1649440-23-2Relevant academic research and scientific papers
New pyrazolyl-nicotinic acids, methyl esters, and 1,3,4-oxadiazolyl- pyrazolyl-pyridine tricyclic scaffold derivatives from 6-hydrazinylnicotinic acid hydrazide hydrate
Bonacorso,Paim,Porte,Pittaluga,Cavinatto,Meyer,Martins,Zanatta
, p. 1171 - 1178 (2014/08/05)
This paper describes an efficient approach for the synthesis of a new series of 6-[3-alkyl(aryl/heteroaryl)-5-trifluoromethyl-1H-pyrazol-1-yl] nicotinic acids (where alkyl = CH3; aryl = Ph, 4-OCH3Ph, 4,4′-BiPh; and heteroaryl = 2-Furyl) from the hydrolysis reaction of alkyl(aryl/heteroaryl)substituted 2-(5-trifluoromethyl-5-hydroxy-4,5-dihydro-1H- pyrazol-1-yl)-5-(5-trifluoromethyl-5-hydroxy-4,5-dihydro-1H-1-carbonylpyrazol-1- yl)pyridines, under basic conditions and at 70-95% yields. In a subsequent step, the esterification reaction of pyrazolyl-nicotinic acids done in thionyl chloride and methanol led to the isolation of a series of methyl 6-[alkyl(aryl/heteroaryl)-5-trifluoromethyl-1H-pyrazol-1-yl] nicotinates as stable hydrochloride salts at 64-84% yields, which could be easily converted to hydrazides to give new oxadiazolyl-pyrazolyl-pyridine tricyclic scaffolds at good yields from a [4 + 1] cyclocondensation reaction with 1,1,1-triethoxyethane and 1-(triethoxymethyl)benzene as the reagent/solvent.
