高等学校化学学报 ›› 2003, Vol. 24 ›› Issue (1): 64.

• 论文 • 上一篇    下一篇

咪唑衍生物的一锅法选择性合成

蒋宗林, 肖蓉, 苏晓渝, 鄢家明, 谢如刚   

  1. 四川大学化学学院, 成都 610064
  • 收稿日期:2001-11-13 出版日期:2003-01-24 发布日期:2003-01-24
  • 通讯作者: 谢如刚(1938年出生),男,教授,博士生导师,从事生物有机化学及高选择性有机合成研究.E-mail:schemorg@mail.sc.cninfo.net E-mail:schemorg@mail.sc.cninfo.net
  • 基金资助:

    国家自然科学基金(批准号:29872028,20172038)资助

Selective One-pot Synthetic Method for Imidazole and Benzimidazole Derivatives

JIANG Zong-Lin, XIAO Rong, SU Xiao-Yu, YAN Jia-Ming, XIE Ru-Gang   

  1. College of Chemistry, Sichuan University, Chengdu 610064, China
  • Received:2001-11-13 Online:2003-01-24 Published:2003-01-24

摘要: 1-(2-氰乙基)咪唑与α,ω-二卤代烃、二溴苄及三溴苄选择性地发生季铵化反应,继而在碱作用下发生Hoffmann型消去反应,简便而高效地制备了3个系列咪唑衍生物:1-(ω-卤烷基)咪唑3a~3e、含中心功能基的双咪唑5a~5b和三咪唑6a~6b,并类似地制得相应的苯并咪唑衍生物7和8.

关键词: 咪唑衍生物, 季铵化反应, Hoffmann型消去反应

Abstract: A novel and selective one-pot synthetic method of imidazole and benzimidazole derivatives has been developed. Three series of target compounds, 1-(ω-haloalkyl) imidazoles 3a-3e, bis-imidazoles 5a-5b and tri-imidazoles 6a-6b have been synthesized by the selective quaterisation of 1H-imidazole-1-propanenitrile (1) with α, ω-dihalide, bis(bromomethyl) benzene or tri(bromomethyl) benzene to obtain imidazolium salts, following by Hoffmann-type elimination. Similarly, benzimidazole analogues 7 and 8 were also prepared. It is found that important factors affecting this selective quaterisation are the solvent, temperature, structure and amount of halides.

Key words: Imidazole derivative, Quaterisation, Hoffmann-type elimination

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