A simple method for synthesis of 5-CF3 substituted dienamides via rearrangement of 2H-pyran derivatives

Tetrahedron

Volumn 67, Issue 39, 2011, Pages 7618-7621

  Wang, Xiao Wei ^a   Li, Peng ^a   Xiao, Hua ^b   Zhu, Shi Zheng ^a   Zhao, Gang ^a,b  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

Author keywords

, Dicyanoalkenes; 2H Pyran intermediate; 5 Trifluoromethyl 2,4 dienamides; Aldol reaction; Rearrangement

Indexed keywords

5 TRIFLUOROMETHYL 2,4 DIENAMIDE DERIVATIVE; ALKADIENE; AMIDE; PYRAN DERIVATIVE; TRIETHYLAMINE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CATALYSIS; CATALYST; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 81155161038     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.07.007     Document Type: Article

References (25)

1. R. Filler, and Y. Kobayashi Biomedicinal Aspects of Fluorine Chemistry 1982 Kodansha & Elsevier Biomedical Tokyo
2. R. Filler, and R.E. Banks Organofluorine Chemicals and their Industrial Applications 1979 Horwood London
3. J.T. Welch Tetrahedron 43 1987 3123
4. R. Filler, Y. Kobayashi, and L.M. Yagupolskii Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications 1993 Elsevier Amsterdam
5. H. McAlonan, J.P. Murphy, M. Nieuwenhuyzen, K. Reynolds, P.K.S. Sarma, P.J. Stevenson, and N. Thompson J. Chem. Soc., Perkin Trans. 1 2002 69
6. Y. Huang, T. Iwama, and V.H. Rawal J. Am. Chem. Soc. 122 2000 7843
7. D.A. Evans, S.J. Miller, T. Lectka, and P. von Matt J. Am. Chem. Soc. 121 1999 7559
8. L.E. Overman, D. Lesuisse, and M. Hashimoto J. Am. Chem. Soc. 105 1983 5373
9. L.E. Overman, and R.L. Freerks J. Org. Chem. 46 1981 2833
10. L.C. Dias, and L.G. Oliveira Org. Lett. 3 2001 3951
11. R. Jansen, B. Kunze, H. Reichenbach, and G. Höfle Eur. J. Org. Chem. 2000 913
12. B. Kunze, R. Jansen, F. Sasse, G. Höfle, and H. Reichenbach J. Antibiot. 51 1998 1075
13. K.L. Erickson, J.A. Beutler, J.H. Cardellina II, and M.R. Boyd J. Org. Chem. 62 1997 8188
14. J.-I. Tanaka, and T. Higa Tetrahedron Lett. 37 1996 5535
15. B.R. D'Souza, and J. Louie Org. Lett. 11 2009 4168
16. M. Oshita, K. Yamashita, M. Tobisu, and N. Chatani J. Am. Chem. Soc. 127 2005 761
17. Y. Li, H. Matsumura, M. Yamanaka, and T. Takahashi Tetrahedron 60 2004 1393
18. X. Pan, Q. Cai, and D. Ma Org. Lett. 6 2004 1809
19. R. Tanaka, S. Hirano, H. Urabe, and F. Sato Org. Lett. 5 2003 67
20. S. Ma, and H. Xie J. Org. Chem. 67 2002 6575
21. T. Takahashi, Y. Li, F.Y. Tsai, and K. Nakajima Organometallics 20 2001 595
22. M. Abarbri, J.L. Parrain, and A. Duchene Synth. Commun. 28 1998 239
23. K. Takai, Y. Kataoka, K. Yoshizumi, and Y. Oguchi Chem. Lett. 1991 1479
24. A.C. Williams, P. Sheffels, D. Sheehan, and T. Livinghouse Organometallics 8 1989 1566
25. T.H. Babu, S.P.D. Muralidharan, and P.T. Perumal Synlett 2010 2125