Advertisement

Russian Chemical Bulletin

, Volume 60, Issue 10, pp 2014–2020 | Cite as

Synthesis and properties of cross-conjugated ω,ω′-bis-dimethylamino ketones and dinitriles with N-acetyl- and N-benzylpiperidine cycles

  • Zh. A. Krasnaya
  • E. O. Tret’yakova
  • V. V. Kachala
  • S. G. Zlotin
Full Articles

Abstract

Reactions of N-acetyl- and N-benzyl-4-piperidones with aminal of β-dimethylaminoac-rolein yielded ketocyanines bearing piperidine cycle. Reaction of 3-dimethylamino-1,1,3-trimethoxypropane with 1-acetylpiperidin-4-ylidenemalononitrile in the presence of ionic liquid, 1-butyl-3-methylimidazolium tetrafluoroborate ([bmim]BF4), resulted in cross-conjugated ω,ω’-dimethylamino dinitrile. Protonation of ketocyanines bearing N-acetyl- and N-benzyl-piperidine cycles with Et2O·HBF4 (1 equiv.) furnished piperidinium salts, while protonation of the latter with Et2O·HBF4 (2 equiv.) afforded doubly charged 4-hydroxypolymethine salts. Unlike protonation, reaction of 3,5-bis(3-dimethylaminoprop-2-enylidene)-1-acetylpiperidin-4-one with Me2SO4 involved only the oxygen atom and led to a singly charged 4-methoxypolymethine salt. Methylation of 3,5-bis(3-dimethylaminoprop-2-enylidene)-1-benzylpiperidin-4-one with Me2SO4 (1 equiv.) involved cyclic nitrogen atom and resulted in piperidinium salt; heating of the latter with the excess of Me2SO4 afforded doubly charged bis-methoxysulfonate. Starting from 4-methoxytetrahydropyridinium salts, meso-methoxythiapentacarbocyanine dyes were synthesized.

Key words

ketocyanines malononitrile protonation methylation polymethine salts cyanines absorption spectra 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Zh. A. Krasnaya, L. A. Shvedova, A. S. Tatikolov, E. O. Tret’yakova, V. V. Kachala, S. G. Zlotin, Izv. Akad. Nauk, Ser. Khim., 2009, 315 [Russ. Chem. Bull., Int. Ed., 2009, 58, 317].Google Scholar
  2. 2.
    Zh. A. Krasnaya, A. S. Tatikolov, Izv. Akad. Nauk, Ser. Khim., 2003, 1555 [Russ. Chem. Bull., Int. Ed., 2003, 52, 1641].Google Scholar
  3. 3.
    Zh. A. Krasnaya, E. O. Tret’yakova, V. V. Kachala, S. G. Zlotin, Izv. Akad. Nauk, Ser. Khim., 2010, 796 [Russ. Chem. Bull., Int. Ed., 2010, 59, 812].Google Scholar
  4. 4.
    (a) Zh. A. Krasnaya, T. S. Stytsenko, Izv. Akad. Nauk SSSR, Ser. Khim., 1983, 850 [Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1983, 32, 776]Google Scholar
  5. 4.
    (b) Zh. A. Krasnaya, T. S. Stytsenko, Izv. Akad. Nauk SSSR, Ser. Khim., 1983, 855 [Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1983, 32, 780].Google Scholar
  6. 5.
    Zh. A. Krasnaya, T. S. Stytsenko, E. P. Prokof’ev, V. F. Kucherov, Izv. Akad. Nauk SSSR, Ser. Khim., 1973, 2008 [Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1973, 22, 1959].Google Scholar
  7. 6.
    G. Dörnyei, M. Incze, I. Moldvai, C. Szántay, Synth. Commun., 2003, 33, 2329.CrossRefGoogle Scholar

Copyright information

© Springer-Verlag 2011

Authors and Affiliations

  • Zh. A. Krasnaya
    • 1
  • E. O. Tret’yakova
    • 1
  • V. V. Kachala
    • 1
  • S. G. Zlotin
    • 1
  1. 1.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation

Personalised recommendations