De novo synthesis of 1,4-dihydropyridines and pyridines

Journal of the American Chemical Society

Volumn 134, Issue 22, 2012, Pages 9078-9081

  Gati, Wafa ^a,b   Rammah, Mohamed M ^b   Rammah, Mohamed B ^b   Couty, François ^a   Evano, Gwilherm ^a,c  

^a UNIVERSITÉ DE VERSAILLES SAINT QUENTIN EN YVELINES   (France)

^b UNIVERSITY OF MONASTIR   (Tunisia)

^c UNIVERSITÉ LIBRE DE BRUXELLES   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

1 ,4-DIHYDROPYRIDINES; CARBOLITHIATION; DE NOVO SYNTHESIS; DIHYDROPYRIDINES; GENERAL METHOD; LITHIATION;

CHEMISTRY; SYNTHESIS (CHEMICAL);

PYRIDINE;

1,4 DIHYDROPYRIDINE DERIVATIVE; PYRIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ISOMERIZATION; LITHIATION; SUBSTITUTION REACTION;

MOLECULAR STRUCTURE; PYRIDINES;

EID: 84861916865     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja303002a     Document Type: Article

References (39)

1. Bartholow, M. Top 200 Drugs of 2010. Pharmacy Times [Online], May 2011. http://www.pharmacytimes.com/publications/issue/2011/May2011/ Top-200-Drugs-of-2010 (accessed March 28, 2012).
2. Lukevitz, é. Chem. Heterocycl. Compd. 1995, 31, 639
3. Jones, G. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V.; McKillop, A., Eds.; Pergamon: Oxford, U.K., 1996, Vol. 5, p 167.
4. Henry, G. D. Tetrahedron 2004, 60, 6043
5. Spitzner, D. Sci. Synth. 2004, 15, 11
6. Lavilla, R. J. Chem. Soc., Perkin Trans. 1 2002, 1141
7. Moreau, J.; Hurvois, J.-P.; Mbaye, M. D.; Renaud, J.-L. Targets Heterocycl. Syst. 2009, 13, 201
8. Movassaghi, M.; Hill, M. D.; Ahmad, O. K. J. Am. Chem. Soc. 2006, 128, 4592
9. Movassaghi, M.; Hill, M. D.; Ahmad, O. K. J. Am. Chem. Soc. 2007, 129, 10096
10. Colby, D. A.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2008, 130, 3645
11. Liu, S.; Liebeskind, L. S. J. Am. Chem. Soc. 2008, 130, 6918
12. Manning, J. R.; Davies, H. M. L. J. Am. Chem. Soc. 2008, 130, 8602
13. Donohoe, T. J.; Jones, C. R.; Barbosa, L. C. A. J. Am. Chem. Soc. 2011, 133, 16418
14. Chen, M. Z.; Micalizio, G. C. J. Am. Chem. Soc. 2012, 134, 1352
15. For a review, see: Bull, J. A.; Mousseau, J. J.; Pelletier, G.; Charette, A. B. Chem. Rev. 2012, 112, 2642
16. Hantzsch, A. Justus Liebigs Ann. Chem. 1882, 1, 215
17. Comins, D. L. Tetrahedron Lett. 1983, 24, 2807
18. Mousset, D.; Gillaizeau, I.; Sabatié, A.; Bouyssou, P.; Coudert, G. J. Org. Chem. 2006, 71, 5993
19. Evano, G.; Coste, A.; Jouvin, K. Angew. Chem., Int. Ed. 2010, 49, 2840
20. DeKorver, K. A.; Li, H.; Lohse, A. G.; Hayashi, R.; Lu, Z.; Zhang, Y.; Hsung, R. P. Chem. Rev. 2010, 110, 5064
21. Dunetz, J. R.; Danheiser, R. L. Org. Lett. 2003, 5, 4011
22. Zhang, Y.; Hsung, R. P.; Tracey, M. R.; Kurtz, K. C. M.; Vera, E. L. Org. Lett. 2004, 6, 1151
23. Hamada, T.; Ye, X.; Stahl, S. S. J. Am. Chem. Soc. 2008, 130, 833
24. Coste, A.; Karthikeyan, G.; Couty, F.; Evano, G. Angew. Chem., Int. Ed. 2009, 48, 4381
25. Jouvin, K.; Couty, F.; Evano, G. Org. Lett. 2010, 12, 3272
26. Jouvin, K.; Heimburger, J.; Evano, G. Chem. Sci. 2012, 3, 756
27. Park, Y. S.; Weisenburger, G. A.; Beak, P. J. Am. Chem. Soc. 1997, 119, 10537
28. Curtis, M. D.; Beak, P. J. Org. Chem. 1999, 64, 2996
29. Lim, S. H.; Curtis, M. D.; Beak, P. Org. Lett. 2001, 3, 711
30. Johnson, T. A.; Jang, D. O.; Slafer, B. W.; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2002, 124, 11689
31. Beak, P.; Lee, B. J. Org. Chem. 1989, 54, 458
32. Chechik-Lankin, H.; Livshin, S.; Marek, I. Synlett 2005, 2098
33. Gourdet, B.; Lam, H. W. J. Am. Chem. Soc. 2009, 131, 3802
34. Gourdet, B.; Rudkin, M. E.; Watts, C. A.; Lam, H. W. J. Org. Chem. 2009, 74, 7849
35. Das, J. P.; Chechik, H.; Marek, I. Nat. Chem. 2009, 1, 128
36. Hogan, A.-M. L.; OShea, D. F. Chem. Commun. 2008, 3839
37. Tsuchida, S.; Kaneshige, A.; Ogata, T.; Baba, H.; Yamamoto, Y.; Tomioka, K. Org. Lett. 2008, 10, 3635
38. For a comprehensive review of Baldwins rules for the cyclization of alkynes, see: Gilmore, K.; Alabugin, I. V. Chem. Rev. 2011, 111, 6513
39. For examples of exclusive 5-endo-dig closure during the intramolecular carbolithiation of ynol ethers by stabilized organolithium reagents, see: Funk, R. L.; Bolton, G. L.; Brummond, K. M.; Ellestad, K. E.; Stallman, J. B. J. Am. Chem. Soc. 1993, 115, 7023