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Reaction of 2-(2-oxo-2-arylethylidene)-2,3-dihydropyrimidine-4(1H)-ones with aldehydes

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Abstract

2-(2-Oxo-2-arylethylidene)-2,3-dihydropyrimidine-4(1H)-ones react with aromatic and heteroaromatic aldehydes to form the unsaturated ketones, whereas in the case of 3- and 4-benzaldehydes the corresponding trans-2-styrylpyrimidine-4(3H)-ones were obtained. A possible mechanism of hydrolytic cleavage of the product of condensation of 2-(2-oxo-2-phenylethylidene)-2,3-dihydropyrimidine-4(1H)-one with paraformaldehyde under acid catalysis and mechanochemical activation has been discussed.

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References

  1. Moskvin, A.V., Reznikova, N.R. and Ivin, B.A., Russ. J. Org. Chem., 2002, vol. 38, no. 4, p. 463.

    Article  CAS  Google Scholar 

  2. Perkampus, H.-H. and Bluhm, T., Tetrahedron, 1972, vol. 28, p. 2099.

    Article  CAS  Google Scholar 

  3. Haroutounian, S.A. and Katzenellenboger, J.A., Tetrahedron, 1995, vol. 51, p. 1585.

    Article  CAS  Google Scholar 

  4. Achell, S., Nouira, I., Pfaffinger, B., Ramondenc, Y., Ple, N., and Rodrigues-Lopes, J., J. Org. Chem., 2009, vol. 74, p. 3711.

    Article  Google Scholar 

  5. Lipunova, G.N., Nosova, E.V., Trashakhova, T.V., and Charushin, V.N., Usp. Khim., 2011, vol. 80, no. 11, p. 1166.

    Article  Google Scholar 

  6. Yavolovskii, A.A., Grishchuk, L.V., Rakipov, I.M., Ivanov, Yu.E., Stepanov, D.E., and Kamalov, G.L., Russ. J. Gen. Chem., 2012, vol. 82, no. 4, p. 725.

    Article  CAS  Google Scholar 

  7. Yavolovskii, A.A., Grishchuk, L.V., Rakipov, I.M., Ivanov, Yu.E., Stepanov, D.E., and Kamalov, G.L., Chem. Heterocycl. Comp., 2013, no. 10, p. 1487.

    Google Scholar 

  8. Stepanov, D.E., Grishchuk, L.V., Ivanova, R.Yu., Ivanov, Yu.E., Yavolovskii, A.A., and Kamalov, G.L., Russ. J. Gen. Chem., 2013, vol. 83, no. 3, p. 526.

    Article  CAS  Google Scholar 

  9. Yamauchi, M., Shirota, M., and Watanabe, T., Heterocycles, 1990, vol. 31, no. 9, p. 1699.

    Article  CAS  Google Scholar 

  10. Traven’, N.I. and Safonova, T.S., Chem. Heterocycl. Comp., 1980, vol. 16, no. 6, p. 607.

    Article  Google Scholar 

  11. Safonova, T.S. and Mamaeva, I.E., Chem. Heterocycl. Comp., 1973, vol. 9, no. 1, p. 108.

    Article  Google Scholar 

  12. Gordon, A.J. and Ford, R.A., The Chemist’s Companion, New York: Wiley, 1972.

    Google Scholar 

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Correspondence to S. M. Pluzhnik-Gladyr.

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Original Russian Text © A.A. Yavolovskii, L.V. Grishchuk, E.I. Bevzyuk, Yu.E. Ivanov, D.E. Stepanov, S.M. Pluzhnik-Gladyr, G.L. Kamalov, 2014, published in Zhurnal Obshchei Khimii, 2014, Vol. 84, No. 5, pp. 777–781.

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Yavolovskii, A.A., Grishchuk, L.V., Bevzyuk, E.I. et al. Reaction of 2-(2-oxo-2-arylethylidene)-2,3-dihydropyrimidine-4(1H)-ones with aldehydes. Russ J Gen Chem 84, 869–874 (2014). https://doi.org/10.1134/S1070363214050156

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  • DOI: https://doi.org/10.1134/S1070363214050156

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