4.5 Article

Catalytic Synthesis of N-(5-Methylfurfuryl)aniline from Bio-Derived Carbohydrates

Journal

ASIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 8, Issue 3, Pages 328-334

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.201800690

Keywords

heterogeneous catalysis; 5-methylfurfural; fructose; palladium; biomass

Funding

  1. National Key Research and Development Program of China [2017YFD0800900]
  2. National Young Overseas High-Level Talents Introduction Plan of China
  3. National Natural Science Foundation of China [21808100]
  4. Graduate Student Innovation Special Fund Project of Nanchang University [cx2016010]

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The value-added chemicals derived from lignocellulosic resources are mainly oxygen-containing compounds while nitrogen-containing compounds are also important in the industry and ambitiously desired to be obtained from bio-based carbohydrates. Here we report an efficient two-step approach from fructose under mild conditions to obtain N-(5-methylfurfuryl)aniline, a necessary nitrogenous intermediate for some important epoxyisoindoles which have good combat-Alzheimer's and antitumor biological activities. First, 5-methylfurfural was prepared with HI and H3PO3 in a biphasic solution from fructose, then it was isolated and used for N-(5-methylfurfuryl)aniline synthesis through reductive amination catalyzed by a heterogeneous palladium catalyst. Besides, the substrate scope of the amines was examined, and most of them showed very good results. With this approach, renewable N-(5-methylfurfuryl)aniline was produced from fructose in an overall yield of 62%.

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