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Aldehydic-amide Condensation Reaction to Synthesize Multi-nitrogen Heterocyclic Compounds Catalyzed by Acidic Ionic Liquids
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(School of Chemical Engineer, Nanjing University of Science & Technology, Nanjing 210094, China)

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    Abstract:

    A novel acidic ionic liquid(ILs), 1-dodecyl-3-(3-sulfopropyl)-imidazolium hydrogen sulfate [C3SO3HDoim]HSO4 was designed and synthesized, and used for condensation reaction of aldehyde and amine to synthesize the energetic material intermediates. Taking the synthesis of tetrahydroimidazo[4, 5-d]imidazol-e-2, 5-(1H, 3H)-dione, 2, 5, 7, 9-tetrazobicyclo[4,3,0]nonan-8-one and hexabenzylhexaazaisowurtzitane (HBIW) as the example, the influences of reaction temperature, reaction time, amount of ILs and types of ILs on condensation reaction were investigated. Results show that ILs [C3SO3HDoim]HSO4 has good catalytic activity, high cyclic utilization reusability and the yields of three kinds of multi-nitrogen heterocyclic compounds glycoluril, 2, 5, 7, 9-tetrazobicyclo[4,3,0]nonan-8-one and HBIW, can reach 95%, 89% and 81%, respectively.

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周治雷,王鹏程,陆明.酸性离子液体催化醛胺缩合反应制备多氮杂环化合物[J].含能材料,2016,24(6):532-537.
ZHOU Zhi-lei, WANG Peng-cheng, LU Ming. Aldehydic-amide Condensation Reaction to Synthesize Multi-nitrogen Heterocyclic Compounds Catalyzed by Acidic Ionic Liquids[J]. Chinese Journal of Energetic Materials,2016,24(6):532-537.

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History
  • Received:August 13,2015
  • Revised:September 14,2015
  • Adopted:September 24,2015
  • Online: May 20,2016
  • Published: June 03,2016