Synthesis of 1,6-dihydropyrimidines via copper-catalyzed multistep cascade reactions between O-propargylic aldoximes and isocyanates

Tetrahedron Letters

Volumn 55, Issue 6, 2014, Pages 1178-1182

  Nakamura, Itaru ^a   Onuma, Toshiki ^a   Zhang, Dong ^a   Terada, Masahiro ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

Alkyne; Cascade reaction; Copper catalyzed; Oximes; Rearrangement

Indexed keywords

EID: 84895051749     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.12.105     Document Type: Article

References (44)

1. L.F. Tietze, and U. Beifuss Angew. Chem., Int. Ed. 32 1993 131
2. L.F. Tietze Chem. Rev. 96 1996 115
3. K.C. Nicolaou, D.J. Edmonds, and P.G. Bulger Angew. Chem., Int. Ed. 45 2006 7134
4. S.F. Kirsch Synthesis 2008 3183
5. H.C. Shen Tetrahedron 64 2008 7847
6. B. Crone, and S.F. Kirsch Chem. Eur. J. 14 2008 3514
7. Recent reviews of π-acidic metal catalysis C. Fehr Synlett 2012 990
8. J. Xiao, and X. Li Angew. Chem., Int. Ed. 50 2011 7226
9. A. Corma, A. Leyva-Pérez, and M.J. Sabater Chem. Rev. 111 2011 1657
10. N. Krause, and C. Winter Chem. Rev. 111 2011 1994
11. T. de Haro, and C. Nevado Synthesis 2011 2530
12. H. Huang, Y. Zhou, and H. Liu Beilstein J. Org. Chem. 7 2011 897
13. S. Hummel, and S.F. Kirsch Beilstein J. Org. Chem. 7 2011 847
14. A. Pradal, P.Y. Toullec, and V. Michelet Synthesis 2011 1501
15. N.D. Shapiro, and F.D. Toste Synlett 2010 675
16. S. Wang, G. Zhang, and L. Zhang Synlett 2010 692
17. A. Fürstner Chem. Soc. Rev. 38 2009 3208
18. A.S.K. Hashmi Chem. Rev. 107 2007 3180
19. I. Nakamura, D. Zhang, and M. Terada J. Am. Chem. Soc. 132 2010 7884
20. I. Nakamura, T. Araki, D. Zhang, Y. Kudo, E. Kwon, and M. Terada Org. Lett. 13 2011 3616
21. I. Nakamura, D. Zhang, and M. Terada Tetrahedron Lett. 52 2011 6470
22. I. Nakamura, Y. Kudo, T. Araki, D. Zhang, E. Kwon, and M. Terada Synthesis 44 2012 1542
23. I. Nakamura, M. Okamoto, Y. Sato, and M. Terada Angew. Chem., Int. Ed. 51 2012 10816
24. I. Nakamura, Y. Kudo, and M. Terada Angew. Chem., Int. Ed. 52 2013 7536
25. H. Goldschmidt Ber. Dtsch. Chem. Ges. 23 1890 2746
26. E. Beckmann Ber. Dtsch. Chem. Ges. 23 1890 3319
27. D.S.C. Black, R.F. Crozier, and V.C. Davis Synthesis 7 1975 205
28. T. Ritter, and E.M. Carreira Angew. Chem., Int. Ed. 44 2005 936
29. N-O Bond cleavage followed by decarboxylation T. Hisano, T. Matsuoka, and M. Ichikawa Chem. Pharm. Bull. 24 1976 533
30. T. Hisano, K. Harano, T. Matsuoka, F. Suematsu, and N. Ohizumi Chem. Pharm. Bull. 33 1985 1869
31. P.C. Too, Y.-F. Wang, and S. Chiba Org. Lett. 12 2010 5688
32. K. Okamoto, T. Oda, S. Kohigashi, and K. Ohe Angew. Chem., Int. Ed. 50 2011 11470
33. T.E. Barder, S.D. Walker, J.R. Martinelli, and S.L. Buchwald J. Am. Chem. Soc. 127 2005 4685
34. 1,4-Hydrogen shift S.-H. Chen, S. Huang, Q. Gao, J. Golik, and V. Farina J. Org. Chem. 59 1994 1475
35. P.C. Montevecchi, and M.L. Navacchia Tetrahedron Lett. 37 1996 6583
36. M. Gulea, J.M. López-Romero, L. Fensterbank, and M. Malacria Org. Lett. 2 2000 2591
37. I. Ryu, T. Fukuyama, M. Tojino, Y. Uenoyama, Y. Yonamine, N. Terasoma, and H. Matsubara Org. Biomol. Chem. 9 2011 3780
38. 6π-Electrocyclization of 1,3-diaza-1,3,5-triene E. Rossi, G. Abbiati, and E. Pini Synlett 1999 1265
39. 1,4-Aryl shift A. Studer, and M. Bossart Tetrahedron 57 2001 9649
40. H. Senboku, H. Hasegawa, K. Orito, and M. Tokuda Tetrahedron Lett. 41 2000 5699
41. A.L. Weis, and H.C. van der Plas Heterocycles 24 1986 1433
42. Synthesis of 1,6-dihydropyrimidines F. Kunckell, and O. Sarfert Chem. Ber. 35 1902 3169
43. B. Piqani, and W. Zhang Beilstein J. Org. Chem. 7 2011 1294
44. H. Cho, Y. Nishimura, Y. Yasui, and M. Yamaguchi Tetrahedron Lett. 53 2012 1177