Radical cation salt induced tandem cyclization between anilines and N-vinyl amides: Synthesis of 2-methyl-4-anilino-1,2,3,4-tetrahydroquinoline derivatives

Tetrahedron Letters

Volumn 51, Issue 51, 2010, Pages 6779-6782

  Jia, Xiao Dong ^a,b   Ren, Yan ^a   Huo, Cong De ^a   Wang, Wen Juan ^a   Chen, Xiang Ning ^a   Xu, Xiao Lan ^a   Wang, Xi Cun ^a  

^a NORTHWEST NORMAL UNIVERSITY   (China)

^b LANZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

2 METHYL 4 ANILINO 1,2,3,4 TETRAHYDROQUINOLINE DERIVATIVES; ACETALDEHYDE; AMIDE; ANILINE; N VINYL AMIDE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTRON TRANSPORT; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 78649329187     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.10.106     Document Type: Article

References (51)

1. B. Crousse, J.-P. Bégué, and D. Bonnet-Delpon J. Org. Chem. 65 2000 5009 5013
2. T. Akiyama, H. Morita, and K. Fuchibe J. Am. Chem. Soc. 128 2006 13070 13071
3. D. Cheng, J. Zhou, E. Saiah, and G. Beaton Org. Lett. 4 2002 4411 4414
4. M. Shi, L.-X. Shao, and B. Xu Org. Lett. 5 2003 579 582
5. G. Sundararajan, N. Prabagaran, and B. Varghese Org. Lett. 3 2001 1973 1976
6. Z. Xue, A. Samanta, B.R. Whittlesey, and M.F. Mayer Tetrahedron Lett. 50 2009 6064 6067
7. H. Ishitani, and S. Kobayashi Tetrahedron Lett. 37 1996 7357 7360
8. B. Crousse, J.-P. Bégué, and D. Bonnet-Delpon Tetrahedron Lett. 39 1998 5765 5768
9. F. Fadel, S.L. Titouani, M. Soufiaoui, H. Ajamay, and A. Mazzah Tetrahedron Lett. 45 2004 5905 5908
10. R. Lavilla, M.C. Bernabeu, I. Carranco, and J.L. Díaz Org. Lett. 5 2003 717 720
11. J. Muhuhi, and M.R. Spaller J. Org. Chem. 71 2006 5515 5526
12. V. Gaddam, and R. Nagarajan J. Org. Chem. 72 2007 3573 3576
13. S. Desrat, and P. van de Weghe J. Org. Chem. 74 2009 6728 6734
14. V. Gaddam, and R. Nagarajan Org. Lett. 10 2008 1975 1978
15. G. Savitha, and P.T. Perumal Tetrahedron Lett. 47 2006 3589 3593
16. K. Nagaiah, D. Sreenu, R.S. Rao, G. Vashishta, and J.S. Yadav Tetrahedron Lett. 47 2006 4409 4413
17. M. Xia, and Y.-D. Lu Synlett 2005 2357 2361
18. R. Nagarajan, C.J. Magesh, and P.T. Perumal Synthesis 2004 69 74
19. V.V. Kouznetsov, A.R.R. Bohórquez, and E.E. Stashenko Tetrahedron Lett. 48 2007 8855 8860
20. C.D. Smith, J.I. Gavrilyuk, A.J. Lough, and R.A. Batey J. Org. Chem. 75 2010 702 715
21. A. Kumar, S. Srivastava, and G. Gupta Tetrahedron Lett. 51 2010 517 520
22. X.-F. Lin, S.-L. Cui, and Y.-G. Wang Tetrahedron Lett. 47 2006 4509 4512
23. R.A. Batey, D.A. Powell, A. Acton, and A.J. Lough Tetrahedron Lett. 42 2001 7935 7939
24. R.A. Batey, P.D. Simoncic, D. Lin, R.P. Smyj, and A.J. Lough Chem. Commun. 1999 651 652
25. J. Zhang, and C.-J. Li J. Org. Chem. 67 2002 3969 3971
26. D.A. Powell, and R.A. Batey Org. Lett. 4 2002 2913 2916
27. D.A. Powell, and R.A. Batey Tetrahedron Lett. 44 2003 7569 7573
28. This process is known as Doebner-von Miller reaction. Refs see: A.B. Turner, B.I. McBain, R.A. Howie, and P.J. Cox J. Chem. Soc., Perkin Trans. 1 1986 1151 1155
29. U. Westerwelle, R. Keuper, and N. Risch J. Org. Chem. 60 1995 2263 2266
30. S. Talukdar, C.-T. Chen, and J.-M. Fang J. Org. Chem. 65 2000 3148 3153
31. A.R. Katritzky, B. Rachwal, and S. Rachwal J. Org. Chem. 60 1995 7631 7640
32. N.L. Bauld Tetrahedron 45 1989 5307 5363
33. M. Schmittel, and A. Burghart Angew. Chem., Int. Ed. 36 1997 2550 2589
34. S.F. Nelsen Acc. Chem. Res. 20 1987 269 276
35. X.-D. Jia, X.-E. Wang, C.-X. Yang, C.-D. Huo, W.-J. Wang, Y. Ren, and X.-C. Wang Org. Lett. 12 2010 732 735
36. X.-D. Jia, H.-C. Lin, C.-D. Huo, W. Zhang, J.-M. Lu, L. Yang, G.-Y. Zhao, and Z.-L. Liu Synlett 2003 1707 1709
37. X.-D. Jia, B. Han, W. Zhang, X.-L. Jin, L. Yang, and Z.-L. Liu Synthesis 2006 2831 2836
38. X.-D. Jia, X.-E. Wang, C.-X. Yang, Y. Da, L. Yang, and Z.L. Liu Tetrahedron 65 2009 2334 2338
39. X.-D. Jia, Y. Da, C. Yang, L. Yang, and Z.-L. Liu Tetrahedron Lett. 49 2008 1786
40. C. Huo, X. Jia, W. Zhang, L. Yang, J. Lu, and Z. Liu Synlett 2004 251 254
41. 2+H: 392.9597, found: 392.9601.
42. P.G. Gassman, and D.A. Singleton J. Am. Chem. Soc. 106 1984 6085 6086
43. F.G. Bordwell, and M.J. Bausch J. Am. Chem. Soc. 108 1986 2473 2474
44. R. Lapouyade, P. Villeneuve, A. Nourmamode, and J.P. Morand J. Chem. Soc., Chem. Commun. 1987 776 778
45. F. Ciminale, L. Lopez, V. Paradiso, and A. Nacci Tetrahedron 52 1996 13971 13980
46. F. Ciminale, L. Lopez, A. Nacci, L. D'Accolti, and F. Vitale Eur. J. Org. Chem. 70 2005 1597 1604
47. F. Ciminale, L. Lopez, G.M. Farinola, S. Sportelli, and A. Nacci Eur. J. Org. Chem. 67 2002 3850 3854
48. F. Ciminale, L. Lopez, G.M. Farinola, and S. Sportelli Tetrahedron Lett. 42 2001 5685 5687
49. M. Schmittel Top. Curr. Chem. 169 1994 183 230
50. M. Schmittel, A. Abufarag, O. Luche, and M. Levis Angew. Chem., Int. Ed. Engl. 29 1990 1144 1146
51. +, was produced, which suggested that redox reactions occurred.