Synthesis of substituted 2-arylimino-3-oxopropanenitriles and 2-(arylimino)propanedinitriles by oxidative coupling of primary aromatic amines with aroylacetonitriles and malononitrile

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Abstract

Aromatic amines enter into an oxidative coupling reaction with 3-aryl-3-oxopropanenitriles in the presence of selenium(IV) oxide to form the corresponding 2-arylimino-3-oxopropanenitriles. In the case of a similar reaction of arylamines with malononitrile, 2-aryliminopropanedinitritles are formed.

About the authors

A. V. Kachanov

Far-Eastern Federal University

Email: kachanov.av@dvfu.ru
Universitetskii pr., L901, Russky Island, Vladivostok, 690922 Russia

M. A. Kucheshov

Far-Eastern Federal University

Universitetskii pr., L901, Russky Island, Vladivostok, 690922 Russia

O. Y. Slabko

Far-Eastern Federal University

Universitetskii pr., L901, Russky Island, Vladivostok, 690922 Russia

References

  1. Boulechfar C., Ferkous H., Delimi A., Djedouani A., Kahlouche A., Boublia A., Darwish A.S., Lemaoui T., Verma R., Benguerba Y. Inorg. Chem. Commun. 2023, 150, 110451. doi: 10.1016/j.inoche.2023.110451
  2. Ravula M., Bandalla S., Dosarapu V., Kurra M., Mavurapu S., Vasam Ch.S. Orient. J. Chem. 2024, 40, 611–629. doi: 10.13005/ojc/400301
  3. Irfan M., Maqbool A., Muhammad S., Adnan A. Futuret J. Pharm. Sci. 2024. doi: 10.1186/s43094-024-00594-5
  4. Layer R.W. Chem. Rev. 1963, 63, 489–510. doi: 10.1021/cr60225a003
  5. Patil R.D., Adimurtthy S. Asian J. Org. Chem. 2013, 2, 726–744. doi: 10.1002/ajoc.201300012
  6. Yasukava T., Nakajima H, Masuda R., Yamashita Y., Kobayashi S. J. Org. Chem. 2022, 87, 13750–13756. doi: 10.1021/acs.joc.2c01411
  7. Laskar D.D., Prajapati D., Sandhu J.S. Synth. Commun. 2001, 31, 1427–1432. doi: 10.1081/SCC-100104052
  8. Gupta D.R., Ojha A.C. J. Indian Chem. Soc. 1972, 49, 807–810. doi: 10.5281/zenodo.6447496
  9. Беспалов Б.П., Аболин А.Г., Бельский В.К., Заводник В.Е., Соболев А.Н., Четкина Л.А. ЖОрХ. 1991, 27, 836–845.
  10. Park L.H., Leitao E.M., Weber C.C. Org. Biomolec. Chem. 2024, 22, 202–227. doi: 10.1039/D3OB01730C
  11. Kachanov A.V., Zamaraev A.V., Gerasimenko A.V., Maslov K.V., Slabko O.Yu., Kaminskii V.A. Synlett. 2018, 29, 2035–2038. doi: 10.1055/s-0037-1609939
  12. Gupta D.R., Singh Yu., Tayal H.D. J. Indian Chem. Soc. 1969, 46, 164–166. doi: 10.5281/zenodo.6460872
  13. Leśniak S., Chrostowska A., Kuc D., Maciejczyk M., Khayar S., Nazarski R.B., Urbaniak L. Tetrahedron. 2009, 65, 10581–10589. doi: 10.1016/j.tet.2009.10.080
  14. Baba A., Yasuma T., Tawada H., Yamashita M., Междунар. заявка WO 2005111046 A1; Сhem. Аbstr., 2005, 144, 6780.
  15. Goldstein D.M., Labadie S.S., Rotstein D.M., Sjog- ren E.B., Talamas F.X., Междунар. заявка. WO 2001021591 A1; Сhem. Аbstr. 2001, 134, 266303.

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