Cercetarea proprietăților catalitice ale amestecurilor eutectice pe baza 1-metilimidazolului pentru sinteza 3,4-dihidropirimidin-2(1H)-tionelor

Natalia Ciobanu; Eugenia Stîngaci; Fliur Macaev

doi:10.52673/18570461.25.1-76.02

Authors

Natalia Ciobanu Institute of Chemistry, MSU https://orcid.org/0000-0002-1321-9277
Eugenia Stingaci Institute of Chemistry, MSU https://orcid.org/0000-0003-0731-3424
Fliur Macaev Institute of Chemistry, MSU https://orcid.org/0000-0002-3094-1990

DOI:

https://doi.org/10.52673/18570461.25.1-76.02

Keywords:

utectic mixtures, imidazole, 3, 4-dihydropyrimidin-2(1H)-thiones, monastrol

Abstract

This work was aimed at the synthesis of new eutectic mixtures based on 1-methyl-1H-imidazole. The structure of compounds was confirmed by physicochemical methods of analysis, IR-, 1H and 13C NMR spectroscopy and elemental analysis data. The catalytic activity of the eutectic mixtures synthesized in the Biginelli reaction was studied. The possibility of the synthesis of 3,4-dihydropyrimidin-2(1H)-thiones has been demonstrated, thereby initiating a new direction for the production of optically active organic substances, including the compound with significant practical applications Monastrol

References

1. Hansen, B.B., Spittle, S., Chen, B., Poe, D., Zhang, Y., Klein, J. M., Horton, A., Adhikar, L.i, Zelovich, T., Dohert,y B.W., Gurkan, B., Maginn, E.J., Ragauskas, A., Dadmun, M., Zawodzinski, T.A., Baker, G.A., Tuckerman, M.E., Savinel, R.F., Sangoro, J.R. Deep Eutectic Solvents: A Review of Fundamentals and Applications. In: Chemical Review. 2021, 121 (3), 1232-1285, https://pubs.acs.org/doi/10.1021/acs.chemrev.0c00385

2. de Andrade, D.C., Monteiro, S.A., Merib, J. A review on recent applications of deep eutectic solvents in microextraction techniques for the analysis of biological matrices. In: Advances in Sample Preparation. 2022, 1. 100007, https://doi.org/10.1016/j.sampre.2022.100007

3. Makos´-Chełstowska, P., Kaykhai, M.i, Płotka Wasylka, J., de la Guardia, M. Magnetic deep eutectic solvents – Fundamentals and applications. In: Journal of Molecular Liquids. 2022, 365, 120158, https://doi.org/10.1016/j.molliq.2022.120158

4. Kappe, C.O. Biologically active dihydropyrimidones of the Biginelli-type – a literature survey. In: Journal of Medicinal Chemistry. 2000, 35, 1043-1052, https://doi.org/10.1016/S0223-5234(00)01189-2

5. Russowsky, D., Canto, R.F.S., Sanches, S.A.A., D’Oca, M.G.M., de Fátima, Â., Pilli, R.A., Kohn, L.K., Antônio, M.A., de Carvalho, J.E. Synthesis and differential antiproliferative activity of Biginelli compounds against cancer cell lines: Monastrol, oxo-monastrol and oxygenated analogues. In: Bioorganic Chemistry, 2006, 173-182, https://doi.org/10.1016/j.bioorg.2006.04.003

6. El-Nassan, H.B. Advances in the discovery of kinesin spindle protein (Eg5) inhibitors as antitumor agents. In: European Journal of Medicinal Chemistry, 2013, 62, 614-631, https://doi.org/10.1016/j.ejmech.2013.01.031

7. Kappe, C.O., Shishkin, O.V., Uraya, G., Verdinoa, P. X-Ray Structure, Conformational Analysis, Enantioseparation, and Determination of Absolute Configuration of the Mitotic Kinesin Eg5 Inhibitor Monastrol. In: Tetrahedron, 2000, 1859-1862, https://doi.org/10.1016/S0040-4020(00)00116-2

8. Chobanu, N.G., Makaev, F.Z. Evtekticheskie rastvory na osnove 3-(karboksimetil)-1-vinil-1H-imidazol-3-ium khlorida i tiomocheviny dlya polucheniya Monastrola. In: Vestnik Bashkirskogo Universiteta, 2021, 26(2), 384-387, https://doi.org/10.33184/bulletin-bsu-2021.2.19

9. Șargarovschi, V., Styngach, E., Macaev, F. Specific ”Ionic Liquids” as new organocatalysts of Biginelli reactii. In: Chem. J. Moldova, 2008, 3, 95-97, https://doi.org/10.19261/cjm.2008.03(2).05

10. Macaev, F., Styngach, E., Shargarovskii, V., Bets, L., Vlad, L., Barba, A. Imidazolium salts with a free carboxy group as new catalysts of the Biginelli reaction. In: Russian Journal of Organic Chemistry, 2010 (4), 610-611, https://doi.org/10.1134/S1070428010040354

11. Prodius D., Macaev F., Lan Y., Novitchi G., Pogreb¬noi S., Stingaci E., Mereacre V., Anson C. E., Powell A. K. Evidence of slow relaxation of magnetization in dysprosium-based ionic liquids. Chemical Communications. 2013, 49, 9215-9217. https://doi.org/10.1039/C3CC45554H