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- Title
New Pyrazolyl-Nicotinic Acids, Methyl Esters, and 1,3,4-Oxadiazolyl-pyrazolyl-pyridine Tricyclic Scaffold Derivatives from 6-Hydrazinylnicotinic Acid Hydrazide Hydrate.
- Authors
Bonacorso, H. G.; Paim, G. R.; Porte, L. M. F.; Pittaluga, E. P.; Cavinatto, S.; Meyer, A. R.; Martins, M. A. P.; Zanatta, N.
- Abstract
This paper describes an efficient approach for the synthesis of a new series of 6-[3-alkyl(aryl/heteroaryl)-5-trifluoromethyl-1 H-pyrazol-1-yl]nicotinic acids (where alkyl = CH3; aryl = Ph, 4-OCH3Ph, 4,4′-BiPh; and heteroaryl = 2-Furyl) from the reaction of alkyl(aryl/heteroaryl)substituted 2-(5-trifluoromethyl-5-hydroxy-4,5-dihydro-1 H-pyrazol-1-yl)-5-(5-trifluoromethyl-5-hydroxy-4,5-dihydro-1 H-1-carbonylpyrazol-1-yl)pyridines, under basic conditions and at 70-95% yields. In a subsequent step, the 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-1 H-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] reaction with 1,1,1-triethoxyethane and 1-(triethoxymethyl)benzene as the reagent/solvent.
- Subjects
PYRAZOLES; HETEROCYCLIC compounds synthesis; HYDRAZIDES; METHANOL; PYRIDINE; BENZENE compound synthesis
- Publication
Journal of Heterocyclic Chemistry, 2014, Vol 51, Issue 4, p1171
- ISSN
0022-152X
- Publication type
Article
- DOI
10.1002/jhet.2110