NHC-catalyzed regiodivergent syntheses of difunctionalized 3-pyrazolidinones from α-bromoenal and monosubstituted hydrazine?

Organic & Biomolecular Chemistry Pub Date: 2017-10-13 DOI: 10.1039/C7OB02041D

Abstract

A formal [3 + 2] annulation of α-bromoenal with monosubstituted hydrazine could give 1,5 or 2,5-difunctionalized 3-pyrazolidinone regiodivergently by tuning the structure of the N-Heterocyclic Carbene (NHC) catalyst. Moderate to high yields, mild reaction conditions, good regioselectivity and potential biological significance of the final product have made this protocol attractive for the assembly of 3-pyrazolidinone.

Graphical abstract: NHC-catalyzed regiodivergent syntheses of difunctionalized 3-pyrazolidinones from α-bromoenal and monosubstituted hydrazine
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