GO-Catalyzed Formation Of Carbon-Carbon/Carbon-Hetero Bond Of Nitrogen-Containing Heterocyclic Compounds

Nitrogen-containing heterocyclic compounds are an important class of heterocyclic compounds,which are widely found in natural products with biological activities and pharmaceutically active molecules.Therefore,rapid and efficient synthesis of nitrogen heterocyclic compounds has been a hot research area in organic chemistry.Because of its simplicity,efficiency and high atomic economy,green chemistry have aroused great interest among chemists and drug scientists,and gradually become one of the trend in the development of organic synthesis.This paper mainly discusses the synthesis of nitrogen-containing heterocyclic compounds containing quinoline derivatives or benzothiazole derivatives by using graphene oxide or transition metals as catalysis and includes the following three parts:(a)A method for cyanation of quinoline N-oxides was reported by GO catalysis using quinoline N-oxides as raw material and TMSCN as “CN” source.The method of this reaction contained transition metal-free and retained N-O bond,which may enhance its biological activity.The reaction had many advantages with good tolerance of substrate functional groups,simplicity,easy availability of raw materials and greenness.(b)One-pot synthesis of benzothiazole derivatives from aniline,benzylamine and sulfur catalyzed by GO catalysis was developed.This method was a three-component reaction in one pot with elemental sulfur as the sole source of sulfur and tolerated a wide range of substrates,transition metal-free,directly formed C-N/C-S bond,and the products had potential application value.(c)The bisamination of methyl group from 8-methylquinoline as raw material and sulfonyl azide as amine source by using transition metal Cp*Ir(?)as catalysis was firstly reported.In this method,two different C-H bonds from the methyl of C(sp3)-H and the quinoline C(sp2)-H at position 7 were simultaneously activated by transition metal Cp*Ir(?)catalysis.The establishment of the catalytic system provided an effective way for the C-H bisamination of quinoline.