有机化学 ›› 2022, Vol. 42 ›› Issue (11): 3740-3746.DOI: 10.6023/cjoc202204059 上一篇    下一篇

研究论文

三组分一锅法合成3,4-二氢喹唑啉衍生物

赵龙, 阳茂林, 陈皓冉, 丁明武*()   

  1. 华中师范大学 农药与化学生物学教育部重点实验室 武汉 430079
  • 收稿日期:2022-04-25 修回日期:2022-06-28 发布日期:2022-07-20
  • 通讯作者: 丁明武
  • 基金资助:
    国家自然科学基金(21572075)

One-Pot Three-Component Synthesis of 3,4-Dihydroquinazoline Derivatives

Long Zhao, Maolin Yang, Haoran Chen, Mingwu Ding()   

  1. Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, Central China Normal University, Wuhan 430079
  • Received:2022-04-25 Revised:2022-06-28 Published:2022-07-20
  • Contact: Mingwu Ding
  • Supported by:
    National Natural Science Foundation of China(21572075)

提出了一种通过偶氮二甲酸二乙酯(DEAD)促进的氧化Ugi/氮杂Wittig反应合成3,4-二氢喹唑啉的新方法. 该方法应用膦亚胺5N-芳基-1,2,3,4-四氢异喹啉6和羧酸7在DEAD存在下发生串联氧化型Ugi/氮杂Wittig反应, 以中等到良好的产率生成3-(四氢异喹啉-1-甲酰基)取代的3,4-二氢喹唑啉8.

关键词: 3,4-二氢喹唑啉, 膦亚胺, 异腈, 氧化型Ugi反应, 氮杂Wittig反应

A new one-pot synthesis of 3,4-dihydroquinazolines by diethyl azodicarboxylate (DEAD)-promoted oxidative Ugi/ aza-Wittig reaction was developed. The reactions of iminophosphoranes 5, N-aryl-1,2,3,4-tetrahydroisoquinolines 6 and acids 7 produced 3-(tetrahydroisoquinolin-1-formyl) substituted 3,4-dihydroquinazolines 8 in moderate to good yields in the presence of DEAD by tandem oxidative Ugi/aza-Wittig reaction.

Key words: 3,4-dihydroquinazoline-one, iminophosphorane, isocyanide, oxidative Ugi reaction, aza-Wittig reaction