Reaction of N-vinylic phosphazenes with α,β-unsaturated aldehydes. Azatriene-mediated synthesis of dihydropyridines and pyridines derived from β-amino acids

Journal of Organic Chemistry

Volumn 71, Issue 16, 2006, Pages 6020-6030

  Palacios, Francisco ^a   Herrán, Esther ^a   Alonso, Concepción ^a   Rubiales, Gloria ^a   Lecea, Begoña ^a   Ayerbe, Mirari ^a   Cossío, Fernando P ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

AZA-WITTIG REACTION; PERISELECTIVITY; PHOSPHAZENE; PYRIDINE;

ADDITION REACTIONS; ALKYLATION; AMINO ACIDS; AROMATIC COMPOUNDS; NITROGEN COMPOUNDS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

ALDEHYDES;

ALDEHYDE; AZATRIENE; BETA AMINO ACID; DIHYDROPYRIDINE DERIVATIVE; DIPHENYLMETHYLPHOSPHINE; HETEROCYCLIC COMPOUND; N VINYLIC PHOSPHAZENE; PHOSPHATE; PHOSPHAZENE DERIVATIVE; PHOSPHINE DERIVATIVE; PYRIDINE DERIVATIVE; TRIMETHYLPHOSPHINE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ADDITION REACTION; ARTICLE; AZA WITTIG REACTION; CYCLIZATION; CYCLOADDITION; CYCLOREVERSION; STEREOCHEMISTRY; SYNTHESIS; WITTIG REACTION;

ALDEHYDES; AMINO ACIDS; AZA COMPOUNDS; COMPUTER SIMULATION; CYCLIZATION; DIHYDROPYRIDINES; ELECTROSTATICS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PHOSPHORANES; PYRIDINES; STATIC ELECTRICITY;

EID: 33746871160     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060775b     Document Type: Article

References (74)

1. For a review, see: Nitta, M. In Reviews on Heteroatom Chemistry; Oae, S. Ed.; MYU: Tokyo, 1993: Vol. 9, p 87.
2. (a) Palacios, F.; Alonso, C.; Amezua, P.; Rubiales, G. J. Org. Chem. 2002, 67, 1941.
3. (b) Palacios, F.; Alonso, C.; Rubiales, G. J. Org. Chem. 1997, 62, 1146.
4. (a) Palacios, F.; Alonso, C.; Rubiales, G.; Villegas, M. Tetrahedron 2005, 61, 2779.
5. (b) Palacios, F.; Alonso, C.; Rubiales, G.; Villegas, M. Tetrahedron Lett. 2004, 45, 4031.
6. Palacios, F.; Ochoa de Retana, A. M.; Martínez de Marigorta, E.; Rodríguez, M.; Pagalday, J. Tetrahedron 2003, 59, 2617
7. (a) Barluenga, J.; Ferrero, M.; Palacios, F. Tetrahedron Lett. 1990, 31, 3497.
8. (b) Barluenga, J.; Ferrero, M.; Palacios, F. J. Chem. Soc., Perkin Trans. 1 1990, 2193.
9. (c) Barluenga, J.; Ferrero, M.; Palacios, F. Tetrahedron Lett. 1988, 29, 4863.
10. (a) Palacios, F.; Herrán, E.; Rubiales, G.; Ezpeleta, J. M. J. Org. Chem. 2002, 67, 2131.
11. (b) Palacios, F.; Herrán, E.; Rubiales, G. J. Org. Chem. 1999, 64, 6239.
12. (c) Palacios, F.; Pérez de Heredia, I.; Rubiales, G. J. Org. Chem. 1995, 60, 2384.
13. Wamhoff, H.; Warnecke, H.; Sohar, P.; Csámpai, A. Synlett 1998, 1193.
14. (a) Barluenga, J.; Ferrero, M.; Palacios, F. Tetrahedron 1997, 53, 4521.
15. (b) Barluenga, J.; Ferrero, M.; Lopez, F.; Palacios, F. J. Chem Soc., Perkin Trans. 1 1990, 2193.
16. (a) Katritzky, A. R.; Mazurkiewicz, R.; Stevens, C. V.; Gordeev, M. F. J. Org. Chem. 1994, 59, 2740.
17. (b) Molina, P.; Pastor, A.; Vilaplana, M. J. Tetrahedron Lett. 1993, 34, 3773.
18. (c) Oikawa, T.; Kanomata, N.; Tada, M. J. J. Org. Chem. 1993, 58, 2046.
19. (d) Krutosikova, A.; Dandarova, M.; Chylova, J.; Vegh, D. Monatsh. Chem. 1992, 123, 807.
20. Palacios, F.; Alonso, C.; Rubiales, G. Tetrahedron 1995, 51, 3683.
21. (a) Wamhoff, H.; Schmidt, A. J. Org. Chem. 1993, 58, 6976.
22. (b) Nitta, M.; Iino, Y.; Mori, S.; Takayasu, T. J. Chem. Soc., Perkin Trans. 1 1995, 1001.
23. (a) Chavignon, O.; Teulade, J. C.; Roche, D.; Madesclaire, M.; Blache, Y.; Gueiffier, A.; Chabard, J. L.; Dauphin, G. J. Org. Chem. 1994, 59, 6413.
24. (b) Rodrigues, J.; Augusto, R.; Leiva, G. C.; de Sousa, D. F. Tetrahedron Lett. 1995, 36, 59.
25. Reactive centers of phosphazenes I (see Scheme 1) are numbered 1.2.3. and 4, and reactive centers of aldehydes II are numbered 1′, 2′, 3′, and 4′.
26. For reviews, see: (a) Palacios, F.; Aparicio, D.; Alonso, C.; Rubiales, G.; de los Santos, J. M., Curr. Org. Chem. 2006, 10, 000.
27. (b) Wamhoff, H.; Richardt, G.; Stoelben, S. Adv. Heterocycl. Chem. 1995, 64, 159.
28. (c) Barluenga, J.; Palacios, F. Org. Prep. Proc. Int. 1991, 23, 1.
29. (a) Palacios, F.; Alonso, C.; Rubiales, G.; Ezpeleta, J. M. Tetrahedron 2004, 60, 2469.
30. (b) Palacios, F.; Aparicio, D.; de los Santos, J. M. Tetrahedron 1996, 52, 4857.
31. Molina, P.; Aller, E.; López-Lázaro, A.; Alajarin, M.; Lorenzo, A. Tetrahedron Lett. 1994, 55, 3817.
32. Nitta, M.; Iino, Y. J. Chem. Soc., Perkin Trans. 1 1990, 435.
33. Nitta, M.; Ohnuma, M.; Iino, Y. J. Chem. Soc., Perkin Trans. 1 1991, 1115.
34. Oikawa, T.; Kanomata, N.; Tada, M. J. Org. Chem. 1993, 58, 2046.
35. Cossío, F. P.; Alonso, C.; Lecea, B.; Ayerbe, M.; Rubiales, G.; Palacios, F. J. Org. Chem. 2006, 71, 2839.
36. (a) Bonini, C.; D'Auria, M.; Funicello, M.; Romaniello, G. Tetrahedron 2002, 58, 3507.
37. (b) Rossi, E.; Abbiati, G.; Fini, E. Synlett 1999, 1265.
38. (c) Molina, P.; Pastor, A.; Vilaplana, M. J. Tetrahedron 1995, 51, 1265.
39. Molina, P.; Pastor, A.; Vilaplana, M. J. J. Org. Chem. 1996, 61, 8094.
40. 42 (vide infra, computational studies).
41. Palacios, F.; Ochoa de Retana, A.; Oyarzabal, J. Tetrahedron Lett. 1996, 37, 4577.
42. Robinson, J. M.; Brent, L. W.; Chau, Ch.; 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.
43. 1H NMR showing the disappearance of phosphazene 6 and the formation of azatrienes 11.
44. Palacios, F.; Gil, M. J.; Martínez de Marigorta, E.; Rodríguez, M. Tetrahedron 2000, 56, 6319.
45. Palacios, F.; Gil, M. J.; Martínez de Marigorta, E.; Rodríguez, M. Tetrahedron Lett. 1999, 40, 2411.
46. Gerasyuts, A. I.; Hsung, R. P.; Sydorenko, N.; Slafer, B. J. Org. Chem. 2005, 70, 4248 and references therein.
47. Parr, R. G.; Yang, W. Density-Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989.
48. (a) Kohn, W.; Becke, A. D.; Parr, R. G. J. Phys. Chem. 1996, 100, 12974.
49. (b) Becke, A. D. J. Chem. Soc. 1993, 98, 5648.
50. (c) Becke, A. D. Phys. Rev. A 1988, 38, 3098.
51. (a) Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986; pp 76-87.
52. (b) Ditchfield, R.; Hehre, W. J.; Pople, J. A. J. Chem. Phys. 1971, 54, 724.
53. (c) Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257.
54. Gaussian 98, Revision A.5: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Koinaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian, Inc., Pittsburgh, PA, 1998.
55. Borden, W. T.; Loncharich, R. J.; Houk, K. N. Annu. Rev. Phys. Chem. 1988, 39, 213.
56. (a) Moyano, A.; Pericás, M. A.; Valentí, E. J. Org. Chem. 1989, 54, 573.
57. (a) Lecea, B.; Arrieta, A.; Roa, G.; Ugalde, J. M.; Cossío, F. P. J. Am. Chem. Soc. 1994, 116, 9613.
58. (b) Lecea, B.; Arrieta, A.; Lopez, X.; Ugalde, J. M.; Cossío, F. P. J. Am. Chem. Soc. 1995, 117, 12314.
59. (a) Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88. 899.
60. (b) Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735.
61. Schleyer, P. v. R.; Maerker, C.; Dransfeld, A.; Jiao, H.; Hommes, N. J. R. v. E. J. Am. Chem. Soc. 1996, 118, 6317.
62. (a) Morao, I.; Lecea, B.; Cossío, F. P. J. Org. Chem. 1997, 62, 7033.
63. (b) Bader, R. F. W. Atoms in Molecules-A Quantum Theory; Clarendon Press: Oxford, 1990; pp 13-52. According to Bader, a critical point of the electron density is characterized by its (ω,σ) pair of values, ω and σ being the rank and the signature, respectively. The rank is the number of non-zero curvatures of the electron density at the critical point and the signature is the algebraic sum of the signs of these eigenvalues.
64. Wolinski, K.; Hilton, J. F.; Pulay, P. J. Am. Chem. Soc. 1990, 112, 8251.
65. (a) Bader, R. F. W. Atoms in Molecules-A Quantum Theory; Clarendon Press: Oxford, 1990; pp 276-277.
66. (b) Cremer, D.; Kraka, E. Croat. Chim. Acta 1984, 57, 1259.
67. Collard, K.; Hall, G. C. Int. J. Quantum Chem. 1977, 12, 623.
68. For a more detailed quantitative treatment of the relevance of electrostatic (Coulombic) and orbital interactions within the second-order perturbation theory framework, see: Vivanco, S.; Lecea, B.; Arrieta, A.; Prieto, P.; Morao, I.; Linden, A.; Cossío, F. P. J. Am. Chem. Soc. 2000, 122, 6078.
69. For reviews, see: (a) Plunkett, A. O. Nat. Prod. Rep. 1994, 11, 581.
70. (b) Numata, A.; Ibuka, T. The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1987; Vol. 31.
71. (c) Gould, S. J.; Weinreb, S. M. Forsch. Chem. Org. Naturist, 1982, 4177.
72. (d) Daly, J. L.; Spande, T. F. Alkaloids. Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Wiley: New York, 1986; Vol. 4, pp 1-274.
73. For recent reviews, see: (a) Schneider, M. J. Alkaloids. Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Pergamon: Oxford, 1996; Vol. 10, pp 155-299.
74. (b) Shipman, M. Contemp. Org. Synth. 1995, 2, 1.