1,2,4-oksadiazolilmetil grubu taşıyan bazı yeni sidnonların sentezi ve halkalı katılma tepkimeleri

In this work, the synthesis of 5-(chloromethyl)-1,2,4-oxadiazole substituted sydnones is firstly described. Then, 5-(azidomethyl)-1,2,4-oxadiazole substituted sydnones were easily synthesized from the reaction between 5-(chloromethyl)-1,2,4-oxadiazole substituted sydnones and sodium azide in acetone/water. To best our knowledge of literature, both 5-(chloromethyl)-1,2,4-oxadiazole and 5-(azidomethyl)-1,2,4-oxadiazole substituted sydnones are novel heterocyclic compounds not known yet. Also, the 1,3-dipolar cycloaddition reactions of these 5-(azidomethyl)-1,2,4-oxadiazole substituted sydnones with dipolarophiles such as N-phenylmaleimide, phenyl vinyl sulfone and phenyl propiolic acid were performed to afford products which might be expected to exhibit biological acitivity. The structures of these novel products were elucidated by means of IR, NMR (1H, 13C), Mass spectra, X-ray diffraction spectra and physical characteristics (melting points and Rf values).