Synthesis of 2-R-4,6-Dinitro-2H-indazoles from 2,4,6-Trinitrotoluene

All articles of this category An efficient synthesis of 2-R-4,6-dinitro-2 H -indazoles (R = aryl or substituted amine) from 2,4,6-trinitrotoluene was elaborated. The proposed method includes formation of C-(2,4,6-trinitrophenyl)- N -R-azomethines 1 ( a - g) from TNT or the product of its transformation 2,4,6-trinitrobenzaldehyde (TNBA) with the further regiospecific substitution of the ortho -nitro group in 1 ( a - g ) by the azido group under the action of NaN 3 . Thermolysis of the azides 2 ( a - g ) gives previously unknown 2-R-4,6-dinitro-2 H -indazoles 3 ( a - g ) in high yields. 2,4,6-trinitrotoluene - 2,4,6-trinitrobenzaldehyde - azomethines - aromatic nucleophilic substitution - aromatic azides - 2- R -4,6-dinitro-2 H -indazoles