One step conversion of heteroaromatic-N-oxides to imidazolo-heteroarenes

Journal of Organic Chemistry

Volumn 73, Issue 1, 2008, Pages 327-330

  Keith, John M ^a  

^a JOHNSON AND JOHNSON PHARMACEUTICAL RESEARCH AND DEVELOPMENT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; ORGANIC SOLVENTS; PYRIDINE; SULFUR;

IMIDAZOLO-HETEROARENES; ISOQUINOLINE; QUINOLINE;

NITROGEN OXIDES;

AROMATIC COMPOUND; IMIDAZOLE DERIVATIVE; ISOQUINOLINE DERIVATIVE; OXIDE; PYRIDINE 1 OXIDE; PYRIMIDINE DERIVATIVE; QUINOLINE DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; REACTION ANALYSIS;

CYCLIC N-OXIDES; IMIDAZOLES; MOLECULAR STRUCTURE; STEREOISOMERISM; SULFHYDRYL COMPOUNDS;

EID: 37549011319     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo702038g     Document Type: Article

References (30)

1. (a) Keith, J. M. J. Org. Chem. 2006, 71, 9540-9543.
2. (b) Letavic, M. A.; Ly, K. S. Tetrahedron Lett. 2007, 48, 2339-2343.
3. (c) Dvorak, C. A.; Rudolph, D. A.; Ma, S.; Carruthers, N. I. J. Org. Chem. 2005, 70, 4188-4190.
4. (d) Deng, X.; Mani, N. S. Org. Lett. 2006, 8, 3505-3508.
5. Vanotti, E.; D'Alessio, R.; Tibolla, M.; Varasi, M.; Montagnoli, A.; Santocanale, C.; Martina, K.; Menichincheri, M. PCT Int. Appl. 2005, 65, WO2005013986.
6. Choudary, B. M.; Sridhar, C.; K.; Mannepalli, L.; Venkanna, G. T.; Sreedhar, B. J. Am. Chem. Soc. 2005, 127, 9948-9949.
7. Zhang, H.; Cai, Q.; Ma, D. J. Org. Chem. 2005, 70, 5164-5173.
8. Hou, Y.; Zeng, X.; Wang, T.; Xia, Z.; Wei, M. Chinese Patent 2003, 7, CN1453269
9. Singh, S. K.; Reddy, M. S.; Mangle, M.; Ganesh, K. R. Tetrahedron 2007, 63, 126-130.
10. Yoo, B. W.; Choi, J. W.; Yoon, C. M. Tetrahedron Lett. 2006, 47, 125-126.
11. Park, E. S.; Lee, S. H.; Lee, J. H.; Rhee, H. J.; Yoon, C. M. Synthesis 2005, 20, 3499-3501.
12. Connon, S. J.; Hegarty, A. F. Eur. J. Org. Chem. 2004, 16, 3477-3483.
13. Trejo, A.; Arzeno, H.; Browner, M.; Chanda, S.; Cheng, S.; Comer, D. D.; Dalrymple, S. A.; Dunten, P.; Lafargue, J.; Lovejoy, B.; Freire-Moar, J.; Lim, J.; McIntosh, J.; Miller, J.; Papp, E.; Reuter, D.; Roberts, R.; Sanpablo, F.; Saunders, J.; Song, K.; Villasenor, A.; Warren, S. D.; Welch, M.; Weller, P.; Whiteley, P. E.; Zeng, L.; Goldstein, D. M. J. Med. Chem. 2003, 46, 4702-4713.
14. Louerat, F.; Gros, P. C.; Fort, Y. Synlett 2006, 1379-1383.
15. Blackaby, W. P.; Atack, J. R.; Bromidge, F.; Castro, J. L.; Goodacre, S. C.; Hallett, D. J.; Lewis, R. T.; Marshall, G. R.; Pike, A.; Smith, A. J.; Street, L. J.; Tattersall, D. F. D.; Wafford, K. A. Bioorg. Med. Chem. Lett. 2006, 16, 1175-1179.
16. Anderson, R. J.; Hill, J. B.; Morris, J. C. J. Org. Chem. 2005, 70, 6204-6212.
17. Ford, N. F.; Browne, L. J.; Campbell, T.; Gemenden, C.; Goldstein, R.; Gude, C.; Wasley, J. W. F. J. Med. Chem. 1985, 28 164-70.
18. Traynelis, V. J.; Kimball, J. P. J. Org. Chem. 1975, 40, 2365-9.
19. Yin, J.; Xiang, B.; Huffman, M. A.; Raab, C. E.; Davies, I. W. J. Org. Chem. 2007, 72, 4554-4557.
20. (a) Stowell, J. C. J. Org. Chem. 1970, 35, 244-245.
21. (b) Henrick, C. A. Tetrahedron 1977, 33, 1845-1889.
22. (c) Feely, W.; Lehn, W. L.; Boekelheide, V. J. Org. Chem. 1957, 22, 1135.
23. Chen, Z-C.; Stang, P. Tett. Lett. 1984, 25, 3923-3926.
24. We also obtained a small amount (1%) of dimeric product (A). A similar product was obtained in a previous project (ref 1a) utilizing sulfuryl chloride. (Chemical Equation Presented)
25. 3). Although product was formed under these conditions (54%), such neat preparations should be avoided.
26. Barnes, R. S.; Harris, J. E. G.; Thomas, J. U.S. Patent 1921497, 1933.
27. 3 complex of product 5 was isolated and characterized, but such complexes were detected by M.S. with many of the substrates examined.
28. See ref 1a.
29. For discussion and examples of poor substrates, please see the Supporting Information.
30. Alternatively, the flask may be rinsed with MeOH when the N-oxide substrate does not possess a nitrile.