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.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 1978–1983, October, 2011.
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Krasnaya, Z.A., Tret’yakova, E.O., Kachala, V.V. et al. Synthesis and properties of cross-conjugated ω,ω′-bis-dimethylamino ketones and dinitriles with N-acetyl- and N-benzylpiperidine cycles. Russ Chem Bull 60, 2014–2020 (2011). https://doi.org/10.1007/s11172-011-0306-5
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DOI: https://doi.org/10.1007/s11172-011-0306-5