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

Abstract

AbstractThe 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%.