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One-step preparation method for adamantyl-containing isocyanates, precursors of epoxide hydrolase inhibitors

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Abstract

One-step preparation method was developed for adamantyl-containing isocyanates obtained by Curtius reaction from adamantanecarboxylic and acetic acids. Synthesis of isocyanate was performed without the isolation of intermediate acid chloride which solution was added to sodium azide in boiling toluene. In the reactor the acid azide formation and its rearrangement in isocyanate occurred simultaneously. Yields of target products were 83–94% with respect to the acid.

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Authors and Affiliations

  1. Volzhsky Polytechnic University (Branch) Volgograd State Technical University, ul. Engelsa 42а, Volzhsky, Volgograd oblast, 404121, Russia

    G. M. Butov, V. V. Burmistrov & D. A. Pitushkin

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  1. G. M. Butov
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  2. V. V. Burmistrov
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  3. D. A. Pitushkin
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Correspondence to G. M. Butov.

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Original Russian Text © G.M. Butov, V.V. Burmistrov, D.А. Pitushkin, 2017, published in Zhurnal Organicheskoi Khimii, 2017, Vol. 53, No. 5, pp. 667–671.

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Butov, G.M., Burmistrov, V.V. & Pitushkin, D.A. One-step preparation method for adamantyl-containing isocyanates, precursors of epoxide hydrolase inhibitors. Russ J Org Chem 53, 673–678 (2017). https://doi.org/10.1134/S1070428017050050

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  • DOI: https://doi.org/10.1134/S1070428017050050

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