Synthesis of polysubstituted pyridines under combined microwave and ultrasound irradiation: K 2CO 3-promoted tandem addition/cyclization/hydrogen shift process

Tetrahedron Letters

Volumn 53, Issue 9, 2012, Pages 1160-1162

  Feng, Huangdi ^a,b   Li, Yuan ^a   Van Der Eycken, Erik V ^b   Peng, Yanqing ^a   Song, Gonghua ^a  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b UNIVERSITY OF LEUVEN   (Belgium)

Author keywords

Heterogeneous; Microwave; Pyridines; Ultrasound

Indexed keywords

CHALCONE; MALONONITRILE; METHANOL; PYRIDINE DERIVATIVE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; IRRADIATION; MICHAEL ADDITION; MICROWAVE IRRADIATION; SYNTHESIS; TANDEM ADDITION CYCLIZATION HYDROGEN SHIFT; ULTRASOUND IRRADIATION;

EID: 84862823367     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.12.103     Document Type: Article

References (58)

1. J.J. Zhang, and C.W.T. Chang J. Org. Chem. 74 2009 4414
2. See: M.T. Cocco, C. Congiu, V. Lilliu, and V. Onnis Eur. J. Med. Chem. 40 2005 1365
3. Anderson, D. R.; Stehle, N. W.; Kolodziej, S. A.; Reinhard, E. J. PCT Int. Appl. WO 2004055015 A1 20040701, 2004.
4. Nirschl, A. A.; Hamann, L. G. U.S. Pat. Appl. 2005182105 A1 20050818, 2005.
5. Chen, H.; Zhang, W.; Tam, R.; Raney, A. K. PCT Int. Appl. WO 2005058315 A1 20050630, 2005.
6. Levy, S. B.; Alekshun, M. N.; Podlogar, B. L.; Ohemeng, K.; Verma, A. K.; Warchol, T.; Bhatia, B.; Bowser, T.; Grier, M. U.S. Pat. Appl. 2005124678 A1 20050609, 2005.
7. K. Guo, R. Mutter, W. Heal, T.R.K. Reddy, H. Cope, S. Pratt, M.J. Thompson, and B.N. Chen Eur. J. Med. Chem. 43 2008 93
8. Selective review: M.D. Hill Chem. Eur. J. 16 2010 12052
9. V.V. Lipson, and N.Y. Gorobets Mol. Divers. 13 2009 399
10. J.A. Varela, and C. Saá Chem. Rev. 103 2003 3787
11. Selective paper: M.D. Fletcher, T.E. Hurst, T.J. Miles, and C.J. Moody Tetrahedron 62 2006 5454
12. M. Movassaghi, and M.D. Hill J. Am. Chem. Soc. 128 2006 4592
13. M. Komatsu, H. Ohgishi, S. Takamatsu, Y. Ohshiro, and T. Agawa Angew. Chem., Int. Ed. Engl. 21 1982 213
14. E.R. Anabha, K.N. Nirmala, A. Thomas, and C.V. Asokan Synthesis 2007 428
15. Selective review: B. Jiang, T. Rajale, W.R. Wever, S.J. Tu, and G.G. Li Chem. Asian J. 5 2010 2318
16. N. Isambert, M.D.S. Duque, J.C. Plaquevent, Y. Genisson, J. Rodriguez, and T. Constantieux Chem. Soc. Rev. 40 2011 1347
17. J.E. Biggs-Houcka, A. Younaia, and J.T. Shawa Curr. Opin. Chem. Biol. 14 2010 371
18. I. Ugi, and S. Heck Comb. Chem. High Throughput Screening 4 2001 1
19. L.F. Tietze, and A. Modi Med. Res. Rev. 20 2000 304
20. V. Nair, C. Rajesh, A.U. Vinod, S. Bindu, A.R. Sreekanth, J.S. Mathen, and L. Bala-gopal Acc. Chem. Res. 26 2003 899
21. H.M. Hügel Molecules 14 2009 4936
22. D. Dallinger, and C.O. Kappe Chem. Rev. 107 2007 2563
23. P. Appukkuttan, V.P. Mehtaa, and E.V. Van der Eycken Chem. Soc. Rev. 39 2010 1467
24. C.O. Kappe, and E.V. Van der Eycken Chem. Soc. Rev. 39 2010 1280
25. G. Cracotto, and P. Cintas Chem. Soc. Rev. 35 2006 180
26. G. Cracotto, and P. Cintas Chem. Eur. J. 13 2007 1902
27. T.J. Mason Chem. Soc. Rev. 26 1997 443
28. V. Polshettiwar, and R.S. Varma Acc. Chem. Res. 41 2008 629
29. Selectived paper: N.M. Evdokimov, I.V. Magedov, A.S. Kireev, and A. Kornienko Org. Lett. 8 2006 899
30. B.C. Ranu, R. Jana, and S. Sowmiah J. Org. Chem. 72 2007 3152
31. S.L. Zhu, S.J. Ji, X.M. Su, C. Sun, and Y. Liu Tetrahedron Lett. 49 2008 1777
32. J.J. Xia, and G.W. Wang Synthesis 2005 2379
33. F. Shi, G. Zhang, Y. Zhang, N. Ma, B. Jiang, and S.J. Tu J. Heterocycl. Chem. 46 2009 965
34. F.E.M. El-Baih J. Saudi Chem. Soc. 8 2004 279
35. F.E. Goda, A.A.-M. Abdel-Aziz, and O.A. Attef Bioorg. Med. Chem. 12 2004 1845
36. S.J. Tu, B. Jiang, Y. Zhang, R.H. Jia, J.Y. Zhang, C.S. Yao, and F. Shi Org. Biomol. Chem. 5 2007 355
37. S.R. Sarda, J.D. Kale, S.K. Wasmatkar, V.S. Kadam, P.G. Ingole, W.N. Jadhav, and R.P. Pawar Mol. Divers. 13 2009 545
38. N.M. Evdokimov, A.S. Kireev, A.A. Yakovenko, M.Y. Antipin, I.V. Magedov, and A. Kornienko J. Org. Chem. 72 2007 3443
39. X.H. Wang, X.D. Cao, S.J. Tu, X.H. Zhang, W.J. Hao, S. Yan, S.S. Wu, Z.G. Han, and F. Shi J. Heterocycl. Chem. 46 2009 886
40. M.N. Nasr, M.M. Gineinah, and A.P. Maaarouf Sci. Pharm. 71 2003 9
41. M.M. Al-Arab J. Heterocycl. Chem. 26 1989 1665
42. F.E. Goda, A.A.M. Abdel-Aziz, and O.A. Attef Bioorg. Med. Chem. 12 2004 1845
43. D.V. Tyndall, T. Al Nakib, and M.J. Meegan Tetrahedron Lett. 29 1988 2703
44. F.F. Barsoum Eur. J. Med. Chem. 45 2010 5176
45. A.S. Girgis, N. Mishriky, M. Ellithey, H.M. Hosnia, and H. Farag Bioorg. Med. Chem. 15 2007 2403
46. Y.Q. Peng, and G.H. Song Green Chem. 3 2001 302
47. Y.Q. Peng, and G.H. Song Green Chem. 4 2002 349
48. Y.Q. Peng, and G.H. Song Green Chem. 5 2003 704
49. Y.Q. Peng, R.L. Dou, G.H. Song, and J. Jiang Synlett 2005 573
50. Y.Q. Peng, R.L. Dou, and G.H. Song Green Chem. 8 2006 507
51. D.J. Wallace, A.D. Gibb, I.F. Cottrell, D.F. Kennedy, K.M.J. Brands, and U.H. Dolling Synthesis 2001 1784
52. K. Guo, M.J. Thompson, T.R.K. Reddy, R. Mutter, and B.N. Chen Tetrahedron 63 2007 5300
53. S.D. Sharma, P. Hazarika, and D. Konwar Catal. Commun. 9 2008 709
54. Z.Y. Chen, and W. Zhang Chin. Chem. Lett. 18 2007 1443
55. T. Razzaq, J.M. Kremsner, and C.O. Kappe J. Org. Chem. 73 2008 6321
56. M.C. Bagley, and M.C. Lubinu Synthesis 2006 1283
57. J. Lu, Y.J. Bai, Z.J. Wang, B.Q. Yang, and W.H. Li Synth. Commun. 31 2001 2625
58. Y.C. Wu, L. Liu, Y.L. Liu, D. Wang, and Y.J. Chen J. Org. Chem. 72 2007 9383