Synthesis of 2,5-bis-arylpyridines by [4 + 2] cycloaddition of 1,4-bis aryl-2-aza-1,3-butadienes with electron-poor dienophiles

Journal of Heterocyclic Chemistry

Volumn 37, Issue 2, 2000, Pages 411-418

  Paparin, Jean Laurent ^a   Crévisy, Christophe ^a   Grée, René ^a   Toupet, Loïc ^b  

^a CNRS   (France)

^b UNIVERSITÉ DE RENNES 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 BUTADIENE DERIVATIVE; PYRIDINE DERIVATIVE;

ARTICLE; DIMERIZATION; SYNTHESIS;

EID: 0343183188     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570370230     Document Type: Article

References (37)

1. [1a] Combinatorial Chemistry: Synthesis and Application; S. R. Wilson, A. W. Eds. Czarnik, J. Wiley and Sons, Inc.: New York, 1-269 (1997) and references cited therein.
2. [b] A. Nefzi, J. M. Ostresh, R. A. Hougten, Chem. Rev., 97, 449 (1997);
3. [c] P. H. H. Hermkens, H. C. J. Ottenheijm, D. C. Rees, Tetrahedron, 53, 5643 (1997);
4. [d] E. M. Gordon, M. A. Gallop, D. V. Patel, Acc. Chem. Res., 29, 144 (1996);
5. [e] N. K. Terrett, M. Gardner, D. W. Gordon, R. J. Kobylecki, J. Steele, Tetrahedron, 51, 8135 (1995).
6. See for instance: F. Palacios, I. Perez de Heredia, G. Rubiales, J. Org. Chem., 60, 2384 (1995) and references therein.
7. J. Barluenga, M. Tomas, Adv. Heterocycl. Chem., 57, 1 (1993).
8. B. Serckx-Poncin, A. M. Hesbain-Frisque, L. Ghosez, Tetrahedron Letters, 23, 3261 (1982).
9. S. J. Allcock, T. L. Gilchrist, F. D. King, Tetrahedron Letters, 32, 125 (1991).
10. M. Behforouz, Z. Gu, L. S. Stelzer, M. Ahmadian, J. Haddad, J. A. Scherschel, Tetrahedron Letters, 38, 2211 (1997).
11. [7a] C. Goulaouic-Dubois, D. R. Adams, N. J. Sisti, F. W. Fowler, D. S. Grierson, Tetrahedron Letters, 39, 4283 (1998);
12. [b] N. J. Sisti, E. Zeller, D. S. Grierson, F. W. Fowler, J. Org. Chem., 62, 2093 (1997);
13. [c] M. Teng, F. W. Fowler, J. Org. Chem., 55, 5646 (1990).
14. [8a] D. L. Boger, J. Heterocyclic Chem., 35, 1003 (1998);
15. [b] D. L. Boger, J. Heterocyclic Chem., 33, 1519 (1996);
16. [c] D. L. Boger, Comprehensive Organic Synthesis, Vol 5, Chapter 4.3, Pergamon, Oxford, (1991).
17. [9a] A. Demoulin, H. Gorissen, A. M. Hesbain-Frisque, L. Ghosez, J. Am. Chem. Soc., 97, 4409 (1975);
18. [b] F. Sainte, B. Serckx-Porcin, A. M. Hesbain-Frisque, L. Ghosez, J. Am. Chem. Soc., 104, 1428 (1982);
19. [c] R. Gompper, U. Heinemann, Angew. Chem. Int. Ed. Engl., 19, 217 (1980);
20. [d] R. Gompper, U. Heinemann, Angew. Chem. Int. Ed. Engl., 20, 296 (1981).
21. J. Barluenga, M. Tomas, A. Ballesteros, V. Gotor, J. Chem. Soc. Chem. Commun., 1195 (1987).
22. [11a] J. Barluenga, Bull. Soc. Chim. Belg., 97, 545 (1988);
23. [b] J. Barluenga, F. Aznar, S. Fustero, M. Tomas, Pure and Appl. Chem., 62, 1957 (1990).
24. F. Palacios, C. Alonso, G. Rubiales, J. Org. Chem., 62, 1146 (1997).
25. M. Komatsu, S. Takamotsu, M. Uesaka, S. Yamamoto, Y. Ohshiro, T. Agawa, J. Org. Chem., 49, 2691 (1984).
26. Y. S. Cheng, E. Ho, P. S. Mariano, H. L. Ammon, J. Org. Chem., 50, 5678 (1985).
27. A. R. Katritzky, G. Zhang, J. Jiang, J. Org. Chem., 59, 4556 (1994).
28. Atomic coordinates for structures 4b and 6b have been deposited with the Cambridge Crystallographic Data Centre. The coordinates can be obtained on request from Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB21EZ, U K.
29. [17a] P. Bayard, L. Ghosez, Tetrahedron Letters, 29, 6115 (1988);
30. [b] S. T. Handy, P. A. Grieco, C. Mineur, L. Ghosez, Synlett, 565 (1995).
31. [18a] F. Palacios, G. Rubiales, Tetrahedron Letters, 37, 6379 (1996);
32. [b] G. Wulff, M. Böhnke, Angew. Chem. Int. Ed. Engl., 25, 90 (1986).
33. T. L. Gilchrist, A. M. d'A. Rocha Gonsalves, T. M. V. D. Pinho e Melo, Pure and Appl. Chem., 68, 859 (1996).
34. T. L. Gilchrist, A. M. d'A Rocha Gonsalves, T. M. V. D. Pinho e Melo, Tetrahedron, 50, 13709 (1994).
35. C. Balsamini, A. Bedini, R. Galarini, G. Spadoni, G. Tarzia, M. Hamdan, Tetrahedron 50, 12375 (1994).
36. T. M. V. D. Pinho e Melo, R. Fausto, A. M. d'A Rocha Gonsalves, T. L. Gilchrist, J. Org. Chem., 63, 5350 (1998).
37. Due to the formation of many by-products during the reaction this compound was isolated in very slightly impure form after column chromatography on silicagel. Nevertheless, pure form can be obtained after crystallization or trituration in diethyl ether. This was accomplished from the very small quantity isolated so yield obtained after this further purification is not representative and therefore is not given.