Diversion of the Arbuzov reaction: alkylation of C-Cl instead of phosphonic ester formation on the fullerene cage.

Kraevaya, Ol'ga A; Peregudov, Alexander S; Troyanov, Sergey I; Godovikov, Ivan; Fedorova, Natalya E; Klimova, Regina R; Sergeeva, Vasilina A; Kameneva, Larisa V; Ershova, Elizaveta S; Martynenko, Vyacheslav M; Claes, Sandra; Kushch, Alla A; Kostyuk, Svetlana V; Schols, Dominique; Shestakov, Alexander F; Troshin, Pavel A

Kraevaya, Ol'ga A; Peregudov, Alexander S; Troyanov, Sergey I; Godovikov, Ivan; Fedorova, Natalya E; Klimova, Regina R; Sergeeva, Vasilina A; Kameneva, Larisa V; Ershova, Elizaveta S; Martynenko, Vyacheslav M; Claes, Sandra; Kushch, Alla A; Kostyuk, Svetlana V; Schols, Dominique; Shestakov, Alexander F; Troshin, Pavel A.

Afiliación

Kraevaya OA; Skolkovo Institute of Science and Technology, Nobel St. 3, Moscow, 143026, Russia. troshin2003@inbox.ru and IPCP RAS, Semenov Prospect 1, Chernogolovka, 141432, Russia.
Peregudov AS; INEOS RAS, Vavylova St. 28, B-334, Moscow, 119991, Russia.
Troyanov SI; Department of Chemistry, Moscow Lomonosov State University, Leninskie gory, Moscow, 119991, Russia.
Godovikov I; INEOS RAS, Vavylova St. 28, B-334, Moscow, 119991, Russia.
Fedorova NE; Honored Academician N.F.Gamaleya National Research Centre for Epidemiology and Microbiology of the Ministry of Health of the Russian Federation, Gamaleya st. 18, 123098, Moscow, Russia.
Klimova RR; Honored Academician N.F.Gamaleya National Research Centre for Epidemiology and Microbiology of the Ministry of Health of the Russian Federation, Gamaleya st. 18, 123098, Moscow, Russia.
Sergeeva VA; Research Centre for Medical Genetics RAMS, Moskvorech'e St. 1, Moscow, 115478, Russia.
Kameneva LV; Research Centre for Medical Genetics RAMS, Moskvorech'e St. 1, Moscow, 115478, Russia.
Ershova ES; Research Centre for Medical Genetics RAMS, Moskvorech'e St. 1, Moscow, 115478, Russia.
Martynenko VM; IPCP RAS, Semenov Prospect 1, Chernogolovka, 141432, Russia.
Claes S; Rega Institute for Medical Research, KU Leuven, Herestraat 49, 3000, Leuven, Belgium.
Kushch AA; Honored Academician N.F.Gamaleya National Research Centre for Epidemiology and Microbiology of the Ministry of Health of the Russian Federation, Gamaleya st. 18, 123098, Moscow, Russia.
Kostyuk SV; Research Centre for Medical Genetics RAMS, Moskvorech'e St. 1, Moscow, 115478, Russia.
Schols D; Rega Institute for Medical Research, KU Leuven, Herestraat 49, 3000, Leuven, Belgium.
Shestakov AF; IPCP RAS, Semenov Prospect 1, Chernogolovka, 141432, Russia and Faculty of Fundamental Physics & Chemical Engineering, Moscow Lomonosov State University, GSP 1, 1-51 Leninskie Gory, Moscow, 119991, Russia.
Troshin PA; Skolkovo Institute of Science and Technology, Nobel St. 3, Moscow, 143026, Russia. troshin2003@inbox.ru and IPCP RAS, Semenov Prospect 1, Chernogolovka, 141432, Russia.

Org Biomol Chem ; 17(30): 7155-7160, 2019 08 14.

Article en En | MEDLINE | ID: mdl-31169856

RESUMEN

We report an "inversed" Arbuzov reaction of the fullerene derivatives C60Ar5Cl with trialkyl phosphites P(OR)3 producing alkylated fullerene derivatives C60Ar5R (R = Me, Et, iPr, nBu) with almost quantitative yields. This reaction provides a convenient synthetic route for the preparation of a large variety of functionalized fullerene derivatives with tailored properties, e.g. water-soluble compounds demonstrating promising antiviral activities against HCMV, HSV1, HIV and several influenza virus strains.

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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Org Biomol Chem Asunto de la revista: BIOQUIMICA / QUIMICA Año: 2019 Tipo del documento: Article País de afiliación: Rusia Pais de publicación: Reino Unido

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