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Synthesis of 3-adamantylated hydantoins and their 2-thio(seleno) analogs

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Chemistry of Heterocyclic Compounds Aims and scope

A series of 3-(adamantan-1-ylalkyl)-2-(O,S,Se)hydantoins were synthesized in the reaction of (adamantan-1-ylalkyl)heteroallenes with glycine ethyl ester hydrochloride under mild conditions in 75–85% yields. A method was developed for the synthesis of novel adamantan-1-ylalkyl isoselenocyanates, precursors in the synthesis of adamantylated 2-selenohydantoins. For the first time, 3-(adamantan-1-yl)-2-(O,S)hydantoins were synthesized via the reaction of 2-(O,S)hydantoins with 1,3-dehydroadamantane in 1,4-dioxane heated to reflux for 1 h in 75–80% yields.

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The work was done with support of the Ministry of Education and Science of the Russian Federation within the framework of the baseline of the State Assignment for 2017–2019 (project 4.7491.2017/BCh) on equipment acquired under the Strategic Development Program of Volgograd State Technical University for 2012–2016.

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Authors and Affiliations

  1. Volzhsky Polytechnic Institute (branch), Volgograd State Technical University, 42a Engelsa St., Volzhsky, 404121, Russia

    Vladimir V. Burmistrov, Dmitry А. Pitushkin, Vladimir S. D’yachenko & Gennady M. Butov

  2. Federal Research Center N. I. Vavilov All-Russian Research Institute of Plant Genetic Resources (VIR), 42–44 Bol’shaya Morskaya St., Saint Petersburg, 190121, Russia

    Vladimir V. Vasipov

Authors
  1. Vladimir V. Burmistrov
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  2. Dmitry А. Pitushkin
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  3. Vladimir V. Vasipov
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  4. Vladimir S. D’yachenko
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  5. Gennady M. Butov
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Correspondence to Gennady M. Butov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(7), 619–622

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Burmistrov, V.V., Pitushkin, D.А., Vasipov, V.V. et al. Synthesis of 3-adamantylated hydantoins and their 2-thio(seleno) analogs. Chem Heterocycl Comp 55, 619–622 (2019). https://doi.org/10.1007/s10593-019-02507-4

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  • DOI: https://doi.org/10.1007/s10593-019-02507-4

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