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1-Carbamoylhydantoins. New Aspects of Reactivity

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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. 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

    Article  CAS  PubMed  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  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

    Article  CAS  PubMed  Google Scholar 

  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

    Article  CAS  Google Scholar 

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Authors and 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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  • DOI: https://doi.org/10.1134/S107042802012012X

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