activation remain relatively limited. Herein, an efficient multi-component synthetic protocol was reported using low-cost, readily available t-butyl hydroperoxide as the oxidant and paraformaldehyde as the C1 synthon, enabling the synthesis of a series of tetrahydroimidazo[1,5-a]quinoxalin-4(5H)-ones. This reaction proceeds without the need for special apparatus under ambient air, featuring mild conditions, simple operation, and low cost. This strategy holds great potential as a practical approach for the synthesis of tetrahydroimidazoquinoxalinone compounds.

Key words: quinoxalin-2(1H)-ones, N-phenylglycines, paraformaldehyde, decarboxylation, cyclization reaction