A valuable synthesis of pyrrolo[1,2-a]quinoxalines, indolo[1,2-a] quinoxalines and their aza-analogues by palladium-catalyzed intramolecular carbon-nitrogen bond formation

Synthesis

Volumn , Issue 17, 2005, Pages 2881-2886

  Abbiati, Giorgio ^a   Beccalli, Egle M ^a   Broggini, Gianluigi ^b   Paladino, Giuseppe ^a   Rossi, Elisabetta ^a  

^a UNIVERSITY OF MILAN   (Italy)

^b UNIVERSITY OF INSUBRIA   (Italy)

Author keywords

Aminations; Cyclizations; Fused ring systems; Indoles; Lactams; Palladium catalyst

Indexed keywords

AMINATION; CARBON; CATALYSTS; NITROGEN; PALLADIUM COMPOUNDS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

CYCLIZATIONS; FUSED-RING SYSTEMS; INDOLES; LACTAMS; PALLADIUM CATALYSTS;

AMINES;

2 CHLORO 5 METHYLINDOLO[1,2 A]QUINOXALIN 6(5H) ONE; 2,5 DIMETHYLINDOLO[1,2 A]QUINOXALIN 6(5H) ONE; 2,5 DIMETHYLPYRIDO[2',3':5'6]PYRAZINO[1,2 A]INDOL 6(5H) ONE; 2,5 DIMETHYLPYRIDO[3,2 E]PYRROLO[1,2 A]PYRAZIN 6(5H) ONE; 5 METHYLINDOLO[1,2 A]QUINOXALIN 6(5H) ONE; 5 METHYLPYRIDO[3',2':5'6]PYRAZINO[1,2 A]INDOL 6(5H) ONE; 5 METHYLPYRIDO[3,2 E]PYRROLO[1,2 A]PYRAZIN 6(5H) ONE; 5 METHYLPYRROLO[1,2 A]QUINOXALIN 4(5H) ONE; 5,8 DIMETHYLPYRROLO[1,2 A]QUINOXALIN 4(5H) ONE; 8 CHLORO 5 METHYLPYRROLO[1,2 A]QUINOXALIN 4(5H) ONE; CARBON; HETEROCYCLIC COMPOUND; INDOLO[1,2 A]QUINOXALINE DERIVATIVE; NITROGEN; PALLADIUM; PYRROLO[1,2 A]QUINOXALINE DERIVATIVE; QUINOXALINE DERIVATIVE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CYCLIZATION; DRUG SYNTHESIS;

EID: 27944443607     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-916033     Document Type: Article

References (40)

1. (a) Campiani, G.; Aiello, F.; Fabbrini, M.; Morelli, E.; Ramunno, A.; Armaroli, S.; Nacci, V.; Garofano, A.; Graco, G.; Novellino, E.; Maga, G.; Spadari, S.; Bergamini, A.; Ventura, L.; Bongiovanni, B.; Capozzi, M.; Bolacchi, F.; Marini, S.; Coletta, M.; Guiso, G.; Caccia, S. J. Med. Chem. 2001, 44, 305.
2. (b) Mikiciuk-Olasik, E.; Trzebinski, P.; Nowak, R.; Kotelko, B. Acta Pol. Pharm. 1994, 51, 231.
3. Guillon, J.; Dallemagne, P.; Pfeiffer, B.; Renard, P.; Manechez, D.; Kervran, A.; Rault, S. Eur. J. Med. Chem. 1998, 33, 293.
4. (a) Campiani, G.; Cappelli, A.; Nacci, V.; Anzini, M.; Vomero, S.; Hamon, M.; Cagnotto, A.; Fracasso, C.; Uboldi, C.; Caccia, S.; Console, S.; Mennini, T. J. Med. Chem. 1997, 40, 3670.
5. (b) Prunier, H.; Rault, S.; Lancelot, J.-C.; Robba, M.; Renard, P.; Delagrange, P.; Pfeiffer, B.; Caignard, D.-H.; Misslin, R.; Guardiola-Lemaitre, B.; Hamon, M. J. Med. Chem. 1997, 40, 1808.
6. Campiani, G.; Morelli, E.; Gemma, S.; Nacci, V.; Butini, S.; Hamon, M.; Novellino, E.; Greco, G.; Cagnotto, A.; Goegan, M.; Cervo, L.; Dalla Valle, F.; Fracasso, C.; Caccia, S.; Pennini, T. J. Med. Chem. 1999, 42, 4362.
7. (a) Lancelot, J.-C.; Prunier, H.; Robba, M.; Delagrange, P.; Renard, P.; Adam, G. Adir et Compagnie Fr., Eur. Pat. Appl. EP 623620, 1994; Chem. Abstr. 1994, 122, 105922.
8. (b) Dieter, H.-R.; Engel, J.; Klinger, K.-H.; Kutscher, B.; Szelenyi, S.; Achterrath-Tuckermann, U.; Schmidt, J.; Metzenauer, P. Asta Medica Ge., Eur. Pat. Appl. EP 584497, 1994; Chem. Abstr. 1994, 122, 31559.
9. Ager, I. R.; Barnes, A. C.; Danswan, G. W.; Hairsine, P. W.; Kay, D. P.; Kennewell, P. D.; Matharu, S. S.; Miller, P.; Robson, P.; Rowlands, D. A.; Tully, W. R.; Westwood, R. J. Med. Chem. 1988, 31, 1098.
10. Abou-Gharbia, M.; Freed, M. E.; McGaully, R. J.; Silver, P. J.; Wendt, R. L. J. Med. Chem. 1984, 27, 1743.
11. (a) Campiani, G.; Nacci, V.; Corelli, F.; Anziani, M. Synth. Commun. 1991, 21, 1567.
12. (b) Lancelot, J.-C.; Rault, S.; Ladureè, D. Chem. Pharm. Bull. 1985, 33, 2798.
13. Cheeseman, G. W. H.; Tuck, B. J. Chem. Soc. 1966, 852.
14. Molina, P.; Alajarin, M.; Vidal, A. Tetrahedron Lett 1989, 30, 2847.
15. Lopez-Alvarado, P.; Avendano, C.; Menendez, C. J. Org. Chem. 1995, 60, 5678.
16. Smith, W. J.; Sawyer, S. Tetrahedron Lett. 1996, 37, 299.
17. Khan, M. A.; Polya, J. B. J. Chem. Soc. 1970, 85.
18. Molina, P.; Alajarin, M.; Vidal, A. Tetrahedron 1990, 46, 1063.
19. (a) Joseph, M. S.; Basanagoudar, L. D. Synth. Commun. 2003, 33, 851.
20. (b) Beach, M. J.; Hope, R.; Klaubert, D. H.; Russell, R. K. Synth. Commun. 1995, 25, 2165.
21. Chicharro, R.; de Castro, S.; Reino, J. L.; Aran, V. J. Eur. J. Org. Chem. 2003, 68, 2314.
22. (a) Miller, J.; Moran, P. J. S.; Da Silva, I. L. G. J. Chem. Res. 1993, 52.
23. (b) Aftah, A.; Abu-Shuheil, M. Y.; Hill, J. Tetrahedron 1990, 46, 6483.
24. Nakamura, I.; Yamamoto, Y. Chem. Rev. 2004, 104, 2127.
25. (a) Gribble, G. W.; Li, J. J. Palladium in Heterocyclic Chemistry: A Guide for the Synthetic Chemist; Pergamon: New York, 2000.
26. (b) Zeni, G.; Larock, R. C. Chem. Rev. 2004, 104, 2285.
27. (a) Paul, F.; Matt, J.; Hartwig, J. F. J. Am. Chem. Soc. 1994, 116, 5969.
28. (b) Guram, A. S.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 7901.
29. Hartwig, J. F. Angew. Chem. Int. Ed. 1998, 37, 2046.
30. Anderson, K. W.; Mendez-Perez, M.; Priego, J.; Buchwald, S. J. J. Org. Chem. 2003, 68, 9563.
31. (a) Mann, G.; Hartwig, J. F.; Driver, M. S.; Fernandez-Rivas, C. J. Am. Chem. Soc. 1998, 120, 827.
32. (b) Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575.
33. Watanabe, M.; Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 2000, 41, 481.
34. (a) Beccalli, E. M.; Broggini, G.; Paladino, G.; Zoni, C. Tetrahedron 2005, 61, 61.
35. (b) Beccalli, E. M.; Broggini, G.; Paladino, G.; Penoni, A.; Zoni, C. J. Org. Chem. 2004, 69, 5627.
36. Abbiati, G.; Beccalli, E. M.; Broggini, G.; Zoni, C. J. Org. Chem. 2003, 68, 7625.
37. Beccalli, E. M.; Broggini, G.; Marchesini, A.; Rossi, E. Tetrahedron 2002, 58, 6673.
38. Larock, R. C.; Harrison, L. W. J. Am. Chem. Soc. 1984, 106, 4218.
39. Hellwinkel, D.; Lammerzahl, F.; Hofmann, G. Chem. Ber. 1983, 116, 3375.
40. Jones, K.; Ho, T. C. T.; Wilkinson, J. Tetrahedron Lett. 1995, 36, 6743.