Recyclization of 1-amino-3.5-diaryl-2.6,6-tricyanocyclohexa-1,3,-dienes to pyridine derivatives

Solvent-free 1H-tetrazole, 1,2,5,6-tetrahydronicotinonitrile and pyrazole synthesis using quinoline based ionic fluoride salts (QuFs): thermal and theoretical studies

“…In second step, QuF again abstracts proton from a-methyl group to promote dimerization via multistep sequence to afford 2-dicyanomethylene-6-methyl-4,6-bis(m-methoxyphenyl)-1,2,5,6-tetrahydronicotinonitrile (13) (Scheme 3). [27][28][29] Moreover, a reaction between acetylacetonate (13) and p-methoxyphenyl hydrazine hydrochloride (14) in the presence of QuF (4) under solvent-free condition afforded corresponding 3,5-dimethyl-1-(p-methoxyphenyl)-1H-pyrazole (15) in good yield (63%) as shown in the Scheme 4. The applications of QuFs in 1H tetrazole (7), 1,2,5,6-tetrahydronicotinonitrile (12) or pyrazole (15) formation signify their catalytic activity in organic reactions.…”