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2-Acyl(aroyl)-1,1,3,3-tetracyanopropenides: VI. Reaction with hydrogen halides

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Abstract

Reactions of 2-aroyl-1,1,3,3-tetracyanopropenides with hydrogen halides in solvents of low dielectric permittivity result in the formation of 6-amino-2-aroyl-2-halopyridine-3,5-dicarbonitriles. 2-Acyl-1,1,3,3-tetracyanopropenides under similar conditions afford 2-(2-alkylidene-5-amino-4-cyano-2,3-dihydrofuran-3-ylidene)propanedinitriles. In solvents of high dielectric permittivity the result of the reaction depends on the nature of the hydrogen halide and the acyl(aroyl) substituent: With HCl and HBr 2-aroyl-1,1,3,3-tetracyanopropenides form 2-(5-amino-2-aryl-2-halo-4-cyano-2,3-dihydrofuran-3-ylidene)-propanedinitriles, and 2-acyl-1,1,3,3-tetracyanopropenides give 2-(2-alkylidene-5-amino-4-cyano-2,3-dihydrofuran-3-ylidene)propanedinitriles; with HI depending on the reaction conditions and the structure of the acyl substituent 2-(5-amino-2-aryl-4-cyano-2,3-dihydrofuran-3-ylidene)propanedinitriles, 2-(5-amino-4-cyano-2,3-dihydrofuran-3-ylidene) propane-dinitrile, 2-amino-4-(dimethoxybenzyl)-6-iodo-5-cyanonicotinamide, 4-amino-6-iodo-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridine-7-carbonitrile, or 4-amino-6-iodo-3-oxo-1-ethylidene-1,3-dihydrofuro[3,4-c]pyridine-7-carbonitrile are obtained.

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Authors and Affiliations

  1. I.N. Ul’yanov Chuvash State University, Moskovskii pr. 15, Cheboksary, 428015, Russia

    Ya. S. Kayukov, S. V. Karpov, O. V. Ershov & O. E. Nasakin

  2. Chuvash State Agricultural Academy, Cheboksary, Russia

    O. V. Kayukova

Authors
  1. Ya. S. Kayukov
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  2. S. V. Karpov
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  3. O. V. Kayukova
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  4. O. V. Ershov
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  5. O. E. Nasakin
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Correspondence to Ya. S. Kayukov.

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Original Russian Text © Ya.S. Kayukov, S.V. Karpov, O.V. Kayukova, O.V. Ershov, O.E. Nasakin, 2014, published in Zhurnal Organicheskoi Khimii, 2014, Vol. 50, No. 8, pp. 1116–1125.

For communication V, see [1].

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Kayukov, Y.S., Karpov, S.V., Kayukova, O.V. et al. 2-Acyl(aroyl)-1,1,3,3-tetracyanopropenides: VI. Reaction with hydrogen halides. Russ J Org Chem 50, 1097–1106 (2014). https://doi.org/10.1134/S1070428014080053

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  • DOI: https://doi.org/10.1134/S1070428014080053

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