Regiodivergent Cyclizations of Donor-Acceptor Cyclopropanes with Hydrazines under Solventless, Mechanochemical
Srinivasarao Yaragorla1, Rajeshwari Tangellapally1
1School of Chemistry, University of Hyderabad, P.O. Central University, Gachibowli, Hyderabad 500046, India.
Abstract:
We developed a regiodivergent synthesis of highly diastereoselective pyridazines and pyrazoles from DACs and hydrazines under solventless ball milling with HFIP. This HFIP-promoted mechanochemical approach eliminates the need for metal catalysts, hazardous solvents, inert atmospheres, or external heating, representing a significant advancement in sustainable heterocycle synthesis. We delineate the structural parameters that dictate the regioselectivity, providing a clear roadmap for the synthesis of either heterocyclic core. 13C NMR studies helped to elucidate the activation of DAC by HFIP.
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