12-Acylindolo[1,2-c]quinazolines by Palladium-Catalyzed Cyclocarbonylation of o-Alkynyltrifluoroacetanilides

Organic Letters

Volumn 4, Issue 8, 2002, Pages 1355-1358

  Battistuzzi, Gianfranco ^a   Cacchi, Sandro ^a   Fabrizi, Giancarlo ^a   Marinelli, Fabio ^b   Parisi, Luca M ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b UNIVERSITY OF L'AQUILA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ACETANILIDE DERIVATIVE; ALKYNE; PALLADIUM;

ANIMAL; ARTICLE; BRYOZOA; CATALYSIS; CHEMISTRY; CYCLIZATION;

ACETANILIDES; ALKYNES; ANIMALS; BRYOZOA; CATALYSIS; CYCLIZATION; PALLADIUM;

EID: 0037129385     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0256769     Document Type: Article

References (17)

1. Cacchi, S.; Fabrizi, G.; Pace, P.; Marinelli, F. Synlett 1999, 620-622.
2. For a recent reference on the chemistry of indolo[1,2-c]quinazolines, see: Billimoria, A. D.; Cava, M. P. J. Org. Chem. 1994, 59, 6777-6782. Merour, J.-Y.; Savelon, L. Heterocycles 1991, 32, 849-853. Molina, P.; Alajarin, M.; Vidal, A. Tetrahedron 1990, 46, 1063-1078.
3. For a recent reference on the chemistry of indolo[1,2-c]quinazolines, see: Billimoria, A. D.; Cava, M. P. J. Org. Chem. 1994, 59, 6777-6782. Merour, J.-Y.; Savelon, L. Heterocycles 1991, 32, 849-853. Molina, P.; Alajarin, M.; Vidal, A. Tetrahedron 1990, 46, 1063-1078.
4. For a recent reference on the chemistry of indolo[1,2-c]quinazolines, see: Billimoria, A. D.; Cava, M. P. J. Org. Chem. 1994, 59, 6777-6782. Merour, J.-Y.; Savelon, L. Heterocycles 1991, 32, 849-853. Molina, P.; Alajarin, M.; Vidal, A. Tetrahedron 1990, 46, 1063-1078.
5. For a review on indolo[1, 2-c]quinazolines, see: Billimoria, A. D.; Cava, M. P. Heterocycles 1996, 42, 453-473.
6. Blackman, A. J.; Hamley, T. W.; Picker, R.; Taylor, W. C.; Thirasana, N. Tetrahedron Lett. 1987, 28, 5561-5562.
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9. Arcadi, A.; Cacchi, S.; Carnicelli, V.; Marinelli, F. Tetrahedron 1994, 50, 437-452.
10. For other examples of preparation of indole derivatives via the aminopalladation-reductive elimination domino methodology, see: (a) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F. Synlett 2000, 394-396. (b) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F. Synlett 2000, 647-649. (c) Cacchi, S.; Fabrizi, G. Pace, P. J. Org. Chem. 1998, 63, 1001-1011. (d) Cacchi, S.; Fabrizi, G.; Marinelli, F.; Moro, L.; Pace, P. Synlett 1997, 1363-1366. (e) Collini, M. D.; Ellingboe, J. W. Tetrahedron Lett. 1997, 38, 7963-7966. (f) Saulnier, M. G.; Frennesson, D. B.; Deshpande, M. S.; Vyas, D. M. Tetrahedron Lett. 1995, 36, 7841-7844. (g) Arcadi, A.; Cacchi, S.; Marinelli, F. Tetrahedron Lett. 1992, 33, 3915-3918.
11. For other examples of preparation of indole derivatives via the aminopalladation-reductive elimination domino methodology, see: (a) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F. Synlett 2000, 394-396. (b) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F. Synlett 2000, 647-649. (c) Cacchi, S.; Fabrizi, G. Pace, P. J. Org. Chem. 1998, 63, 1001-1011. (d) Cacchi, S.; Fabrizi, G.; Marinelli, F.; Moro, L.; Pace, P. Synlett 1997, 1363-1366. (e) Collini, M. D.; Ellingboe, J. W. Tetrahedron Lett. 1997, 38, 7963-7966. (f) Saulnier, M. G.; Frennesson, D. B.; Deshpande, M. S.; Vyas, D. M. Tetrahedron Lett. 1995, 36, 7841-7844. (g) Arcadi, A.; Cacchi, S.; Marinelli, F. Tetrahedron Lett. 1992, 33, 3915-3918.
12. For other examples of preparation of indole derivatives via the aminopalladation-reductive elimination domino methodology, see: (a) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F. Synlett 2000, 394-396. (b) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F. Synlett 2000, 647-649. (c) Cacchi, S.; Fabrizi, G. Pace, P. J. Org. Chem. 1998, 63, 1001-1011. (d) Cacchi, S.; Fabrizi, G.; Marinelli, F.; Moro, L.; Pace, P. Synlett 1997, 1363-1366. (e) Collini, M. D.; Ellingboe, J. W. Tetrahedron Lett. 1997, 38, 7963-7966. (f) Saulnier, M. G.; Frennesson, D. B.; Deshpande, M. S.; Vyas, D. M. Tetrahedron Lett. 1995, 36, 7841-7844. (g) Arcadi, A.; Cacchi, S.; Marinelli, F. Tetrahedron Lett. 1992, 33, 3915-3918.
13. For other examples of preparation of indole derivatives via the aminopalladation-reductive elimination domino methodology, see: (a) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F. Synlett 2000, 394-396. (b) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F. Synlett 2000, 647-649. (c) Cacchi, S.; Fabrizi, G. Pace, P. J. Org. Chem. 1998, 63, 1001-1011. (d) Cacchi, S.; Fabrizi, G.; Marinelli, F.; Moro, L.; Pace, P. Synlett 1997, 1363-1366. (e) Collini, M. D.; Ellingboe, J. W. Tetrahedron Lett. 1997, 38, 7963-7966. (f) Saulnier, M. G.; Frennesson, D. B.; Deshpande, M. S.; Vyas, D. M. Tetrahedron Lett. 1995, 36, 7841-7844. (g) Arcadi, A.; Cacchi, S.; Marinelli, F. Tetrahedron Lett. 1992, 33, 3915-3918.
14. For other examples of preparation of indole derivatives via the aminopalladation-reductive elimination domino methodology, see: (a) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F. Synlett 2000, 394-396. (b) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F. Synlett 2000, 647-649. (c) Cacchi, S.; Fabrizi, G. Pace, P. J. Org. Chem. 1998, 63, 1001-1011. (d) Cacchi, S.; Fabrizi, G.; Marinelli, F.; Moro, L.; Pace, P. Synlett 1997, 1363-1366. (e) Collini, M. D.; Ellingboe, J. W. Tetrahedron Lett. 1997, 38, 7963-7966. (f) Saulnier, M. G.; Frennesson, D. B.; Deshpande, M. S.; Vyas, D. M. Tetrahedron Lett. 1995, 36, 7841-7844. (g) Arcadi, A.; Cacchi, S.; Marinelli, F. Tetrahedron Lett. 1992, 33, 3915-3918.
15. For other examples of preparation of indole derivatives via the aminopalladation-reductive elimination domino methodology, see: (a) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F. Synlett 2000, 394-396. (b) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F. Synlett 2000, 647-649. (c) Cacchi, S.; Fabrizi, G. Pace, P. J. Org. Chem. 1998, 63, 1001-1011. (d) Cacchi, S.; Fabrizi, G.; Marinelli, F.; Moro, L.; Pace, P. Synlett 1997, 1363-1366. (e) Collini, M. D.; Ellingboe, J. W. Tetrahedron Lett. 1997, 38, 7963-7966. (f) Saulnier, M. G.; Frennesson, D. B.; Deshpande, M. S.; Vyas, D. M. Tetrahedron Lett. 1995, 36, 7841-7844. (g) Arcadi, A.; Cacchi, S.; Marinelli, F. Tetrahedron Lett. 1992, 33, 3915-3918.
16. For other examples of preparation of indole derivatives via the aminopalladation-reductive elimination domino methodology, see: (a) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F. Synlett 2000, 394-396. (b) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F. Synlett 2000, 647-649. (c) Cacchi, S.; Fabrizi, G. Pace, P. J. Org. Chem. 1998, 63, 1001-1011. (d) Cacchi, S.; Fabrizi, G.; Marinelli, F.; Moro, L.; Pace, P. Synlett 1997, 1363-1366. (e) Collini, M. D.; Ellingboe, J. W. Tetrahedron Lett. 1997, 38, 7963-7966. (f) Saulnier, M. G.; Frennesson, D. B.; Deshpande, M. S.; Vyas, D. M. Tetrahedron Lett. 1995, 36, 7841-7844. (g) Arcadi, A.; Cacchi, S.; Marinelli, F. Tetrahedron Lett. 1992, 33, 3915-3918.
17. Arcadi, A.; Cacchi, S.; Cassetta, A.; Fabrizi, G.; Parisi, L. M. Synlett 2001, 1605.