Novel regioselectivity: Three-component cascade synthesis of unsymmetrical 1,4- and 1,2-dihydropyridines

Journal of Organic Chemistry

Volumn 74, Issue 7, 2009, Pages 2862-2865

  Wan, Jie Ping ^a   Gan, Shi Feng ^a   Sun, Gong Lei ^b   Pan, Yuan Jiang ^a  

^a ZHEJIANG UNIVERSITY   (China)

^b ZHEJIANG NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 DIHYDROPYRIDINE; 1,4 DIHYDROPYRIDINE; ALDEHYDE; AMINE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL REACTION; STEREOCHEMISTRY;

DIHYDROPYRIDINES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 64249158227     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo900068z     Document Type: Article

References (42)

1. For related reviews, sse: (a) Janis, R. A.; Silver, P. J.; Triggle, D. J. Adv. Drug Res. 1987, 16, 309.
2. (b) Lavilla, R. J. Chem. Soc., Perkin 1 2002, 1141.
3. (c) Kappe, C. O. Eur. J. Med. Chem. 2000, 35, 1043.
4. (a) Varache-Lemebge, M.; Nuhrich, A.; Zemb, V.; Devaux, G.; Vacher, P.; Vacher, A. M.; Dufy, B. Eur. J. Med. Chem. 1996, 31, 547.
5. (b) Alker, D.; Campbell, S. F.; Cross, P. E.; Burges, R. A.; Carter, A. J.; Gardiner, D. G. J. Med. Chem. 1990, 33, 585.
6. (a) Wetzel, J. M.; Miao, S. W.; Forray, C.; Borden, L. A.; Branchek, T. A.; Gluchowski, C. J. Med. Chem. 1995, 38, 1579.
7. (b) Wong, W. C.; Chiu, G.; Wetzel, J. M.; Marzabadi, M. R.; Nagarathnam, D.; Wang, D.; Fang, J.; Miao, S. W.; Hong, X.; Forray, C.; Vaysse, P. J.-J.; Branchek, T. A.; Gluchowski, C.; Tang, R.; Lepor, H. J. Med. Chem. 1998, 41, 2643.
8. (a) Donkor, I. O.; Zhou, X.; Schmidt, J.; Agrawal, K. C.; Kishore, V. Bioorg. Med. Chem. 1998, 6, 563.
9. (b) Bretzel, R. G.; Bollen, C. C.; maeser, E.; Federlin, K. F. Drug Fut. 1992, 17, 465.
10. (c) Klusa, V. Drug Fut. 1995, 20, 135.
11. (d) Hilgeroth, A. Mini-Rev. Med. Chem. 2002, 2, 235.
12. (a) Rudler, H.; Parlier, A.; Hamon, L.; Herson, P.; Daran, J.-C. Chem. Commun. 2008, 4150.
13. (b) Rudler, H.; Parlier, A.; Sandoval-Chavez, C.; Herson, P.; Daran, J.-C. Angew. Chem., Int. Ed. 2008, 47, 6843.
14. For representative reviews, see: (a) Zhu, J.; Bienaymé, H. Multicomponent Reactions, 1st ed.; Wiley-VCH: Weinheim, Germany, 2005.
15. (b) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168.
16. (c) Zhu, J. Eur. J. Org. Chem. 2003, 1133.
17. (d) Dömling, A. Chem. Rev. 2006, 106, 17.
18. Hantzsch, A. Justus Liebigs Ann. Chem. 1882, 1, 215.
19. For recent reviews on Hantsche 1,4-DHP synthesis, see: (a) Simon, C.;Constantieux, T.; Rodriguez, J. Eur. J. Org. Chem. 2004, 4957.
20. (b) Langer, P. Chem. Eur. J. 2001, 7, 3858.
21. (c) Langer, P. Synthesis 2002, 441.
22. For alternative synthesis of Hantsch-type 1,4-DHP, see: (a) Cui, S.-L.; Wang, J.; Lin, X.-F.; Wang, Y.-G. J. Org. Chem. 2007, 72, 7779.
23. (b) Kikuchi, S.; Iwai, M.; Murayama, H.; Fukuzawa, S. Tetrahedron Lett. 2008, 49, 114.
24. See also:(a) Rovnyak, G. C.; Kimball, S. D.; Beyer, B.; Cucinotta, G.; Dimarco, J. D.; Gougoutas, J.; Hedberg, A.; Malley, M.; McCarthy, J. P.; Zhang, R.; Moreland, S. J. Med. Chem. 1995, 38, 119.
25. (b) Peri, R.; Padmanabhan, S.; Rutledge, A.; Singh, S.; Triggle, D. J. J. Med. Chem. 2000, 43, 2906.
26. (c) Shan, R.; Velazquez, C.; Knaus, E. E. J. Med. Chem. 2004, 47, 254.
27. (a) Öhberg, L.; Westman, J. Synlett 2001, 1296.
28. (b) Cotterill, I. C.; Usyatinsky, A. Y.; Arnold, J. M.; Clark, D. S.; Dordick, J. S.; Michels, P. C.; Khmelnitsky, Y. L. Tetrahedron Lett. 1998, 39, 1117.
29. (c) Chowdhurv, U. S. Tetrahedron 1990, 46, 7893.
30. For selected examples, see: (a) Bossert, F.; Meyer, H.; Wehinger, E. Angew. Chem. 1981, 93, 755.
31. (b) Wang, G.-W.; Miao, C.-B. Green Chem. 2006, 8, 1080.
32. (a) Vohra, R. K.; Bruneau, C.; Renaud, J.-L. Adv. Synth. Catal. 2006, 348, 2571.
33. (b) Moreau, J.; Duboc, A.; Hubert, C.; Hurvois, J.-P.; Renaud, J.-L. Tetrahedron Lett. 2007, 48, 8647.
34. (c) Sridharan, V.; Perumal, P. T.; Anvendaño, C.; Menéndez, J. C. Tetrahedron 2007, 63, 4407.
35. (d) Kumar, A.; Maurya, R. A. Tetrahedron 2008, 64, 3477.
36. (e) Das, B.; Suneel, K.; Venkateswarlu, K.; Ravikanth, B. Chem. Pharm. Bull. 2008, 56, 366.
37. Recently, Ishar et al. reported the [4+2] cycloaddition of azadienes with allenic esters to give novel unsymmetrical 1,4-DHPs, see:(a) Ishar, M. P. S.; Kumar, K.; Kaur, S.; Kumar, S.; Girdhar, N. K.; Sachar, S.; Marwaha, A.; Kapoor, A. Org. Lett. 2001, 3, 2133.
38. (b) Singh, L.; Ishar, M. P. S.; Elango, M.; Subramanian, V.; Gupta, V.; Kanwal, P. J. Org. Chem. 2008, 73, 2224.
39. (a) Zhu, Y.-L.; Huang, S.-L.; Pan, Y.-J. Eur. J. Org. Chem. 2005, 2354.
40. (b) Huang, S.-L.; Pan, Y.-J.; Zhu, Y.-L.; Wu, A.-X. Org. Lett. 2005, 7, 3797.
41. (c) Zhu, Y.-L.; Huang, S.-L.; Wan, J.-P.; Yan, L.; Pan, Y.-J.; Wu, A.-X. Org. Lett. 2006, 8, 2599.
42. (e) Wan, J.-P.; Zhou, J.; Mao, H.; Pan, Y.-J.; Wu, A.-X. Tetrahedron 2008, 64, 11115.