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Novel [4 + 2] Cycloaddition Reaction of Aryl-Methylidenemalononitriles to Unsaturated Chalcogen Amides. Synthesis, Structure, and Properties of Triethylammonium 3,5,5-Tricyano-1,4,5,6-Tetrahydropyridine-2-Selenolates and -Thiolates

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Chemistry of Heterocyclic Compounds Aims and scope

Reaction of arylmethylidenemalononitriles with 3-aryl-2-cyanoprop-2-eneselenoamides in the presence of Et3N gave triethylammonium 4,6-diaryl-3,5,5-tricyano-1,4,5,6-tetrahydropyridine-2-selenolates. A similar reaction with cyclohexylidenecyanothioacetamide yields triethylammonium 4-aryl-1,5,5-tri-cyano-3-azaspiro[5.5]undec-1-ene-2-thiolate. Alkylation of the obtained selenolates and thiolates gives 6-(alkylseleno)-2,4-diaryl-1,4-dihydropyridine-3,3,5(2H)-tricarbonitriles and 4-(alkylthio)-2-aryl-3-aza- spiro[5.5]undec-4-ene-1,1,5-tricarbonitriles, respectivelly. The structure of 2,4-di(2-furyl)-6-{[2-(4-methylphenyl)-2-oxoethyl]seleno}-1,4-dihydropyridine-3,3,5(2H)-tricarbonitrile has been confirmed by the X-ray structural analysis.

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The authors are grateful to Prof. O. V. Shishkina (Scientific-Technological Complex "Institute of Monocrystals", National Academy of Sciences of Ukraine, Kharkov) for carrying out the X-ray structural analysis.

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Authors and Affiliations

  1. “ChemEx” Laboratory, Vladimir Dal’ East Ukrainian National University, 20-A Molodyozhnyi Kv., Luhansk, 91034, Ukraine

    K. A. Frolov, V. V. Dotsenko & S. G. Krivokolysko

  2. A. A. Bogomolets National Medical University, 13 T. Shevchenka Blvd., Kyiv, 01601, Ukraine

    E. O. Kostyrko

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  1. K. A. Frolov
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  2. V. V. Dotsenko
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  3. S. G. Krivokolysko
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  4. E. O. Kostyrko
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Correspondence to V. V. Dotsenko.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1384-1396, September, 2013.

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Frolov, K.A., Dotsenko, V.V., Krivokolysko, S.G. et al. Novel [4 + 2] Cycloaddition Reaction of Aryl-Methylidenemalononitriles to Unsaturated Chalcogen Amides. Synthesis, Structure, and Properties of Triethylammonium 3,5,5-Tricyano-1,4,5,6-Tetrahydropyridine-2-Selenolates and -Thiolates. Chem Heterocycl Comp 49, 1289–1300 (2013). https://doi.org/10.1007/s10593-013-1378-y

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