Sc(OTf)3-catalyzed three-component cyclization of arylamines, β,γ-unsaturated α-ketoesters, and 1,3-dicarbonyl compounds for the synthesis of highly substituted 1,4-dihydropyridines and tetrahydropyridines

Journal of Organic Chemistry

Volumn 78, Issue 11, 2013, Pages 5751-5755

  Liu, Lu ^a   Sarkisian, Ryan ^a   Deng, Yongming ^a   Wang, Hong ^a  

^a MIAMI UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

UNSATURATED COMPOUNDS;

1 ,3-DICARBONYL COMPOUNDS; 1 ,4-DIHYDROPYRIDINES; ARYL AMINES; CYCLIZATION REACTIONS; KETO ESTER; TETRAHYDROPYRIDINES; THREE COMPONENT;

CYCLIZATION;

1,3 DICARBONYL; 1,4 DIHYDROPYRIDINE DERIVATIVE; AROMATIC AMINE; BETA,GAMMA UNSATURATED ALPHA KETOESTER; CARBON NITROGEN MONOCYCLE; ESTER DERIVATIVE; KETONE; PYRIDINE DERIVATIVE; TETRAHYDROPYRIDINE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE; SYNTHESIS;

EID: 84879288206     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo400578m     Document Type: Article

References (49)

1. Tietze, L. F.; Brasche, G.; Gericke, K. Domino Reactions in Organic Synthesis; Wiley-VCH: Weinheim, 2006.
2. Zhu, J.; Bienaymé, H. Multicomponent Reactions; Wiley-VCH: Weinheim, 2005.
3. Simon, C.; Constantieux, T.; Rodriguez, J. Eur. J. Org. Chem. 2004, 4957
4. Bonne, D.; Constantieux, T.; Coquerel, Y.; Rodriguez, J. Chem.-Eur. J. 2013, 19, 2218
5. Bonne, D.; Coquerel, Y.; Constantieux, T.; Rodriguez, J. Tetrahedron: Asymmetry 2010, 21, 1085
6. Allais, C.; Lieby-Muller, F.; Constantieux, T.; Rodriguez, J. Adv. Synth. Catal. 2012, 354, 2537
7. Zhong, C.; Liao, T.; Tuguldur, O.; Shi, X. Org. Lett. 2010, 12, 2064
8. Li, N.; Chen, X. H.; Song, J.; Luo, S. W.; Fan, W.; Gong, L. Z. J. Am. Chem. Soc. 2009, 131, 15301
9. Liang, B.; Kalidindi, S.; Porco, J. A., Jr.; Stephenson, C. R. J. Org. Lett. 2010, 12, 572
10. Liu, W. B.; Jiang, H. F.; Zhang, M.; Qi, C. R. J. Org. Chem. 2010, 75, 966
11. Maiti, S.; Biswas, S.; Jana, U. J. Org. Chem. 2010, 75, 1674
12. Sadek, K. U.; Mekheimer, R. A.; Mohamed, T. M.; Moustafa, M. S.; Elnagdi, M. H. Beilstein J. Org. Chem. 2012, 8, 18
13. Alizadeh, A.; Mikaeili, A.; Firuzyar, T. Synthesis 2012, 44, 1380
14. Wang, J. L.; Liu, B. K.; Yin, C.; Wu, Q.; Lin, X. F. Tetrahedron 2011, 67, 2689
15. Li, H.; Yan, C. G. Tetrahedron 2011, 67, 2863
16. Khan, A. T.; Das, D. K. Tetrahedron Lett. 2012, 53, 2345
17. Chen, W. B.; Wu, Z. J.; Pei, Q. L.; Cun, L. F.; Zhang, X. M.; Yuan, W. C. Org. Lett. 2010, 12, 3132
18. Bossert, F.; Vater, W. Med. Res. Rev. 1989, 9, 291
19. Kawase, M.; Shah, A.; Gaveriya, H.; Motohashi, N.; Sakagami, H.; Varga, A.; Molnar, J. Bioorg. Med. Chem. 2002, 10, 1051
20. Aouam, K.; Berdeaux, A. Therapie 2003, 58, 333
21. Straub, T.; Boesenberg, C.; Gekeler, V.; Boege, F. Biochemistry 1997, 36, 10777
22. Donkor, I. O.; Zhou, X.; Schmidt, J.; Agrawal, K. C.; Kishore, V. Bioorg. Med. Chem. 1998, 6, 563
23. Kuzmin, A.; Semenova, S.; Ramsey, N. F.; Zvartau, E. E.; Van Ree, J. M. Eur. J. Pharmacol. 1996, 295, 19
24. Boumendjel, A.; Baubichon-Cortay, H.; Trompier, D.; Perrotton, T.; Di Pietro, A. Med. Res. Rev. 2005, 25, 453
25. Hilgeroth, A. Mini Rev. Med. Chem. 2002, 2, 235
26. Comins, D. L.; O'Connor, S. Adv. Heterocycl. Chem. 1988, 44, 199
27. Kumar, R.; Chandra, R. Adv. Heterocycl. Chem. 2001, 78, 269
28. Lavilla, R. J. Chem. Soc., Perkin Trans. 1 2002, 1141
29. Wan, J. P.; Liu, Y. RSC Adv. 2012, 2, 9763
30. Hantzsch, A. Justus Liebigs Ann. Chem. 1882, 1, 215
31. Ji, S. J.; Jiang, Z. Q.; Lu, J.; Lo, T. P. Synlett 2004, 831
32. Sridhar, R.; Perumal, P. T. Tetrahedron 2005, 61, 2465
33. Breitenbucher, J. G.; Figliozzi, G. Tetrahedron Lett. 2000, 41, 4311
34. Wang, L. M.; Sheng, J.; Zhang, L.; Han, J. W.; Fan, Z. Y.; Tian, H.; Qian, C. T. Tetrahedron 2005, 61, 1539
35. Vohra, R. K.; Bruneau, C.; Renaud, J. L. Adv. Synth. Catal. 2006, 348, 2571
36. Ishar, M. P. S.; Kumar, K.; Kaur, S.; Kumar, S.; Girdhar, N. K.; Sachar, S.; Marwaha, A.; Kapoor, A. Org. Lett. 2001, 3, 2133
37. Bartoli, G.; Babiuch, K.; Bosco, M.; Carlone, A.; Galzerano, P.; Melchiorre, P.; Sambri, L. Synlett 2007, 2897
38. Kantam, M. L.; Ramani, T.; Chakrapani, L.; Choudary, B. M. Catal. Commun. 2009, 10, 370
39. Das, B.; Suneel, K.; Venkateswarlu, K.; Ravikanth, B. Chem. Pharm. Bull. 2008, 56, 366
40. Kumar, A.; Maurya, R. A.; Sharma, S.; Kumar, M.; Bhatia, G. Eur. J. Med. Chem. 2010, 45, 501
41. Kumar, A.; Maurya, R. A. Tetrahedron 2008, 64, 3477
42. Sridharan, V.; Perumal, P. T.; Avendaňo, C.; Menéndez, J. C. Tetrahedron 2007, 63, 4407
43. Jiang, J.; Yu, J.; Sun, X. X.; Rao, Q. Q.; Gong, L. Z. Angew. Chem., Int. Ed. 2008, 47, 2458
44. Deng, Y.; Liu, L.; Sarkisian, R. G.; Wheeler, K.; Wang, H.; Xu, Z. Angew. Chem., Int. Ed. 2013, 52, 3663
45. Monbaliu, J. C. M.; Masschelein, K. G. R.; Stevens, C. V. Chem. Soc. Rev. 2011, 40, 4708
46. Eisch, J. J.; Sanchez, R. J. Org. Chem. 1986, 51, 1848
47. Palacios, F.; Vicario, J.; Aparicio, D. Eur. J. Org. Chem. 2006, 2843
48. Cao, C. L.; Sun, X. L.; Kang, Y. B.; Tang, Y. Org. Lett. 2007, 9, 4151
49. Palacios, F.; Vicario, J.; Aparicio, D. Eur. J. Org. Chem. 2006, 2843