A general and efficient 2-amination of pyridines and quinolines

Journal of Organic Chemistry

Volumn 72, Issue 12, 2007, Pages 4554-4557

  Yin, Jingjun ^a   Xiang, Bangping ^a   Huffman, Mark A ^a   Raab, Conrad E ^a   Davies, Ian W ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FUNCTIONAL GROUP; PYRIDINE N-OXIDES; QUINOLINES;

AMINATION; AROMATIC COMPOUNDS; OXIDATION; REACTION KINETICS;

NITROGEN COMPOUNDS;

2 AMINO (ISO)QUINOLINE; 2 AMINOPYRIDINE; PYRIDINE 1 OXIDE; PYRIDINE DERIVATIVE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; DEPROTECTION REACTION; SUBSTITUTION REACTION;

AMINATION; AMINOPYRIDINES; AMINOQUINOLINES; PYRIDINES; QUINOLINES;

EID: 34250202185     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070189y     Document Type: Article

References (57)

1. (a) Scriven, E. F. V. In Comprehensive Heterocyclic Chemistry, Part 2; Boulton, A. J., McKillop, A., Eds.; Pergamon: New York, 1984; Vol. 2, pp 165-314.
2. (b) Leffler, M. T. Org. React. 1942, 1, 91.
3. (c) McGill, C. K.; Rappa, A. Adv. Heterocycl. Chem. 1988, 44, 1-79.
4. For examples: (a) Song, Y. H.; Clizbe, L.; Bhakta, C.; Teng, W.; Li, W.; Wong, P.; Huang, B.; Sinha, U.; Park, G.; Reed, A.; Scarborough, R. M.; Zhu, B.-Y. Bioorg. Med. Chem. Lett. 2002, 12, 2043.
5. (b) Lam, P. Y. S.; Clark, C. G.; Li, R.; Pinto, D. J. P.; Orwat, M. J.; Galemmo, R. A.; Fevig, J. M.; Teleha, C. A.; Alexander, R. S.; Smallwood, A. M.; Rossi, K. A.; Wright, M. R.; Bai, S. A.; He, K.; Luettgen, J. M.; Wong, P. C.; Knabb, R. M.; Wexler, R. R. J. Med. Chem. 2003, 46, 4405.
6. For examples: (a) Taylor, E. C.; Corvetti, A. J. J. Org. Chem. 1954, 19, 1633.
7. (b) Ikemoto, T.; Kawamoto, T.; Wada, H.; Ishida, T.; Ito, T.; Isogami, Y.; Miyano, Y. o.; Mizuno, Y.; Tomimatsu, K.; Hamamura, K.; Takatani, M.; Wakimasu, M. Tetrahedron 2002, 58, 489.
8. (c) Gudmundsson, K. S.; Johns, B. A. Org. Lett. 2003, 5, 1369.
9. (d) Kuramochi, T.; Kakefuda, A.; Yamada, H.; Tsukamoto, I.; Taguchi, T.; Sakamoto, S. Bioorg. Med. Chem. 2005, 13, 4022.
10. (a) Huang, X.; Buchwald, S. L. Org. Lett. 2001, 3, 3417.
11. (b) Mathes, B. M.; Filla, S. A. Tetrahedron Lett. 2003, 44, 725.
12. (c) Bolm, C.; Frison, J.-C.; Paih, J. L.; Moessner, C.; Raabe, G. J. Organomet. Chem. 2004, 689, 3767.
13. (a) Lang, F.; Zewge, D.; Houpis, I. N.; Volante, R. P. Tetrahedron Lett. 2001, 42, 3251.
14. (b) Vedejs, E.; Trapencieris, P.; Suna, E. J. Org. Chem. 1999, 64, 6724.
15. Even complete 4-chlorination is known: (a) Alcázar, J.; Alonso, J. M.; Bartolomé, J. M.; Iturino, L.; Matesanz, E. Tetrahedron Lett. 2003, 44, 8983.
16. For other examples: (b) Yamanaka, H.; Araki, T.; Sakamoto, T. Chem. Pharm. Bull. 1988, 36, 2244.
17. (c) Klemm, L. H.; Louris, J. N.; Boisvert, W.; Higgins, C.; Muchiri, D. R. J. Heterocycl. Chem. 1985, 22, 1249.
18. (d) Miura, Y.; Takaku, S.; Nawata, Y.; Hamana, M. Heterocycles 1991, 32, 1579.
19. (e) Bremner, D. H.; Dunn, A. D.; Wilson, K. A. Synthesis 1992, 6, 528.
20. (f) Ohta, A.; Takahashi, N.; Shirokoma, Y. Heterocycles 1990, 30, 875.
21. (g) Itoh, T.; Ono, K.; Sugawara, T.; Mizuno, Y. J. Heterocycl. Chem. 1982, 19, 513.
22. Deprotonation at the 2-position with a strong base followed by halogenation is known, but with limited scope. For examples: (a) Cuperly, D.; Gros, P.; Fort, Y. J. Org. Chem. 2002, 67, 238.
23. (b) Mathieu, J.; Gros, P.; Fort, Y. Chem. Commun. 2000, 951.
24. (c) Imahori, T.; Uchiyama, M.; Sakamoto, T.; Kondo, Y. Chem. Commun. 2001, 2450.
25. Chichibabin, A. E.; Zeide, O. A. J. Russ. Phys. Chem. Soc. 1914, 46, 1216.
26. 4 or via vicarious nucleophilic substitution has been reported. (a) Wozniak, M.; Baranski, A.; Szpakiewicz, B. Liebigs Ann. Chem. 1991, 875.
27. (b) Seko, S.; Miyake, K. Chem. Commun. 1998, 1519.
28. (c) Makosza, M.; Bialecki, M. J. Org. Chem. 1998, 63, 4878.
29. (d) Bakke, J. M.; Svensen, H.; Trevisan, R. J. Chem. Soc., Perkin Trans. 1 2001, 376.
30. For examples: (a) Itoh, T.; Nagano, T.; Hirobe, M. Chem. Pharm. Bull. 1986, 34, 2013.
31. (b) Jain, S. L.; Sain, B. Chem. Commun. 2002, 1040.
32. (c) Ferrer, M.; Sanchez-Baeza, F.; Messeguer, A. Tetrahedron 1997, 53, 15877.
33. (d) Fields, J. D.; Kropp, P. J. J. Org. Chem. 2000, 65, 5937.
34. (a) Abramovich, R. A.; Singer, G. M. J. Am. Chem. Soc. 1969, 91, 5672.
35. (b) Abramovich, R. A.; Singer, G. M. J. Org. Chem. 1974, 39, 1795.
36. (c) Abramovich, R. A.; Rogers, R. B. J. Org. Chem. 1974, 39, 1802.
37. (d) Abramovich, R. A.; Pilski, J.; Konitz, A.; Tomasik, P. J. Org. Chem. 1983, 48, 4391.
38. (e) Abramovitch, R. A.; Wang, Y.-X. Heterocycles 1987, 26, 2065.
39. (a) Manley, P. J.; Bilodeau, M. T. Org. Lett. 2002, 4, 3127.
40. (b) Couturier, M.; Caron, L.; Tumidajski, S.; Jones, K.; White, T. D. Org. Lett. 2006, 8, 1929.
41. For examples: (a) Wachi, K.; Terada, A. Chem. Pharm. Bull. 1980, 28, 465.
42. (b) Ujjainwalla, F.; Walsh, T. F. Tetrahedron Lett. 2001, 42, 6441.
43. (a) Glennon, R. A.; Slusher, R. M.; Lyon, R. A.; Titeler, M. McKenney, J. D. J. Med. Chem. 1986, 29, 2375.
44. (b) Miura, Y.; Takaku S.; Fujimura, Y.; Hamana, M. Heterocycles 1992, 34, 1055.
45. (c) Storz, T. Marti, R.; Meier, R.; Nury, P.; Roeder, M.; Zhang, K. Org. Process Res. Dev. 2004, 8, 663.
46. (d) Couturier, M.; Le, T. Org. Process Res. Dev. 2006, 10, 534.
47. (e) Gerster, J. F.; Lindstrom, K. J.; Miller, R. L.; Tomai, M. A. Birmachu, W.; Bomersine, S. N.; Gibson, S. J.; Imbertson, L. M.; Jacobson J. R.; Knafla, R. T.; Maye, P. V.; Nikolaides, N.; Oneyemi, F. Y.; Parkhurst, G. J.; Pecore, S. E.; Reiter, M. J.; Scribner, L. S.; Testerman, T. L. Thompson, N. J.; Wagner, T. L.; Weeks, C. E.; Andre, J.-D.; Lagain, D. Bastard, Y.; Lupu, M. J. Med. Chem. 2005, 48, 3481.
48. Solekhova, M. A.; Kurbatov, Y. V. Russ. J. Org. Chem. 2002, 38, 1192.
49. Only methylated (A = Me) or acylated [A = Ac or RC(O)-] N-oxides are observed. The formation of the former is low yielding (ref 6a); the latter was only used for Grignard addition: (a) Webb, T. R. Tetrahedron Lett. 1985, 26, 3191.
50. (b) Fakhfakh, M. A.; Franck, X.; Fournet, A.; Hocquemiller, R.; Figadère, B. Tetrahedron Lett. 2001, 42, 3847.
51. Umemoto, T.; Tomizawa, G.; Hachisuka, H.; Kitano, M. J. Fluorine Chem. 1996, 77, 161.
52. (a) Kelly, T. R.; Bridger, G. J.; Zhao, C. J. Am. Chem. Soc. 1990, 112, 8024.
53. (b) Bashir, M.; Kingston, D. G. I.; Carman, R. J.; Tassell, R. L. v.; Wilkins, T. D. Heterocycles 1987, 26, 2877.
54. 2O is readily available on both small and large scales.
55. 2O and low conversion.
56. The 2-/4-amination selectivity was improved significantly by lowering the temperature from rt to 0°C, but it is not clear how it was affected by solvents and activating reagents.
57. 2O.