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Heteryladamantanes. Communication 6. Synthesis and some properties of 6-(1-adamantyl)-3-cyanopyridin-2(1H)-one

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

Conclusions

  1. 1.

    6-(1-Adamantyl)-3-cyanopyridin-2(1H)-one has been obtained for the first time by reaction of the sodium salt of 3-(1-adamantyl)-1-hydroxyprop-1-en-3-one with cyanoacetamide.

  2. 2.

    The regioselectivity of the alkylation reaction on the oxygen atom of the substituted pyridone by halomethylene-active compounds has been established.

  3. 3.

    A nucleophilic substitution reaction where an OCH2COOR group is replaced by an OR group has been discovered in 6-(1-adamantyl)-2-alkoxycarbonylmethoxy-3-cyanopyridines when they are treated with excess sodium alkoxide in alcohol.

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Literature cited

  1. E. É. Apenova, Yu. A. Sharanin, B. M. Zolotarev, and V. P. Litvinov, Izv. Akad. Nauk SSSR, Ser. Khim., 406 (1986).

  2. V. P. Litvinov, E. É. Apenova, Yu. A. Sharanin, V. N. Nesterov, V. E. Shklover, and Yu. T. Struchkov, Izv. Akad. Nauk SSSR, Ser. Khim., 145 (1986).

  3. V. P. Litvinov, E. É. Spenova, Yu. A. Sharanin, and A. M. Shestopalov, Zh. Org. Khim.,21, 669 (1985).

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  4. Z. A. Bomika, M. B. Andaburskaya, Yu. É. Pelcher, and G. Ya. Dubur, Khim. Geterotsikl. Soedin., 1089 (1976).

  5. L. Paquette, Fundamentals of the Contemporary Chemistry of Heterocyclic Compounds [Russian translation], Mir, Moscow (1971), p. 221.

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Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow

    V. P. Litvinov, E. É. Apenova & Yu. A. Sharanin

Authors
  1. V. P. Litvinov
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  2. E. É. Apenova
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  3. Yu. A. Sharanin
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Additional information

For Communication 5, see [1].

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 2, pp. 386–391, February, 1987.

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Litvinov, V.P., Apenova, E.É. & Sharanin, Y.A. Heteryladamantanes. Communication 6. Synthesis and some properties of 6-(1-adamantyl)-3-cyanopyridin-2(1H)-one. Russ Chem Bull 36, 345–349 (1987). https://doi.org/10.1007/BF00959379

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  • DOI: https://doi.org/10.1007/BF00959379

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