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Catalytic Synthesis of N ‐(5‐Methylfurfuryl)aniline from Bio‐Derived Carbohydrates
Author(s) -
Xiao Jianjun,
Jin Qi,
Yang Jiaqi,
Xiong Lingheng,
Qiu Jumin,
Jiang Jun,
Peng Yang,
Li Teng,
Qiu Zumin,
Yang Weiran
Publication year - 2019
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201800690
Subject(s) - chemistry , aniline , reductive amination , amination , catalysis , substrate (aquarium) , yield (engineering) , fructose , organic chemistry , combinatorial chemistry , oceanography , materials science , metallurgy , geology
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 H 3 PO 3 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%.