Studies On The Synthesis Of N-containing Hrteroarens Via Amine Oxidation

Nitrogen-containing heteroarenes(NCHs) have found a wide range of applications in the field of pharmacology, organic synthesis and materials, etc. However, most of current synthetic methods have defects in some aspects. Based on the previous proposed synthetic methods, we have conducted the selection of reactants and catalysts, and the synthesis of benzothiazole, benzimidazole, benzoxazole and other NHCs are achieved. The whole paper could be divided into four parts:Detailedly, reviews about recent application and research progress in synthetic methods of NCHs are presented. Based on our previous imines’ work, a single [Cu] catalyzed for the synthesis of such NCHs, under base and ligand free, air assist oxidation coupling, is developed.Furthermore, The synthesis of NCHs under TEMPO catalyzed, especially the synthesis of oxazoles and quinazolinones,which compansate the weakness in CuI catalyzed reaction, is elaborate. This system uses a catalytic amount of 2,2,6,6-tetramethylpiperidine oxide(TEMPO), making cyclization greener and more economic.Combining recent cataylst-free reactions in heterocycles synthesis and our exploration in this field, the self-catalyzed oxidation and coupling of amines is developed under aerobic conditions.Above all, we have elvolved the substrates from aldehyde, nitrile and carboxylic acid to aromatic or aliphatic amines. And developed a systematic methods to form a series of NCHs, with CuI or TEMPO catalyzed oxidation coupling of amines with 2-aminothiolphenol, 2-aminophenol, phenylenediamine and anthranilamide under air or dioxygen.