138000-87-0Relevant academic research and scientific papers
Blue-light-promoted radical C-H azolation of cyclic nitrones enabled by Selectfluor
Akulov, Alexey A.,Varaksin, Mikhail V.,Tsmokalyuk, Anton N.,Charushin, Valery N.,Chupakhin, Oleg N.
supporting information, p. 2049 - 2057 (2021/03/26)
An original approach to achieve the C(sp2)-H azolation of cyclic aldonitrones mediated by Selectfluor has first been employed. By exploiting a metal-free, visible-light-promoted cross-dehydrogenative C-N coupling reaction between model aldonitrones, 2H-imidazole 1-oxides, and NH-containing azoles, a series of novel azaheterocyclic derivatives have been obtained in yields up to 94%. The elaborated protocol has proved to be appropriate for gram-scale processes and displayed potential for utilization in the synthesis of novel structural analogues of lanabecestat. Besides, mechanistic studies have revealed that this coupling reaction is likely to proceedviaa nitroxide-involving radical pathway, encompassing a chain of electron transfer events, such as hydrogen atom transfer (HAT) and single electron transfer (SET).
SYNTHESIS OF 2H-IMIDAZOLE 1-OXIDES AND STABLE NITROXYL RADICALS BASED ON THEM
Kirilyuk, I. A.,Grigor'ev, I. A.,Volodarskii, L. B.
, p. 1871 - 1879 (2007/10/02)
2H-Imidazole 1-oxides containing an aldonitrone group in the heterocyclic ring are obtained by the condensation of hydroxyiminomethyl ketones with ketones and ammonium acetate.Their oxidation with lead dioxide in methanol gives stable nitroxyl radicals -
