The Synthesis Amide Derivatives Via N=N Bond Cleavage Of Azobenzenes

In this thesis, a Pd-catalyzed reaction of aryl azo compound with benzyl amine to construct a new C-N bond via N=N bond cleavage has been investigated, which has applied to synthesize a series of amides. The main results obtained are shown as below:The amides are widely present in biological medicine, functional materials and natural products. Inspired by the universal application of amides, many protocols to prepare amide compounds have been reported previously. However, some problems still exist in these procedures, such as the long reaction time, the harsh conditions, and the low yield in industry or pharmaceutical field. Therefore, developing a simple, highly efficient and rapid method to synthesize amides is a big challenge.This thesis has developed a very simple and efficient protocol to synthesize a series of amide derivatives. The reaction of aryl azo compound with benzyl amine could proceed smoothly in chlorobenzene using palladium acetate(10 mol%) as the catalyst, and TBHP as the oxidant, affording a series of bioactive amide derivatives in up to 94% yields. Moreover, it is noteworthy that this method features with a simple system, high efficiency, mild conditions, and the addition of acids, bases, ligands and additives are free(Scheme 1). Based on the obtained results and reported literatures, a plausible reaction mechanism is proposed as follows(Scheme 2):...