Nitrosation of adamantyl dichlorocyclopropanes as a new approach to adamantyl isoxazoles


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Abstract

Nitrosation of 2-(1-adamantylmethyl)-1,1-dichlorocyclopropane with either adduct NOCl•(SO3)n or nitrosonium tetrafluoroborate gives 3- and 4-(1-adamantylmethyl)-5-chloroisoxazoles in good yields. The presence of a linker between cyclopropane ring and adamantane moiety is essential for enabling nitrosation—heterocyclization of adamantyl 1,1-dichlorocyclopropanes.

About the authors

O. B. Bondarenko

Department of Chemistry, M. V. Lomonosov Moscow State University

Author for correspondence.
Email: bondarenko@org.chem.msu.ru
Russian Federation, Build. 3, 1 Leninskie Gory, Moscow, 119991

M. R. Baimuratov

Samara State Technical University

Email: bondarenko@org.chem.msu.ru
Russian Federation, 244 ul. Molodogvardeiskaya, Samara, 443100

Yu. N. Klimochkin

Samara State Technical University

Email: bondarenko@org.chem.msu.ru
Russian Federation, 244 ul. Molodogvardeiskaya, Samara, 443100

N. V. Zyk

Department of Chemistry, M. V. Lomonosov Moscow State University; Institute of Physiologically Active Compounds, Russian Academy of Sciences

Email: bondarenko@org.chem.msu.ru
Russian Federation, Build. 3, 1 Leninskie Gory, Moscow, 119991; 1 Severnyi proezd, Chernogolovka, Moscow Region, 142432

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