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Reaction of Cyanoselenoacetamide with 1,3-Dicarbonyl Compound Anilinomethylene Derivatives

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Chemistry of Heterocyclic Compounds Aims and scope

The reaction of cyanoselenoacetamide with a 2-anilinomethylene derivative of Meldrum’s acid (2 equiv. KOH, EtOH, 20°C) gives the 5-cyano-6-hydroseleno-2-oxo-1,2-dihydropyridine-3-carboxylic acid dipotassium salt. The latter reacts with alkyl halides to yield 5-cyano-6-(R-methylseleno)-2-oxo-1,2-dihydropyridine-3-carboxylic acids. Treatment of cyanoselenoacetamide with 2-anilinomethyl derivatives of dimedone and 1,3-cyclohexanedione is accompanied by oxidation and gives 2,2'-di-selane-1,2-diylbis(5-oxo-5,6,7,8-tetrahydroquinoline-3-carbonitriles). The obtained diselanes undergo cleavage using alkyl halides in KOH to give 2-(R-methylseleno)-5-oxo-5,6,7,8-tetrahydroquinoline-3-carbonitriles or selenopheno[2,3-b]quinolines as Thorpe–Ziegler cyclization products of the latter in low yields.

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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

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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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Correspondence to V. V. Dotsenko.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1397-1403, September, 2013.

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Frolov, K.A., Dotsenko, V.V. & Krivokolysko, S.G. Reaction of Cyanoselenoacetamide with 1,3-Dicarbonyl Compound Anilinomethylene Derivatives. Chem Heterocycl Comp 49, 1301–1307 (2013). https://doi.org/10.1007/s10593-013-1379-x

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  • DOI: https://doi.org/10.1007/s10593-013-1379-x

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