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Synthesis and Properties of N,N′-Disubstituted Ureas and Their Isosteric Analogs Containing Polycyclic Fragments: XIV. N-[(Adamantan-1-yl)(phenyl)methyl]-N′-substituted Ureas and Symmetrical Bis-ureas

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Abstract

A procedure has been developed for the synthesis of rac-1-[isocyanato(phenyl)methyl]adamantane from rac-2-(adamantan-1-yl)-2-phenylacetic acid in 95% yield. The reactions of rac-1-[isocyanato(phenyl)­methyl]adamantane with aliphatic diamines and trans-4-[(4-aminocyclohexyl)oxy]benzoic acid afforded a series of N,N′-disubstituted ureas in 60–91% yields, and its hydrolysis in the presence of a catalytic amount of 1,8-diazabicyclo[5.4.0]undec-7-ene gave 94% of symmetrical N,N′-bis[(adamantan-1-yl)(phenyl)methyl]urea. The structure of rac-2-(adamantan-1-yl)-2-phenylacetic acid was confirmed by X-ray analysis of its single crystal.

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ACKNOWLEDGMENTS

The X-ray diffraction study was carried out using the equipment of the joint Spectral and Analytical Center (Kazan Scientific Center Federal Research Center, Russian Academy of Science).

Funding

This study was performed under financial support by the Russian Science Foundation (project no. 19-73-10002). The crystal structure of rac-2-(adamantan-1-yl)-2-phenylacetic acid was determined by R.R. Fayzullin in the framework of state assignment for Kazan Scientific Center Federal Research Center, Russian Academy of Science.

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Authors and Affiliations

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

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

  2. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center Federal Research Center, Russian Academy of Sciences, 420088, Kazan, Russia

    R. R. Fayzullin

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

    G. M. Butov

Authors
  1. V. V. Burmistrov
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  2. V. M. Mokhov
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  3. D. V. Danilov
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  4. R. R. Fayzullin
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  5. G. M. Butov
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Corresponding author

Correspondence to G. M. Butov.

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Additional information

Translated from Zhurnal Organicheskoi Khimii, 2022, Vol. 58, No. 3, pp. 235–247 https://doi.org/10.31857/S0514749222030028.

For communication XIII, see [1].

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Burmistrov, V.V., Mokhov, V.M., Danilov, D.V. et al. Synthesis and Properties of N,N′-Disubstituted Ureas and Their Isosteric Analogs Containing Polycyclic Fragments: XIV. N-[(Adamantan-1-yl)(phenyl)methyl]-N′-substituted Ureas and Symmetrical Bis-ureas. Russ J Org Chem 58, 259–267 (2022). https://doi.org/10.1134/S1070428022030022

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