A concise route to pyridines from hydrazides by metal carbene N-H insertion, 1,2,4-triazine formation, and Diels-Alder reaction

Organic Letters

Volumn 11, Issue 16, 2009, Pages 3686-3688

  Shi, Baolu ^a   Lewis, William ^a   Campbell, Ian B ^b   Moody, Christopher J ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CARBENE; DRUG DERIVATIVE; HYDRAZINE DERIVATIVE; METHANE; PYRIDINE DERIVATIVE; TRIAZINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; SYNTHESIS;

CATALYSIS; CYCLIZATION; HYDRAZINES; METHANE; MOLECULAR STRUCTURE; PYRIDINES; TRIAZINES;

EID: 68949111606     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol901502u     Document Type: Article

References (36)

1. Neunhoeffer, H. In Comprehensive Heterocyclic Chemistry II; Boulton, A. J., Ed.; Pergamon: Oxford. 1996; Vol. 6, p 507.
2. Seela, F.; He, Y. J. Org. Chem. 2003, 68, 367.
3. Seela, F.; Chittepu, P. J. Org. Chem. 2007, 72, 4358.
4. Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press: San Diego, 1987; Vol. 47.
5. Barluenga, J.; Tomas, M. Adv. Heterocycl. Chem. 1993, 57, 1.
6. Tietze, L. F.; Kettschau, G. Top. Curr. Chem. 1997, 189, 1.
7. For recent examples, see refs 7-12; Stanforth, S. P.; Tarbit, B.; Watson, M. D. Tetrahedron Lett. 2002, 43, 6015.
8. Stanforth, S. P.; Tarbit, B.; Watson, M. D. Tetrahedron 2004, 60, 8893.
9. Raw, S. A.; Taylor, R. J. K. J. Chem. Soc., Chem. Commun. 2004, 508.
10. Raw, S. A.; Taylor, R. J. K. J. Am. Chem. Soc. 2004, 126, 12260.
11. Sainz, Y. F.; Raw, S. A.; Taylor, R. J. K. J. Org. Chem. 2005, 70, 10086.
12. Catozzi, N.; Wasnaire, P.; Taylor, R. J. K. Tetrahedron Lett. 2008, 49, 2865.
13. Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; John Wiley: New York, 1998.
14. Zhang, Z.; Wang, J. Tetrahedron 2008, 64, 6577.
15. Moody, C. J.; Swann, E. Synlett 1998, 135.
16. Bashford, K. E.; Cooper, A. L.; Kane, P. D.; Moody, C. J.; Muthusamy, S.; Swann, E. J. Chem. Soc., Perkin Trans. 1 2002, 1672.
17. Lee, S. H.; Clapham, B.; Koch, G.; Zimmermann, J.; Janda, K. D. J. Comb. Chem. 2003, 5, 188.
18. Bagley, M. C.; Buck, R. T.; Hind, S. L.; Moody, C. J. J. Chem. Soc., Perkin Trans. 1 1998, 591.
19. Davies, J. R.; Kane, P. D.; Moody, C. J. Tetrahedron 2004, 60, 3967.
20. Moody, C. J.; Bagley, M. C. J. Chem. Soc., Perkin Trans. 1 1998, 601.
21. Davies, J. R.; Kane, P. D.; Moody, C. J.; Slawin, A. M. Z. J. Org. Chem. 2005, 70, 5840.
22. Bagley, M. C.; Hind, S. L.; Moody, C. J. Tetrahedron Lett. 2000, 41, 6897.
23. Bagley, M. C.; Moody, C. J.; Pepper, A. G. Tetrahedron Lett. 2000, 41, 6901.
24. Davies, J. R.; Kane, P. D.; Moody, C. J. J. Org. Chem. 2005, 70, 7305.
25. Palmer, F. N.; Lach, F.; Poriel, C.; Pepper, A. G.; Bagley, M. C.; Slawin, A. M. Z.; Moody, C. J. Org. Biomol. Chem. 2005, 3, 3805.
26. Lachia, M.; Moody, C. J. Nat. Prod. Rep 2008, 25, 227.
27. Bagley, M. C.; Bashford, K. E.; Hesketh, C. L.; Moody, C. J. J. Am. Chem. Soc. 2000, 122, 3301.
28. Hughes, R. A.; Thompson, S. P.; Alcaraz, L.; Moody, C. J. J. Am. Chem. Soc. 2005, 127, 15644.
29. Linder, J.; Blake, A. J.; Moody, C. J. Org. Biomol. Chem. 2008, 6, 3908.
30. Clapham, B.; Spanka, C.; Janda, K. D. Org. Lett. 2001, 3, 2173.
31. Clapham, B.; Lee, S. H.; Koch, G.; Zimmermann, J.; Janda, K. D. Tetrahedron Lett. 2002, 43, 5407.
32. Konno, S.; Sagi, M.; Takaharu, E.; Fujimura, S.; Hayashi, K.; Yamanaka, H. Chem. Pharm. Bull. 1988, 36, 1721.
33. Ohsumi, T.; Neunhoeffer, H. Tetrahedron 1992, 48, 651.
34. For other examples of use of norbornadiene, see refs 34-36; Barlow, M. G.; Haszeldine, R. N.; Simpkin, D. J. J. Chem. Soc., Chem. Commun. 1979, 658.
35. Pabst, G. R.; Sauer, J. Tetrahedron Lett. 1998, 39, 6687.
36. Altuna-Urquijo, M.; Gehre, A.; Stanforth, S. P.; Tarbit, B. Tetrahedron 2009, 65, 975.