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

Kota Sathish; Sakkani Nagaraju; Dhurke Kashinath

doi:10.1055/a-1480-9837

SynOpen, Table of Contents

CC BY-NC-ND 4.0 · SynOpen 2021; 05(02): 123-133
DOI: 10.1055/a-1480-9837

paper

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

Kota Sathish

,

Sakkani Nagaraju

,

Dhurke Kashinath ∗

Abstract

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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

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References

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