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Four-Component Condensation of Ethyl Acetoacetate, Phenylglyoxal Hydrate, Barbituric Acid, and Primary Amines

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Abstract

The four-component condensation of ethyl acetoacetate, phenylglyoxal hydrate, barbituric acid, and primary amines was used to obtain polysubstituted pyrroles containing a barbituric acid fragment. In some cases, by-products formed by the three-component condensation of phenylglyoxal hydrate, barbituric acid, and amines were isolated.

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The authors declare no conflict of interest.

REFERENCES

  1. Abdolmohammadi, S. and Balalaie, S., Int. J. Org. Chem., 2012, vol. 2, p. 7. https://doi.org/10.4236/ijoc.2012.21002

    Article  CAS  Google Scholar 

  2. Mosslemin, M.H. and Nateghi, M.R. Ultrason. Sonochem., 2010, vol. 17, p. 162. https://doi.org/10.1016/j.ultsonch.2009.07.002

    Article  CAS  PubMed  Google Scholar 

  3. Nemati, F. and Saeedirad, R., Chin. Chem. Lett., 2013, vol. 24, p. 370. https//doi.org/10.1016/j.cclet.2013.02.018

    Article  CAS  Google Scholar 

  4. Verma, G.K., Raghuvanshi, K., Kumar, R., and Singh, M.S., Tetrahedron Lett., 2012, vol. 53, p. 399. https://doi.org/10.1016/j.tetlet.2011.11.047

    Article  CAS  Google Scholar 

  5. Khalafi-Nezhad, A. and Panahi, F., Synthesis, 2011, p. 984. https://doi.org/10.1055/s-0030-1258446

  6. Jadhav, C., Khillare, L.D., and Bhosle, M.R., Synth. Commun., 2018, vol. 48, p. 233. https://doi.org/10.1080/00397911.2017.1390685

    Article  CAS  Google Scholar 

  7. Kolos, N.N. and Chechina, N.V., Chem. Heterocycl. Compd., 2019, vol. 55, p. 1278. https://doi.org/10.1007/s10593-019-02613-3

    Article  CAS  Google Scholar 

  8. Andina, A.V. and Andin, A.N., Russ. J. Org. Chem., 2015, vol. 51, p. 1043. htps://doi.org/10.1134/S1070428015070295

    Article  CAS  Google Scholar 

  9. Bavadi, M., Niknam, K., and Shahraki, O., J. Mol. Struct., 2017, vol. 1146, p. 242. https://doi.org/10.1016/j.molstruc.2017.06.003

    Article  CAS  Google Scholar 

  10. Ghandi, M., Jourablou, A., and Abbasi, A., J. Heterocycl. Chem., 2017, vol. 54, p. 3108. https://doi.org/10.1002/jhet.2924

    Article  CAS  Google Scholar 

  11. Dommaraju, Y., Borthakur, S., Rajesh, N., and Prajapati, D., RSC Adv., 2015, vol. 5, p. 24327. https://doi.org/10.1039/c5ra00796h

    Article  CAS  Google Scholar 

  12. Wilkerson, W.W., Copeland, R.A., Covington, M., and Trzaskos, J.M., J. Med. Chem., 1995, vol. 38, p. 3895. https://doi.org/10.1021/jm00020a002

    Article  CAS  PubMed  Google Scholar 

  13. Laszlo, S.E., Visco, D., Agarwal, L., Chang, L., Chin, J., Croft, G., Forsyth, A., Fletcher, D., Frantz, B., Hacker, C., Hanlon, W., Harper, C., Kostura, M., Li, B., Luell, S., MacCoss, M., Mantlo, N., O’Neill, E.A., Orevillo, C., Pang, M., Parsons, J., Rolando, A., Sahly, Y., Sidler, K., Widmer, W.R., and O’Keefe, S.J., Bioorg. Med. Chem. Lett., 1998, vol. 8, p. 2689. https://doi.org/10.1016/S0960-894X(98)00495-8

    Article  PubMed  Google Scholar 

  14. Nagarajan, K., Shenoy, S.J., and Talwalker, P.K., Indian J. Chem. Sect. B, 1989, vol. 28, p. 326.

    Google Scholar 

  15. Sulsky, R., Magnin, D.R., Huang, Y., Simpkins, L., Taunk, P., Patel, M., Zhu, Y., Stouch, T.R., Bassolino-Klimas, D., Parker, R., Harrity, T., Stoffel, R., Taylor, D.D., Lavoie, T.B., Kish, K., Jacobson, B.L., Sheriff, S., Adam, L.P., Ewinga, W.R., and Robl, J.A., Bioorg. Med. Chem. Lett., 2007, vol. 17, p. 3511. https://doi.org/10.1016/j.bmcl.2006.12.044

    Article  CAS  PubMed  Google Scholar 

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Correspondence to A. N. Andin.

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Translated from Zhurnal Organicheskoi Khimii, 2023, Vol. 59, No. 8, pp. 1050–1056 https://doi.org/10.31857/S0514749223080062.

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Andin, A.N., Kukharev, A.V. Four-Component Condensation of Ethyl Acetoacetate, Phenylglyoxal Hydrate, Barbituric Acid, and Primary Amines. Russ J Org Chem 59, 1329–1334 (2023). https://doi.org/10.1134/S1070428023080067

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  • DOI: https://doi.org/10.1134/S1070428023080067

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