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Three-Component Condensation of Urea with Formaldehyde and Propane-1,3-diamine or Butane-1,4-diamine

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Abstract

Three-component condensation of urea with formaldehyde and propane-1,3-diamine in a molar ratio of 1 : 3 : 1 leads to the tricyclic 1,3,5,7,11,13,15,17-octaazatricyclo[15.3.1.17,11]docosane-4,14-dione. Condensation of urea with 1,3,7,9,13,15,19,21-octaazapentacyclo[19.3.1.13,7.19,13.115,19]octacosane (2 : 1) also leads to the formation of tricyclic product. As a result of the condensation of urea with formaldehyde and butane-1,4-diamine in the ratio of 2 : 4 : 1, 5,5′-butane-1,4-diylbis(1,3,5-triazinan-2-one) was obtained.

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REFERENCES

  1. Ghosh, A.K. and Brindisi, M., J. Med. Chem., 2020, vol. 63, no. 6, p. 2751. https://doi.org/10.1021/acs.jmedchem.9b01541

    Article  CAS  PubMed  Google Scholar 

  2. Dandia, A., Arya, K. and Sati, M., Synth. Commun., 2004, vol. 34, no. 6, p. 1141. https://doi.org/10.1081/scc-120028646

    Article  CAS  Google Scholar 

  3. Ramsh, S.M., Ivanenko, A.G., Shpilevyi, V.A., Medvedskiy, N.L., and Kushakova, P.M., Chem. Heterocycl. Compd., 2005, vol. 41, no. 7, p. 921. https://doi.org/10.1007/s10593-005-0249-6

    Article  CAS  Google Scholar 

  4. Paquin, A.M., Angew. Chem. (A), 1948, vol. 60, no. 10, p. 267.

    Google Scholar 

  5. Paquin, A.M., J. Org. Chem., 1949, vol. 14, no. 2, p. 189. https://doi.org/10.1021/jo01154a001

    Article  CAS  PubMed  Google Scholar 

  6. Yawer, M.A., Necas, M., and Sindelar, V., Tetrahedron, 2016, vol. 72, no. 22, p. 2943. https://doi.org/10.1016/j.tet.2016.04.009

    Article  CAS  Google Scholar 

  7. Dave, P.R., Doyle, G., Axenrod, T., Yazdekhasti, H., and Ammon, H.L., Tetrahedron Lett., 1992, vol. 33, no. 8, p. 1021. https://doi.org/10.1016/s0040-4039(00)91849-5

    Article  CAS  Google Scholar 

  8. Burke, W.J., J. Am. Chem. Soc., 1947, vol. 69, no. 9, p. 2136. https://doi.org/10.1021/ja01201a024

    Article  CAS  Google Scholar 

  9. Burke, W.J., Patent USA 2304624A, 1942; C. A., 1943, vol. 37, no. 10, p. 2852.

    Google Scholar 

  10. McCormick, L.J., McDonnell-Worth, C., Platts, J.A., Alison, J. Edwards, A.J., and Turner, D.R., Chem. Asian J., 2013, vol. 8, p. 2642. https://doi.org/10.1002/asia.201300530

    Article  CAS  PubMed  Google Scholar 

  11. Hamoud, F., Ramsh, S.M., Pevzner, L.M., Fundamensky, V.S., Gurzhiy, V.V., Zakharov, V.I., Kuznetsov, V.A., Krivorotov, D.V., and Khrabrova, E.S., Chem. Heterocycl. Compd., 2014, vol. 50, no. 7, p. 1053. https://doi.org/10.1007/s10593-014-1562-8

    Article  CAS  Google Scholar 

  12. Dale, J. and Sigvartsen, T., Acta Chem. Scand., 1991, vol. 45, no. 10, p. 1064. https://doi.org/10.3891/acta.chem.scand.45-1064

    Article  CAS  Google Scholar 

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Funding

This work was carried out within the framework of the governmental task of the Ministry of Science and Higher Education of the Russian Federation (program 785.00X60.19).

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Correspondence to F. Hamoud.

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No conflict of interest was declared by the authors.

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Translated from Zhurnal Obshchei Khimii, 2021, Vol. 91, No. 11, pp. 1801–1804 https://doi.org/10.31857/S0044460X21110123.

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Hamoud, F., Bedouh, Y., Ramsh, S.M. et al. Three-Component Condensation of Urea with Formaldehyde and Propane-1,3-diamine or Butane-1,4-diamine. Russ J Gen Chem 91, 2327–2329 (2021). https://doi.org/10.1134/S1070363221110116

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  • DOI: https://doi.org/10.1134/S1070363221110116

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