1-Carbamoylhydantoins. New Aspects of Reactivity

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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REFERENCES

  1. 1

    Lewis, R.T., MacLeod, A.M., Merchant, K.J., Kelleher, F., Sanderson, I., Herbert, R.H., Cascieri, M.A., Sadowski, S., Ball, R.G., and Hoogsteen, K., J. Med. Chem., 1995, vol. 38, p. 923. https://doi.org/10.1021/jm00006a011

    CAS  Article  PubMed  Google Scholar 

  2. 2

    Biltz, H. and Heidrich, D., Justus Liebigs Ann. Chem., 1927, vol. 457, p. 190. https://doi.org/10.1002/jlac.19274570107

    CAS  Article  Google Scholar 

  3. 3

    Chung II Hong and Chheda, G.B., J. Med. Chem., 1975, vol. 18, p. 79. https://doi.org/10.1021/jm00235a018

    Article  Google Scholar 

  4. 4

    Capuano, L., Lazik, W., and Zander, R., Chem. Ber., 1974, vol. 107, p. 3237. https://doi.org/10.1002/cber.19741071010

    CAS  Article  Google Scholar 

  5. 5

    Poje, N., Palkovic, A., and Poje, M., J. Heterocycl. Chem., 1997, vol. 34, p. 477. https://doi.org/10.1002/jhet.5570340220

    CAS  Article  Google Scholar 

  6. 6

    Fraenkel-Conrat, H., Cooper, M., and Olcott, H., J. Am. Chem. Soc., 1945, vol. 67, p. 314. https://doi.org/10.1021/ja01218a049

    CAS  Article  Google Scholar 

  7. 7

    Belafdal, O., Bergon, M., Calmon, M., and Calmon, J.P., J. Org. Chem., 1989, vol. 54, p. 4193. https://doi.org/10.1021/jo00278a037

    CAS  Article  Google Scholar 

  8. 8

    Bellucci, M., Frigerio, M., Marcelli, T., and Volonterio, A., Synlett, 2013, vol. 24, p. 727. https://doi.org/10.1055/s-0032-1318432

    CAS  Article  Google Scholar 

  9. 9

    Mukherjee-Mueller, G., Helv. Chim. Acta, 1979, vol. 62, p. 1429. https://doi.org/10.1002/hlca.19790620507

    CAS  Article  Google Scholar 

  10. 10

    Poje, N. and Poje, M., Tetrahedron Lett., 1995, vol. 36, p. 8885. https://doi.org/10.1016/0040-4039(95)01847-B

    CAS  Article  Google Scholar 

  11. 11

    Kavina, M.A. and Sizov, V.V., Russ. J. Org. Chem., 2020, vol. 56, p. 1046. https://doi.org/10.1134/S1070428020060135

    CAS  Article  Google Scholar 

  12. 12

    Anisuzzaman, A.K.M., Storehalder, T., Williams, D.C., Ogg, N., and Kilbourne, T.D., J. Agric. Food Chem., 2008, vol. 56, p. 502. https://doi.org/10.1021/jf0720483

    CAS  Article  PubMed  Google Scholar 

  13. 13

    Belafdal, O., Bergon, M., Calmon, M., and Calmon, J.P., J. Org. Chem., 1989, vol. 54, p. 4193. https://doi.org/10.1021/jo00278a037

    CAS  Article  Google Scholar 

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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