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Synthesis and Properties of N,N′-Disubstituted Ureas and Their Isosteric Analogs Containing Polycyclic Fragments: VIII. Synthesis and Properties of N-[(3-Chloroadamantan-1-yl)methyl]-N′-(Fluoro, chlorophenyl)ureas and Symmetrical Bis-ureas

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Abstract

A new procedure has been proposed for the synthesis of 3-chloroadamantan-1-ylmethyl isocyanate starting from 2-(3-chloroadamantan-1-yl)acetic acid. Reactions of 3-chloroadamantan-1-ylmethyl isocyanate with fluoro- and chloroanilines and alkane-α,ω-diamines afforded two series of N,N′-disubstituted ureas containing a 3-chloroadamantan-1-yl substituent in 53–94% yields. The synthesized ureas are promising as inhibitors of human soluble epoxide hydrolase.

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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, Ya. P. Kuznetsov, V. S. D’yachenko, E. V. Rasskazova & G. M. Butov

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

    V. V. Burmistrov, V. S. D’yachenko, E. V. Rasskazova & G. M. Butov

Authors
  1. D. V. Danilov
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  2. V. V. Burmistrov
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  3. Ya. P. Kuznetsov
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  5. E. V. Rasskazova
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  6. G. M. Butov
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Correspondence to G. M. Butov.

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Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 3, pp. 339–351 https://doi.org/10.31857/S0514749221030022.

For communication VII, see [1].

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Danilov, D.V., Burmistrov, V.V., Kuznetsov, Y.P. et al. Synthesis and Properties of N,N′-Disubstituted Ureas and Their Isosteric Analogs Containing Polycyclic Fragments: VIII. Synthesis and Properties of N-[(3-Chloroadamantan-1-yl)methyl]-N′-(Fluoro, chlorophenyl)ureas and Symmetrical Bis-ureas. Russ J Org Chem 57, 327–337 (2021). https://doi.org/10.1134/S1070428021030027

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