Palladium-catalyzed reaction of o-alkynyltrifluoroacetanilides with 1-bromoalkynes. An approach to 2-substituted 3-alkynylindoles and 2-substituted 3-acylindoles

Journal of Organic Chemistry

Volumn 70, Issue 16, 2005, Pages 6213-6217

  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

HYDRATION; ORGANIC COMPOUNDS; PALLADIUM; REACTION KINETICS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

1-BROMOALKYNES; CYCLIZATION; PALLADIUM-CATALYZED REACTION; REGIOSELECTIVE SYNTHESIS;

CATALYSIS;

ACETANILIDE DERIVATIVE; ALKYNE DERIVATIVE; INDOLE DERIVATIVE; PALLADIUM; TRIFLUOROACETANILIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; ELIMINATION REACTION; HYDRATION; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 23044490214     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050517z     Document Type: Article

References (52)

1. For a review, see: (a) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Eur. J. Org. Chem. 2002, 2671.
2. See also: (b) Cacchi, S.; Fabrizi, G.; Parisi, L. M. Synthesis 2004, 1889.
3. (c) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Parisi, L. M. Tetrahedron Lett. 2004, 45, 2431
4. (d) Cacchi, S.; Fabrizi, G.; Lamba, D.; Marinelli, F.; Parisi, L. M. Synthesis 2003, 728.
5. (e) Flynn, B. L.; Hamel, E.; Jung, M. K. J. Med. Chem. 2002, 45, 2670.
6. (a) Cacchi, S.; Fabrizi, G.; Pace, P.; Marinelli, F. Synlett 1999, 620.
7. (b) Arcadi, A.; Cacchi, S.; Carnicelli, V.; Marinelli, F. Tetrahedron 1994, 50, 437.
8. For recent reviews on this type of chemistry, see the following. Cyclization with nitrogen nucleophiles: (a) Cacchi, S.; Marinelli, F. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; John Wiley & Sons: New York, 2002; Vol. 2, p 2227.
9. (b) Cacchi, S.; Fabrizi, G.; Parisi, L. M. Heterocycles 2002, 58, 667.
10. Cyclization with oxygen nucleophiles: (c) Cacchi, S.; Arcadi, A. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; John Wiley & Sons: New York, 2002; Vol. 2, p 2193.
11. (d) Cacchi, S.; Fabrizi, G.; Goggiamani, A. Heterocycles 2002, 56, 613.
12. Cyclization with carbon nucleophiles: (e) Balme, G.; Bouyssi, D.; Monteiro, N. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; John Wiley & Sons: New York, 2002; Vol. 2, p 2245.
13. See also: (f) Balme, G. Bossharth, E. Monteiro, N. Eur. J. Org. Chem. 2003, 4101.
14. (g) Balme, G.; Bouyssi, D.; Lomberget, T. Monteiro, N. Synthesis 2003, 2115.
15. Bouyssi, D.; Gore, J.; Balme, G. Tetrahedron Lett. 1992, 33, 2811.
16. Dai, G.; Larock, R. C. J. Org. Chem. 2003, 68, 920.
17. (a) Hewkin, C. T.; Fabio, R.; Conti, N.; Cugola, A.; Gastaldi, P.; Micheli, F.; Quaglia, A. M. Arch. Pharm. Pharm. Med. Chem. 1999, 332, 55.
18. (b) Cugola, A.; Gaviraghi, G.; Micheli, F. Patent WO 9420465, 1994; Chem. Abstr. 1994, 121, 300763.
19. (a) Zhang, H.; Larock, R. C. J. Org. Chem. 2002, 67, 7048.
20. (b) Kanekiyo, N.; Kuwada, T.; Choshi, T.; Nobuhiro, J.; Hibino, S. J. Org. Chem. 2001, 66, 8793.
21. (c) Abbiati, G.; Beccalli, E. M.; Marchesini, A.; Rossi, E. Synthesis 2001, 2477.
22. Battistuzzi, G.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Parisi, L. M. Org. Lett. 2002, 4, 1355.
23. For some recent utilizations of 3-acylindoles as intermediates, see: (a) Hendrickson, J. B.; Wang, J. Org. Lett. 2004, 6, 3.
24. (b) Na, Y.-M.; Le Borgne, M.; Pagniez, F.; Le Baut, G.; Le Pape, P. Eur. J. Med. Chem. 2003, 75.
25. (c) Fresneda, P. M.; Molina, P.; Delgado, S.; Bleda, J. A. Tetrahedron Lett. 2000, 41, 4777.
26. (d) Fresneda, P. M.; Molina, P.; Saoz, M. A. Synlett 1999,1651.
27. (e) Faul, M. M.; Winneroski, L. L.; Krumrich, C. A. J. Org. Chem. 1998, 63, 6053.
28. (f) Wang, S.-P. Heterocycles 1997, 45, 347.
29. For some references on biological activities of 3-acylindoles, see: (a) Curtin, M. L.; Davidsen, S. K.; Heyman, H. R.; Garland, R. B.; Sheppard, G. S.; Florjancic, A. S.; Xu, L.; Carrera, G. M., Jr.; Steinman, D. H.; Trautmann, J. A.; Albert, D. H.; Magoc, T. J.; Tapang, P.; Rhein, D. A.; Conway, R. G.; Luo, G.; Denissen, J. F.; Marsh, K. C.; Morgan, D. W.; Summers, J. B. J. Med. Chem. 1998, 41, 74.
30. (b) Lehr, M. J. Med. Chem. 1997, 40, 2694.
31. (c) Eissenstat, M. A.; Bell, M. R.; D'Ambra, T. E.; Alexander, E. J.; Daum, S. J.; Ackerman, J. H.; Gruett, M. D.; Kumar, V.; Estep, K. G.; Olefirowicz, E. M.; Wetzel, J. R.; Alexander, M. D.; Weaver, J. D.; Haycock, D. A.; Luttinger, D. A.; Casiano, F. M.; Chippari, S. M.; Kuster, J. E.; Stevenson, J. I.; Ward, S. J. J. Med. Chem. 1995, 38, 3094.
32. (d) D'Ambra, T. E.; Estep, K. G.; Bell, M. R.; Eissenstat, M. A.; Josef, K. L.; Ward, S. J.; Haycock, D. A.; Baizman, E. R.; Casiano, F. M.; Beglin, N. C.; Chippari, S. M.; Grego, J. D.; Kullnig, R. K.; Daley, G. T. J. Med. Chem. 1992, 35, 124.
33. (e) Bell, M. R.; D'Ambra, T. E.; Kumar, V.; Eissenstat, M. A.; Herrmann, J. L., Jr.; Wetzel, J. R.; Rosi, D.; Philion, R. E.; Daum, S. J.; Hlasta, D. J.; Kullnig, R. K.; Ackerman, J. H.; Haubrich, D. R.; Luttinger, D. A.; Baizman, E. R.; Miller, M. S.; Ward, S. J. J. Med. Chem. 1991, 34, 1099.
34. For a kinetic study on the substituent effects on the acid hydration of alkynes, see: Allen, A. D.; Chiang, Y.; Kresge, A. J.; Tidwell, T. T. J. Org. Chem. 1982, 47, 775.
35. Quantum mechanical calculations (PC Spartan Pro 1.0) indicated that the addition of water to acetylenic moiety of 3 should occur with high regioselectivity to give 3-acylindole derivatives.
36. Arcadi, A.; Cacchi, S.; Carnicelli, V.; Marinelli, F. Tetrahedron 1994, 50, 437.
37. Rao, M. L. N.; Periasamy, M. Synth. Commun. 1995, 25, 2295.
38. Damle, S. V.; Seomoon, D.; Lee, P. H. J. Org. Chem. 2003, 68, 7085.
39. Li, L.-S.; Wu, Y.-L. Tetrahedron Lett. 2002, 43, 2427.
40. Amatore, C.; Jutand, A.; M'Barki, M. A. Organometallics 1992, 11, 3009.
41. Netherton, M.; Fu, G. C, Org. Lett. 2001, 3, 4295.
42. For a masterful review on the transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes, see: Alonso, F.; Beletskaya, I. P.; Yus, M. Chem. Rev. 2004, 104, 3079.
43. For some recent references, see: (a) Okauchi, T.; Itonaga, M.; Minami, T.; Owa, T.; Kitoh, K.; Yoshino, H. Org. Lett. 2000, 2, 1485.
44. (b) Nicolaou, I.; Demopoulos, V. J. J. Heterocycl. Chem. 1998, 35, 1345.
45. (c) Nakatsuka, S.; Teranishi, K.; Goto, T. Tetrahedron Lett. 1994, 35, 2699.
46. (d) Tani, M.; Aoki, T.; Ito, S.; Matsumoto, S.; Hideshima, M.; Fukushima, K.; Nozawa, R.; Maeda, T.; Tashiro, M.; Yokoyama, Y.; Murakami, Y. Chem. Pharm. Bull. 1990, 38, 3261.
47. For a recent reference, see: Allen, M. S.; Hamaker, L. K.; LaLoggia, A. J.; Cook, J. M. Synth. Commun. 1992, 22, 2077.
48. For some recent references, see: (a) Yang, C. X.; Patel, H. H.; Ku, Y.-Y.; Shah, R.; Sawick, D. Synth. Commun. 1997, 27, 2125.
49. (b) Faul, M. M.; Winneroski, L. L. Tetrahedron Lett. 1997, 38, 4749.
50. (c) Davidsen, S. K.; Summers, J. B.; Albert, D. H.; Holms, J. H.; Heyman, H. R.; Magoc, T. J.; Conway, R. G.; Rhein, D. A.; Carter, G. W. J. Med. Chem. 1994, 37, 4423.
51. (d) Macor, J. E.; Blank, D. H.; Fox, C. B.; Lebel, L. A.; Newman, M. E.; Post, R. J.; Ryan, K.; Schmidt, A. W.; Schulz, D. W.; Koe, B. K. J. Med. Chem. 1994, 37, 2509.
52. (e) Bergman, J.; Venemalm, L. Tetrahedron 1990, 46, 6061.