SYNTHESIS AND AMINOMETHYLATION OF 9-AZA-3-AZONIASPIRO[5,5]UNDECA-7,10-DIENE-8-SELENOLATES

Authors

  • К. А. Фролов "ChemEx" Laboratory, Vladimir Dal' East Ukrainian National University
  • В. В. Доценко "ChemEx" Laboratory, Vladimir Dal' East Ukrainian National University
  • С. Г. Кривоколыско "ChemEx" Laboratory, Vladimir Dal' East Ukrainian National University
  • Р. И. Зубатюк Scientific-Technological Complex "Institute of Monocrystals", National Academy of Sciences of Ukraine
  • О. В. Шишкин Scientific-Technological Complex "Institute of Monocrystals", National Academy of Sciences of Ukraine

DOI:

https://doi.org/10.1007/475

Keywords:

N-alkylpiperidin-4-ones, cyanoselenoacetamide, malononitrile, Michael adducts, pyridine-2 selenolates, cyclocondensation, Mannich reaction, X-ray structural analysis

Abstract

10-Amino-7,11-dicyano-9-aza-3-azoniaspiro[5,5]undeca-7,10-diene-8-selenolates have been obtained by the interaction of N-alkylpiperidin-4-ones with 2 equiv. cyanoselenoacetamide or with malononitrile and cyanoselenoacetamide. Aminomethylation of the obtained compounds proceeded under mild conditions and led to the formation of 8'-selenoxo-3',5',7',11'-tetraazaspiro[piperidine-4,13'-tri-cyclo[7.3.1.02,7]tridec[2]ene]-1',9'-dicarbonitriles. The structure of 1-methyl-5',11'-di(4-methyl-phenyl)-8'-selenoxo-3',5',7',11'-tetraazaspiro[piperidine-4,13'-tricyclo[7.3.1.02,7]tridec[2]ene]-1',9'-di-carbonitrile was determined by X-ray structural analysis.

Authors: K. A. Frolov, V. V. Dotsenko, S. G. Krivokolysko, R. I. Zubatyuk, and O. V. Shishkin

English Translation in Chemistry of Heterocyclic Compounds, 2013, 49 (3), pp 472-478

http://link.springer.com/article/10.1007/s10593-013-1270-9

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Published

2013-04-09

Issue

No. 3 (2013)

Section

Original Papers