Synthesis of Cyclopenta[b]indol-1-ones and Carbazol-4-ones from N-(2-Halophenyl)-Substituted Enaminones by Intramolecular Heck Reaction

Helvetica Chimica Acta

Volumn 87, Issue 1, 2004, Pages 82-89

  Sørensen, Ulrik S ^a   Pombo Villar, Esteban ^a  

^a NOVARTIS PHARMA AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; SUBSTRATES; SYNTHESIS (CHEMICAL);

CHEMOSELECTIVITY; HECK REACTION;

KETONES;

1,2,3,9 TETRAHYDROCARBAZOL 4(4H) ONE; 3 (7 BROMO 3 METHYL 1H INDOL 1 YL)CYCLOPENT 2 EN 1 ONE; 3 [(2 BROMOPHENYL)(PROP 2 ENYL)AMINO]CYCLOPENT 2 EN 1 ONE; 3 [(2,6 DIBROMOPHENYL)(PROP 2 ENYL)AMINO]CYCLOPENT 2 EN 1 ONE; 3,4 DIHYDROCYCLOPENT[B]INDOL 1(2H) ONE DERIVATIVE; 4,5,7,8 TETRAHYDRO 4 METHYLIDENE 9H CYCLOPENTA[B]PYRROLO[3,2,1 HI]INDOL 9 ONE; ALOSETRON; CARBAZOL 4 ONE DERIVATIVE; CARBAZOLE DERIVATIVE; CYCLOPENTA[B]INDOL 1 ONE DERIVATIVE; ONDANSETRON; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; HECK REACTION; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 1342281510     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.200490020     Document Type: Article

References (22)

1. a) S. R. Prakash, K. M. Cable, I. D. Correa, I. Fellows, S. Montgomery, J. J. Newman, I. Waterhouse, G. N. Wells, D. R. Sutherland, J. Labelled Compd. Radiopharm. 1995, 36, 993;
2. b) I. H. Coates, A. W. Oxford, P. C. North, T. Miller, A. D. Baxter, K. I. Hammond, Eur. Pat. Appl. 385721, 1990;
3. c) I. H. Coates, P. C. North, A. W. Oxford, Eur. Pat. Appl. 306323, 1988.
4. D. Gardette, J.-C. Gramain, M.-E. Lepage, Y. Troin, Can. J. Chem. 1989, 67, 213.
5. J. Bergman, J. E. Bäckvall, Tetrahedron 1975, 31, 2063.
6. a) H. Iida, Y. Yuasa, C. Kibayashi, J. Org. Chem. 1980, 45, 2938;
7. b) T. Sakamoto, T. Nagano, Y. Kondo, H. Yamanaka, Synthesis 1990, 215;
8. c) L.-C. Chen, S.-C. Yang, H.-M. Wang, Synthesis 1995, 385;
9. d) C. F. Masaguer, E. Raviña, J. A. Fontenla, J. Brea, H. Tristán, M. I. Loza, Eur. J. Med. Chem. - Chim. Ther. 2000, 35, 83.
10. A. Osuka, Y. Mori, H. Suzuki, Chem. Lett. 1982, 2031; J. d'Angelo, D. Desmaele, Tetrahedron Lett. 1990, 31, 879; H. Suzuki, S. V. Thiruvikraman, A. Osuka, Synthesis 1984, 616; S.-C. Yang, H.-M. Wang, C.-S. Kuo, L.-C. Chen, Heterocycles 1991, 32, 2399; D. Desmaële, J. d'Angelo, J. Org. Chem. 1994, 59, 2292.
11. A. Osuka, Y. Mori, H. Suzuki, Chem. Lett. 1982, 2031; J. d'Angelo, D. Desmaele, Tetrahedron Lett. 1990, 31, 879; H. Suzuki, S. V. Thiruvikraman, A. Osuka, Synthesis 1984, 616; S.-C. Yang, H.-M. Wang, C.-S. Kuo, L.-C. Chen, Heterocycles 1991, 32, 2399; D. Desmaële, J. d'Angelo, J. Org. Chem. 1994, 59, 2292.
12. J. d'Angelo, D. Desmaele, Tetrahedron Lett. 1990, 31, 879; H. Suzuki, S. V. Thiruvikraman, A. Osuka, Synthesis 1984, 616; S.-C. Yang, H.-M. Wang, C.-S. Kuo, L.-C. Chen, Heterocycles 1991, 32, 2399; D. Desmaële, J. d'Angelo, J. Org. Chem. 1994, 59, 2292.
13. J. d'Angelo, D. Desmaele, Tetrahedron Lett. 1990, 31, 879; H. Suzuki, S. V. Thiruvikraman, A. Osuka, Synthesis 1984, 616; S.-C. Yang, H.-M. Wang, C.-S. Kuo, L.-C. Chen, Heterocycles 1991, 32, 2399; D. Desmaële, J. d'Angelo, J. Org. Chem. 1994, 59, 2292.
14. J. d'Angelo, D. Desmaele, Tetrahedron Lett. 1990, 31, 879; H. Suzuki, S. V. Thiruvikraman, A. Osuka, Synthesis 1984, 616; S.-C. Yang, H.-M. Wang, C.-S. Kuo, L.-C. Chen, Heterocycles 1991, 32, 2399; D. Desmaële, J. d'Angelo, J. Org. Chem. 1994, 59, 2292.
15. R.C. Larock, E. K. Yum, M. D. Refvik, J. Org. Chem. 1998, 63, 7652.
16. S. Caddick, Tetrahedron 1995, 51, 10403; C. R. Strauss, R. W. Trainor, Aust. J. Chem. 1995, 48, 1665; S. A. Galema, Chem. Soc. Rev. 1997, 26, 233; F. Langa, P. D. L. Cruz, A. D. L. Hoz, A. Díaz-Ortiz, E. Díez-Barra, Contemp. Org. Synth. 1997, 4, 373; N. Kuhnert, Angew. Chem., Int. Ed. 2002, 41, 1863.
17. S. Caddick, Tetrahedron 1995, 51, 10403; C. R. Strauss, R. W. Trainor, Aust. J. Chem. 1995, 48, 1665; S. A. Galema, Chem. Soc. Rev. 1997, 26, 233; F. Langa, P. D. L. Cruz, A. D. L. Hoz, A. Díaz-Ortiz, E. Díez-Barra, Contemp. Org. Synth. 1997, 4, 373; N. Kuhnert, Angew. Chem., Int. Ed. 2002, 41, 1863.
18. S. Caddick, Tetrahedron 1995, 51, 10403; C. R. Strauss, R. W. Trainor, Aust. J. Chem. 1995, 48, 1665; S. A. Galema, Chem. Soc. Rev. 1997, 26, 233; F. Langa, P. D. L. Cruz, A. D. L. Hoz, A. Díaz-Ortiz, E. Díez-Barra, Contemp. Org. Synth. 1997, 4, 373; N. Kuhnert, Angew. Chem., Int. Ed. 2002, 41, 1863.
19. S. Caddick, Tetrahedron 1995, 51, 10403; C. R. Strauss, R. W. Trainor, Aust. J. Chem. 1995, 48, 1665; S. A. Galema, Chem. Soc. Rev. 1997, 26, 233; F. Langa, P. D. L. Cruz, A. D. L. Hoz, A. Díaz-Ortiz, E. Díez-Barra, Contemp. Org. Synth. 1997, 4, 373; N. Kuhnert, Angew. Chem., Int. Ed. 2002, 41, 1863.
20. S. Caddick, Tetrahedron 1995, 51, 10403; C. R. Strauss, R. W. Trainor, Aust. J. Chem. 1995, 48, 1665; S. A. Galema, Chem. Soc. Rev. 1997, 26, 233; F. Langa, P. D. L. Cruz, A. D. L. Hoz, A. Díaz-Ortiz, E. Díez-Barra, Contemp. Org. Synth. 1997, 4, 373; N. Kuhnert, Angew. Chem., Int. Ed. 2002, 41, 1863.
21. J. Barluenga, J. Perez-Prieto, G. Asensio, Tetrahedron 1990, 46, 2453.
22. J. G. Rodriguez, F. Temprano, C. Esteban-Calderon, M. Martinez-Ripoll, S. Garcia-Blanco, Tetrahedron 1985, 41, 3813.