Cyclization of ethyl [cyano(4,6-dimethylpyrimidin-2-yl)amino]-acetate

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Abstract

Imidazolin-4-one derivatives have been prepared by a reaction of ethyl [cyano(4,6-dimethylpyrimidin-2-yl)amino]acetate (2) with morpholine, piperidine and hydrazides. In the presence of sulfuric acid, cyanoester 2 gives 2-iminooxazolin-5-one which is acylated on the nitrogen atom of imino group and is rearranged to imidzolidin-2,4-dione in the presence of KCNO.

About the authors

A. K. Shiryaev

Samara State Technical University

Email: shiryaev.ak@samgtu.ru
Russia, 443100 Samara, ul. Molodogvardeiskaya, 244

M. S. Krasavina

Samara State Technical University

Russia, 443100 Samara, ul. Molodogvardeiskaya, 244

V. A. Shiryaev

Samara State Technical University

Russia, 443100 Samara, ul. Molodogvardeiskaya, 244

References

  1. Thakur A., Verma M., Bharti R., Sharma R. Tetrahedron. 2022, 119, 132813. doi: 10.1016/j.tet.2022.132813
  2. Joshi S., Mehra M., Singh R., Kakar S. Egypt. J. Basic Appl. Sci. 2023, 10, 1, 218–239. doi: 10.1080/2314808X.2023.2171578
  3. Kushwaha N., Kushwaha S. Biointerface Res. Appl. Chem. 2022, 12, 5, 6460–6486. doi: 10.33263/BRIAC125.64606486
  4. Rulhania S., Kumar S., Nehra B., Gupta G.D., Monga V. J. Mol. Struct. 2021, 1232, 129982. doi: 10.1016/j.molstruc.2021.129982
  5. Alghamdi S.S., Suliman R.S., Almutairi K., Kahtani K., Aljatli D. Drug Design Develop. Ther. 2021, 15, 3289–3312. doi: 10.2147/DDDT.S307113
  6. Siwach A., Verma P.K. BMC Chem. 2021, 15, 12, 1–69. doi: 10.1186/s13065-020-00730-1
  7. Gujjarappa R., Kabi A.K., Sravani S., Garg A., Vodna- la N., Tyagi U., Kaldhi D., Velayutham R., Singh V., Gupta S. Overview on Biological Activities of Imidazole Derivatives. Ed. B.P. Swain. Singapore: Springer. Publ. 2022, 135–227. doi: 10.1007/978-981-16-8399-2_6
  8. Gujjarappa R., Sravani S., Kabi A.K., Garg A., Vodna- la N., Tyagi U., Kaldhi D., Singh V., Gupta S., Mala- kar C.C. An Overview on Biological Activities of Oxazole, Isoxazoles and 1,2,4-Oxadiazoles Derivatives. Ed. B.P. Swain. Singapore: Springer. Publ. 2022, 379–400. doi: 10.1007/978-981-16-8399-2_10
  9. Tolomeu H.V., Fraga C.A.M. Molecules 2023, 28, 838. doi: 10.3390/molecules28020838
  10. Sharma P., LaRosa C., Antwi J., Govindarajan R., Werbovetz K.A. Molecules 2021, 26, 4213. doi: 10.3390/molecules26144213
  11. Guerrero-Pepinosa N.Y., Cardona-Trujillo M.C., Garzґon-Casta˜no S.C., Veloza L.A., Sepúlveda-Arias J.C. Biomed. Pharmacother. 2021, 138, 111495. doi: 10.1016/j.biopha.2021.111495
  12. Albayatia M.R., Mohamed M.F.A., Moustafa A.H. Synth. Commun. 2020, 50, 8, 1217–1231. doi: 10.1080/00397911.2020.1735443
  13. Moustafa A.H., Ahmed W.W., Awad M.F., Aboelez M.O., Khodairy A., Amer A.A. Mol. Div. 2022, 26, 2813–2823. doi: 10.1007/s11030-022-10401-z
  14. Dovlatyan V.V., Eliazyan K.A., Pivazyan V.A. Chem. Heterocycl. Compd. 1994, 30 (9), 1074–1076. doi: 10.1007/BF01171168
  15. Shestakov A.S., Moustafa A.H., Bushmarinov I.S., Goloveshkin A.S., Shapovalov A.V., Shikhaliev K.S., Prezent M.A., Sidorenko O.E. J. Heterocycl. Chem. 2017, 54, 551–560. doi: 10.1002/jhet.2621
  16. Fodor G., Koczka K. J. Chem. Soc. 1952, 850-854. doi: 10.1039/JR9520000850
  17. Dutta S., Higginson C.J., Ho B.T., Rynearson K.D., Dibrov S.M., Hermann T. Org. Lett. 2010, 12 (2), 360–363. doi: 10.1021/ol9026914
  18. Dutta S., Dibrov S.M., Ho B.T., Higginson C.J., Hermann T. J. Chem. Crystallogr. 2012, 42, 119–129. doi: 10.1007/s10870-011-0212-6
  19. Basavaprabhu H., Sureshbabu V.V. Org. Biomol. Chem. 2012, 10 (13), 2528–2533. doi: 10.1039/c2ob06916d
  20. Wildermuth R.E., Steinborn C., Barber D.M., Muhlfenzl K.S., Kendlbacher M., Mayer P., Wurst K., Magauer T. Chem. Eur. J. 2021, 27, 12181–12189. doi: 10.1002/chem.202101849
  21. Steinborn C., Wildermuth R.E., Barber D.M., Magauer T. Angew. Chem. Int. Ed. 2020, 59, 17282–17285. doi: 10.1002/anie.202008158
  22. Masumoto E., Maruoka H., Okabe F., Fujioka T., Yamagata K. J. Heterocycl. Chem. 2015, 52, 48–53. doi: 10.1002/jhet.1946
  23. Birtwell S. J. Chem. Soc. 1953, 1725–1730. doi: 10.1039/JR9530001725

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