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Facile One-Pot Synthesis of 3,5-Disubstituted 1H-Pyrazoles from Propargylic Alcohols via Propargyl Hydrazides
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2013
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Acid-catalyzed Propargylation3,5-Disubstituted 1H-pyrazolesDiversity Oriented SynthesisEngineeringNatural SciencesDiversity-oriented SynthesisPropargylic AlcoholsOne-pot ApproachOrganic ChemistryPropargyl HydrazidesCatalysisStereoselective SynthesisChemistryHeterocycle ChemistrySynthesis MethodSynthetic ChemistryBiomolecular Engineering
A new and efficient metal-free, two-component, one-pot approach to a variety of 3,5-disubstituted 1<i>H</i>-pyrazoles has been developed from propargylic alcohols. This transformation proceeds via an acid-catalyzed propargylation of N,N-diprotected hydrazines followed by base-mediated 5-<i>endo</i>-dig cyclization leading to 3,5-disubstituted 1<i>H</i>-pyrazoles in good overall yields.