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Fluorinated 1,3,4-oxadiazoles and other azoles in cycloaddition reactions

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Chemistry of Heterocyclic Compounds Aims and scope

This review covers reported cycloaddition reactions of fluorinated 1,3,4-oxadiazoles and certain other fluorinated azoles, leading to the formation of a wide range of new oxygen-containing cage structures. The considered reactions represent cascade (tandem) (2+4) cycloaddition processes leading to the formation of oxadiazabicycloheptenes, followed by retro-(2+3) cycloaddition, extrusion of nitrogen molecule, and another (2+3) cycloaddition. Preparative applications of the reactions are discussed, along with the stereochemical and orbital effects that influence their direction.

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The authors gratefully acknowledge the financial support received from the Russian Foundation for Basic Research (grant No. 16-29-10755-ofi_m) as well as from the Moscow Region State University (grant No. 2016-1).

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Authors and Affiliations

  1. Moscow Region State University, 10 Radio St., Moscow, 107005, Russia

    Nikolai V. Vasil’ev

  2. State Scientific Research Institute of Biological Engineering, 75-1 Volokolamskoe Shosse, Moscow, 123424, Russia

    Nikolai V. Vasil’ev, Tatiana S. Kostryukova & Georgy V. Zatonsky

  3. Moscow M. V. Lomonosov State University, 1 Leninskie Gory, Moscow, 119991, Russia

    Sergey Z. Vatsadze

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  1. Nikolai V. Vasil’ev
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Correspondence to Nikolai V. Vasil’ev.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(9), 675–686

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Vasil’ev, N.V., Kostryukova, T.S., Zatonsky, G.V. et al. Fluorinated 1,3,4-oxadiazoles and other azoles in cycloaddition reactions. Chem Heterocycl Comp 52, 675–686 (2016). https://doi.org/10.1007/s10593-016-1948-x

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  • DOI: https://doi.org/10.1007/s10593-016-1948-x

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