Synthesis of Alkynyl Hydrazones from Unprotected Hydrazine and Their Reactivity as Diazo Precursors
Akashdeep Sharma, Paru Jamwal, Himani Vaid, Ramani Gurubrahamam
Abstract
Alkynyl hydrazones are synthesized conveniently from 2-oxo-3-butynoates and hydrazine by suppressing the susceptible formation of pyrazoles. The resultant hydrazones are transformed into alkynyl diazoacetates under metal-free and mild oxidative conditions in excellent yields. Further, the alkynyl cyclopropane and propargyl silane carboxylates are synthesized in good yields by developing an unprecedented copper-catalyzed alkynyl carbene transfer reaction.
Topics & Concepts
ChemistryDiazoHydrazine (antidepressant)PropargylSilaneHydrazoneCatalysisCarbeneCyclopropaneOrganic chemistryReactivity (psychology)Medicinal chemistryPropargyl alcoholCopperAlkyneCombinatorial chemistryMedicinePathologyAlternative medicineChromatographyRing (chemistry)Cyclopropane Reaction MechanismsCatalytic Alkyne ReactionsCatalytic C–H Functionalization Methods