Advertisement

Chemistry of Heterocyclic Compounds

, Volume 14, Issue 1, pp 49–54 | Cite as

Synthesis of condensed structures from 3-cyano-2-pyridylacrylic acids

  • L. N. Zhukauskaite
  • A. P. Stankevichyus
  • A. N. Kost
Article

Abstract

Ammonolysis of the methyl esters of trans-β-(3-cyano-2-pyridyl)acrylic (I) and trans-β-(6-methyl-3-cyano-2-pyridyl)acrylic (II) acids gave the amides of these acids. The addition of bromine, diazomethane, and hydrogen to the double bond of cis- and trans-acids I and II is described. Hydrogenation of the methyl esters of trans-acids I and II over Raneynickel at room temperature and atmospheric pressure occurs with intramolecular cyclization to two-ring lactams — 7-oxo-5, 6,8,9-tetrahydropyrid[3,2-c]azepine and 2-methyl-7-oxo-5,6,8,9-tetrahydropyrid[3,2-c]azepine. Under the conditons of acid hydrolysis of acids I and II the elements of water add to the nitrile group with intramolecular cyclization to give, respectively, 3-carboxymethyl-1-oxo-2,3-dihydrofuro [4,3-b]pyridine and 5-methyl-3-carboxymethyl-1-oxo-2,3-dihydrofuro[4,3-b]pyridine, whereas refluxing these acids with aqueous sodium hydroxide gives two-ring lactams — 3-carboxymethyl-1-oxo-2, 3-dihydropyrrolo[4,3-b]pyridine and its 5-methyl homolog. The structures of the compounds were confirmed by the UV, IR, PMR, and mass spectra.

Keywords

Hydrolysis Hydroxide Amide Pyridine Methyl Ester 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    V. G. Granik, N. B. Marchenko, E. O. Sochneva, R. G. Glushkov, T. F. Vlasova, and Yu. N. Sheinker, Khim. Geterotsikl. Soedin., No. 6, 805 (1976).Google Scholar
  2. 2.
    H.-J. Sattler and W. Schunack, Ber.,108, 1003 (1975).Google Scholar
  3. 3.
    G. Tarzta, G. Panzone, P. Carminati, P. Schiatti, and D. Selva, Farmaco, Sci. E.,31, 81 (1976).Google Scholar
  4. 4.
    A. N. Kost, L. N. Zhukauskaite, and A. P. Stankevichyus, Khim. Geterotsikl. Soedin., No. 4, 504 (1971).Google Scholar
  5. 5.
    A. N. Kost, A. P. Stankevichyus, L. N. Zhukauskaite, and I. I. Shulyakene, Khim. Geterotsikl. Soedin., No. 4, 509 (1971).Google Scholar
  6. 6.
    P. B. Terent'ev, S. M. Vinogradova, A. N. Kost, and A. G. Strukovskii, Khim. Geterotsikl. Soedin., No. 1, 64 (1973).Google Scholar
  7. 7.
    A. N. Kost and A. P. Stankevichyus, Khim. Geterotsikl. Soedin., No. 9, 1288 (1971).Google Scholar
  8. 8.
    D. H. Williams and J. Ronayne, Chem. Commun., 1129 (1967).Google Scholar
  9. 9.
    A. P. Stankevichyus and A. N. Kost, Nauchn. Tr. Vyssh. Uchebn. Zaved. LitSSR, Khim. Khim. Tekhnol.,13, 163 (1971).Google Scholar
  10. 10.
    A. N. Kost, L. N. Zhukauskaite, and A. P. Stankevichyus, USSR Author's Certificate No. 445669 (1974); Byull. Izobr., No. 37, 65 (1974).Google Scholar
  11. 11.
    L. P. Yurkina, N. D. Rus'yanova, L. F. Lipatova, and V. K. Kondratov, Khim. Geterotsikl. Soedin., No. 3, 390 (1970).Google Scholar
  12. 12.
    W. Ciusa and G. Fiorenci, Boll. Sci. Fac. Chim. Ind. Bologna,18, 12 (1959); Chem. Abstr.,54, 22636 (1960).Google Scholar

Copyright information

© Plenum Publishing Corporation 1978

Authors and Affiliations

  • L. N. Zhukauskaite
    • 1
  • A. P. Stankevichyus
    • 1
  • A. N. Kost
    • 1
  1. 1.Kaunas Medical InstituteKaunas

Personalised recommendations