6-Aryl-11H-indolo[3,2-c]quinolines through the palladium-catalyzed carbonylative cyclization of o-(o-aminophenyl)trifluoroacetanilide with aryl iodides

Synlett

Volumn , Issue 5, 1999, Pages 620-622

  Cacchi, Sandro ^a   Fabrizi, Giancarlo ^a   Pace, Paola ^a   Marinelli, Fabio ^b  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b UNIVERSITY OF L'AQUILA   (Italy)

Author keywords

Alkynes; Carbonylation; Cyclization; Indoloquinolines; Palladium catalysis

Indexed keywords

11H INDOLO[3,2 C]QUINOLINE; 2 (2 AMINOPHENYL)TRIFLUOROACETANILIDE; ACETANILIDE DERIVATIVE; CARBONYL DERIVATIVE; INDOLE DERIVATIVE; INDOLOQUINOLINE DERIVATIVE; IODIDE; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0032953559     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2659     Document Type: Article

References (16)

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2. Arcadi, A.; Cacchi, S.; Marinelli, F. Tetrahedron Lett. 1992, 33, 3915.
3. Arcadi, A.; Cacchi, S.; Carnicelli, V.; Marinelli, F. Tetrahedron 1994, 50, 437.
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5. Saulnier, M.G.; Frennesson, D.B.; Deshpande, M.S.; Vyas, D.M. Tetrahedron Lett. 1995, 36, 7841.
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7. For a recent reference, see: Helissey, P.; Giorgi-Renault, S.; Renault, J.; Cros, S. Chem. Pharm. Bull. 1989, 37, 675; Werbel L.M.; Kesten, S.J.; Turner, W.R. Eur. J. Med. Chem. 1993, 28, 837; Koh, H.L.; Go, M.L.; Ngiam, T.L.; Mak, J.W. Eur. J. Med. Chem. 1994, 29 107;
8. For a recent reference, see: Helissey, P.; Giorgi-Renault, S.; Renault, J.; Cros, S. Chem. Pharm. Bull. 1989, 37, 675; Werbel L.M.; Kesten, S.J.; Turner, W.R. Eur. J. Med. Chem. 1993, 28, 837; Koh, H.L.; Go, M.L.; Ngiam, T.L.; Mak, J.W. Eur. J. Med. Chem. 1994, 29 107;
9. For a recent reference, see: Helissey, P.; Giorgi-Renault, S.; Renault, J.; Cros, S. Chem. Pharm. Bull. 1989, 37, 675; Werbel L.M.; Kesten, S.J.; Turner, W.R. Eur. J. Med. Chem. 1993, 28, 837; Koh, H.L.; Go, M.L.; Ngiam, T.L.; Mak, J.W. Eur. J. Med. Chem. 1994, 29 107;
10. See for example: Molina, A.; Vaquero, J.J.; Garcia-Navio, J.L.; Alvarez-Builla, J. Tetrahedron Lett. 1993, 34, 2673; Molina, A.; Vaquero, J.J.; Garcia-Navio, J.L.; Alvarez-Builla, J.; de Pascual-Teresa, B.; Gago, F.; Rodrigo, M.M.; Ballesteros, M. J. Org. Chem. 1996, 61, 5587.
11. See for example: Molina, A.; Vaquero, J.J.; Garcia-Navio, J.L.; Alvarez-Builla, J. Tetrahedron Lett. 1993, 34, 2673; Molina, A.; Vaquero, J.J.; Garcia-Navio, J.L.; Alvarez-Builla, J.; de Pascual-Teresa, B.; Gago, F.; Rodrigo, M.M.; Ballesteros, M. J. Org. Chem. 1996, 61, 5587.
12. 3), 114.9, 113.9, 106.4, 94.9, 88.3.
13. o-Ethynylaniline was prepared according to: Arcadi, A.; Cacchi, S.; Marinelli, F. Tetrahedron Lett. 1989, 30, 2581.
14. 3: C, 65.75; H, 3.91. Found: C, 65.68; H, 3.84.
15. 4) and concentrated under vacuum. The residue was purified by chromatography on silica gel eluting with a n-hexane/EtOAc 50/50 (v/v) mixture to give 0.095 g of 4a (86% yield).
16. 2O: C, 81.46; H, 4.97. Found: C, 81.40; H, 4.93.