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Synthesis and Properties of N,N′-Disubstituted Ureas and Their Isosteric Analogs Containing Polycyclic Fragments: III. Synthesis and Properties ofN-[2-(Adamantan-1-yl)ethyl]-N′-R-ureas

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Abstract

Methods have been developed for the synthesis of N,N′-disubstituted ureas containing an adamantane fragment separated from the urea nitrogen atom by an ethylene spacer in 29–88% yields on the basis of 2-(adamantan-1-yl)ethyl isocyanate and 2-(adamantan-1-yl)ethanamine. 1,1′-Carbonyldiimidazole was used for the first time to obtain 2-(adamantan-1-yl)ethyl isocyanate. The latter was formed through a stable intermediate product, N-[2-(adamantan-1-yl)ethyl]-1H-imidazole-1-carboxamide which could be isolated and used in the synthesis of symmetrically and unsymmetrically substituted ureas.

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Funding

This study was performed under financial support by the Russian Science Foundation (project no. 19-73-10002).

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Authors and Affiliations

  1. Volgograd State Technical University, 400005, Volgograd, Russia

    D. V. Danilov, V. V. Burmistrov & G. M. Butov

  2. Volzhsky Polytechnic Institute (Branch), Volgograd State Technical University, 404121, Volzhsky, Volgograd oblast, Russia

    V. V. Burmistrov & G. M. Butov

Authors
  1. D. V. Danilov
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  2. V. V. Burmistrov
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  3. G. M. Butov
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Correspondence to G. M. Butov.

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For communication II, see [1].

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Danilov, D.V., Burmistrov, V.V. & Butov, G.M. Synthesis and Properties of N,N′-Disubstituted Ureas and Their Isosteric Analogs Containing Polycyclic Fragments: III. Synthesis and Properties ofN-[2-(Adamantan-1-yl)ethyl]-N′-R-ureas. Russ J Org Chem 56, 1132–1139 (2020). https://doi.org/10.1134/S1070428020070027

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