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Synthesis of isomeric 2,3,5‐trisubstituted perhydropyrrolo[3,4‐d]‐isoxazole‐4,6‐diones via 1,3‐dipolar cycloaddition reactions
Author(s) -
Özkan Hamdi,
Yildirir Yilmaz
Publication year - 2010
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.395
Subject(s) - chemistry , isoxazole , maleimide , cycloaddition , 1,3 dipolar cycloaddition , diastereomer , column chromatography , carbon 13 nmr , proton nmr , medicinal chemistry , organic chemistry , stereochemistry , catalysis
A series of isoxazolidine derivates (isomeric 2,3,5‐trisubstitutedperhydropyrrolo[3,4‐d]isoxazole‐4,6‐diones) used as anti‐inflammatory, immunosuppressive, antibacterial agent, and inhibitor for some enzymes were synthesized. These compounds were prepared by 1,3‐dipolar cycloaddition of N ‐methyl maleimide and N ‐phenyl maleimide with nitrones. Diastereomeric products obtained in this reaction were separated by column chromatography and recrystallized. All compounds synthesized were characterized by elemental analysis and spectroscopic methods ( 1 H NMR, 13 C NMR, and FTIR). J. Heterocyclic Chem., (2010).