Copper Catalyzed Reaction Of Halogeated Aromatic Amine

Nitrogen-containing heterocyclic compounds in the formation of biologically active drugs or agents play an important role in the pharmaceutical and agrochemical industries. For example, quinazolinone derivatives, dihydroquinazolinones and benzimidazoles are now known to show various useful biological and medicinal activities, such as hypnotic, sedative, analgesic, anticonvulsant, antitussive, antibacterial, diuretic, antihistamine, antidepressant and so on.At present, their preparation depends on the availability of the requisite 2-aminobenzoic acid derivatives,2-aminobenzamide derivatives and 1,2-diaminoarene derivatives. But the previous preparation methods of those arylamines are not convenient.Fortunately, we have developed a simple copper-catalyzed amination of o-functionalized haloarenes (2-halobenzoic acid,2-halobenzamide, and N-(2-bromophenyl)acetamide derivatives) using NaN3 as the amino source in ethanol, and the corresponding 2-aminobenzoic acid,2-aminobenzamide, and N-(2-aminophenyl) acetamide derivatives were obtained in good to excellent yields. The protocol undergoes one-pot Ullmann-type coupling of ortho-functionalized haloarenes with NaN3 to give orthofunctionalized azidoarenes, followed reduction with ethanol, and ethanol acted as solvent and reductive agent.The method is of economical and practical advantages, and the synthesized compounds can be widely used in the synthesis of various nitrogen-containing heterocyclic compounds.