Synthesis of 3,4-disubstituted isoquinolines via palladium-catalyzed cross-coupling of 2-(1-Alkynyl)benzaldimines and organic halides

Journal of Organic Chemistry

Volumn 68, Issue 3, 2003, Pages 920-928

  Dai, Guangxiu ^a   Larock, Richard C ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ISOQUINOLINES;

CATALYSIS; PALLADIUM; SYNTHESIS (CHEMICAL);

ORGANIC COMPOUNDS;

3,4 DIPHENYLISOQUINOLINE; ALKYNE; ALKYNYL GROUP; ESTER; HALIDE; ISOQUINOLINE DERIVATIVE; ORGANOMETALLIC COMPOUND; PALLADIUM COMPLEX; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

EID: 0037423348     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026294j     Document Type: Article

References (57)

1. For recent leading references, see: (a) Cacchi, S.; Fabrizi, G.; Moro, L. Tetrahedron Lett. 1998, 39, 5101 and references therein.
2. (b) Chaudhuri, G.; Chowdhury, C.; Kundu, N. G. Synlett 1998, 1273.
3. (c) Montiero, N.; Balme, G. Synlett 1998, 746.
4. (d) Chowdhury, C.; Chaudhuri, G.; Guha, S.; Mukherjee, A. K.; Kundu, N. G. J. Org. Chem. 1998, 63, 1863.
5. (e) Cacchi, S.; Fabrizi, G.; Moro, L. J. Org. Chem. 1997, 62, 5327.
6. (f) Khan, M. W.; Kundu, N. G. Synlett 1997, 1435.
7. (g) Cacchi, S.; Fabrizi, G.; Marinelli, F.; Moro, L.; Pace, P. Synlett 1997, 1363.
8. (h) Arcadi, A.; Cacchi, S.; Del Rosario, M.; Fabrizi, G.; Marinelli, F. J. Org. Chem. 1996, 61, 9280.
9. (i) Chowdhury, C.; Kundu, N. G. J. Chem. Soc., Chem. Commun. 1996, 1067.
10. (j) Kundu, N. G.; Pal, M. J. Chem. Soc., Chem. Commun. 1993, 86.
11. (k) Candiani, I.; DeBernardinis, S.; Cabri, W.; Marchi, M.; Bedeschi, A.; Penco, S. Synlett 1993, 269.
12. (l) Zhang, H.; Brumfield, K. K.; Jaroskova, L.; Maryanoff, B. E. Tetrahedron Lett. 1998, 39, 4449.
13. (m) Fancelli, D.; Fagnola, M. C.; Severino, D.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2311.
14. (n) Fagnola, M. C.; Candiani, I.; Visentin, G.; Cabri, W.; Zarini, F.; Mongelli, N.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2307.
15. (o) Gabriele, B.; Salerno, G.; Fazio, A.; Bossio, M. Tetrahedron Lett. 2001, 42, 1339.
16. (p) Monteiro, N.; Arnold, A.; Balme, G. Synlett 1998, 1111.
17. (q) Larock, R. C.; Pace, P.; Yang, H.; Russell, C. E. Tetrahedron 1998, 54, 9961.
18. (r) Cacchi, S.; Fabrizi, G.; Moro, L. Synlett 1998, 741.
19. (s) Cacchi, S.; Fabrizi, G.; Moro, L. J. Org. Chem. 1997, 62, 527 and references therein.
20. (t) Balme, G.; Bouyssi, D. Tetrahedron 1994, 50, 403.
21. (a) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F. Synlett 2000, 3, 394.
22. (b) Cacchi, S.; Fabrizi, G.; Pace, P.; Marinelli, F. Synlett 1999, 620.
23. (c) Cacchi, S.; Fabrizi, G.; Pace, P. J. Org. Chem. 1998, 63, 1001.
24. (d) Cacchi, S.; Fabrizi, G.; Marinelli, F.; Moro, L.; Pace, P. Synlett 1997, 1363.
25. (e) Arcadi, A.; Cacchi, S.; Carnicelli, V.; Marinelli, F. Tetrahedron 1994, 50, 437.
26. (f) Mandai, T.; Ohat, K.; Baba, N.; Kawada, M.; Tsuji, J. Synlett, 1992, 671.
27. (g) Tsuda, T.; Ohashi, Y.; Nagahama, M.; Sumiya, R.; Saegusa, T. J. Org. Chem. 1988, 53, 2650.
28. (a) Monteiro, N.; Balme, G. Synlett 1998, 746.
29. (b) Cacchi, S.; Fabrizi, G.; Moro, L. Synlett 1998, 741.
30. (c) Arcadi, A.; Cacchi, S.; Del Rosario, M.; Fabrizi, G.; Marinelli, F. J. Org. Chem. 1996, 61, 9280 and references therein.
31. (a) Fukuda, Y.; Shiragami, H.; Utimoto, K.; Nozaki, H. Tetrahedron 1985, 41, 3655.
32. (b) Fukuda, Y.; Shiragami, H.; Utimoto, K.; Nozaki, H. J. Org. Chem. 1991, 56, 5816.
33. (c) Arcadi, A.; Burini, A.; Cacchi, S.; Delmastro, M.; Marinelli, F.; Pietroni, B. R. J. Org. Chem. 1992, 57, 976.
34. (d) Cacchi, S.; Fabrizi, G.; Moro, L. J. Org. Chem. 1997, 62, 5327.
35. (e) Cavicchioli, M.; Decortiat, S.; Bouyssi, D.; Gore, J.; Balme, G. Tetrahedron 1996, 52, 11463.
36. (f) Bouyssi, D.; Cavicchioli, M.; Balme, G. Synlett 1997, 944.
37. (g) Arcadi, A. Synlett 1997, 941.
38. (h) Arcadi, A.; Anacardio, R.; D'Anniballe, G.; Gentile, M. Synlett 1997, 1315.
39. (i) Arcadi, A.; Cacchi, S.; Marinelli, F. Tetrahedron Lett 1992, 33, 3915.
40. (j) Arcadi, A.; Cacchi, S.; Larock, R. C.; Marinelli, F. Tetrahedron Lett 1993, 34, 2813.
41. Bentley, K. W. The Isoquinoline Alkaloids; Harwood Academic: Australia, 1998; Vol 1.
42. Organic Reactions; Wiley & Sons: London, 1951; Vol. VI, Chapters 2-4.
43. Maassarani, F.; Pfeffer, M.; Le Borgne, G. J. Chem. Soc., Chem. Commun. 1987, 565.
44. Wu, G.; Geib, S. J.; Rheingold, A. L.; Heck, R. F. J. Org. Chem. 1988, 53, 3288.
45. Girling, I. R.; Widdowson, D. A. Tetrahedron Lett. 1982, 23, 4281.
46. (a) Roesch, K. R.; Larock, R. C. Org. Lett. 1999, 1, 553.
47. (b) Roesch, K. R.; Larock, R. C. J. Org. Chem. 2002, 67, 86.
48. (a) Roesch, K. R.; Larock, R. C. J. Org. Chem. 1998, 63, 5306.
49. (b) Roesch, K. R.; Zhang, H.; Larock, R. C. J. Org. Chem. 2001, 66, 8042.
50. (a) Huang, Q.; Hunter, J. A.; Larock, R. C. Org. Lett. 2001, 3, 2973.
51. (b) Huang, Q.; Hunter, J. A.; Larock, R. C. J. Org. Chem. 2002, 67, 3437.
52. Dai, G.; Larock, R. C. Org. Lett. 2001, 3, 4035.
53. Sonogashira, K. Comprehensive Organic Synthesis; Pergamon Press: Elmsford, NY, 1990; Vol. 3, p 251.
54. 3.
55. Wu, G.; Rheingold, A. L.; Geib, S. J.; Heck, R. F. Organometallics 1987, 6, 1941.
56. Stille, J. K.; Lau, K. S. Y. Acc. Chem. Res. 1977, 10, 434.
57. Tsuji, J.; Takahashi, H.; Morikawa, M. Tetrahedron Lett. 1965, 4387.