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CC BY-NC-ND 4.0 · SynOpen 2021; 05(02): 123-133
DOI: 10.1055/a-1480-9837
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
K.S. thanks DST for an INSPIRE fellowship. S.N. thanks UGC-New Delhi for a Fellowship. D.K. thanks DST (SERB), New Delhi for financial support (SB/FT/CS-136/2012 and SB/EMEQ-103/2014).
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 conditionsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1480-9837.
- Supporting Information
Publikationsverlauf
Eingereicht: 22. März 2021
Angenommen nach Revision: 12. April 2021
Accepted Manuscript online:
13. April 2021
Artikel online veröffentlicht:
20. Mai 2021
© 2021. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)
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