Chromato-mass-spectrometric analysis of the reaction between 1,2-diaminoimidazole and 1-aryl-3-(dimethylamino)prop-2-en-1-one

  • Х. С. Шихалиев Shikhaliev Khidmet S. – professor, head of Department of Organic Chemistry, Voronezh State University, Voronezh
  • Д. Ю. Вандышев Vandyshev Dmitriy Yu. – the postgraduate student of organic chemistry department, Voronezh State University, Voronezh. e-mail: francy_2007@mail.ru
  • А. Ю. Потапов Potapov Andrey Yu. - dr. sci., associate professor of organic chemistry department, Voronezh State University, Voronezh.
  • М. Ю. Крысин Krysin Michael Yu. - professor of organic chemistry department
  • А. В. Коконова Kononova Anna V. – student , Voronezh State University, Voronezh
Keywords: High performance liquid chromatography, mass spectrometry, diaminoimidazole, enaminone, the reaction mass, imidazopyridine.

Abstract

Diaminoimidazoles are actively used in the creation of various substances with a given physiological
activity. However, the main problem in the chemistry of this polynucleophilic substrate is: the determination
of the sequence of transformations leading to final products during various cascade processes, as well as
the time that is necessary to form the maximum number of desired substances. By the method of highperformance
liquid chromatography in combination with mass spectrometry, we studied the interaction of
1,2-diaminoimidazole with 1-phenyl-3-(dimethylamino)prop-2-en-1-one. In the course of the analysis, it was
found that the reaction takes place over two hours of boiling and leads to a single product - 4-phenyl-5-
phenylimidazo[1,5-b]pyridazine-7-amine.

Downloads

Download data is not yet available.

References

1. Huang W.S., Metcalf C.A., Sundaramorthi R., Wang Y. et al., Journal of Medicinal Chemistry, 2010, Vol. 53, No 12, pp. 4701-4719.
2. Miller G.D., Woessner D.W., Sirch M.J., Lim C.S., Molecular Pharmaceutics, 2013, Vol. 10, No 9, pp. 3475-3483.
3. Foulks J.M., Carpenter K.J., Luo B., Xu Y. et al., Neoplasia, 2014, Vol. 16, No 5, pp. 403-412.
4. Roberts L.R., Bradley P.A., Bunnage M.E., England K.S. et al., Bioorganic and Medicinal Chemistry Letters, 2011, Vol. 21, No 21, pp. 6515-6518.
5. Livermore D.G.H., Bethell R.C., Cammack N., Hancock A.P. et al., Journal of Medicinal Chemistry, 1993, Vol. 36, No 24, pp. 3784-3794.
6. Kolos N.N., Orlov V.D., Paponov B.V., Baumer V.N., Chemistry of Heterocyclic Compounds, 1998, Vol. 34, No 10, pp. 1189-1194.
7. Kolos N.N., Kovalenko L.Yu., Shishkina S.V., Shishkin O.V. et al., Chemistry of Heterocyclic Compounds, 2007, Vol. 43, No 3, pp. 1397-1405.
8. Kutlescha K., Irragang T., Kempe R., Advanced Synthesis and Catalysis, 2010, Vol. 352, No 18, pp. 3126-3130.
9. Lipson V.V., Svetlichnaya N.V., Shirobokov M.G., Musatov V.I.,et al., Russian Journal of Organic Chemistry, 2012, Vol. 48, No 2, pp.273-277.
10. Lipson V.V., Svetlichnaya N.V., Shishkina S.V., Shishkin O.V., Mendeleev Communication, 2008, Vol. 18, No 4, pp. 141 -143.
11. Medvedeva S.M., Shikhlaliev Kh.S., Krysin M.Yu., Gotsak I.V., Chemistry of Heterocyclic Compounds, 2016, Vol. 52, No 5, pp.309-315.
12. Shihaliev Kh.S., Selemenev V.F., Medvedeva S.M., Ponomareva L.F. et al., Sorbtsionnye i khromatograficheskie protsessy,2014, Vol. 14, No 2, pp. 332-337.
13. Medvedeva S.M., Shihaliev Kh.S., Sorbtsionnye i khromatograficheskie protsessy, 2014, Vol. 14, No 4, pp. 696-702.
14. Medvedeva S.M., Shihaliev Kh.S., Kryl'skij D.V., Sinjaeva L.A., Sorbtsionnye i khromatograficheskie protsessy, 2014, Vol. 14, No 6, pp. 970-976.
15. Vandyshev D.Yu., Shikhaliev Kh.S., Kokonova A.V. et al., Chemistry of Heterocyclic Compounds, 2016, Vol. 52, No 7, pp. 493-497.
Published
2018-02-21
How to Cite
Шихалиев, Х. С., Вандышев, Д. Ю., Потапов, А. Ю., Крысин, М. Ю., & Коконова, А. В. (2018). Chromato-mass-spectrometric analysis of the reaction between 1,2-diaminoimidazole and 1-aryl-3-(dimethylamino)prop-2-en-1-one. Sorbtsionnye I Khromatograficheskie Protsessy, 17(3), 490-495. https://doi.org/10.17308/sorpchrom.2017.17/405