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Synthesis and Properties of N,N′-Disubstituted Ureas and Their Isosteric Analogs Containing Polycyclic Fragments: XIII. N-[(3-Bromoadamantan-1-yl)methyl]ureas and Symmetrical Diureas

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Abstract

A one-step procedure has been developed for the synthesis of (3-bromoadamantan-1-yl)methyl isocyanate from 2-(3-bromoadamantan-1-yl)acetic acid and diphenylphosphoryl azide in 85% yield. The reac­tions of (3-bromoadamantan-1-yl)methyl isocyanate with aliphatic diamines and 4-(trans-4-aminocyclohexyl­oxy)benzoic acid gave a series of N,N′-disubstituted ureas and diureas in 52–85% yield. The hydrolysis of (3-bromoadamantan-1-yl)methyl isocyanate in the presence of a catalytic amount of DBU afforded symmetrical N,N′-bis[(3-bromoadamantan-1-yl)methyl]urea in 52% yield.

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ACKNOWLEDGMENTS

The study was performed using the equipment of the “New Materials and Sustainable Technologies” joint center at the Lobachevsky Nizhny Novgorod State University under support by the Russian Science Foundation.

Funding

This study was financially supported by the Russian Science Foundation (project no. 21-73-20123).

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Authors and Affiliations

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

    D. V. Danilov, V. S. D’yachenko, Ya. P. Kuznetsov, E. K. Degtyarenko, V. V. Burmistrov, G. M. Butov & I. A. Novakov

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

    G. M. Butov

Authors
  1. D. V. Danilov
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  2. V. S. D’yachenko
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  3. Ya. P. Kuznetsov
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  4. E. K. Degtyarenko
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  5. V. V. Burmistrov
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  6. G. M. Butov
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  7. I. A. Novakov
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Corresponding author

Correspondence to G. M. Butov.

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Additional information

Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 12, pp. 1684–1693 https://doi.org/10.31857/S051474922112003X.

For communication XII, see [1].

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Danilov, D.V., D’yachenko, V.S., Kuznetsov, Y.P. et al. Synthesis and Properties of N,N′-Disubstituted Ureas and Their Isosteric Analogs Containing Polycyclic Fragments: XIII. N-[(3-Bromoadamantan-1-yl)methyl]ureas and Symmetrical Diureas. Russ J Org Chem 57, 1913–1920 (2021). https://doi.org/10.1134/S1070428021120034

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