Síntese de Amino-N-heteroaromáticos via SNAr

Abstract

N-heteroaromatic derivatives containing amine groups in their structures are of great interest in the development of new drugs, due to the reported biological activities that these compounds present. The development of novel protocols for obtaining amino-N-heteroaromatic compounds in a mild manner and without the use of metal catalysts is much desired in synthetic organic chemistry. In this work a method was developed to obtain quinoxalinic derivatives through a SNAr reaction using 2,3-dichloro-6,7-dinitroquinoxaline and substituted anilines. After optimization, 13 examples of unpublished products were obtained under mild conditions and without the use of metallic catalysts, with yields varying from low to excellent (trace-98%). In addition to the use of the quinoxalinic derivative, the C-H functionalization reaction with pyridine and tert-butylamine was studied. The use of molecular iodine (I2) as an additive in this transformation allowed the formation of the disubstituted product N2,N6-di-tert-butylpyridine-2,6-diamine from a direct synthesis and formation of an unpublished compound with potential biological activity.