2-(o-aminoaryl)indole derivatives via the coupling-cyclization of o-alkynylanilines with o-halotrifluoroacetanilides in the presence of a palladium catalyst

Heterocycles

Volumn 64, Issue , 2004, Pages 475-482

  Arcadi, Antonio ^a   Cacchi, Sandro ^b   Fabrizi, Giancarlo ^b   Marinelli, Fabio ^a   Parisi, Luca M ^b  

^a UNIVERSITY OF L'AQUILA   (Italy)

^b SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 22944473776     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-04-S(P)23     Document Type: Article

References (28)

1. Battistuzzi G., Cacchi S., and Fabrizi G. Eur. J. Org. Chem. (2002) 2671
2. For pioneering works on the palladium-catalyzed coupling of terminal alkynes with aryl halides in the absence of copper salts, see:. Cassar L. J. Organomet. Chem. 93 (1975) 253
3. Dieck H.A., and Heck F.R. J. Organomet. Chem. 93 (1975) 259
4. Baudoin O., Cesario M., Guénard D., and Guéritte F. J. Org. Chem. 67 (2002) 1199
5. Barraja P., Diana P., Lauria A., Passannanti A., Almerico A.M., Minnei C., Longu S., Congiu D., Musiu C., and La Colla P. Bioorgan. Med. Chem. 7 (1997) 1591
6. Cirrincione G., Almerico A.M., Barraja P., Diana P., Lauria A., Passannanti A., Musiu C., Pani A., Murtas P., Minnei C., Marongiu M.E., and La Colla P. J. Med. Chem. 42 (1999) 2561
7. Billimoria A.D., and Cava M.P. J. Org. Chem. 59 (1994) 6777
8. WO 2004030635, 2004. Wrasidlo W., Doukas J., Royston I., Noronha G., Hood J.D., Dneprovskaia E., Gong X., Splittgerber U., and Zhao. Chem. Abstr. 140 (2004) 321386
9. EP 406734, 1991. Tegeler J.J., Gardenhire E.M., and Helsley G.C. Chem. Abstr. 115 (1991) 49397
10. Sonogashira K., Tohda Y., and Hagihara N. Tetrahedron Lett. (1975) 4467
11. Arcadi A., Cacchi S., and Marinelli F. Tetrahedron Lett. 30 (1989) 2581. Compound (1a) and the other o-ethynylanilines were prepared as according to literature:
12. Fagnola F.C., Candiani I., Visentin G., Cabri W., Zarini F., Monelli N., and Tedeschi A. Tetrahedron Lett. 38 (1997) 2307
13. Sakamoto T., Kondo Y., Iwashita S., Nagano T., and Yamanaka H. Chem. Pharm. Bull. 36 (1988) 1305
14. Suzuki N., Yasaki S., Yasuhara A., and Sakamoto T. Chem. Pharm. Bull. 51 (2003) 1170
15. Dai W.-M., Sun L.-P., and Guo D.-S. Tetrahedron Lett. 42 (2002) 7699
16. Dai W.-M., Guo D.-S., and Sun L.-P. Tetrahedron Lett. 42 (2001) 5275
17. Kondo Y., Kojima S., and Sakamoto T. J. Org. Chem. 62 (1997) 6507
18. Kondo Y., Kojima S., and Sakamoto T. Heterocycles 43 (1996) 2741
19. Shin K., and Ogasawara K. Synlett 922 (1996)
20. Shin K., and Ogasawara K. Synlett (1995) 859
21. Shin K., and Ogasawara K. Chem. Lett. (1995) 289
22. Yasuhara A., Kanamori Y., Kaneko M., Numata A., Kondo Y., and Sakamoto T. J. Chem. Soc., Perkin Trans. 1 (1999) 529
23. Koradin C., Dohle W., Rodriguez A.L., Schmid B., and Knochel P. Tetrahedron 59 (2003) 1571
24. Rodriguez A.L., Koradin C., Dohle W., and Knochel P. Angew. Chem. Int. Ed. 39 (2000) 2488
25. ref. 7b.
26. Amatore C., Blart E., Genêt J.P., Jutand A., Lemaire-Audoire S., and Savignac M. J. Org. Chem. 60 (1995) 6829
27. Cacchi S., Fabrizi G., Pace P., and Marinelli F. Synlett (1999) 620
28. Taylor E.C., Katz A.H., Salgado-Zamora H., and McKillop A. Tetrahedron Lett. 26 (1985) 5963