Abstract
The reactions of heterocyclic paramagnetic aldonitrone,viz., 2,2,5,5-tetramethyl-3-imidazoline-1-oxyl 3-oxide, with mono- and disubstituted alkynes afford unstable isoxazoline derivatives. The reactions with monosubstituted alkynes yield predominantly 5-substituted regioisomers. The resulting isoxazoline derivatives are readily (and often spontaneously) converted into enaminoketones,viz, imidazolidine-1-oxyl derivatives. In the presence of tolan, the title paramagnetic aldonitrone gives a dimer in which one imidazoline ring undergoes profound transformation. The structure of the resulting dimer was established by X-ray diffraction analysis.
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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 112–117, January, 2000.
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Berezina, T.A., Reznikov, V.A., Volodarsky, L.B. et al. Reactions of heterocyclic paramagnetic aldonitrone, 2,2,5,5-tetramethyl-3-imidazoline-1-oxyl 3-oxide, with alkynes. Russ Chem Bull 49, 116–121 (2000). https://doi.org/10.1007/BF02499075
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DOI: https://doi.org/10.1007/BF02499075