1-Carbamoylhydantoins. New Aspects of Reactivity

Russian Journal of Organic Chemistry volume 56, pages2119–2131(2020)Cite this article

Abstract

Some derivatives of 1-carbamoylhydantoins undergo cleavage at the N1–C(O) bond on heating in solution. 1-Carbamoylhydantoins in aqueous and alcoholic ammonia rearrange via opening of the imidazole ring, followed by recyclization. Prolonged treatment of 1-carbamoylhydantoins with aqueous ammonia can lead to elimination of the C2=O carbonyl group.

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Affiliations

  1. CHEM Ltd. Scientific and Production Company, Kuzʼmolovskii, 188663, Leningrad oblast, Russia

    M. A. Kavina & V. V. Sizov

  2. St. Petersburg State Chemical Pharmaceutical University, 197022, St. Petersburg, Russia

    M. A. Kavina

Authors
  1. M. A. Kavina
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  2. V. V. Sizov
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Correspondence to V. V. Sizov.

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Kavina, M.A., Sizov, V.V. 1-Carbamoylhydantoins. New Aspects of Reactivity. Russ J Org Chem 56, 2119–2131 (2020). https://doi.org/10.1134/S107042802012012X

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Keywords:

  • cleavage of 1-carbamoylhydantoins
  • isocyanate
  • rearrangement of hydantoins
  • cyclization to isomeric hydantoin
  • elimination of cyanic acid
  • substituted ureas