A 'one pot' synthesis of polysubstituted pyridines from metallated alkylphosphonates, nitriles and α,β-unsaturated ketones

Tetrahedron Letters

Volumn 37, Issue 26, 1996, Pages 4577-4580

  Palacios, Francisco ^a   Ochoa De Retana, Ana M Ochoa ^a   Oyarzabal, Julen ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

KETONE; NITRILE; PHOSPHONIC ACID DERIVATIVE; PYRIDINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; ORGANIC CHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0030600197     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00850-7     Document Type: Article

References (53)

1. 1. For an excellent review see: "Comprehensive Heterocyclic Chemistry," Katritzky, A. R.; Rees, C. W.; Boulton, A. J.; McKillop, A. Eds.; Pergamon Press, Oxford, 1984, Vol. 2. Toomey, J. F.; Murugan, R. in "Progress in Heterocyclic Chemistry". Suschitzky, H.; Scriven, E. F. V. Eds.; Pergamon Press, Oxford, 1994, Vol. 6., pp. 206.
2. 1. For an excellent review see: "Comprehensive Heterocyclic Chemistry," Katritzky, A. R.; Rees, C. W.; Boulton, A. J.; McKillop, A. Eds.; Pergamon Press, Oxford, 1984, Vol. 2. Toomey, J. F.; Murugan, R. in "Progress in Heterocyclic Chemistry". Suschitzky, H.; Scriven, E. F. V. Eds.; Pergamon Press, Oxford, 1994, Vol. 6., pp. 206.
3. 2 For reviews see: a) Plunkett, A. O., Nat. Prod. Rep. 1994, 11, 581.
4. b) Wang, C. L. J.; Wuonola, M. A. Org. Prep. Proc. Int. 1992, 24, 585.
5. c) Pinder, A. R. Nat. Prod. Rep. 1992, 9, 491.
6. d) Numata, A.; Ibuka, T. in the "The Alkaloids," Brossi, A. Ed.; Academic Press, New York, 1987, Vol. 31.
7. e) Daly, J. W.; Spande, T. F. in "Alkaloids. Chemical and Biological Respectives," Pelletier, S. W. Ed.; Willey, New York, 1980, Vol. 4, pp. 1.
8. 3. For a review see: Gould, S. J.; Weinreb, S. M. Fortsch. Chem. Org. Naturist. 1982, 41, 77.
9. 4. a) Keys, L.D.; Hamilton, G.A. J. Am. Chem. Soc, 1987, 109, 2156.
10. b) Krogsgaard-Lassen, P.; Falch, E.; Christensen, V. Drugs Future. 1984, 9, 597.
11. c) Allen, R. D.; Johnston, G. A. R. Med. Res. Rev. 1983, 3, 91.
12. d) Coults, R. T.; Casy, A. F. in "Pyridines and its Derivatives," Abramovitch, R. A. Ed.; Willey, New York, 1975, Suppl. IV, p. 445.
13. 5. For a recent review see: Shipman, M. Contemp. Org. Synth. 1995, 2, 1.
14. 6. a) Alpha, B.; Lehn, J.M.; Perathoner, S.; Sabbatini, N. Angew. Chem. Int. Ed. Engl. 1987, 26, 1266.
15. b) Ziessel, R.; Lehn, J. M. Helv. Chim. Acta. 1990, 73, 1149.
16. 7. a) Macedo, E.; Moberg, C. Tetrahedron: Asymmetry 1995, 6, 549.
17. b) Chen, C.; Tagami, K.; Kishi, Y. J. Org. Chem. 1995, 60, 5386.
18. 8. For reviews in the synthesis of pyridines see: a) McKillop, A.; Boulton, A. J. in Ref. 1, p.67.
19. b) Meth-Cohn, O. Heterocycles 1993, 35, 539.
20. 9. a) Katritzky, A. R.; Mazurkiewicz, R.; Stevens, C.V.; Gordur, M. F. J. Org. Chem. 1994, 59, 2740.
21. b) Molina, P.; Fresneda, P. M.; García-Zafra, S. Tetrahedron Lett. 1995, 36, 3581.
22. c) Molina, P,; Pastor, A.; Vilaplana, M. J. Tetrahedron Lett. 1993, 34, 3773.
23. d) Barluenga, J.; Gonzalez, F. J.; Carlón, R. P.; Fustero, S. J. Org. Chem. 1991, 56, 6751.
24. e) Barluenga, J.; Ferrero, M.; Palacios, F. J. Chem. Soc., Perkin Trans, 1, 1990, 2193.
25. 10. For reviews see: a) Barluenga, J.; Tomas, M. Adv. Heterocycol. Chem. 1993, 57, 1
26. b) Boger, D. L. in "Comprehensive Organic Synthesis," Trost, B. H.; Paquette, L. A, Eds.; Pergamon Press, Oxford, 1991, Vol. 1, pp. 451.
27. c) Fringelli, F.; Tatichi, A. in "Dienes in the Diels-Alder Reaction," Willey, New York, 1990.
28. d) Barluenga, J.; Joglar, J.; Gonzalez, F. J.; Fustero S. Synlett 1990, 129.
29. 11. a) Palacios, F.; Perez de Heredia, I.; Rubiales, G. J. Org. Chem. 1995, 60, 2384 and references cited therein,
30. b) Gilchrist, T. L.; Rocha Gonzalves, A.; Pinho e Melo, T. Tetrahedron 1994, 50, 13709,
31. c) Balsamini, C.; Bedini, A.; Galarini, R.; Spadoni, G.; Tarsia, G.; Hamdan, H. Tetrahedron 1994, 50, 12375.
32. d) Barluenga, J.; Ferrero, M.; Pelaez, E.; López, F.; Palacios, F. Chem. Commun. 1994, 865.
33. 12. a) Kelly, T. R.; Liu, H.T; J. Am. Chem. Soc. 1985, 107, 4918.
34. b) Khanapene, S. P.; Biehl, E. L. Heterocycles 1990, 31, 505.
35. 13. Robinson, J. M.; Brent, L. W.; Chan, Ch.; Floyd, K. A.; Gillham, S. L.; McMahan, T. L.; Majda, D. J.; Mutycka, T. J.; Pack, M. J.; Roberts, A. L.; Seally, L. A.; Simpson, S. L.; Smith, R. R.; Zalesny, K. N. J. Org. Chem. 1992, 57, 7352 and references cited therein.
36. 14. a) Palacios, F.; Aparicio, D.; García, J. Synlett, 1994, 260.
37. b) Barluenga, J.; Merino, I.; Palacios, F. Tetrahedron Lett. 1989, 30, 5493.
38. c) Barluenga, J.; Merino, I.; Palacios, F. Tetrahedron Lett. 1990, 31, 6713.
39. d) Palacios, F.; Aparicio, D.; de los Santos, J. M. Tetrahedron Lett. 1993, 34, 3481.
40. e) Palacios, F.; Aparicio, D.; de los Santos, J. M. Tetrahedron 1994, 50, 12727.
41. f) Palacios, F.; Aparicio, D.; de los Santos, J. M.; Rodriguez, E. Tetrahedron Lett. 1996, 37, 1289.
42. 15. Barluenga, J.; López, F.; Palacios F.; Cano, F. M.; Foces, M. C. J. Chem. Soc., Perkin Trans, 1, 1988, 2329.
43. 16. Palacios, F.; García, J.; Ochoa de Retana, A.; Oyarzabal, J. Heterocycles 1995, 41, 1915.
44. 17. a) Barluenga, J.; López, F.; Palacios, F. Tetrahedron Lett. 1987, 28, 2875.
45. b) Barluenga, J.; López, F.; Palacios, F. Chem. Commun. 1985, 1681.
46. 18. López, F.; Pelaez, E.; Palacios, F.; Barluenga, J.; García, S.; Tejerino, B.; García, A. J. Org. Chem. 1994, 59, 1484.
47. 19. Kiselyov, A. S. Tetrahedron Lett. 1995, 36, 9297.
48. 5) have been obtained.
49. 21. Shin, W. S.; Lee, K.; Oh, D. Y. Tetrahedron Lett. 1995, 36, 281.
50. 22. Lee, K.; Oh, D. Y. Synthesis 1991, 213.
51. 4, and filtered. Evaporation of the solvent followed by flash chromatography (neutral aluminum oxide; eluent, hexane), afforded 1.43g. of compound 1a, which was recrystallized from hexane.
52. 3), 117.0-157.7 (C arom.) ppm.
53. 3), 115.8-158.7 (C arom.) ppm.