Rhodium-catalyzed gram-scale synthesis of highly substituted pyridine derivatives

Synthesis

Volumn , Issue 8, 2009, Pages 1400-1402

  Parthasarathy, Kanniyappan ^a   Cheng, Chien Hong ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

C H activation; Ketoxime; Pyridine; Rhodium

Indexed keywords

C-H ACTIVATION; C-H BOND; GRAM-SCALE SYNTHESIS; KETOXIME; KETOXIMES; ONE-POT SYNTHESIS; PYRIDINE DERIVATIVES; RHODIUM-CATALYZED;

ACETYLENE; ACTIVATION ANALYSIS; RHODIUM;

PYRIDINE;

ALKYNE; PYRIDINE DERIVATIVE; RHODIUM;

ARTICLE; CATALYST; CHELATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDROGEN BOND; ONE POT SYNTHESIS;

EID: 67650069346     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0028-1088009     Document Type: Article

References (25)

1. For recent syntheses of highly substituted pyridines, see: (a) Colby, D. A.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2008, 130, 3645.
2. (b) Barluenga, J.; Fernandez-Rodriguez, M. A.; Garcia-Garcia, P.; Aguilar, E. J. Am. Chem. Soc. 2008, 130, 2764.
3. (c) Movassaghi, M.; Hill, M. D.; Ahmad, O. K. J. Am. Chem. Soc. 2007, 129, 10096.
4. (a) Rama Rao, A. V.; Ravindra Reddy, G.; Venkateswara Rao, B. J. Org. Chem. 1991, 56, 4545.
5. (b) Henry, G. D. Tetrahedron 2004, 60, 6043.
6. (c) Michael, J. P. Nat. Prod. Rep. 2005, 22, 627.
7. For reviews, see: (a) Boger, D. L. J. Heterocycl. Chem. 1998, 35, 1003.
8. (b) Zeni, G.; Larock, R. C. Chem. Rev. 2004, 104, 2285.
9. (c) Varela, J. A.; Saa, C. Chem. Rev. 2003, 103, 3787.
10. (a) Schiess, P.; Chia, H.; Ringele, P. Tetrahedron Lett. 1972, 13, 313.
11. (b) Tanaka, K.; Mori, H.; Yamamoto, M.; Katsumura, S. J. Org. Chem. 2001, 66, 3099.
12. (c) Trost, B. M.; Gutierrez, A. C. Org. Lett. 2007, 9, 1473.
13. (a) Varela, J. A.; Castedo, L.; Saá, C. J. Org. Chem. 2003, 68, 8595.
14. (b) Sangu, K.; Fuchibe, K.; Akiyama, T. Org. Lett. 2004, 6, 353.
15. (c) Zhang, X.; Campo, M. A.; Yao, T.; Larock, R. C. Org. Lett. 2005, 7, 763.
16. (d) McCormick, M. M.; Duong, H. A.; Zuo, G.; Louie, J. J. Am. Chem. Soc. 2005, 127, 5030; and references cited therein.
17. Parthasarathy, K.; Jeganmohan, M.; Cheng, C.-H. Org. Lett. 2008, 10, 325.
18. (a) Shinada, T.; Yoshihara, K. Tetrahedron Lett. 1995, 36, 6701.
19. (b) Booth, S. E.; Jenkins, P. R.; Swain, C. J.; Sweeney, J. B. J. Chem. Soc., Perkin Trans. 1 1994, 3499.
20. (a) Kakiuchi, F.; Yamamoto, Y.; Chatani, N.; Murai, S. Chem. Lett. 1995, 681.
21. (b) Jun, C.-H.; Moon, C. W.; Lee, D.-Y. Chem. Eur. J. 2002, 8, 2422.
22. (c) Jun, C.-H.; Moon, C. W.; Kim, Y. M.; Lee, J.; Lee, H. Tetrahedron Lett. 2002, 43, 4233.
23. (d) Kuninobu, Y.; Tokunaga, Y.; Kawata, A.; Takai, K. J. Am. Chem. Soc. 2006, 128, 202.
24. Perrin, D. D.; Armarego, W. L. F. Purification of Laboratory Chemicals, 3rd ed.; Pergamon Press: New York, 1988.
25. Osborn, J. A.; Wilkinson, G. In Reagents for Transition Metal Complex and Organometallic Syntheses, Vol. 28; Angelici, R., Ed.; Wiley: New York, 1989, 77-79.