Synthesis of oxazines and N-arylpyrroles by reaction of unfunctionalized dienes with nitroarenes and carbon monoxide, catalyzed by palladium-phenanthroline complexes

Journal of Organic Chemistry

Volumn 68, Issue 2, 2003, Pages 460-466

  Ragaini, Fabio ^a   Cenini, Sergio ^a   Brignoli, Daniela ^a   Gasperini, Michela ^a   Gallo, Emma ^a  

^a CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

STERIC HINDRANCE;

CARBON MONOXIDE; CATALYSTS; PALLADIUM COMPOUNDS;

ORGANIC COMPOUNDS;

1,10 PHENANTHROLINE; CARBON MONOXIDE; OXAZINE DERIVATIVE; PALLADIUM COMPLEX; PYRROLE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; DIELS ALDER REACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

EID: 0037462342     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0260589     Document Type: Article

References (52)

1. (a) Gilchrist, T. L. J. Chem. Soc., Perkin Trans. 1 1998, 615.
2. (b) Korostova, S. E.; Mikhaleva, A. I.; Vasil'tsov, A. M.; Trofimov, B. A. Russ. J. Org. Chem. 1998, 34, 911.
3. (c) Korostova, S. E.; Mikhaleva, A. I.; Vasil'tsov, A. M.; Trofimov, B. A. Russ. J. Org. Chem. 1998, 34, 1691.
4. (d) Sundberg, R. J. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. S., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: Oxford, U.K., 1996; Vol. 2, p 207.
5. (e) Gilchrist, T. L. J. Chem. Soc., Perkin Trans. 1 1999, 2849.
6. (f) Bean, G. P. In The Chemistry of Heterocyclic Compounds; Jones, A. R., Ed.; Wiley: New York, 1990; Vol. 48, Part I, Chapter. 2, p 105.
7. (a) Boger, D. L.; Weinreb, S. N. Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press: New York, 1987.
8. (b) Weinreb, S. M.; Staib, R. R. Tetrahedron 1982, 39, 3087.
9. Møller, E. R.; Jørgensen, K. A. J. Org. Chem. 1996, 61, 5770.
10. McClure, K. F.; Danishefsky, S. J. J. Org. Chem. 1991, 56, 850.
11. 5b-d which gives good yields in the absence of substituents in the 2 and 5 positions. However, in this case the pyrrole nucleus must be synthesized before and this procedure has been applied only to unsubstituted pyrrole.
12. (b) Mann, G.; Hartwig, J. F.; Driver, M. S.; Fernández-Rivas, C. J. Am. Chem. Soc. 1998, 120, 827.
13. (c) Hartwig, J. F.; Kawatsura, M.; Hauck, S. H.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575.
14. (d) Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727.
15. Cenini, S.; Ragaini, F.; Tollari, S.; Paone, D. J. Am. Chem. Soc. 1996, 118, 11964.
16. Ragaini, F.; Cenini, S.; Tollari, S.; Tummolillo, G.; Beltrami, R. Organometallics 1999, 18, 928.
17. (a) Srivastava, A.; Nicholas, K. M. J. Chem Soc., Chem. Commun. 1998, 2705.
18. (b) Kolev-Veetil, M. K.; Khan, M. A.; Nicholas, K. M. Organometallics 2000, 19, 3754.
19. (c) Srivastava, A.; Kolev-Veetil, M. K.; Nicholas, K. M. Tetrahedron Lett. 2002, 43, 931.
20. (d) Penoni, A.; Volkmann, J.; Nicholas, K. M. Org. Lett. 2002, 4, 699.
21. (e) Penoni, A.; Nicholas, K. M. Chem. Commun. 2002, 484.
22. Ragaini, F.; Cenini, S.; Borsani, E.; Dompé, M.; Gallo, E. Organometallics 2001, 20, 3390.
23. Cenini, S.; Ragaini, F. Catalytic Reductive Carbonylation of Organic Nitro Compounds; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1997; and references therein.
24. (a) Wehman, P.; Borst, L.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Mol. Catal., A 1996, 112, 23.
25. (b) Wehman, P.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Chem. Commun. 1996, 217.
26. (c) Santi, R.; Romano, A. M.; Panella, F.; Mestroni, G.; Sessanta o Santi, A. J. Mol. Catal., A 1999, 144, 41.
27. Ragaini, F.; Cenini, S.; Querci, C. It. Pat. Appl. M12000A 000548, 2000.
28. (a) Hamer, J.; Ahmad, M.; Holliday, R. E. J. Org. Chem. 1963, 28, 3034.
29. (b) Kresze, G.; Firl, J.; Zimmer, H.; Wollnik, U. Tetrahedron 1974, 20, 1605.
30. (a) Leach, A. G.; Houk, K. N. J. Org. Chem. 2001, 66, 5192.
31. (b) McCarrick, M. A.; Wu, Y.-D.; Houk, K. N. J. Org. Chem. 1993, 58, 3330.
32. Sasaki, T.; Eguchi, S.; Ishii, T.; Yamada, H. J. Org. Chem. 1970, 35, 4273.
33. Kresze, G.; Korpiun, O. Tetrahedron 1966, 22, 2493.
34. 1H NMR spectra of the crude mixtures and their similarity with the ones of the nitrobenzene-derived products
35. 3N/butadiene; 100 °C; Pco = 10 bar; in 30 mL of THF for 6 h.
36. Okuro, K.; Dang, T. D.; Khumtaveeporn, K.; Alper, H. Tetrahedron Lett. 1996, 37, 2713.
37. Ittel, S. D.; Johnson, L. K.; Brookhart, M. Chem. Rev. 2000, 100, 1169.
38. (a) Kinoshita, A.; Sakakibara, N.; Mori, M. J. Am. Chem. Soc. 1997, 119, 12388.
39. (b) Kinoshita, A.; Sakakibara, N.; Mori, M. Tetrahedron 1999, 55, 8155.
40. (c) Mori, M.; Tonogaki, K.; Nishiguchi, N. J. Org. Chem. 2002, 67, 224.
41. (d) Smulik, J. A.; Driver, S. T. J. Org. Chem. 2000, 65, 1788.
42. (e) Smulik, J. A.; Driver, S. T. Org. Lett. 2000, 2, 2271.
43. (f) Smulik, J. A.; Giessert, A. J.; Driver, S. T. Tetrahedron Lett. 2002, 43, 209.
44. (g) Tonogaki, K.; Mori, M. Tetrahedron Lett. 2002, 43, 2235.
45. (a) Bontempi, A.; Alessio, E.; Chanos, G.; Mestroni, G. J. Mol. Catal. 1997, 42, 67.
46. (b) Milani, B.; Anzilutti, A.; Vicentini, L.; Sessanta o Santi, A.; Zangrando, E.; Geremia, S.; Mestroni, G. Organometallics 1997, 16, 5064.
47. Vorbrueggen, H.; Krolikiewicz, K. Tetrahedron 1994, 50, 6549.
48. Augelmann, G.; Streith, J.; Fritz, H. Helv. Chim. Acta 1985, 68, 95.
49. Wichterle, O. Collect. Czech. Chem. Commun. 1947, 12, 292.
50. Jones, A., R.; Spotswood, T. McL.; Cheuychit, P. Tetrahedron 1967, 23, 4469.
51. Jones, R. A. Aust. J. Chem. 1966, 19, 289.
52. Rocek, J. Collect. Czech. Chem. Commun. 1954, 19, 275.