Efficient one-pot synthesis of cyclic β-enaminoamides by thermal Wolff rearrangement of cyclic 2-diazo-1,3-dicarbonyls and conversion to uracil derivatives

Tetrahedron

Volumn 68, Issue 11, 2012, Pages 2496-2508

  Neupane, Pratik ^a   Li, Xin ^a   Jung, Jae Hak ^a   Lee, Yong Rok ^a   Kim, Sung Hong ^b  

^a Yeungnam University   (South Korea)

^b Korea Basic Science Institute (KBSI)   (South Korea)

Author keywords

Enaminoamides; Diazodicarbonyls; Uracil; Wolff rearrangement

Indexed keywords

AMIDE; AMINE; AMINO ACID DERIVATIVE; CARBONYL DERIVATIVE; PROPYL 2 (PROPYLAMINO)CYCLOPENT 1 ENECARBOXAMIDE; UNCLASSIFIED DRUG; URACIL DERIVATIVE;

ARTICLE; ONE POT SYNTHESIS; PRIORITY JOURNAL; SPIN TRAPPING; WOLFF REARRANGEMENT;

EID: 84862777312     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.01.060     Document Type: Article

References (44)

1. M.P. Doyle, M.A. McKervey, and T. Ye Modern Catalytic Methods for Organic Synthesis with Diazo Compounds 1998 Wiley New York, NY
2. G. Maas Angew. Chem., Int. Ed. 48 2009 8186
3. H.M.L. Davies, and J.R. Manning Nature 451 2008 417
4. S.-F. Zhu, C. Chen, Y. Cai, and Q.-L. Zhou Angew. Chem., Int. Ed. 47 2008 932
5. E.C. Lee, and G.C. Fu J. Am. Chem. Soc. 129 2007 12066
6. B. Liu, S.-F. Zhu, W. Zhang, C. Chen, and Q.-L. Zhou J. Am. Chem. Soc. 129 2007 5834
7. C. Chen, S.-F. Zhu, B. Liu, L.-X. Wang, and Q.-L. Zhou J. Am. Chem. Soc. 129 2007 12616
8. T.C. Maier, and G.C. Fu J. Am. Chem. Soc. 128 2006 4594
9. D. Rix, R. Ballesteros-Garrido, W. Zeghida, C. Besnard, and J. Lacour Angew. Chem., Int. Ed. 50 2011 7308
10. Z. Zhang, Y. Liu, L. Ling, Y. Li, Y. Dong, M. Gong, X. Zhao, Y. Zhang, and J. Wang J. Am. Chem. Soc. 133 2011 4330
11. L. Zhou, Y. Liu, Y. Zhang, and J. Wang Chem. Commun. 2011 3622
12. L. Dumitrescu, K. Azzouzi-Zriba, D. Bonnet-Delpon, and B. Crousse Org. Lett. 13 2011 692
13. Y. Li, Y. Shi, Z. Huang, X. Wu, P. Xu, J. Wang, and Y. Zhang Org. Lett. 13 2011 1210
14. M. Austeri, D. Rix, W. Zeghida, and J. Lacour Org. Lett. 13 2011 1394
15. W. Kirmse Eur. J. Org. Chem. 2002 2193
16. C. Wentrup, W. Heilmayer, and G. Kollenz Synthesis 1994 1219
17. M. Presset, Y. Coquerel, and J. Rodriguez J. Org. Chem. 74 2009 415
18. M. Presset, Y. Coquerel, and J. Rodriguez Org. Lett. 11 2009 5706
19. M. Presset, Y. Coquerel, and J. Rodriguez Org. Lett. 12 2010 4212
20. M. Presset, K. Mohanam, M. Hamann, Y. Coquerel, and J. Rodriguez Org. Lett. 13 2011 4124
21. Y.R. Lee, and J.C. Hwang Eur. J. Org. Chem. 2005 1568
22. Y.R. Lee, J.Y. Suk, and B.S. Kim Tetrahedron Lett. 40 1999 6603
23. Y.R. Lee, and J.Y. Suk Tetrahedron Lett. 41 2000 4795
24. Y.R. Lee, and J.Y. Suk Tetrahedron 58 2002 2359
25. Y.R. Lee Synth. Commun. 28 1998 865
26. Y.R. Lee, and J.Y. Suk Heterocycles 48 1998 875
27. Y.R. Lee, and J.Y. Suk Chem. Commun. 1998 2621
28. Y.R. Lee, and D.H. Kim Tetrahedron Lett. 42 2001 6561
29. Y.R. Lee, B.S. Cho, and H.J. Kwon Tetrahedron 59 2003 9333
30. Y.R. Lee, J.Y. Suk, and B.S. Kim Tetrahedron Lett. 40 1999 8219
31. A.R. Haight, T.L. Stuk, J.A. Menzia, and T.A. Robbins Tetrahedron Lett. 38 1997 4191
32. J.C. Combret, J.L. Klein, and M. Mouslouhoudine Synthesis 1984 493
33. J. Barluenga, F. Aznar, R. Liz, and M.P. Cabal Synthesis 1986 960
34. J. Cossy, D. Belotti, A. Thellend, and J.P. Pete Synthesis 1988 720
35. G. Jager Chem. Ber. 105 1972 137
36. D.F. Taber, R.E. Ruckle Jr., and M.J. Hennessy J. Org. Chem. 51 1986 4077
37. M. Presset, D. Mailhol, Y. Coquerel, and J. Rodriguez Synthesis 2011 2549
38. F. Medda, R.J.M. Russell, M. Higgins, A.R. MaCarthy, J. Campbell, A.M.Z. Slawin, D.P. Lane, S. Lain, and N.J. Westwood J. Med. Chem. 52 2009 2673
39. C. Chen, D. Wu, Z. Guo, Q. Xie, G.J. Reinhart, A. Madan, J. Wen, T. Chen, C.Q. Huang, M. Chen, Y. Chen, F.C. Tucci, M. Rowbottom, J. Pontillo, Y.-F. Zhu, W. Wade, J. Saunders, H. Bozigian, and R.S. Struthers J. Med. Chem. 51 2008 7478
40. C.F. Regan, Z. Guo, Y. Chen, C.Q. Huang, M. Chen, W. Jiang, J.K. Rueter, T. Coon, C. Chen, J. Saunders, M.S. Brown, S.F. Betz, R.S. Struthers, C. Yang, J. Wen, A. Madan, and Y.-F. Zhu Bioorg. Med. Chem. Lett. 18 2008 4503
41. M. Ćerňová, I. Ćerňa, R. Pohl, and M. Hocek J. Org. Chem. 76 2011 5309
42. V. Malik, P. Singh, and S. Kumar Tetrahedron 61 2005 4009
43. M. Botta, V. Summa, R. Saladino, and R. Nicoletti Synth. Commun. 21 1991 2181
44. J. Cossy, and A. Bouzide Tetrahedron 55 1999 6483