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

1,3-Dipolar Cycloaddition of a Nitronyl Nitroxide-Substituted Alkyne to Heteroaromatic N-Imines

Vasiliy Romanov A B , Aleksey Vorob’ev A B , Irina Bagryanskaya A B , Dmitriy Parkhomenko A and Evgeny Tretyakov A B C
+ Author Affiliations
- Author Affiliations

A N. N. Vorozhtsov Institute of Organic Chemistry, 9 Ac. Lavrentiev Avenue, Novosibirsk 630090, Russia.

B National Research University – Novosibirsk State University, 2 Pirogova Street, Novosibirsk 630090, Russia.

C Corresponding author. Email: tretyakov@nioch.nsc.ru

Australian Journal of Chemistry - https://doi.org/10.1071/CH17476
Submitted: 18 August 2017  Accepted: 6 September 2017   Published online: 21 September 2017

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 (hfac = hexafluoroacetylacetonate ion) 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.


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[14]  Selected bond lengths (Å) in 4a: O1–N1 1.280(2), O2–N2 1.283(2), N1–C1 1.349(3), N1–C2 1.496(3), N2–C1 1.342(3), N2–C3 1.500(3), N3–N4 1.366(3), N3–C14 1.327(3), N4–C9 1.384(3), N4–C13 1.368(3), C1–C8 1.436(3); in 4b (average for two independent molecules): O1–N1 1.277(4), O2–N2 1.271(4), O3–C16 1.355(5), N1–C1 1.322(5), N1–C2 1.499(5), N2–C1 1.343(5), N2–C3 1.479(5), N3–N4 1.363(5), N3–C18 1.324(5), N4–C9 1.376(4), N4–C17 1.388(5), C1–C8 1.449(5).

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