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

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
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).


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.

Supporting Information

Publication History

Received: 22 March 2021

Accepted after revision: 12 April 2021

Publication Date:
13 April 2021 (online)

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