P 17 Palladium(II)-Catalyzed Oxidative C–H/C–H Coupling and Eliminative SNH Reactions in Direct Functionalization of Imidazole Oxides with Indoles / M. V. Varaksin, I. A. Utepova, O. N. Chupakhin, V. N. Charushin // Journal of Organic Chemistry. - 2012. - Vol.77, №20. - С. 9087-9093 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): IMIDAZOLE OXIDES -- INDOLES Аннотация: Two novel synthetic approaches to realize the direct C(sp2)–H bond functionalization in cyclic nitrones are reported. Palladium(II)-catalyzed oxidative C–C coupling of 2,2-dialkyl-4-phenyl-2H-imidazole 1-oxides with indoles was shown to result in the formation of 5-indolyl-3-yl derivatives, while nucleophilic substitution of hydrogen (SNH) at C(5) of the same imidazole system was found to afford the corresponding deoxygenated compounds \\\\Expert2\\nbo\\Journal of Organic Chemistry\\2010, v.77, p.9087.pdf |
S 98 Synthesis of nitroxyl radical by direct nucleophilic functionalization of a C-H bond in the azadiene systems [Electronic resource] / M. V. Varaksin, E. V. Tretyakov, I. A. Utepova, G. V. Romanenko, A. S. Bogomyakov, D. V. Stass, R. S. Sagdeev, V. Ovcharenko, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2012. - Vol.61, №7. - С. 1469-1473. - Bibliogr. : p. 1473 (15 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): NITRONES -- NITRONYL NITROXYLS -- ESR SPECTRA Аннотация: Cyclic dinitrones underwent nucleophilic substitution of the hydrogen atom in the reaction with a paramagnetic carbanion, the lithium derivative of 4,4,5,5 tetramethyl 4,5 dihydro 1H imidazol 1 oxyl 3 oxide, to give polyfunctional nitronyl nitroxyls \\\\expert2\\NBO\\Russian Chemical Bulletin\\2012, 61 (7), 1469-1473.pdf |
B 68 Blue-light-promoted radical c-h azolation of cyclic nitrones enabled by selectfluor® / A. A. Akulov, M. V. Varaksin, A. N. Tsmokalyuk [et al.] // Green Chemistry. - 2021. - Vol. 23, № 5. - P2049-2057 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: 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 proceed via a nitroxide-involving radical pathway, encompassing a chain of electron transfer events, such as hydrogen atom transfer (HAT) and single electron transfer (SET). |
Radical C–H amination of cyclic nitrones enabled by iodine catalysis / А. A. Akulov, M. V. Varaksin, A. A. Nelyubina [et al.] // Современные синтетические методологии для создания лекарственных препаратов и функциональных материалов : сборник тезисов VI Международной конференции. - Екатеринбург, 2022. - Ст. I-31. - P82 Рубрики: ХИМИЧЕСКИЕ НАУКИ ЗДРАВООХРАНЕНИЕ. МЕДИЦИНСКИЕ НАУКИ |