Synthesis of pentasubstituted pyridines. Cycloadditions of N-vinylic heterocumulenes with 1-(N,N-diethylamine)prop-1-yne

Tetrahedron

Volumn 53, Issue 12, 1997, Pages 4521-4530

  Barluenga, José ^a   Ferrero, Miguel ^a   Palacios, Francisco ^b  

^a UNIVERSITY OF OVIEDO   (Spain)

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

Author keywords

[No Author keywords available]

Indexed keywords

ISOQUINOLINE DERIVATIVE; PYRIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; TEMPERATURE;

EID: 0031585094     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00126-9     Document Type: Article

References (44)

1. 1. For recent reviews see: a) Schneider, M. J. Alkaloids: Chemical and Biological Perspectives, Pelletier, S. W. (Ed.), Pergamon Press, Oxford 1996, Vol. 10, p 155.
2. b) Shipman, M. Contemp. Org. Synth. 1995, 2, 1.
3. 2. a) For a review see: Jones, G. Comprehensive Heterocyclic Chemistry, Katritzky, A. R.; Rees, C. W.; Boulton, A. J.; Mckillop, A. (Eds.), Pergamon Press, Oxford 1984, Vol. 2, p 395.
4. b) Epsztajn, J.; Bieniek, A.; Kowalska, J. A. Tetrahedron 1991, 47, 1697-1706.
5. c) Robinson, J. M.; Brent, L. W.; Chau, C.; Floyd, K. A.; Gillham, S. L.; McMahan, T. L.; Magda, D. J.; Motycka, 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, 7352-7355, and literature therein cited.
6. d) Barluenga, J.; Fustero, S.; Gotor, V. Synthesis 1975, 191-192.
7. e) Guzman, A.; Romero, M.; Maddox, M. L.; Muchowski, J. M. J. Org. Chem. 1990, 55, 5793-5797.
8. f) Barluenga, J.; González, F. J.; Carlón, R. P.; Fustero, S. J. Org. Chem. 1991, 56, 6751-6754.
9. g) Oikawa, T.; Kanomata, N.; Tada, M. J. Org. Chem. 1993, 58, 2046-2051.
10. h) Molina, P.; Pastor, A.; Vilaplana, M. J. Tetrahedron Lett. 1993, 34, 3773-3776.
11. i) Katritzky, A. R.; Mazurkiewicz, R.; Stevens, C. V.; Gordeev, M. F. J. Org. Chem. 1994, 59, 2740-2742.
12. 3. For reviews see: a) Boger, D. L. Comprehensive Organic Synthesis, Trost, B. M.; Raquette, L. A.; (Eds.), Pergamon Press, Oxford 1991, Vol. 5, p. 451-512;
13. b) Fringelli, F.; Tatichi, A. Dienes in the Diets-Aider Reaction, John Wiley, New York 1990;
14. c) Barluenga, J.; Joglar, J.; González, F. J.; Fustero, S. Synlett 1990, 129-138.
15. 4. a) Palacios, F.; Perez de Heredia, I.; Rubiales, G. J. Org. Chem. 1995, 60, 2384-2390.
16. b) Palacios, F.; Rubiales, G. Tetrahedron Lett. 1996, 37, 6379-6382.
17. c) Palacios, F.; Aparicio, D.; de los Santos, J. M. Tetrahedron 1996, 52, 4857-4866.
18. 5. a) Kelly, T. R.; Liu, H. T. J. Am. Chem. Soc. 1985, 107, 4998-4999.
19. b) Khanapure, S. P.; Blehl, E. R. Heterocycles 1990, 31, 505-516.
20. 6. Dondoni, A.; Kniezo, L.; Medici, A. J. Org. Chem. 1982, 47, 3994-3998.
21. 7. a) Barluenga, J.; Ferrero, M.; Peláez-Arango, E.; López-Ortiz, F.; Palacios, F. J. Chem. Soc., Chem. Commun. 1994, 865-866.
22. b) Peláez-Arango, E.; López-Ortiz, F.; Barluenga, J.; Ferrero, M.; Palacios, F. Magn. Reson. Chem. 1994, 32, 646-651.
23. 8. For a review see: Barluenga, J.; Palacios, F. Org. Prep. Proc. Int. 1991, 23, 1-65.
24. 9. a) Barluenga, J.; Ferrero, M.; Palacios, F. Tetrahedron Lett. 1990, 31, 3497-3500,
25. b) Barluenga, J.; Ferrero, M.; Palacios, F. J. Chem. Soc., Perkin Trans. 1 1990, 2193-2197.
26. 10. Tietze, L. F.; Beifus, U. Angew. Chem. Int. Ed. Engl. 1993, 32, 131-163.
27. 11. For recent reviews of the aza-Wittig reaction see: a) Eguchi, S.; Matsushita, Y.; Yamashita, K. Org. Prep. Proc. Int. 1992, 24, 209.
28. b) Gololobov, Y. G.; Kasukhin, L. F. Tetrahedron 1992, 48, 1353-1406.
29. c) Molina, P.; Vilaplana, M. J. Synthesis 1994, 1197-1218.
30. 12. Barluenga, J.; Ferrero, M.; Palacios, F. Tetrahedron Lett. 1988, 29, 4863-4864.
31. 13. a) Molina, P.; Fresneda, P. M.; García-Zafra, S. Tetrahedron Lett. 1995, 36, 3581-3582.
32. b) Molina, P.; Fresneda, P. M.; García-Zafra, S.; Almendros, P. Tetrahedron Lett. 1994, 35, 8851-8854.
33. c) Molina, P.; Murcia, F.; Fresneda, P. M. Tetrahedron Lett. 1994, 35, 1453-1456.
34. d) Molina, P.; García-Zafra, S.; Fresneda, P. M. Synlett. 1995, 43-45.
35. e) Chavignon, O.; Teulade, J. C.; Roche, D.; Madesclaire, M.; Blache, Y.; Gueiffier, A.; Chabard, J. L.; Dauphin, G. J. Org. Chem. 1994, 59, 6413-6418.
36. f) Molina, P.; Almendros, P.; Fresneda, P. M. Tetrahedron 1994, 50, 2241-2254.
37. 14. Ferrero, M. Ph. D. Thesis, Universidad de Oviedo, 1992.
38. 15. A synthesis of this compound through an alternative route using [(methylthio)carbonyl]amino derivatives has been reported: Alvarez-Ibarra, C.; Barbolla, M.; López-Ranz, M.; Quiroga, M. L.; Ruiz, M. P. J. Org. Chem. 1994, 59, 2648-2651.
39. 16. Peláez-Arango, E.; Ferrero, M.; López-Ortiz, F. Magn. Reson. Chem. 1996, 34, 368-372.
40. 17. Previously described by: Molina, P.; Tárraga, A.; Lidón, M. J. J. Chem. Soc., Perkin Trans. 1 1990, 1727-1731.
41. 18. Capuano, L.; Braun, C.; Kühn, F. Liebigs Ann. Chem. 1992, 15-18.
42. 19. Knittel, D. Synthesis 1985, 186-188.
43. 20. Smith, L. I.; Hoehn, H. H. Org. Synth. 1955, Coll. Vol. III, p. 356-358.
44. 21. Brandsma, L. Studies in Organic Chemistry 34. Preparative Acetylenic Chemistry, 2nd ed., Eisevier, 1988.