Advertisement

Chemistry of Heterocyclic Compounds

, Volume 48, Issue 2, pp 334–342 | Cite as

Features of reactions of quaternary salts derived from (4Z)-5-(bromomethyl)-2,2,6,6-tetra-methylhept-4-en-3-one. Synthesis of azolo[a]azepine and indolizine derivatives

  • L. M. PotikhaEmail author
  • A. R. Turelik
  • V. A. Kovtunenko
Article

The alkylation of 1-alkyl-2-methyl-1H-imidazoles, 1,2-dimethyl-1H-benzimidazole, and 2-R-pyridines by (4Z)-5-(bromomethyl)-2,2,6,6-tetramethylhept-4-en-3-one gives 1-alkyl-3-[(2Z)-2-tert-butyl-5,5-di-methyl-4-oxohex-2-en-1-yl]-2-methyl-1H-imidazol-3-ium, -1H-benzimidazol-3-ium, and 2-R-pyridinium bromides. Heating solutions of these diazolium salts in ethanol with potassium carbonate leads to 1,5-dihydroimidazo[1,2-a]azepinium and 5,10-dihydroazepino[1,2-a]benzimidazolium derivatives, while heating the pyridinium salts with triethylamine leads to indolizine derivatives. Heating solutions of quaternary salts derived from 1,2-dimethyl-1H-imidazole and 2-methylpyridine in acetic anhydride gives allylic rearrangement products, namely, 3-[(2Z)-2-tert-butyl-5,5-dimethyl-4-oxohex-1-en-1-yl]-1,2-dimethyl-1H-imidazol-3-ium and -2-methylpyridinium bromides, which under the action of base (MeONa for the diazolium salt and Et3N for the pyridinium salt) are converted into 1,5-dihydroimid-azo[1,2-a]azepinium and indolizine derivatives, respectively.

Keywords

azepino[1,2-a][1,3]benzimidazole hept-4-en-3-one imidazo[1,2-a]azepine allylic rearrange- ment cyclization 

References

  1. 1.
    L. M. Potikha, A. R. Turelik, and V. A. Kovtunenko, Khim. Geterotsikl. Soedin., 901 (2011). [Chem. Heterocycl. Compd., 47, 745 (2011)].Google Scholar
  2. 2.
    L. M. Potikha, A. R. Turelik, and V. A. Kovtunenko, Khim. Geterotsikl. Soedin., 1725 (2011). [Chem. Heterocycl. Compd., 47, 1436 (2011)].Google Scholar
  3. 3.
    L. M. Potikha, A. R. Turelik, and V. A. Kovtunenko, Khim. Geterotsikl. Soedin., 552 (2011). [Chem. Heterocycl. Compd., 47, 452 (2011)].Google Scholar
  4. 4.
    R. Ricard, P. Sauvage, C. S. K. Wan, A. C. Weedon, and D. F. Wong, J. Org. Chem., 51, 62 (1986).CrossRefGoogle Scholar
  5. 5.
    C. S. K. Wan, A. C. Weedon, and D. F. Wong, J. Org. Chem., 51, 3335 (1986).CrossRefGoogle Scholar
  6. 6.
    L. M. Potikha, A. R. Turelik, A. V. Shelepyuk, and V. A. Kovtunenko, Khim. Geterotsikl. Soedin., 364 (2012). [Chem. Heterocycl. Compd., 48, 452 (2012)].Google Scholar
  7. 7.
    Y. Tamura, N. Tsujimoto, Y. Sumida, and M. Ikeda, Tetrahedron, 28, 21 (1973).CrossRefGoogle Scholar
  8. 8.
    E. Pohjala, Tetrahedron Lett., 13, 2585 (1972).CrossRefGoogle Scholar
  9. 9.
    E. E. van Tamelen and T. H. Whitesides, J. Am. Chem. Soc., 90, 3894 (1968).CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, Inc. 2012

Authors and Affiliations

  • L. M. Potikha
    • 1
    Email author
  • A. R. Turelik
    • 1
  • V. A. Kovtunenko
    • 1
  1. 1.Taras Shevchenko Kyiv National UniversityKyivUkraine

Personalised recommendations