有机化学 ›› 2024, Vol. 44 ›› Issue (5): 1686-1690.DOI: 10.6023/cjoc202311010 上一篇    下一篇

研究简报

一锅法还原胺化/N-酰基化/Aza-Wittig反应合成3,4-二氢喹唑啉

张文生*(), 郑伟, 左国强, 马科友, 肖合全, 刘改云   

  1. 济源职业技术学院材料工程学院 河南济源 459000
  • 收稿日期:2023-11-08 修回日期:2024-01-11 发布日期:2024-01-30
  • 基金资助:
    河南省科技攻关计划(212102310883)

One-Pot Reductive Amination/N-Acylation/Aza-Wittig Reaction for the Synthesis of 3,4-Dihydroquinazolines

Wensheng Zhang(), Wei Zheng, Guoqiang Zuo, Keyou Ma, Hequan Xiao, Gaiyun Liu   

  1. School of Material Engineering, Jiyuan Vocational and Technical College, Jiyuan, Henan 459000
  • Received:2023-11-08 Revised:2024-01-11 Published:2024-01-30
  • Contact: *E-mail: tongjizws@163.com
  • Supported by:
    Program for Science and Technology Development of Henan Province(212102310883)

发展了一种三步骤一锅法合成3,4-二氢喹唑啉的方法. 该方法包括邻叠氮苯甲醛与胺的还原胺化, 酰氯的N-酰基化和P(Bu-n)3作用下的Aza-Wittig反应. 芳香胺、苄胺和脂肪族链胺都可以顺利参加该多步骤反应, 其中脂肪族丁胺的收率略低. 芳香酰氯中含有供电子基团时可以获得满意的收率, 但是含有吸电子氯原子的芳香酰氯和丙烯酰氯则不能得到目标产物.

关键词: 3,4-二氢喹唑啉, 合成, 还原胺化, 分子内N-维悌希反应

A one-pot three-step synthesis for the preparation of 3,4-dihydroquinazolines is developed. This method involves a reductive amination of o-azidebenzaldehydes with amines followed by N-acylation using azoyl chloride and Staudinger/ intramolecular aza-Wittig sequence in the presence of P(Bu-n)3. Aromatic amines, benzylamines, and aliphatic chain amines could complete this multi-step reaction. The yield of butylamine, however, was slightly lower. Satisfactory yields can be obtained when aromatic acyl chloride containing electron-donating groups on the benzene ring was used. However, aromatic acyl chloride with electron withdrawing chlorine atoms and acryloyl chloride failed to give the corresponding products.

Key words: 3,4-dihydroquinazoline, synthesis, reductive amination, intramolecular aza-Wittig reaction