A new synthesis of 2-substituted pyridines via aluminum chloride induced heteroarylation of arenes and heteroarenes

Journal of Organic Chemistry

Volumn 70, Issue 6, 2005, Pages 2376-2379

  Pal, Manojit ^a   Batchu, Venkateswara Rao ^a   Dager, Indu ^a   Swamy, Nalivela Kumara ^a   Padakanti, Srinivas ^a  

^a DR REDDY'S LABORATORIES LTD   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALUMINUM COMPOUNDS; CHEMICAL BONDS; REACTION KINETICS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

ALUMINUM CHLORIDE; ELECTRON-WITHDRAWING GROUPS; HETEROARYLATION; PYRIDINES;

NITROGEN COMPOUNDS;

ALUMINUM CHLORIDE; CARBON; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PYRIDINE DERIVATIVE;

ARTICLE; ARYLATION; ELECTRON; SUBSTITUTION REACTION;

ALUMINUM COMPOUNDS; CHLORIDES; MOLECULAR STRUCTURE; PYRIDINES;

EID: 15444378698     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo047944h     Document Type: Article

References (63)

1. For reviews, see: (a) Plunkett, A. O. Nat. Prod. Rep. 1994, 11, 581-590. (b) Daly, J. W.; Pinder, A. R. Nat. Proc. Rep. 1992, 9, 491-504. (c) Spande, T. F. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1987; Vol. 31.
2. For reviews, see: (a) Plunkett, A. O. Nat. Prod. Rep. 1994, 11, 581-590. (b) Daly, J. W.; Pinder, A. R. Nat. Proc. Rep. 1992, 9, 491-504. (c) Spande, T. F. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1987; Vol. 31.
3. For reviews, see: (a) Plunkett, A. O. Nat. Prod. Rep. 1994, 11, 581-590. (b) Daly, J. W.; Pinder, A. R. Nat. Proc. Rep. 1992, 9, 491-504. (c) Spande, T. F. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1987; Vol. 31.
4. (a) Wang, Y.; Dong, X.; Larock, R. C. J. Org. Chem. 2003, 68, 3090-3098.
5. (b) Moody, C. J.; Hughes, R. A.; Thompson, S. P.; Alcaraz, L. Chem. Commun. 2002, 1760-1761.
6. (c) Bach, T.; Heuser, S. Synlett 2002, 2089-2091.
7. For selected example, see: (a) Sutherland, A.; Gallagher, T.; Sharples, C. G. V.; Wonnacott, S. J. Org. Chem. 2003, 68, 2475-2478. (b) Cosford, N. D. P.; Tehrani, L.; Roppe, J.; Schweiger, E.; Smith, N. D.; Anderson, J.; Bristow, L.; Brodkin, J.; Jiang, X.; McDonald, I.; Rao, S.; Washburn, M.; Varney, M. A. J. Med. Chem. 2003, 46, 204-206. (c) Enyedy, I. J.; Sakamury, S.; Zaman, W. A.; Johnson, K. M.; Wang, S. Biorg. Med. Chem. Lett. 2003, 13, 513-517. (d) Faul, M. M.; Ratz, A. M.; Sullivan, K. A.; Trankle, W. G.; Winnerroski, L. L. J. Org. Chem. 2001, 66, 5772-5782. Bouras, A.; Boggetto, N.; Benatalah, Z.; de Rosny, E.; Sicsic, S.; Reboud-Ravaux, M. J. Med. Chem. 1999, 42, 957-962. (e) Phillips, G.; Davey, D. D.; Eagen, K. A.; Koovakkat, S. K.; Liang, A.; Ng, H. P.; Pinkerton, M.; Trinh, L.; Whiltow, M.; Beatty, A. M.; Morrissey, M. M. J. Med. Chem. 1999, 42, 1749-1756.
8. For selected example, see: (a) Sutherland, A.; Gallagher, T.; Sharples, C. G. V.; Wonnacott, S. J. Org. Chem. 2003, 68, 2475-2478. (b) Cosford, N. D. P.; Tehrani, L.; Roppe, J.; Schweiger, E.; Smith, N. D.; Anderson, J.; Bristow, L.; Brodkin, J.; Jiang, X.; McDonald, I.; Rao, S.; Washburn, M.; Varney, M. A. J. Med. Chem. 2003, 46, 204-206. (c) Enyedy, I. J.; Sakamury, S.; Zaman, W. A.; Johnson, K. M.; Wang, S. Biorg. Med. Chem. Lett. 2003, 13, 513-517. (d) Faul, M. M.; Ratz, A. M.; Sullivan, K. A.; Trankle, W. G.; Winnerroski, L. L. J. Org. Chem. 2001, 66, 5772-5782. Bouras, A.; Boggetto, N.; Benatalah, Z.; de Rosny, E.; Sicsic, S.; Reboud-Ravaux, M. J. Med. Chem. 1999, 42, 957-962. (e) Phillips, G.; Davey, D. D.; Eagen, K. A.; Koovakkat, S. K.; Liang, A.; Ng, H. P.; Pinkerton, M.; Trinh, L.; Whiltow, M.; Beatty, A. M.; Morrissey, M. M. J. Med. Chem. 1999, 42, 1749-1756.
9. For selected example, see: (a) Sutherland, A.; Gallagher, T.; Sharples, C. G. V.; Wonnacott, S. J. Org. Chem. 2003, 68, 2475-2478. (b) Cosford, N. D. P.; Tehrani, L.; Roppe, J.; Schweiger, E.; Smith, N. D.; Anderson, J.; Bristow, L.; Brodkin, J.; Jiang, X.; McDonald, I.; Rao, S.; Washburn, M.; Varney, M. A. J. Med. Chem. 2003, 46, 204-206. (c) Enyedy, I. J.; Sakamury, S.; Zaman, W. A.; Johnson, K. M.; Wang, S. Biorg. Med. Chem. Lett. 2003, 13, 513-517. (d) Faul, M. M.; Ratz, A. M.; Sullivan, K. A.; Trankle, W. G.; Winnerroski, L. L. J. Org. Chem. 2001, 66, 5772-5782. Bouras, A.; Boggetto, N.; Benatalah, Z.; de Rosny, E.; Sicsic, S.; Reboud-Ravaux, M. J. Med. Chem. 1999, 42, 957-962. (e) Phillips, G.; Davey, D. D.; Eagen, K. A.; Koovakkat, S. K.; Liang, A.; Ng, H. P.; Pinkerton, M.; Trinh, L.; Whiltow, M.; Beatty, A. M.; Morrissey, M. M. J. Med. Chem. 1999, 42, 1749-1756.
10. For selected example, see: (a) Sutherland, A.; Gallagher, T.; Sharples, C. G. V.; Wonnacott, S. J. Org. Chem. 2003, 68, 2475-2478. (b) Cosford, N. D. P.; Tehrani, L.; Roppe, J.; Schweiger, E.; Smith, N. D.; Anderson, J.; Bristow, L.; Brodkin, J.; Jiang, X.; McDonald, I.; Rao, S.; Washburn, M.; Varney, M. A. J. Med. Chem. 2003, 46, 204-206. (c) Enyedy, I. J.; Sakamury, S.; Zaman, W. A.; Johnson, K. M.; Wang, S. Biorg. Med. Chem. Lett. 2003, 13, 513-517. (d) Faul, M. M.; Ratz, A. M.; Sullivan, K. A.; Trankle, W. G.; Winnerroski, L. L. J. Org. Chem. 2001, 66, 5772-5782. Bouras, A.; Boggetto, N.; Benatalah, Z.; de Rosny, E.; Sicsic, S.; Reboud-Ravaux, M. J. Med. Chem. 1999, 42, 957-962. (e) Phillips, G.; Davey, D. D.; Eagen, K. A.; Koovakkat, S. K.; Liang, A.; Ng, H. P.; Pinkerton, M.; Trinh, L.; Whiltow, M.; Beatty, A. M.; Morrissey, M. M. J. Med. Chem. 1999, 42, 1749-1756.
11. For selected example, see: (a) Sutherland, A.; Gallagher, T.; Sharples, C. G. V.; Wonnacott, S. J. Org. Chem. 2003, 68, 2475-2478. (b) Cosford, N. D. P.; Tehrani, L.; Roppe, J.; Schweiger, E.; Smith, N. D.; Anderson, J.; Bristow, L.; Brodkin, J.; Jiang, X.; McDonald, I.; Rao, S.; Washburn, M.; Varney, M. A. J. Med. Chem. 2003, 46, 204-206. (c) Enyedy, I. J.; Sakamury, S.; Zaman, W. A.; Johnson, K. M.; Wang, S. Biorg. Med. Chem. Lett. 2003, 13, 513-517. (d) Faul, M. M.; Ratz, A. M.; Sullivan, K. A.; Trankle, W. G.; Winnerroski, L. L. J. Org. Chem. 2001, 66, 5772-5782. Bouras, A.; Boggetto, N.; Benatalah, Z.; de Rosny, E.; Sicsic, S.; Reboud-Ravaux, M. J. Med. Chem. 1999, 42, 957-962. (e) Phillips, G.; Davey, D. D.; Eagen, K. A.; Koovakkat, S. K.; Liang, A.; Ng, H. P.; Pinkerton, M.; Trinh, L.; Whiltow, M.; Beatty, A. M.; Morrissey, M. M. J. Med. Chem. 1999, 42, 1749-1756.
12. For selected example, see: (a) Sutherland, A.; Gallagher, T.; Sharples, C. G. V.; Wonnacott, S. J. Org. Chem. 2003, 68, 2475-2478. (b) Cosford, N. D. P.; Tehrani, L.; Roppe, J.; Schweiger, E.; Smith, N. D.; Anderson, J.; Bristow, L.; Brodkin, J.; Jiang, X.; McDonald, I.; Rao, S.; Washburn, M.; Varney, M. A. J. Med. Chem. 2003, 46, 204-206. (c) Enyedy, I. J.; Sakamury, S.; Zaman, W. A.; Johnson, K. M.; Wang, S. Biorg. Med. Chem. Lett. 2003, 13, 513-517. (d) Faul, M. M.; Ratz, A. M.; Sullivan, K. A.; Trankle, W. G.; Winnerroski, L. L. J. Org. Chem. 2001, 66, 5772-5782. Bouras, A.; Boggetto, N.; Benatalah, Z.; de Rosny, E.; Sicsic, S.; Reboud-Ravaux, M. J. Med. Chem. 1999, 42, 957-962. (e) Phillips, G.; Davey, D. D.; Eagen, K. A.; Koovakkat, S. K.; Liang, A.; Ng, H. P.; Pinkerton, M.; Trinh, L.; Whiltow, M.; Beatty, A. M.; Morrissey, M. M. J. Med. Chem. 1999, 42, 1749-1756.
13. (a) Lin, L.-F.; Lee, S.-J.; Chen, C.-T. Heterocycles 1977, 7, 347-352.
14. (b) Du Priest, M. T.; Schmidt, C. L.; Kuzmich, D.; Williams, S. B. J. Org. Chem. 1986, 51, 2021-2023.
15. Maarse, H.; Visscher, C. A. In Volatile Compounds in Food; Grafische Industrie Kreon Zeist: The Netherlands, 1989; Vol II, pp 648, 703, 1059.
16. Thomas, A. F.; Bassols, F. J. Agric. Food Chem. 1992, 40, 2236-2243.
17. (a) Sakamoto, T.; Kondo, Y.; Murata, N.; Yamanaka, H. Tetrahedron Lett. 1992, 33, 5373-5374.
18. (b) Sakamoto, T.; Kondo, Y.; Murata, N.; Yamanaka, H. Tetrahedron 1993, 49, 9713-9720.
19. (c) Kondo, Y.; Murata, N.; Sakamoto, T. Heterocycles 1994, 37, 1467-1468.
20. (d) Gosmini, C.; Lasry, S.; Nedelec, J.-Y.; Perichon, J. Tetrahedron 1998, 54,1289-1298.
21. (e) Zhang, N.; Thomas, L.; Wu, B. J. Org. Chem. 2001, 66, 1500-1502.
22. (f) Hassan, J.; Hathroubi, C.; Gozzi, C.; Lemaire, M. Tetrahedron 2001, 57, 7845-7856.
23. (a) Negishi, E.-i.; Luo, P.-T.; Frisbee, R.; Matsushita, H. Heterocycles 1982, 18, 117-122.
24. (b) Gauthier, D. R.; Szumigala, R. H.; Dormer, P. G.; Armstrong, J. D.; Volante, R. P.; Reider, P. J. Org. Lett. 2002, 4, 375-378.
25. (c) Riguet, E.; Alami, M.; Cahiez, G. Tetrahedron Lett. 1997, 38, 4397-4400.
26. Lee, H. M.; Nolan, S. P. Org. Lett. 2000, 2, 2053-2056.
27. (e) Journal; T., Kazuaki; Yorimitsu, H.; Shinokubo, H.; Matsubara, S.; Oshima, K. Org. Lett. 2001, 3, 1997-2000.
28. (f) Rao, M. L. N.; Yamazaki, O.; Shimada, S.; Tanaka, T.; Suzuki, Y.; Tanaka, M. Org. Lett. 2001, 3, 4103-4106.
29. (g) Bonnet, V.; Mongin, F.; Trecourt, F.; Queguiner, G.; Knochel, P. Tetrahedron 2002, 55, 4429-4438.
30. (h) Molander, G. A.; Biolatto, B. J. Org. Chem. 2003, 68, 4302-4314.
31. (a) Feuerstein, M.; Doucet, H.; Santelli, M. J. Organomet. Chem. 2003, 687, 327-336.
32. (b) Leadbeater, N. E.; Marco, M. J. Org. Chem. 2003, 68, 5660-5667.
33. (c) Zhao, Y.; Zhou, Y.; Ma, D.; Liu, J.; Li, L.; Zhang, T. Y.; Zhang, H. Org. Biomol, Chem. 2003, 1, 1643-1646.
34. (d) Leadbeater, N. E.; Marco, M. Angew. Chem., Int. Ed. 2003, 42, 1407-1409.
35. (e) Feuerstein, M.; Doucet, H.; Santelli, M. Tetrahedron Lett. 2001, 42, 5659-5662.
36. (f) Villemin, D.; Frederic, C. Tetrahedron Lett. 2001, 42, 639-642.
37. (g) Stavenuiter, J.; Hamzink, M.; Van der Hulst, R.; Zomer, G.; Westra, G.; Kriek, E. Heterocycles 1987, 26, 2711-2716.
38. (h) Feuerstein, M.; Doucet, H.; Santelli, M. J. Organomet. Chem. 2003, 687, 327-336.
39. (i) Adjabeng, G.; Brenstrum, T.; Wilson, J.; Frampton, C.; Robertson, A.; Hillhouse, J.; McNulty, J.; Capretta, A. Org. Lett. 2003, 5, 953-956.
40. (j) Kogan, V.; Aizenshtat, Z.; Popovitz-Biro, R.; Neumann, R. Org. Lett. 2002, 4, 3529-3532.
41. (k) Botella, L.; Najera, C. J. Organomet. Chem. 2002, 663, 46-57.
42. (l) Liu, S.-Y.; Choi, M. J.; Fu, G. C. Chem. Commun. 2001, 23, 2408-2409.
43. (m) Lohse, O.; Thevenin, P.; Waldvogel, E. Synlett 1999, 45-48.
44. For example, see: (a) Pal, M.; Rao, V. V.; Srinivas P.; Murali N.; Akhila V.; Premkumar M.; Rao, C. S.; Misra, P.; Ramesh M.; Rao Y. K. Indian J. Chem. 2003, 42B, 593-601.
45. (b) Pal, M.; Veeramaneni, V. R.; Nagaballi, M.; Kalleda, S. R.; Misra, P.; Casturi, S. R.; Yeleswarapu, K. R. Bioorg. Med. Chem. Lett. 2003, 13, 1639-1643.
46. (c) Pal, M.; Madan, M.; Srinivas, P.; Pattabiraman, V. R.; Kalleda, S. R.; Akhila, V.; Ramesh, M.; Rao Mamidi, N. V. S.; Casturi, S. R.; Malde, A.; Gopalakrishnan, B.; Yeleswarapu, K. R. J. Med. Chem. 2003, 46, 3975-3984.
47. (a) Pal, M.; Batchu, V. R.; Khanna, S.; Yeleswarapu, K. R. Tetrahedron 2002, 58, 9933-9940.
48. (b) Pal, M.; Batchu, V. R.; Parasuraman, K.; Yeleswarapu, K. R. J. Org. Chem. 2003, 68, 6806-6809.
49. Also see: (c) Pal, M.; Dakarapu, R.; Padakanti, S. J. Org. Chem. 2004, 69, 2913-2916.
50. 3, see: Kepinskaya, I. B.; Makarova, Z. S.; Koptyug, V. A. Zh. Org. Khim. 1980, 16, 1263-1268. Chem. Abstr. 1980, 93, 185326.
51. 3, see: Kepinskaya, I. B.; Makarova, Z. S.; Koptyug, V. A. Zh. Org. Khim. 1980, 16, 1263-1268. Chem. Abstr. 1980, 93, 185326.
52. (a) Kelly, T. R.; Lang, P. J. Org. Chem. 1996, 61, 4623-4633.
53. (b) The use of arenes possessing a single electron-donating group such as anisole, N,N-dimethylaniline, was examined. These arenes failed to react with 1b under the condition studied,
54. (c) Merchant, J. R.; Kulkarni, S. D.; Venkatesh, M. S. Indian J. Chem. Sect. B 1980, 914-916.
55. 4/acetonitrile, 0/40, 5/40, 30/70, 40/70, 45/ 40, 50/40, 1.0 ml/min, 210 nm, retention time 11.1 min.
56. It has been observed that the yields of cross-coupled products in a palladium-catalyzed reaction are higher when phenyl bromide is substituted with electron-withdrawing groups. These groups make aryl bromide more electron deficient and thus facilitate the oxidative addition to Pd(0). For phenyl bromides substituted with electrondonating groups, the desired coupled products were obtained in much lower yields. For related studies, see ref 7e.
57. Pal, M.; Subramanian, V.; Batchu, V. R.; Dager, I. Synlett 2004, 1965-1969.
58. (a) Amat, M.; Hadida, S.; Pshenichnyi, G.; Bosch, J. J. Org. Chem. 1997, 62, 3158-3175.
59. (b) For a list of references on other methods see ref 16a.
60. (a) Ketcha, D. M.; Gribble, G. W. J. Org. Chem. 1985, 50, 5451-5457.
61. (b) Le Borgne, M.; Marchand, P.; Delevoye-Seiller, B.; Robert, J.-M.; Le Baut, G.; Hartmann, R. W.; Falzer, M. Bioorg. Med. Chem. Lett. 1999, 9, 333-336.
62. (c) Jiang, J.; Gribble, G. W. Synth. Commun. 2002, 32, 2035-2040.
63. No product was detected in the reaction mixture even after 4 days.