Synthesis of polysubstituted 3H-pyrimidin-4-ones from cyanoacetamides under Vilsmeier conditions

Tetrahedron

Volumn 67, Issue 37, 2011, Pages 7081-7084

  Zhang, Zhiguo ^a   Xue, Can ^b   Liu, Xiao ^b   Zhang, Qian ^b   Liu, Qun ^b  

^a HENAN NORMAL UNIVERSITY   (China)

^b NORTHEAST NORMAL UNIVERSITY   (China)

Author keywords

Cyclopropanes; Polysubstituted 3H pyrimidin 4 ones; Ring expansion; Vilsmeier reagent

Indexed keywords

6 CHLORO 3,5 DISUBSTITUTED 3H PYRIMIDIN 4 ONE DERIVATIVE; ACETANILIDE DERIVATIVE; CYCLOPROPANE; PYRIMIDINE DERIVATIVE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; PRIORITY JOURNAL; RING OPENING; VILSMEIER HAACK REACTION;

EID: 80051703585     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.07.006     Document Type: Article

References (42)

1. A.J. Balmforth, S.E. Bryson, A.J. Aylett, P. Warburton, S.G. Ball, K.T. Pun, D. Middlemiss, and G.M. Drew Br. J. Pharmacol. 112 1994 277 281
2. G.R. Madhavan, R. Chakrabarti, R.K. Vikramadithyan, R.N.V.S. Mamidi, V. Balraju, B.M. Rajesh, P. Misra, S.K.B. Kumar, B.B. Lohray, V.B. Lohray, and R. Rajagopalan Bioorg. Med. Chem. 10 2002 2671 2680
3. M. Eerdekens, I. Van Hove, B. Remmerie, and E. Mannaert Schizophr. Res. 70 2004 91 100
4. D. Engel, A. Nudelman, N. Tarasenko, I. Levovich, I. Makarovsky, S. Sochotnikov, I. Tarasenko, and A. Rephaeli J. Med. Chem. 51 2008 314 323
5. M.S. Phoujdar, M.K. Kathiravan, J.B. Bariwal, A.K. Shah, and K.S. Jain Tetrahedron Lett. 49 2008 1269 1273
6. I. Shcherbakova, G. Huang, O.J. Geoffroy, S.K. Nair, K. Swierczek, M.F. Balandrin, J. Fox, W.L. Heatona, and R.L. Conklina Bioorg. Med. Chem. Lett. 2005 2537 2540
7. T. Takahashi, S. Hirokami, and M. Nagata J. Chem. Soc., Perkin Trans. 1 1988 2653 2662
8. J.U. Jeong, X. Chen, A. Rahman, D.S. Yamashita, and J.I. Luengo Org. Lett. 6 2004 1013 1016
9. R.N. Daniels, K. Kim, E.P. Lebois, H. Muchalski, M. Hughes, and C.W. Lindsley Tetrahedron Lett. 49 2008 305 310
10. A. Pinner Chem. Ber. 22 1889 1612 1635
11. A. Salimbeni, R. Canevotti, F. Paleari, D. Poma, S. Caliari, F. Fici, R. Cirillo, A.R. Renzetti, A. Subissi, L. Belvisi, G. Bravi, C. Scolastico, and A. Giachetti J. Med. Chem. 38 1995 4806 4820
12. A. Jezewski, J. Jurczak, Z. Lidert, and C.M. Tice J. Heterocycl. Chem. 38 2001 645 648
13. A. Sitte, and H. Paul Chem. Ber. 102 1969 615 622
14. E.C. Taylor, P. Zhou, and C.M. Tice Tetrahedron Lett. 38 1997 4343 4346
15. Z. Zhang, Q. Zhang, S. Sun, T. Xiong, and Q. Liu Angew. Chem., Int. Ed. 46 2007 1726 1729
16. Q. Zhang, Z. Zhang, Z. Yan, Q. Liu, and T. Wang Org. Lett. 9 2007 3651 3653
17. Z. Zhang, Q. Zhang, Z. Yan, and Q. Liu J. Org. Chem. 72 2007 9808 9810
18. T. Xiong, Q. Zhang, Z. Zhang, and Q. Liu J. Org. Chem. 72 2007 8005 8009
19. W. Pan, D. Dong, K. Wang, J. Zhang, R. Wu, D. Xiang, and Q. Liu Org. Lett. 9 2007 2421 2423
20. X. Bi, D. Dong, Q. Liu, W. Pan, L. Zhao, and B. Li J. Am. Chem. Soc. 127 2005 4578 4579
21. L. Chen, Y. Zhao, Q. Liu, C. Chen, and C.R. Piao J. Org. Chem. 72 2007 9259 9263
22. D. Dong, X. Bi, Q. Liu, and F. Cong Chem. Commun. 2005 3580 3582
23. Y. Li, F. Liang, X. Bi, and Q. Liu J. Org. Chem. 71 2006 8006 8010
24. Q. Liu, G. Che, H. Yu, Y. Liu, J. Zhang, Q. Zhang, and D. Dong J. Org. Chem. 68 2003 9148 9150
25. D. Dong, Y. Liu, Y. Zhao, Y. Qi, Z. Wang, and Q. Liu Synthesis 2005 85 91
26. S. Sun, Y. Liu, Q. Liu, Y. Zhao, and D. Dong Synlett 2004 1731 1734
27. L. Zhao, F. Liang, X. Bi, S. Sun, and Q. Liu J. Org. Chem. 71 2006 1094 1098
28. Y. Zhao, Q. Liu, J. Zhang, and Z. Liu J. Org. Chem. 70 2005 6913 6917
29. R. Zhang, D. Zhang, Y. Liang, G. Zhou, and D. Dong J. Org. Chem. 76 2011 2880 2883
30. For details of the preparation of 1, see the Supplementary data; see also: D.A. White Synth. Commun. 7 1977 559 568
31. CCDC-714403 (2a) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via http://www.ccdc.cam.ac.uk/data-request/cif.
32. D. Xiang, K. Wang, Y. Liang, G. Zhou, and D. Dong Org. Lett. 10 2007 345 348
33. D. Xiang, Yang, R. Zhang, Y. Liang, W. Pan, J. Huang, and D. Dong J. Org. Chem. 72 2007 8593 8596
34. C.M. Marson Tetrahedron 48 1992 3659 3726
35. R. Chuch, R. Trust, J.D. Albright, and D.W. Powell J. Org. Chem. 60 1995 3750 3758
36. T.A. Bryson, J.C. Wisowaty, R.B. Dunlap, R.R. Fisher, and P.D. Ellis J. Org. Chem. 39 1974 3436 3438
37. M.C. Otto, N. Bramha, and T. Brian J. Chem. Soc., Perkin Trans. 1 1981 1520 1530
38. M.Á. Alonso, J.I. Úbeda, C. Avendaňo, J.C. MenéCndez, and M. Villacampa Tetrahedron 49 1993 10997 11008
39. J. Bésán, L. Kulcsár, and M. Kovács Synthesis 11 1980 883 884
40. O. Meth-Cohn, S. Rhouati, B. Tarnowski, and A. Robinson J. Chem. Soc., Perkin Trans. 1 1981 1537 1543
41. D.R. Adams, and C. Adams Synth. Commun. 20 1990 469 475
42. S. Selvi, and P.T. Perumal Org. Prep. Proced. Int. 33 2001 194 197