Synthesis of 6,9-Diaryl-5Н-imidazo[2,1-d][1,2,5]triazepines and Their Dihydro Derivatives

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Abstract

2-(2-Benzoyl-1H-imidazol-1-yl)-1-arylethanones were obtained by alkylation of 2-benzoylimidazole with phenacyl bromides; their cyclization with hydrazine hydrate leads to the formation of previously undescribed 6-aryl-9-phenyl-5H-imidazo[2,1-d][1,2,5]triazepines. The reduction of the latter with sodium borohydride in a dioxane medium leads to the production of 6-aryl-9-phenyl-6,7-dihydro-5H-imidazo[2,1-d][1,2,5]triazepines.

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About the authors

Dmitry A. Lomov

Litvinenko Institute of Physical Organic and Coal Chemistry

Author for correspondence.
Email: lomov_dmitrii@mail.ru
ORCID iD: 0000-0001-9955-6225
Russian Federation, Donetsk

References

  1. Elattar K.M., Mert B.D., Abozeid M.A., El-Mekabaty F. // RSC Adv. 2016. N 6. P. 37286. doi: 10.1039/C6RA00590J
  2. Elattar K.M., Abozeid M.A., Etman H.A. // Synth. Commun. 2016. Vol. 46. N 2. P. 93 doi: 10.1080/00397911.2015.1109126
  3. Hassan A.Y., Nabil S., El-Sebaey S., Abou-amra E. // Sci. Rep. 2023. Vol. 13. P. 5585. doi: 10.1038/s41598-023-32421-x
  4. Abuhashem A., Al-Hussain S.A. // Pharmaceuticals. 2022. Vol. 15. P. 1232. doi: 10.3390/ph15101232
  5. Moskvina V., Demydchuk B.A., Mykhalchenko O.A., Rusanov E.B. // Arkivoc. 2022. N 2. P. 204. doi: 10.24820/ark.5550190.p011.689
  6. Alaoui K., Kacimi Y.E., Galai M., Serrar H., Touir R., Kaya S., Ebn Touhami M. // Int. J. Ind. Chem. 2020. Vol. 11. P. 23. doi: 10.1007/s40090-019-00199-5
  7. Komodziński K., Lepczyńska J., Ruszkowski P., Milecki J., Skalski B. // Tetrahedron Lett. 2013. N 54. P. 3781. doi: 10.1016/j.tetlet.2013.05.051
  8. Reddy G.S., Kumar P.A., Anand R.V., Mukkanti K., Reddy P.P. // Synlett. 2009. N 9. P. 1463. doi: 10.1055/s-0029-1217178
  9. Foldesi T., Dancso A., Simig G., Volk B., Milen M. // Tetrahedron. 2016. Vol. 72. P. 5427 doi 10.1016/ j.tet.2016.07.029
  10. Kibal’ny, A.V., Nikolyukin Y.A., Dulenko V.I. // Chem. Heterocycl. Compd. 1994. Vol. 30. P. 895. doi: 10.1007/BF01165026
  11. Demirayak S., Kayagil I. // J. Heterocycl. Chem. 2005. Vol. 42. P. 319. doi: 10.1002/jhet.5570420224
  12. Муратов А.В., Берестнева Ю.В., Ракша Е.В., Ересько А.Б. // Вестник ТвГУ. Серия: Химия. 2018. № 4. С. 109. doi: 10.26456/vtchem2018.4.14
  13. Periasamy M., Thirumalaikumar M. // J. Organomet. Chem. 2000. Vol. 609 P. 137. doi: 10.1016/S0022-328X(00)00210-2
  14. Togo G., Fernandes M. Oxidation of Alcohols to Aldehydes and Ketones. Springer, 2006. P. 1.
  15. Bastiaansen L.A.M., Godefroi E.F. // Synthesis. 1978. N 9. P. 675. doi: 10.1055/S-1978-24848
  16. Hayashi Y., Kayatani T., Sugimoto H., Suzuki M., Inomata K., Uehara A., Mizutani Y., Kitagawa T., Maeda Y. // J. Am. Chem. Soc. 1995. Vol. 117. N 45. P. 11221. doi: 10.1021/ja00150a020
  17. Shen C., Guo X., Yu J., Zeng X-G Peng L., Zhao C-M., Zhang F-L. // Synth. Commun. 2016. Vol. 47. P. 273. doi: 10.1080/00397911.2016.1258579

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