Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science

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1,3-Dipolar Cycloaddition of a Nitronyl Nitroxide-substituted Alkyne to Heteroaromatic N-imines

Vasiliy Romanov , Aleksey Vorob'ev , Irina Bagryanskaya , Dmitriy Parkhomenko , Evgeny Tretyakov

Abstract

1,3-Dipolar cycloaddition of the triple bond in an ethynyl-substituted nitronyl nitroxide to heteroaromatic N-imines is described. The reaction opens a pathway to polyfunctional nitronyl nitroxides with pyrazolo[1,5-a]pyridine or related substituents. According to X-ray diffraction analysis, dihedral angles between the plane of the paramagnetic moiety and heteroaromatic cycle do not exceed 24. Reactions between Cu(hfac)2 and a pyrazolo[1,5-a]pyridine-substituted radical produced a polymer chain complex with a ‘head-to-tail’ motif resembling that in breathing crystals.

CH17476  Accepted 06 September 2017

© CSIRO 2017