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Преподаватель органической химии

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Органическая химия (1.2)

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Доктор химических наук

Наименование направления подготовки и (или) специальности


Общий стаж работы 13 лет (с 01.01.2007)
Стаж работы по специальности 13 лет (с 01.01.2007)


Sukhorukov A. C-h reactivity of the alpha-position in nitrones and nitronates // Advanced Synthesis and Catalysis. — 2019. The review summarizes the chemistry of nitrones and nitronates in the context of the C‐H reactivity of their α‐carbon atom. Electrophilic, nucleophilic and radical reactions leading to functionalization of the α‐position are described. Examples of the application of these processes in total synthesis are outlined. 1. Introduction 2. An overview of the α‐C‐H reactivity of nitrones and nitronates 3. Tautomerization of nitrones and nitronates 4. Nitrones and nitronates as α‐C‐nucleophilic synthons 4.1 Reaction of nitrones with С‐electrophiles 4.2 Halogenation and nitrosation of nitrones 4.3. Addition of electrophiles to N‐siloxyenamines 4.4 Reaction of nitronates with electrophiles 4.5. Addition of electrophiles to N,N‐bis(oxy)enamines 5. Nitrones and nitronates as α‐C‐radical synthons 5.1 Oxidative dimerization of nitrones 5.2 Addition reactions of N‐vinyl nitroxyl radicals 5.3 Radical reactions of N‐(oxy)enamines and N,N‐bis(oxy)enamines 5.4. Oxidation of the α‐position in nitrones 6. Nitrones and nitronates as α‐C‐electrophilic synthons 6.1 Reaction of N‐oxyenamines with nucleophiles 6.2 Introduction of nucleophiles into the α‐position of nitronates via N,N‐bis(oxy)enamines 7. Functionalization of the α‐carbon atom in nitrones and nitronates using [n,3]‐migrations and related processes 7.1 [1,3]‐Migrations in N,N‐bis(oxy)enamines 7.2 [3,3]‐Sigmatropic rearrangements in N‐oxyenamines 8. Applications in target‐oriented organic synthesis 9. Conclusions. [ DOI ]

In situ generated magnesium cyanide as an efficient reagent for nucleophilic cyanation of nitrosoalkenes and parent nitronates / P. Y. Ushakov, A. A. Tabolin, S. L. Ioffe, A. Y. Sukhorukov // European Journal of Organic Chemistry. — 2019. — Vol. 2019, no. 9. — P. 1888–1892. In situ generated magnesium cyanide [NaCN/Mg(ClO4)2] is suggested as a convenient, readily available, non‐volatile and organic‐soluble reagent for hydrocyanation reactions. It was successfully used for nucleophilic cyanation of nitrosoalkenes, nitronates, as well as other typical π‐electrophiles, such as imines, α,β‐unsaturated ketones, alkylidenemalonates and azoalkenes. [ DOI ]

Naumovich Y. A., Ioffe S. L., Sukhorukov A. Y. Michael addition of p-nucleophiles to conjugated nitrosoalkenes // Journal of Organic Chemistry. — 2019. — Vol. 84, no. 11. — P. 7244–7254. A general approach to various α-phosphorus-substituted oximes (β-oximinoalkyl-substituted phosphonates, phosphine oxides, phosphine–borane complexes, and phosphonium salts) was developed. The strategy exploits hitherto unknown Michael addition of PH-containing compounds (diphenylphosphine oxide, diisopropyl phosphite, phosphine–borane complexes, and triphenylphosphonium bromide) to unstable conjugated nitrosoalkenes, which are generated in situ from corresponding nitrosoacetals. The resulting α-phosphorus-substituted oximes can be considered as useful P-, N-, and O-ligands for catalysis and precursors to valuable β-aminophosphonates. [ DOI ]

Nucleophilic halogenation of cyclic nitronates: A general access to 3-halo-1,2-oxazines / R. S. Malykhin, A. O. Kokuev, V. S. Dorokhov et al. // Journal of Organic Chemistry. — 2019. In the article, comprehensive studies on the nucleophilic chlorination and bromination of readily available six-membered cyclic nitronates (1,2-oxazine-N-oxides) are reported. Under optimized conditions (POCl3 or (COBr)2 with Hünig’s base), 3-halo-substituted 1,2-oxazines, which are difficult to access by other routes, were obtained in good to high yields. The latter were shown to be convenient precursors to other 3-substituted 1,2-oxazine derivatives using Lewis/Brønsted acid-assisted substitution of the halide atom for C-, S- and N-nucleophiles. [ DOI ]

Golovanov I. S., Sukhorukov A. Y. Synthesis of stable ate-complexes of heteroaromatic boronic acids // Известия высших учебных заведений. Химия и химическая технология. — 2019. — Vol. 62, no. 4. — P. 60–67.