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Synthesis and crystal structure of 3-(1,5-dimethyl-4-(1H)-pyridon-3-yl)-2-cyanothiobutyramide

  • Organic Chemistry
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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    A method is described for the recyclization of the sodium salt of 3-hydroxymethylene-1,2,5-trimethyl-4-piperidone by treatment with cyanothioacetamide to give 3-(1,5-dimethyl-4-(1H)-pyridon-3-yl)-2-cyanobutyrothioamide, the structure of which has been established by x-ray structural studies.

  2. 2.

    The 1,4-dihydropyridine ring is located anti-perpendicularly to the CN group relative to the C8–C9 bond, has the sofa conformation, and contains the planar conjugated grouping N1-C2=C3-C4=O.

  3. 3.

    The distribution of bond lengths in the thioamide group shows that p,π-delocalization is present therein.

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Authors and Affiliations

  1. A. N. Nesmeyanov Institute of Heteroorganic Chemistry, Academy of Sciences of the USSR, Moscow

    V. N. Nesterov, Yu. A. Sharanin, V. P. Litvinov, V. E. Shklover, Yu. T. Struchkov, V. K. Promonenkov, V. Yu. Mortikov & A. M. Shestopalov

Authors
  1. V. N. Nesterov
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  2. Yu. A. Sharanin
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  3. V. P. Litvinov
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  4. V. E. Shklover
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  5. Yu. T. Struchkov
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  6. V. K. Promonenkov
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  7. V. Yu. Mortikov
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  8. A. M. Shestopalov
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 6, pp. 1378–1383, June, 1986.

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Nesterov, V.N., Sharanin, Y.A., Litvinov, V.P. et al. Synthesis and crystal structure of 3-(1,5-dimethyl-4-(1H)-pyridon-3-yl)-2-cyanothiobutyramide. Russ Chem Bull 35, 1251–1255 (1986). https://doi.org/10.1007/BF00956609

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  • DOI: https://doi.org/10.1007/BF00956609

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