Preparation of indoles from o-alkynyltrifluoroacetanilides through the aminopalladation-reductive elimination process

Synthesis

Volumn , Issue 11, 2004, Pages 1889-1894

  Cacchi, Sandro ^a   Fabrizi, Giancarlo ^a   Parisi, Luca M ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

Alkynes; Catalysis; Cyclization; Indoles; Palladium

Indexed keywords

CARBON MONOXIDE; CATALYSIS; DERIVATIVES; HALIDE MINERALS; PALLADIUM; SYNTHESIS (CHEMICAL);

INDOLE SYSTEMS; PYRROLE NUCLEUS;

ORGANIC COMPOUNDS;

(2 PHENYL 1H INDOL 3 YL)ACETIC ACID ETHYL ESTER; 2 PHENYL 3 (2 PYRIDYL)INDOLE; 2 PHENYL 3 (4 METHOXYBENZOYL)INDOLE; 2 PHENYL 3 CINNAMYLINDOLE; 2 PHENYLETHYNYLTRIFLUOROACETANILIDE; ACETANILIDE DERIVATIVE; ALLYL CARBONATE; CARBON MONOXIDE; CARBONIC ACID DERIVATIVE; INDOLE DERIVATIVE; ORGANOHALOGEN DERIVATIVE; PALLADIUM; TRIFLUOROACETANILIDE DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

AMINOPALLADATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; ELIMINATION REACTION; REDUCTION;

EID: 4043154410     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-815993     Document Type: Article

References (18)

1. For a recent review, see:Gribble, G. W. J. Chem. Soc., Perkin Trans. 1 2000, 1045.
2. Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Eur. J. Org. Chem. 2002, 2671.
3. Arcadi, A.; Cacchi, S.; Marinelli, F. Tetrahedron Lett. 1992, 33, 3915.
4. (a) Sonogashira, K. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-WCH: Weinheim, 1998, 203.
5. (b) Sonogashira, K. In Handbook of Organopalladium Chemistry for Organic Synthesis, Vol. 1; Negishi, E., Ed.; Wiley: New York, 2002, 493.
6. 3
7. Cacchi, S.; Fabrizi, G.; Lamba, D.; Marinelli, F.; Parisi, L. M. Synthesis 2003, 728.
8. Cacchi, S.; Fabrizi, G.; Marinelli, F.; Moro, L.; Pace, P. Synlett 1997, 1363.
9. Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F. Synlett 2000, 394.
10. Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F. Synlett 2000, 647.
11. Cacchi, S.; Fabrizi, G.; Pace, P. J. Org. Chem. 1998, 63, 1001.
12. (a) Arcadi, A.; Cacchi, S.; Carnicelli, V.; Marinelli, F. Tetrahedron 1994, 50, 437.
13. (b) See also: Cacchi, S.; Fabrizi, G.; Pace, P.; Marinelli, F. Synlett 1999, 620.
14. (c) See also: Arcadi, A.; Cacchi, S.; Cassetta, A.; Fabrizi, G.; Parisi, L. M. Synlett 2001, 1605.
15. (d) See also: Battistuzzi, G.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Parisi, L. M. Org. Lett. 2002, 4, 1355.
16. Saulnier, M. G.; Frennesson, D. B.; Deshpande, M. S.; Vyas, D. M. Tetrahedron Lett. 1995, 36, 7841.
17. Flynn, B. L.; Hamel, E.; Jung, M. K. J. Med. Chem. 2002, 45, 2670.
18. Colllini, M. D.; Ellingboe, J. W. Tetrahedron Lett. 1997, 38, 7963.