Regioselectivity on the palladium-catalyzed intramolecular cyclization of indole derivatives

Journal of Organic Chemistry

Volumn 68, Issue 20, 2003, Pages 7625-7628

  Abbiati, Giorgio ^a   Beccalli, Egle M ^a   Broggini, Gianluigi ^b   Zoni, Caterina ^a  

^a UNIVERSITY OF MILAN   (Italy)

^b UNIVERSITY OF INSUBRIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; MOLECULAR STRUCTURE; PALLADIUM;

CYCLIZATION;

ORGANOMETALLICS;

BETA CARBOLINONE; CARBOXYLIC ACID DERIVATIVE; INDOLE 2 CARBOXAMIDE DERIVATIVE; INDOLE DERIVATIVE; METAL COMPLEX; PALLADIUM COMPLEX; PYRAZINO[1,2 A]INDOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; INFRARED SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0141655068     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034636v     Document Type: Article

References (29)

1. Tsuji, J. Palladium Reagents and Catalysts, Innovations in Organic Synthesis; Wiley and Sons: Chichester, U.K., 1995.
2. (a) Poli, G.; Giambastiani, G.; Heuman, A. Tetrahedron 2000, 56, 5959-5989.
3. (b) Li, J. J.; Gribble G. W. Palladium in Heterocyclic Chemistry A Guide for the Synthetic Chemist; Pergamon: New York, 2000.
4. Beccalli, E. M.; Broggini, G.; Marchesini, A.; Rossi, E. Tetrahedron 2002, 58, 6673-6678.
5. (a) Arnold, R. D.; Nutter, W. M.; Stepp, W. L. J. Org. Chem. 1959, 24, 117.
6. (b) Brennan, M. R.; Erickson, K. L.; Smalc, F. S.; Tansey, M. J.; Thornton, J. M. Heterocyles 1986, 24, 2879.
7. (a) Ruppelt, M.; Bartel, S.; Guarnieri, W.; Raddatz, S.; Rosentreter, U. ; Wild, H.; Endermann, R.; Kroll, H. P. Ger. Offen. DE 19802235, 1999; Chem. Abstr. 1999, 131, 129985.
8. (b) McCort, G.; Hoornaert, C.; Duclos, O.; Guilpain, E.; Cadilhac, C.; Dellac, G. Fr. Patent FR 2 761 073, 1998; Chem. Abstr. 1999, 130, 38400.
9. (c) McCort, G.; Hoornaert, C.; Cadilhac, C.; Duclos, O.; Guilpain, E.; Dellac, G. PCT Int. Appl. WO 9 842 710, 1998; Chem. Abstr. 1998, 129, 275933.
10. (a) Gatta, F.; Zaccari, V.; Huidobro-toro, J. P.; Landi Vittory, R. Il Farmaco 1974, 29, 386-397.
11. (b) Saxena, M. P.; Ahmed, S. R. J. Heterocyl. Chem. 1977, 14, 595-598.
12. (c) Suzuki, H.; Shinpo, K.; Yamazaki, T.; Niwa, S.; Yokoyama, Y.; Murakami, Y. Heterocycles 1996, 42, 83-86.
13. (a) Beach, M. J.; Hope, R.; Klaubert, D. H.; Russell, R. K. Synth. Commun. 1995, 25, 2165-2183.
14. (b) Brimble, M. A.; Johnston, A. D. Tetrahedron 1994, 50, 4887-4896.
15. Boger, D. L.; Fink, B. E.; Hedrick, M. P. Bioorg. Med. Chem. Lett. 2000, 10, 1019-1020.
16. Beccalli, E. M.; Broggini, G. Tetrahedron Lett. 2003, 44, 1919-1921.
17. (a) Hegedus, L. S.; Allen, G. F.; Waterman, E. L. J. Am. Chem. Soc. 1976, 98, 2674-2676.
18. (b) Hegedus, L. S.; Allen, G. F.; Bozell, J. J.; Waterman, E. L. J. Am. Chem. Soc. 1978, 5800-5807.
19. (c) Hegedus, L. S. Angew. Chem. 1988, 1113-1226.
20. (d) Larock, R. C.; Hightower, T. R.; Hasvold, L. A.; Peterson, K. P. J. Org. Chem. 1996, 61, 3584-3585.
21. (e) Hegedus, L. S.; McKearin, J. M. J. Am. Chem. Soc. 1982, 104, 2444-2451.
22. Fix, S. R.; Brice J. L.; Stahl, S. S. Angew. Chem., Int. Ed. 2002, 41, 164-166.
23. (a) Amatore, C.; Jutand, A. Acc. Chem. Res. 2000, 33, 314-321.
24. (b) Muller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675-703,
25. (c) Beller, M.; Breindl, C.; Eichberger, M.; Hartung, C. G.; Seayad, J.; Thiel, O. R.; Tillack, A.; Trauthwein, H. Synlett 2002, 10, 1579-1594.
26. (a) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 4206-4207.
27. (b) Casalnuovo, A. L.; Calabrese, J. C.; Milstein, D. Inorg. Chem. 1987, 26, 971-972.
28. (c) Fryzuk, M. D.; Montgomery, C. D. Coord. Chem. Rev. 1989, 95, 1-40.
29. Jeffery T. Tetrahedron 1996, 30, 10113-10130.