Synthesis and structure of 4-(het)aryl-6-methyl-2-cyanoimino-N,N-diethyl-1,2,3,4-tetrahydropyrimidine-5-carboxamides

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Abstract

A series of previously unknown 4-(het)aryl-6-methyl-2-cyanoimino-N,N-diethyl-1,2,3,4-tetrahydropyrimidine-5-carboxamides was synthesized by the reaction of N,N-diethyl-3-oxobutanamide with (het)arylaldehydes and N-cyanoguanidine. The structure of the obtained compounds was established by IR, 1H NMR spectroscopy and single crystal X-ray diffraction analysis.

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About the authors

N. A. Buzmakova

Perm State Pharmaceutical Academy of the Ministry of Health of the Russian Federation

Author for correspondence.
Email: tanyapgfa@yandex.ru
ORCID iD: 0000-0003-3171-0438
Russian Federation, Perm

T. M. Zamaraeva

Perm State Pharmaceutical Academy of the Ministry of Health of the Russian Federation

Email: tanyapgfa@yandex.ru
ORCID iD: 0000-0002-9932-9628
Russian Federation, Perm

N. V. Slepova

Perm State Pharmaceutical Academy of the Ministry of Health of the Russian Federation

Email: tanyapgfa@yandex.ru
ORCID iD: 0000-0003-3924-3715
Russian Federation, Perm

F. V. Sobin

Perm State Pharmaceutical Academy of the Ministry of Health of the Russian Federation

Email: tanyapgfa@yandex.ru
ORCID iD: 0000-0002-8416-6934
Russian Federation, Perm

M. V. Dmitriev

Пермский государственный национальный исследовательский университет

Email: tanyapgfa@yandex.ru
ORCID iD: 0000-0002-8817-0543
Russian Federation, Пермь

References

  1. Biginelli P. // Gazz. Chim. Ital. 1893. 23. P. 360.
  2. Kappe C.O. // Tetrahedron 1993. 49. P. 6937. doi: 10.1016/S0040-4020(01)87971-0
  3. Kappe C.O. // Eur. J. Med. Chem. 2000. 35. P. 1043. doi: 10.1016/s0223-5234(00)01189-2
  4. Wan J.-P., Liu Y. // Synthesis. 2010. P. 3943. doi 10.1055/ s-0030-1258290
  5. Nagarajaiah H., Mukhopadhyay A., Moorthy J.N. // Tetrahedron Lett. 2016. 57. P. 5135. doi 10.1016/ j.tetlet.2016.09.047
  6. Marvaniya H.M., Parikh P.K., Sen D.J. // J. Appl. Pharm. Sci. 2011. Vol. 1. N 5. P. 109.
  7. Kumar B.R.P., Sankar G., Baig R.B.N. // Eur. J. Med. Chem. 2009. Vol. 44. P. 4192. doi 10.1016/ j.ejmech.2009.05.014
  8. Yadlapalli R.K., Chourasia O.P., Vemuri K., Sritharan M., Perali R.S. // Bioorg. Med. Chem. Lett. 2012. Vol. 22. P. 2708. doi: 10.1016/j.bmcl.2012.02.101
  9. Zalavadiya P.D., Ghetiya R.M., Dodiya B.L., Vekariya P.B., Joshi H.S. // J. Heterocycl. Chem. 2013. Vol. 50. P. 973. doi: 10.1002/jhet.728
  10. Гейн В.Л., Замараева Т.М., Бузмакова Н.А., Сыропятов Б.Я., Аликина Н.В. // Хим.-фарм. ж. 2016. T. 50. № 4. C. 19; Gein V.L., Zamaraeva T.M., Buzmakova N.A., Syropyatov B.Y., Alikina N.V. // Pharm. Chem. J. 2016. Vol. 50. N 4. P. 226. doi: 10.1007/s11094-016-1427-9
  11. Бузмакова Н.А., Рудакова И.П., Замараева Т.М. // Разработка и регистрация лекарственных средств. 2022. 11. C. 38. doi: 10.33380/2305-2066-2022-11-4(1)-38-42
  12. Бузмакова Н.А., Андрюков К.В., Замараева Т.М., Рудакова И.П., Подчезерцева К.В., Гоман А.С., Авдеева Е.В., Слепова Н.В., Дозморова Н.В. // Разработка и регистрация лекарственных средств. 2023. 12. C. 13. doi: 10.33380/2305-2066-2023-12-4(1)-1600
  13. Kreutzberger A., Sellheim M. // J. Heterocycl. Chem. 1985. Vol. 22. P. 721. doi: 10.1002/jhet.5570220321
  14. Kosasayama A., Konno T., Higasni K., Ishikawa F. // Chem. Pharm. Bull. 1979. Vol. 27. P. 841. doi: 10.1248/cpb.27.841.
  15. Гейн В.Л., Замараева Т.М., Дмитриев М.В. // ЖОХ. 2017. Т. 87. Вып. 2. С. 336; Gein V.L., Zamaraeva T.M., Dmitriev M.V. // Russ. J. Gen. Chem. 2017. Vol. 87. N 2. P. 350. doi: 10.1134/S1070363217020335
  16. CrysAlisPro, Agilent Technologies, Version 1.171.37.33, release 27-03-2014.
  17. Sheldrick G.M. // Acta Crystallogr. (A). 2008. Vol. 64. P. 112. doi: 10.1107/S0108767307043930
  18. Sheldrick G.M. // Acta Crystallogr. (A). 2015. Vol. 71. P. 3. doi: 10.1107/S2053273314026370

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2. Scheme 1.

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3. Fig.1. General view of the molecule of compound 1 in a crystal, represented by thermal ellipsoids with 50% probability.

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4. Fig.2. General view of the crystal packing of compound 1 (view along the 0a axis).

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