Chemistry of Heterocyclic Compounds

, Volume 12, Issue 8, pp 837–845 | Cite as

Some reactions of pyridines and related heterocycles with acetylenic esters (review)

  • R. M. Acheson
Article

Abstract

The types of compounds obtainable from acetylenemono- and acetylenedicarboxylic esters with a variety of pyridines are reviewed. The structures previously proposed for a number of products formed from 2-methylquinolines and thiazoles have been revised on the basis of x-ray diffraction studies. Mechanisms accounting for the production of the various compounds are considered.

Keywords

Ester Organic Chemistry Pyridine Diffraction Study Thiazole 
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.

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Literature cited

  1. 1.
    O. Diels, K. Alder, and E. Naujoko, Ber., 62, 554 (1929); O. Diels and W. E. Thiele, J. Pr. Chem., 156, 195 (1940).Google Scholar
  2. 2.
    R. M. Acheson and M. L. Burstall, J. Chem. Soc., 3240 (1954).Google Scholar
  3. 3.
    R. M. Acheson, Adv. Heterocyclic Chem., 1, 125 (1963).Google Scholar
  4. 4.
    R. M. Acheson and N. F. Elmore, Adv. Heterocyclic Chem.,(1977).Google Scholar
  5. 5.
    E. Ciganek and C. G. Krespan, J. Org. Chem., 33, 541 (1968).Google Scholar
  6. 6.
    R. M. Acheson, M. G. Bite, and M. W. Cooper, J. C. S. Perkin I (1976).Google Scholar
  7. 7.
    Unpublished observations, R. M. Acheson and others.Google Scholar
  8. 8.
    R. M. Acheson and J. Woollard, J. Chem. Soc., Perkin Trans. 1, 438 (1975).Google Scholar
  9. 9.
    R. M. Acheson and J. Woollard, J. Chem. Soc., Perkin Trans., 1, 446 (1975).Google Scholar
  10. 10.
    E. LeGoff and R. B. LaCount, Tetrahedron Lett., 2333 (1967); J. C. Kauer and H. E. Simmons, J. Org. Chem., 33, 2720 (1968).Google Scholar
  11. 11.
    R. M. Acheson and D. A. Robinson, J. Chem. Soc. (C), 1629 (1968).Google Scholar
  12. 12.
    R. M. Acheson and A. O. Plunkett, J. Chem. Soc., 2676 (1964).Google Scholar
  13. 13.
    R. M. Acheson and G. Proctor, unpublished observations.Google Scholar
  14. 14.
    R. M. Acheson, R. S. Feinberg, and J. M. F. Gagan, J. Chem. Soc., 948 (1965).Google Scholar
  15. 15.
    P. J. Abbott, R. M. Acheson, J. R. Carruthers, U. Eisner, and D. J. Watkin, J. Chem. Soc., Perkin Trans. 1 (1976).Google Scholar
  16. 16.
    R. M. Acheson and B. J. Jones, J. Chem. Soc. (C), 1301 (1970).Google Scholar
  17. 17.
    O. Diels and R. Meyer, Annalen, 513, 129 (1934); A. Crabtree, A. W. Johnson, and J. C. Tebby, J. Chem. Soc., 3497 (1961).Google Scholar
  18. 18.
    R. M. Acheson and D. A. Robinson, J. Chem. Soc. (C), 1633 (1968).Google Scholar
  19. 19.
    R. M. Acheson, J. M. F. Gagan, and D. R. Harrison, J. Chem. Soc. (C), 362 (1968).Google Scholar
  20. 20.
    R. M. Acheson and R. F. Flowerday, J. Chem. Soc., Perkin Trans. 1, 394 (1975).Google Scholar
  21. 21.
    R. M. Acheson, G. Procter, and D. J. Watkin, to be published.Google Scholar
  22. 22.
    R. M. Acheson and D. F. Nisbet, J. Chem. Soc., Perkin Trans. 1, 1338 (1973).Google Scholar
  23. 23.
    P. J. Abbott, R. M. Acheson, J. R. Carruthers, R. A. Fordor, and D. J. Watkin, Acta Crystallogr. (in press).Google Scholar
  24. 24.
    P. J. Abbott, R. M. Acheson, R. A. Fordor, D. J. Watkin, and J. R. Carruthers, Acta Crystallogr. (in press).Google Scholar
  25. 25.
    R. M. Acheson and J. M. Woollard, J. Chem. Soc. (C), 3296 (1971).Google Scholar
  26. 26.
    R. M. Acheson, S. J. Hodgson, and R. G. M. Wright, J. Chem. Soc., Perkin Trans. 1 (1976).Google Scholar
  27. 27.
    E. Winterfeldt and A. Naumann, Chem. Ber., 98, 3537 (1965).Google Scholar
  28. 28.
    R. M. Acheson and J. Woollard, J. Chem. Soc., Perkin Trans. 1, 740 (1975).Google Scholar
  29. 29.
    P. J. Abbott, R. M. Acheson, U. Eisner, D. J. Watkin, and J. R. Carruthers, Chem. Comm., 115 (1975); J. Chem. Soc., Perkin Trans. 1 (1976).Google Scholar
  30. 30.
    H. Ogura, H. Takayanagi, K. Furuhara, and Y. Iitake, Chem. Comm., 759 (1974); H. Ogura, K. Kikuchi, H. Takayanagi, K. Furuhata, Y. Iitaka, and R. M. Acheson, J. Chem. Soc., Perkin Trans. 1, 2316 (1975).Google Scholar
  31. 31.
    R. M. Acheson, M. W. Foxton, and G. R. Miller, J. Chem. Soc., 3200 (1965).Google Scholar
  32. 32.
    R. M. Acheson, M. W. Foxton, P. J. Abbott, and K. J. Milles, J. Chem. Soc. (C), 882 (1967).Google Scholar
  33. 33.
    P. J. Abbott, R. M. Acheson, M. Y. Kornilov, and J. K. Stubbs, J. Chem. Soc., Perkin Trans. 1, 2322 (1975).Google Scholar
  34. 34.
    P. J. Abbott, R. M. Acheson, N. R. Raulins, and G. E. Robinson, J. Chem. Soc., Perkin Trans. 1, 2181 (1972).Google Scholar
  35. 35.
    R. M. Acheson, J. M. Bridson, and T. S. Cameron, J. Chem. Soc., Perkin Trans. 1, 986 (1972); R. M. Acheson, J. N. Bridson, T. R. Cecil, and A. R. Hands, ibid, 1569 (1972).Google Scholar
  36. 36.
    R. M. Acheson, N. D. Wright, and P. A. Tasker, J. Chem. Soc., Perkin Trans. 1, 2918 (1972).Google Scholar
  37. 37.
    P. G. Lehman, Tetrahedron Lett., 4863 (1972).Google Scholar
  38. 38.
    R. M. Acheson, G. Paglietti, and P. A. Tasker, J. Chem. Soc., Perkin Trans. 1, 2496 (1974).Google Scholar
  39. 39.
    J. W. Lown, M. H. Akhtar, and W. M. Dodson, J. Org. Chem., 40, 3363 (1975).Google Scholar

Copyright information

© Plenum Publishing Corporation 1977

Authors and Affiliations

  • R. M. Acheson
    • 1
  1. 1.Department of BiochemistryUniversity of OxfordEngland

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