Synthesis of highly substituted pyrroles via oxidative free radical reactions of β-aminocinnamates

Tetrahedron

Volumn 62, Issue 10, 2006, Pages 2235-2239

  Tsai, An I ^a   Chuang, Che Ping ^a  

^a NATIONAL CHENG KUNG UNIVERSITY   (Taiwan)

Author keywords

Aminocinnamates; Free radical; Oxidative; Tetra n butylammonium cerium(IV) nitrate

Indexed keywords

CINNAMIC ACID DERIVATIVE; FREE RADICAL; PYRROLE DERIVATIVE;

ANALYTIC METHOD; ARTICLE; CHEMICAL REACTION; COVALENT BOND; DIMERIZATION; DRUG SYNTHESIS; OXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS; SUBSTITUTION REACTION;

EID: 32444443956     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.12.011     Document Type: Article

References (39)

1. D.J. Hart Science 223 1984 883
2. W.P. Neumann Synthesis 1987 665
3. D.P. Curran Synthesis 1988 417 and 489
4. G.G. Melikyan Synthesis 1993 833
5. J. Iqbal, B. Bhatia, and N.K. Nayyar Chem. Rev. 94 1994 519
6. B.B. Snider Chem. Rev. 96 1996 339
7. H. Oumar-Mahamat, C. Moustrou, J.-M. Surzur, and M.P. Berstrand J. Org. Chem. 54 1989 5684
8. B.B. Snider, B.Y.F. Wan, B.O. Buckman, and B.M. Foxman J. Org. Chem. 56 1991 328
9. A. Citterio, R. Sebastiano, and M.C. Carvayal J. Org. Chem. 56 1991 5335
10. A. Citterio, R. Sebastiano, and M. Nicolini Tetrahedron 49 1993 7743
11. M.-C. Jiang, and C.-P. Chuang J. Org. Chem. 65 2000 5409
12. Y.-L. Wu, C.-P. Chuang, and P.-Y. Lin Tetrahedron 57 2001 5543
13. A. Gossauer R.R. Kreher Houben-Weyl, Methoden der Organischen Chemie Vol. E 6a 1994 Thieme Stuttgart 556 798 Part 1
14. T.L. Gilchrist J. Chem. Soc., Perkin Trans. 1 1999 2849
15. D.L. Borger, C.W. Boyce, M.A. Labroli, C.A. Sehon, and Q. Jin J. Am. Chem. Soc. 121 1999 54
16. C.-F. Lee, L.-M. Yang, T.-Y. Hwu, A.-S. Feng, J.-C. Tseng, and T.-Y. Luh J. Am. Chem. Soc. 122 2000 4992
17. A.V. Kelin, A.W. Sromek, and V. Gevorgyan J. Am. Chem. Soc. 123 2001 2074
18. P.M.T. Ferreira, H.L.S. Maia, and L.S. Monteiro Tetrahedron Lett. 43 2002 4491
19. G. Bashiardes, I. Safir, F. Barbot, and J. Laduranty Tetrahedron Lett. 44 2003 8417
20. G. Minetto, L.F. Raveglia, and M. Taddei Org. Lett. 6 2004 389
21. M. Alongi, G. Minetto, and M. Taddei Tetrahedron Lett. 46 2005 7069
22. A.S. Demir, and M. Emrullahoglu Tetrahedron 61 2005 10482
23. C.-P. Chuang, and Y.-L. Wu Tetrahedron 60 2004 1841
24. J. Cossy, and A. Bouzide J. Chem. Soc., Chem. Commun. 1993 1218
25. J. Cossy, A. Bouzide, and C. Leblanc Synlett 1993 202
26. J. Cossy, and A. Bouzide Tetrahedron Lett. 34 1993 5583
27. J. Cossy, and A. Bouzide Tetrahedron 55 1999 6483
28. J. Cossy, A. Bouzide, and C. Leblanc J. Org. Chem. 65 2000 7257
29. C.-P. Chuang, and Y.-L. Wu Tetrahedron Lett. 42 2001 1719
30. Y. Zhang, A.J. Raines, and R.A. Flowers II J. Org. Chem. 69 2004 6267
31. Y. Zhang, and R.A. Flowers II J. Org. Chem. 68 2003 4560
32. Y. Zhang, A.J. Raines, and R.A. Flowers II Org. Lett. 5 2003 2363
33. When 1a was treated with ethyl acetoacetate (2a ) and TBACN in methanol, in addition to the desired pyrrole product 3a (31%), dimerization product 4a was also produced in 11% yield.
34. R.M. Carr, R.O.C. Norman, and J.M. Vernon J. Chem. Soc., Perkin Trans. 1 1980 156
35. M.A. Sukari, and J.M. Vernon Tetrahedron 39 1983 793
36. P.-F. Zhang, and Z.-C. Chen Synth. Commun. 31 2001 1619
37. J. Toda, T. Fuse, E. Kishikawa, N. Ando, R. Negishi, Y. Horiguchi, and T. Sano Heterocycles 38 1994 2091
38. A.-H. Li, S. Moro, N. Melman, X. Ji, and K.A. Jacobson J. Med. Chem. 41 1998 3186
39. H.A. Muathen Indian J. Chem. 30B 1991 521