Microwave-assisted intramolecular cyclization of electron-rich heterocycle derivatives by a palladium-catalyzed coupling reaction

Synthesis

Volumn , Issue 1, 2008, Pages 136-140

  Beccalli, Egle M ^a   Broggini, Gianluigi ^b   Martinelli, Michela ^a   Sottocornola, Silvia ^b  

^a UNIVERSITY OF MILAN   (Italy)

^b UNIVERSITY OF INSUBRIA   (Italy)

Author keywords

Carbamates; Indoles; Intramolecular cyclization; Microwaves; Palladium catalyst

Indexed keywords

CARBAMATES; INDOLES; INTRAMOLECULAR CYCLIZATION; PALLADIUM CATALYST;

CATALYST ACTIVITY; CYCLIZATION; DERIVATIVES; MICROWAVES; PALLADIUM; REACTION KINETICS; SYNTHESIS (CHEMICAL);

NITROGEN COMPOUNDS;

CARBOXYLIC ACID DERIVATIVE; ETHYL 11 METHYL 5,11 DIHYDRO 6H INDOLO[3,2 C]ISOQUINOLINE 6 CARBOXYLATE; ETHYL 3,4 DIMETHYLPYRROLO[3,2 B]INDOLE 1(4H) CARBOXYLATE; ETHYL 6 METHYL 4H THIENO[3,2 B]PYRROLE 4 CARBOXYLATE; ETHYL 6 METHYL 4H THIENO[3,2 C]PYRROLE 4 CARBOXYLATE; ETHYL FURO[2,3 C]ISOQUINOLINE 4(5H) CARBOXYLATE; ETHYL FURO[3,2 C]ISOQUINOLINE 4(5H) CARBOXYLATE; ETHYL THIENO[2,3 C]ISOQUINOLINE 4(5H) CARBOXYLATE; ETHYL THIENO[3,2 C]ISOQUINOLINE 4(5H) CARBOXYLATE; HETEROCYCLIC COMPOUND; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CYCLIZATION; DRUG STRUCTURE; ELECTRON; MICROWAVE RADIATION; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 38349156758     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-990947     Document Type: Article

References (27)

1. Li, J. J.; Gobble, G. W. Palladium in Heterocyclic Chemistry: A Guide for the Synthetic Chemist; Pergamon: New York, 2000.
2. Negishi, I. In Handbook of Organopalladium Chemistry for Organic Synthesis, Vol. I; Negishi, E.; de Meijere, A., Eds.; Wiley: New York, 2002, Chap. III.
3. (a) Abbiati, G.; Beccalli, E. M.; Broggini, G.; Martinelli, M.; Paladino, G. Synlett 2006, 73.
4. (b) Beccalli, E. M.; Broggini, G.; Martinelli, M.; Paladino, G.; Rossi, E. Synthesis 2006, 2404.
5. (c) Beccalli, E. M.; Broggini, G.; Martinelli, M.; Paladino, G.; Zoni, C. Eur. J. Org. Chem. 2005, 2091.
6. (d) Beccalli, E. M.; Broggini, G.; Paladino, G.; Penoni, A.; Zoni, C. J. Org. Chem. 2004, 69, 5627.
7. (a) Brugier, D.; Outurquin, F.; Paulmier, C. J. Chem. Soc., Perkin Trans. 1 2001, 37.
8. (b) Liu, B.; Padwa, A. Tetrahedron Lett. 1999, 40, 1645.
9. (a) Desai, P. J.; Dunford, P. J.; Hofstra, C. L.; Karlsson, L.; Leung, W.-P.; Ling, P.; Thumond, R. L. WO 2004021999, 2004; Chem. Abstr. 2004, 140, 207611.
10. (b) Cai, H.; Carruthers, N. I. US 2004048878, 2004; Chem. Abstr. 2004, 140, 235696.
11. (a) Ontoria, J. M.; Martin Hernando, J. I.; Malancona, S.; Attenni, B.; Stansfield, I.; Conte, I.; Ercolani, C.; Habermann, J.; Ponzi, S.; Di Filippo, M.; Koch, U.; Rowley, M.; Narjes, F. Bioorg. Med. Chem. Lett. 2006, 16, 4026.
12. (b) Attenni, B.; Martin Hernando, J. I.; Ignacio, M.; Malancona, S.; Narjes, F.; Ontoria, J. M.; Rowley, M. WO 2005023819, 2005; Chem. Abstr. 2005, 142, 316690.
13. (c) Wang, X. A.; Sun, L.-Q.; Sit, S.-Y.; Sin, N.; Scola, P. M.; Hewawasam, P.; Good, A. C.; Chen, Y.; Campbell, J. A. WO 2003099274, 2003; Chem. Abstr. 2004, 140, 16975.
14. (a) Coghlan, R. D.; Fobare, W. F.; Trybulski, E. J. WO 2006069182, 2006; Chem. Abstr. 2006, 145, 83249.
15. (b) Jagtap, P.; Baloglu, E.; Van Duzer, J. H.; Szabo, C.; Salzman, A. L.; Roy, A.; Williams, W.; Nivorozhkin, A. WO 2005082368, 2005; Chem. Abstr. 2005, 143, 286298.
16. (a) Kumar, P. R.; Raju, S.; Goud, P. S.; Sailaja, M.; Sarma, M. R.; Reddy, G. O.; Kumar, M. P.; Reddy, V. V. R. M. K.; Suresh, T.; Hegde, P. Bioorg. Med. Chem. 2004, 12, 1221.
17. (b) Pellicciari, R.; Moroni, F. WO 2002036599, 2002; Chem. Abstr. 2002, 136, 355165.
18. (a) Sher, P. M.; Ellsworth, B. A. US 2004142938, 2004; Chem. Abstr. 2004, 141, 140474.
19. (b) Nakamura, T.; Takagi, M.; Kiguchi, T.; Ikenogami, T.; Ueda, N. WO 2004113345, 2004; Chem. Abstr. 2005, 142, 93672.
20. (c) Onda, K.; Suzuki, T.; Shiraki, R.; Yonetoku, Y.; Ogiyama, T.; Maruyama, T.; Momose, K. WO 2003091213, 2003; Chem. Abstr. 2003, 139, 364824.
21. (d) Daisy, J. EP 1391460, 2004; Chem. Abstr. 2004, 140, 199313.
22. (a) Campeau, L.-C.; Fagnou, K. Chem. Commun. 2006, 1253.
23. (b) Arai, N.; Takahashi, M.; Mitani, M.; Mori, A. Synlett 2006, 3170.
24. Padwa, A.; Brodney, M. A.; Lynch, S. M.; Rashatasakhon, P.; Wang, Q.; Zhang, H. J. Org. Chem. 2004, 69, 3735.
25. Meth-Cohn, O.; Van Vuuren, G. Tetrahedron Lett. 1986, 27, 1105.
26. Lynch, S. M.; Bur, S. K.; Padwa, A. Org. Lett. 2002, 4, 4643.
27. Sullivan, J. B.; McCarthy, W. C. J. Org. Chem. 1965, 30, 662.