Lomov D. Synthesis and reactions of amino- and oxo-derivatives imidazo[4,5-b]- and imidazo[4,5-c]pyridines

In a series of imidazo[4,5-b]pyridine-2-ones and their 6-chloro(bromo)derivatives the directions of nitration were established. The interaction of 5-nitro-6-chloro(bromo)-1,3-dihydro-2Н-imidazo[4,5-b]pyridine-2-one derivatives with hydrazine hydrate leads to 5-oxy-1,3-dihydro-2Н-imidazo[4,5-b]-1,2,3-triazolo[5,4-b]pyridine-2-ones. The interaction of 5-amino-1,3-dialkyl-1,3-dihydro-2Н-imidazo[4,5-b]pyridine-2-ones with 2,5-dimethoxytetrahydrofurane and itaconic acid gives 1-(1,3-dialkyl-2-oxo-1,3-dihydro-2H-imidazo[4,5-b]-pyridine-5'-yl)pyrroles and 1-(1,3-dihydro- and 1,3-dialkyl-2-oxo-1,3-dihydro-2H-imidazo[4,5-b]pyridine-5'-yl)-5-oxopyrrolidine-3-carboxylic acid. The interaction of 5-amino-1,3-dialkylsubstituted imidazo[4,5-b]pyridine-2-one with acetylacetone and acetoacetic ester leads to 1,3-dialkyl-2,7-dimethyl-2-oxo-1,3-dihydro-2Н-imidazo[5,4-b]-1,8-naphthyridines and 1,3-dialkyl-7-methyl-2,5-dioxo-1,3-dihydro-2Н-imidazo[5,4-b]-1,8-naphthyridines. The synthesis and intermolecular oxidative polycyclization of the N-[3-(2-methyl-3Н-imidazo[4,5-b]pyridin-3-yl)phenyl]-2,3-diaminоpyridine and N-[4-(2-methyl-3Н-imidazo-[4,5-b]pyridin-3-yl)phenyl]-2,3-diaminоpyridine to polyimidazo[4,5-b]pyridine derivatives was carried out for the first time. The recyclization of 2-hetaryl-7-nitroimidazo[4,5-c]pyridin-4-ones under the action of hydrazine hydrate gives the 7-methyl-2-hetarylimidazo[4,5-d]pyridazin-4-one derivatives. The interaction of 1,3-dialkyl-1,3-dihydro-6-nitro-5-oxo-2Н-imidazo[4,5-b]pyridin-2-ones with hydrazine hydrate leads to recyclization and formation of 5-amino-1,3-dialkyl-4-(pyrazol-3-yl)imidazol-2-one derivatives. The results of the virtual biological tests show, that new 1-(1,3-dialkyl-2-oxo-1,3-dihydro-2H-imidazo[4,5-b]pyridin-5'-yl)-3-(1H-benzimidazol-2-yl)-5-pyrrolidines have high probabilities of nootropic and bronchodilatoric activity.