Abstract
The title compound, Methyl 5-Hydroxy-1-Phenyl-1H-Pyrazole-3-Carboxylate (C11H10N2O3), was prepared by a one-pot, two-component reaction of an equimolar mixture of phenyl hydrazine and dimethyl acetylene dicarboxylate (DMAD) at reflux temperature for 2 h in a mixture of toluene and dichloromethane as solvent. C11H10N2O3 was crystallized from an ethanol solution in monoclinic space group P21/c with unit cell dimensions a = 9.5408(16), b = 9.5827(16), c = 11.580(2) Å, β = 105.838(3)°, V = 1018.5(3) Å3, Z = 4.
Highlights
Over the years, pyrazoles have enjoyed a prominent place in heterocyclic chemistry largely due to the wide range of biological activity demonstrated by this class of compounds for uses such as pharmaceuticals and agricultural and veterinary drugs [1,2,3]
We describe a new one pot synthesis and structure of methyl 5-hydroxy-1-phenyl-1Hpyrazole-3-carboxylate (1a) which is a tautomeric form of methyl 5-oxo-1-phenyl-4,5-dihydro-1Hpyrazole-3-carboxylate (1b) (Figure 1)
The tautomeric form 1a is predominant in a DMSO-d6 solution and this form crystallizes from ethanol solution
Summary
Pyrazoles have enjoyed a prominent place in heterocyclic chemistry largely due to the wide range of biological activity demonstrated by this class of compounds for uses such as pharmaceuticals and agricultural and veterinary drugs [1,2,3]. They possess anti-obesity [4], antianxiety [5] and HIV-1 reverse transcriptase inhibitor [6], anti-hyperglycemic, anti-pyretic, analgesic, anti-inflammatory and hypoglycemic activity [7,8]. The structure of the tautomer 1b is found in the Cambridge database and is an organocatalyst for organic reactions [9]
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