Efficient synthesis of polysubstituted pyrrole-3-carbonitriles via reactions of 1,1-dicyano-2,3-diarylcyclopropanes with aromatic imines

Tetrahedron Letters

Volumn 52, Issue 34, 2011, Pages 4497-4500

  Fu, Qin ^a   Yan, Chao Guo ^a  

^a YANGZHOU UNIVERSITY   (China)

Author keywords

Cyclopropane; Imine; Michael addition; Pyrrole; Ring opening reaction

Indexed keywords

AROMATIC AMINE; CARBONITRILE DERIVATIVE; CYANIDE; CYCLOPROPANE; CYCLOPROPANE DERIVATIVE; IMINE; PYRROLE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; MICHAEL ADDITION; RING OPENING; RING OPENING METATHESIS POLYMERIZATION; SYNTHESIS;

EID: 79960837692     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.06.085     Document Type: Article

References (50)

1. S. Danishefsky Acc. Chem. Res. 12 1979 66 72
2. L.A. Paquette Chem. Rev. 86 1986 733 750
3. H.N.C. Wong, M.Y. Hon, C.W. Tse, Y.C. Yip, J. Tanko, and T. Hudlicky Chem. Rev. 89 1989 165 198
4. H.-U. Reissig, and R. Zimmer Chem. Rev. 103 2003 1151 1196
5. M. Yu, and B.L. Pagenkopf Tetrahedron 61 2005 321 347
6. R.K. Bowman, and J.S. Johnson Org. Lett. 8 2006 573 576
7. A.T. Parsons, M.J. Campbell, and J.S. Johnson Org. Lett. 10 2008 2541 2544
8. P.D. Pohlhaus, S.D. Sanders, A.T. Parsons, W. Li, and J.S. Johnson J. Am. Chem. Soc. 130 2008 8642
9. S.D. Sanders, A. Ruiz-Olalla, and J.S. Johnson Chem. Commun. 2009 5135 5137
10. A.T. Parsons, and J.S. Johnson J. Am. Chem. Soc. 131 2009 14202 14203
11. V.S. Korotkov, O.V. Larionov, and A. de Meijere Synthesis 2006 3542 3546
12. K. Sapeta, and M.A. Kerr J. Org. Chem. 72 2007 8597 8599
13. C. Perreault, S.R. Goudreau, L.E. Zimmer, and A.B. Charette Org. Lett. 10 2008 689 692
14. F.S. Liang, X. Cheng, J. Liu, and Q. Liu Chem. Commun. 2009 3636 3638
15. Z.F. Han, S. Uehira, T. Tsuritani, H. Shinokubo, and K. Oshima Tetrahedron 57 2001 987 995
16. P. Moreau, and M. Maffei Tetrahedron Lett. 45 2004 743 746
17. M. Shi, Y.H. Yang, and B. Xu Tetrahedron 61 2005 1893 1901
18. A. Gupta, and V.K. Yadav Tetrahedron Lett. 47 2006 8043 8047
19. X.Y. Tang, and M. Shi Tetrahedron 65 2009 9336 9343
20. Y.V. Tomilov, R.A. Novikov, and O.M. Nefedov Tetrahedron 66 2010 9151 9158
21. D. Du, and Z.W. Wang Tetrahedron Lett. 49 2008 956 959
22. J. Fang, J. Ren, and Z.W. Wang Tetrahedron Lett. 49 2008 6659 6662
23. X. Huang, W.J. Fu, and M.Z. Miao Tetrahedron Lett. 49 2008 2359 2362
24. Q.P. Ding, Z.Y. Wanga, and J. Wu Tetrahedron 65 2009 5385 5392
25. A.O. Chagarovskiy, E.M. Budynina, O.A. Ivanova, Y.K. Grishin, I.V. Trushkov, and P.V. Verteletskii Tetrahedron 65 2009 5385 5392
26. P. Gopinath, and S. Chandrasekaran J. Org. Chem. 76 2011 700 703
27. P.B. Alper, C. Meyers, A. Lerchner, D.R. Siegel, and E.M. Carreira Angew. Chem., Int. Ed. 38 1999 3186 3189
28. C. Fischer, C. Meyers, and E.M. Carreira Helv. Chim. Acta 83 2000 1175 1181
29. A. Lerchner, and E.M. Carreira J. Am. Chem. Soc. 124 2002 14826
30. C. Meyers, and E.M. Carreira Angew. Chem., Int. Ed. 42 2003 694 696
31. M. Lautens, and W. Han J. Am. Chem. Soc. 124 2002 6312 6316
32. M. Lautens, W. Han, and J.H.-C. Liu J. Am. Chem. Soc. 125 2003 4028 4029
33. R.P. Wurz, and A.B. Charette Org. Lett. 7 2005 2313 2316
34. F. Bertozzi, M. Gustafsson, and R. Olsson Org. Lett. 4 2002 3147 3150
35. F. Bertozzi, B.V. Gundersen, M. Gustafsson, and R. Olsson Org. Lett. 5 2003 1551 1554
36. C.A. Carson, and M.A. Kerr J. Org. Chem. 70 2005 8242 8244
37. Y.B. Kang, Y. Tang, and X.L. Sun Org. Biomol. Chem. 4 2006 299 301
38. P.D. Pohlhaus, and J.S. Johnson J. Org. Chem. 70 2005 1057 1059
39. A.T. Parsons, A.G. Smith, A.J. Neel, and J.S. Johnson J. Am. Chem. Soc. 132 2010 9688 9692
40. S.K. Jackson, A. Karadeolian, A.B. Driega, and M.A. Kerr J. Am. Chem. Soc. 130 2008 4196 4201
41. W. Xu, I. Ghiviriga, Q.Y. Chen, and W.R. Dolber J. Fluorine Chem. 131 2010 958 963
42. S. Oudeyer, E. Léonel, J.P. Paugam, and J.V. Nédélec Tetrahedron 59 2003 1073 1081
43. W.G. Cao, H. Zhang, J. Chen, H.M. Deng, M. Shao, L. Lei, J.X. Qian, and Y. Zhu Tetrahedron 64 2008 6670 6674
44. M.J. Campbell, J.S. Johnson, A.T. Parsons, P.D. Pohlhaus, and S.D. Sanders J. Org. Chem. 75 2010 6317 6325
45. G.S. Yang, Y. Shen, K. Li, Y.X. Sun, and Y.Y. Hua J. Org. Chem. 76 2011 229 233
46. Q.F. Wang, X.K. Song, J. Chen, and C.G. Yan J. Comb. Chem. 11 2009 1007 1010
47. 2: C, 73.35; H, 5.10; N, 9.78. Found: C, 73.28; H, 5.53; N, 9.64.
48. Single crystal data for compound 3c (CCDC 819779), 3j (CCDC 817980), 3m (CCDC 817981) have been deposited in the Cambridge Crystallographic Data Center. These data can be obtained free of charge via www.ccdc.ac.ck./data-request/cif.
49. Md.I. Uddin, A. Mimoto, K. Nakano, Y. Ichikawa, and H. Kotsuki Tetrahedron Lett. 49 2008 5867 5870
50. O. Lifchits, and A.B. Charette Org. Lett. 10 2008 2809 2912