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

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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Literature cited

  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. R. M. Acheson and M. L. Burstall, J. Chem. Soc., 3240 (1954).

  3. R. M. Acheson, Adv. Heterocyclic Chem., 1, 125 (1963).

    Google Scholar 

  4. R. M. Acheson and N. F. Elmore, Adv. Heterocyclic Chem.,(1977).

  5. E. Ciganek and C. G. Krespan, J. Org. Chem., 33, 541 (1968).

    Google Scholar 

  6. R. M. Acheson, M. G. Bite, and M. W. Cooper, J. C. S. Perkin I (1976).

  7. Unpublished observations, R. M. Acheson and others.

  8. R. M. Acheson and J. Woollard, J. Chem. Soc., Perkin Trans. 1, 438 (1975).

    Google Scholar 

  9. R. M. Acheson and J. Woollard, J. Chem. Soc., Perkin Trans., 1, 446 (1975).

    Google Scholar 

  10. E. LeGoff and R. B. LaCount, Tetrahedron Lett., 2333 (1967); J. C. Kauer and H. E. Simmons, J. Org. Chem., 33, 2720 (1968).

  11. R. M. Acheson and D. A. Robinson, J. Chem. Soc. (C), 1629 (1968).

  12. R. M. Acheson and A. O. Plunkett, J. Chem. Soc., 2676 (1964).

  13. R. M. Acheson and G. Proctor, unpublished observations.

  14. R. M. Acheson, R. S. Feinberg, and J. M. F. Gagan, J. Chem. Soc., 948 (1965).

  15. P. J. Abbott, R. M. Acheson, J. R. Carruthers, U. Eisner, and D. J. Watkin, J. Chem. Soc., Perkin Trans. 1 (1976).

  16. R. M. Acheson and B. J. Jones, J. Chem. Soc. (C), 1301 (1970).

  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. R. M. Acheson and D. A. Robinson, J. Chem. Soc. (C), 1633 (1968).

  19. R. M. Acheson, J. M. F. Gagan, and D. R. Harrison, J. Chem. Soc. (C), 362 (1968).

  20. R. M. Acheson and R. F. Flowerday, J. Chem. Soc., Perkin Trans. 1, 394 (1975).

    Google Scholar 

  21. R. M. Acheson, G. Procter, and D. J. Watkin, to be published.

  22. R. M. Acheson and D. F. Nisbet, J. Chem. Soc., Perkin Trans. 1, 1338 (1973).

    Google Scholar 

  23. P. J. Abbott, R. M. Acheson, J. R. Carruthers, R. A. Fordor, and D. J. Watkin, Acta Crystallogr. (in press).

  24. P. J. Abbott, R. M. Acheson, R. A. Fordor, D. J. Watkin, and J. R. Carruthers, Acta Crystallogr. (in press).

  25. R. M. Acheson and J. M. Woollard, J. Chem. Soc. (C), 3296 (1971).

  26. R. M. Acheson, S. J. Hodgson, and R. G. M. Wright, J. Chem. Soc., Perkin Trans. 1 (1976).

  27. E. Winterfeldt and A. Naumann, Chem. Ber., 98, 3537 (1965).

    Google Scholar 

  28. R. M. Acheson and J. Woollard, J. Chem. Soc., Perkin Trans. 1, 740 (1975).

    Google Scholar 

  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).

  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).

  31. R. M. Acheson, M. W. Foxton, and G. R. Miller, J. Chem. Soc., 3200 (1965).

  32. R. M. Acheson, M. W. Foxton, P. J. Abbott, and K. J. Milles, J. Chem. Soc. (C), 882 (1967).

  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. P. J. Abbott, R. M. Acheson, N. R. Raulins, and G. E. Robinson, J. Chem. Soc., Perkin Trans. 1, 2181 (1972).

    Google Scholar 

  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. R. M. Acheson, N. D. Wright, and P. A. Tasker, J. Chem. Soc., Perkin Trans. 1, 2918 (1972).

    Google Scholar 

  37. P. G. Lehman, Tetrahedron Lett., 4863 (1972).

  38. R. M. Acheson, G. Paglietti, and P. A. Tasker, J. Chem. Soc., Perkin Trans. 1, 2496 (1974).

    Google Scholar 

  39. J. W. Lown, M. H. Akhtar, and W. M. Dodson, J. Org. Chem., 40, 3363 (1975).

    Google Scholar 

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Published in Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1011–1022, August, 1976.

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Acheson, R.M. Some reactions of pyridines and related heterocycles with acetylenic esters (review). Chem Heterocycl Compd 12, 837–845 (1976). https://doi.org/10.1007/BF00510095

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  • DOI: https://doi.org/10.1007/BF00510095

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