A facile strategy for the one pot multicomponent synthesis of spiro dihydropyridines from amines and activated alkynes

Tetrahedron Letters

Volumn 52, Issue 48, 2011, Pages 6508-6511

  Kiruthika, Selvarangam E ^a   Lakshmi, Neelakandan Vidhya ^a   Banu, Babu Rasidha ^a   Perumal, Paramasivan T ^a  

^a CENTRAL LEATHER RESEARCH INSTITUTE   (India)

Author keywords

Activated alkynes; Diketones; Monoketones; Multi component reactions; Spiro dihydropyridines

Indexed keywords

ACETYLENE DERIVATIVE; ALKYNE DERIVATIVE; AMINE; DIHYDROPYRIDINE DERIVATIVE; ESTER DERIVATIVE; KETONE DERIVATIVE; MALONONITRILE; SPIRO COMPOUND;

ARTICLE; CATALYST; CHEMICAL STRUCTURE; ONE POT SYNTHESIS; QUANTUM YIELD; REACTION ANALYSIS; REACTION TIME; STEREOCHEMISTRY;

EID: 80255138769     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.09.119     Document Type: Article

References (34)

1. (a) Bienayme, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. Eur. J. 2000, 6, 332;
2. (b) Multicomponent Reactions; Zhu, J., Bienayme, H., Eds.; Wiley-VCH: Weinheim, Germany, 2005. p 468;
3. (c) Jingqiang, W.; Jared, T. S. Org. Lett. 2007, 9, 4077.
4. (a) Armstrong, R. W.; Combs, A. P.; Tempest, P. A.; Brown, S. D.; Keating, T. A. Acc. Chem. Res. 1996, 29, 123;
5. (b) Domling, A. Chem. Rev. 2006, 106, 17;
6. (c) Tietze, L. F.; Kinzel, T.; Brazel, C. C. Acc. Chem. Res. 2009, 42, 367;
7. (d) Jing, S.; Er-Yan, X.; Qun, W.; Chao-Guo, Y. ACS Comb. Sci. 2011, 13, 436.
8. (a) Ana, G. N.; Delgado, J.; Cecilia, P.; Marcaccini, S.; Carlos, F. M. Tetrahedron Lett. 2005, 46, 23;
9. (b) Yavari, I.; Mohammad, J. B.; Mehdi, S.; Sanaz, S. Tetrahedron Lett. 2010, 66, 7995;
10. (c) Ugi, I.; Domling, A.; Werner, B. J. Heterocycl. Chem. 2000, 37, 647;
11. (d) Kappe, C. O. Eur. J. Med. Chem. 2000, 35, 1043.
12. (a) Guarna, A.; Occhiato, E. G.; Macheeti, F.; Giacomelli, V. J. Org. Chem. 1999, 64, 4985;
13. (b) Ling, Y. Z.; Li, J. S.; Liu, Y.; Kato, K.; Klus, G. T.; Brodie, A. J. Med. Chem. 1994, 40, 3297;
14. (c) Kozyr, A. V.; Chenko, L. P.; Kolesnikow, A. V.; Zelenova, N. A. Immunol. Lett. 2002, 80, 41.
15. (a) Nair, V.; Devipriya, S.; Suresh, E. Tetrahedron 2008, 64, 3567;
16. (b) Nair, V.; Devipriya, S.; Suresh, E. Tetrahedron Lett. 2007, 48, 3667;
17. (c) Yavari, I.; Mirzaei, A.; Moradi, L.; Khalili, G. Tetrahedron Lett. 2010, 51, 396;
18. (d) Yavari, I.; Mokhtarporyani-Sanandaj, A.; Moradi, L.; Mirzaei, A. Tetrahedron 2008, 64, 5221.
19. (a) Liu, W. B.; Jiang, H. F.; Zhang, M.; Qi, C. R. J. Org. Chem. 2010, 75, 966;
20. (b) Cao, H.; Jiang, H. F.; Yao, W. J. Org. Lett. 2009, 11, 1931;
21. (c) Liu, W. B.; Jiang, H. F.; Qiao, C. L. Tetrahedron 2009, 65, 2110;
22. (d) Jing, S.; Er-Yan, X.; Qun, W.; Chao-Guo, Y. Org. Lett. 2010, 12, 3678.
23. (a) Sridharan, V.; Perumal, P. T.; Avendaño, C.; Carlos, J. M. Tetrahedron 2007, 63, 4407;
24. (b) Adharvana, C. M.; Syamasundar, K. Catal. Commun. 2006, 6, 624;
25. (c) Sridhar, R.; Perumal, P. T. Tetrahedron 2005, 61, 2465;
26. (d) Anniyappan, M.; Muralidharan, D.; Perumal, P. T. Synth. Commun. 2002, 32, 659.
27. Zamponi, G. W.; Stotz, S. C.; Staples, R. J.; Andro, T. M.; Nelson, J. K.; Hulubei, V.; Blumenfeld, A.; Natale, N. R. J. Med. Chem. 2003, 46, 87
28. Peri, R.; Padmanabhan, S.; Rutledge, A.; Singh, S.; Triggle, D. J. J. Med. Chem. 2000, 43, 2906.
29. (a) Kharkar, P. S.; Desai, B.; Gaveria, H.; Varu, B.; Lori ya, R.; Naliapara, Y.; Shah, A.; Kulkarn, V. M. J. Med. Chem. 2002, 45, 4858;
30. (b) McCormack, J. G.; Westergaard, N.; Kristiansen, M.; Brand, C. L.; Lau, J. Curr. Pharm. Des. 2001, 7, 1457.
31. (a) Kotha, B. S.; Deb, C. A.; Lahiri, K. Synthesis 2009, 2, 0165;
32. (b) Augustine, T.; Kanakam, C. C.; Vithiya, S. M.; Ramkumar, V. Tetrahedron Lett. 2009, 50, 5906;
33. (c) Trost, B. M.; Brennan, M. K. Synthesis 2009, 18, 3003.
34. Sharavathi, G. P.; Christopher, F. P. Org. Lett. 2010, 15, 3434.