Synthesis of Spiro Pyrazolone-Oxindole and Bicyclic Pyrazolone Derivatives via Solvent-Dependent Regioselective Aza-1,4/1,6-Michael and Intramolecular Cycloaddition under Catalyst-Free Conditions

Abstract

A solvent-dependent, highly regioselective [3+2]-cyclo­addition reaction of isoxazole-styrenes and azomethine imines under catalyst-free conditions is reported, furnishing a library of pyrazolone–spirooxindole hybrids. Good regioselectivity for the isomeric structures was achieved by the reaction of isoxazole-styrene and azomethine imine in different solvents and temperatures. The developed method was extended for the synthesis of tri-substituted dinitrogen-fused pyrazolones by using a 1,6-Michael addition reaction. Furthermore, the isoxazole moiety was converted into a carboxylic acid as a model study via ring opening.

Key words

spirooxindole-pyrazolone hybrids - bicyclic pyrazolones - isoxazole-styrenes - switchable 1,3-dipolar cycloaddition - solvent-­dependent reactivity - catalyst-free conditions

Publikationsverlauf

Eingereicht: 22. März 2021

Angenommen nach Revision: 12. April 2021

Accepted Manuscript online:
13. April 2021

Artikel online veröffentlicht:
20. Mai 2021

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