ABSTRACT
A facile one-pot synthesis of five- and six-membered fused dihydropyridines such as chromenodihydropyridines, pyrazolodihydropyridines and isoxazolopyridines was accomplished for the first time by employing PPh3-NBS via a formal [3 + 2 + 1] cycloaddition of 1,3-bisnucleophiles (i.e., 2-aminochromone, 4-aminochromone, 5-aminopyrazole and 5-aminoisoxazole), ß-enaminones and aldehydes in aqueous medium. The present approach involves a Michael type addition followed by intramolecular cyclization leading to the formation of two new C-C bonds and one C-N bond. High compatibility and excellent yields are the advantages of this protocol.
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.