Na2S-promoted reduction of azides in water: synthesis of pyrazolopyridines in one pot and evaluation of antimicrobial activity

Abstract

Reduction of various azides using Na₂S has been accomplished in water, and, in situ, the resulting amines on reaction with various ketones lead to pyrazolo[3,4-b]pyridines in one pot. Thus, a number of new trifluoromethyl-substituted pyrazolo[3,4-b]pyridine compounds have been prepared and screened for antimicrobial activity against different Gram-positive and Gram-negative strains. A good number of compounds, 4a, 4b, 4d, 4f, 4i, 4k, 4l, 4m, 4r and 4s, were found to possess promising activity. Notably, Na₂S on hydrolysis in water generates H₂S and NaOH, which facilitate the reduction of azides followed by intramolecular cyclization leading to the title compounds. To the best of our knowledge, this is the first report of the synthesis of the title compounds in aqueous medium in a one-pot reaction.