Bromination of 1(9)H-2,3-dihydroimidazo[1,2-a]benzimidazole and its N-derivatives

Capa

Citar

Texto integral

Acesso aberto Acesso aberto
Acesso é fechado Acesso está concedido
Acesso é fechado Somente assinantes

Resumo

2,3-Dihydro-1 H -imidazo[1,2- a ]benzimidazole in acetic acid, and its N 1-Me derivative in CHCl3, are brominated at position 6 with bromine. Less nucleophilic N 9-R derivatives do not enter into the reaction under these conditions, but, like their N 1-R isomers, they are quite effectively brominated by the KBrO3-HBr system, but at position 7, probably due to the transition of the reaction to the mode of bromination of protonated forms of substrates. N 1- and N 9-alkyl-6(7)-Br-2,3-dihydroimidazo[1,2- a ]benzimidazoles can also be obtained by N -alkylation of 6(7)-Br-2,3-dihydroimidazo[1,2- a ]benzimidazoles under neutral or basic conditions.

Sobre autores

V. Sochnev

Institute of Physical and Organic Chemistry, Southern Federal University

Email: vsochnev@sfedu.ru

Yu. Koshchienko

Institute of Physical and Organic Chemistry, Southern Federal University

T. Kuz'menko

Institute of Physical and Organic Chemistry, Southern Federal University

A. Kolodina

Institute of Physical and Organic Chemistry, Southern Federal University

G. Borodkin

Institute of Physical and Organic Chemistry, Southern Federal University

A. Morkovnik

Institute of Physical and Organic Chemistry, Southern Federal University

Bibliografia

  1. Анисимова В.А., Левченко М.В. // ХГС. 1987. Т. 1. С. 59
  2. Anisimova V.A., Levchenko M.V. // Chem. Heterocycl. Compd. 1987. Vol. 23. N 1. P. 48. doi: 10.1007/BF00475473
  3. Анисимова В.А., Левченко М.В., Ковалев Г.В., Спасов А.А., Дудченко Г.П., Цыбанев А.В., Александрова Е.А. // Хим. -фарм. ж. 1988. Т. 22. № 10. С. 1212
  4. Anisimova V.A., Levchenko M.V., Kovalev G.V., Spasov A.A., Dudchenko G.P., Tsibanev A.V., Alexandrova E.A. // Pharm. Chem. J. 1989. Vol. 22. N 10. P. 774. doi: 10.1007/bf00763272
  5. Анисимова В.А., Балаболкин М.И., Вдовина Г.П., Дедов И.И., Минкин В.И., Петров В.И., Спасов А.А. Пат. РФ 2386634 (2010) // Б. И. 2010. № 11.
  6. Анисимова В.А., Толпыгин И.Е., Спасов А.А., Косолапов В.А., Степанов А.В., Кучерявенко А.Ф. // Хим.-фарм. ж. 2006. Т. 40. С. 27
  7. Anisimova V.A., Tolpygin I.E., Spasov A.A., Kosolapov V.A., Stepanov A.V., Kucheryavenko A.F. // Pharm. Chem. J. 2006. Vol. 40. P. 261. doi: 10.1007/s11094-006-0105-8
  8. Анисимова В.А., Толпыгин И.Е., Аскалепова О.И. // ХГС. 2013. С. 1887
  9. Anisimova V.A., Tolpygin I.E., Askalepova O.I. // Chem. Heterocycl. Compd. 2014. N 49. P. 1748. doi: 10.1007/s10593-014-1427-1
  10. Oh S., Kim S., Kong S., Yang G., Lee N., Han D., Goo J., Siqueira-Neto J. L., Freitas-Junior L. H., Song R. // Eur. J. Med. Chem. 2014. N 84. P. 395. doi: 10.1016/j.ejmech.2014.07.038
  11. Спасов A.A., Анисимова В.А., Петров В.И., Кучерявенко А.Ф., Толпыгин И.Е., Минкин В.И. Пат. РФ 2453312 (2012) // Б. И. 2012. № 17.
  12. North R.J., Day A.R. // J. Heterocycl. Chem. 1969. N 6. P. 655. doi: 10.1002/jhet.5570060511
  13. Sochnev V.S., Kuz'menko T.A., Morkovnik A.S., Divaeva L.N., Podobina A.S., Zubenko A.A., Chepurnoy P.B., Borodkin G.S., Klimenko A.I. // Mendeleev Commun. 2021. N 31. P. 555. doi: 10.1016/j.mencom.2021.07.040
  14. Анисимова В.А., Симонов А.М., Борисова Т.А. // ХГС. 1973. Т. 6. С. 791
  15. Anisimova V.A., Simonov A.M., Borisova T.A. // Chem. Heterocycl. Compd. 1973. Vol. 9. P. 726. doi: 10.1007/BF00472317
  16. Гельман Н.Э., Терентьева Е.А., Шанина Т.М., Кипаренко Л.М. Методы количественного органического элементного анализа. М: Химия, 1987. 295 c.
  17. Granovsky A.A. Firefly version 8. http://classic.chem.msu.su/gran/firefly/index.html
  18. Schmidt M.W., Baldridge K.K., Boatz J.A., Elbert S.T., Gordon M.S., Jensen J.H., Koseki S., Matsunaga N., Nguyen K.A., Su S., Windus T.L., Dupuis M., Montgomery J.A. // J. Comput. Chem. 1993. N. 14. P. 1347. doi: 10.1002/jcc.540141112
  19. CrysAlisPro. Version 171.42., Rigaku Oxford Diffraction, 2015, https://www.rigaku.com/products/crystallography/crysalis
  20. Sheldrick G.M. // Acta Crystallogr. (A). 2015. Vol. 71. P. 3. doi: 10.1107/S2053273314026370
  21. Sheldrick G.M. // Acta Crystallogr. (C). 2015. Vol. 71. P. 3. doi: 10.1107/S2053229614024218

Arquivos suplementares

Arquivos suplementares
Ação
1. JATS XML
Baixar

Declaração de direitos autorais © Russian Academy of Sciences, 2023