One-step, three-component synthesis of highly substituted pyridines using silica nanoparticle as reusable catalyst

Tetrahedron Letters

Volumn 50, Issue 50, 2009, Pages 6959-6962

  Banerjee, Subhash ^a   Sereda, Grigoriy ^a  

^a University of South Dakota   (United States)

Author keywords

2 Amino 3,5 dicarbonitrile 6 sulfanylpyridines; Catalysis; Multicomponent reaction; Silica nanoparticles

Indexed keywords

ALDEHYDE DERIVATIVE; MALONONITRILE; NANOPARTICLE; PYRIDINE DERIVATIVE; SILICON DIOXIDE; THIOL DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; INFRARED SPECTROSCOPY; ONE POT SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; TRANSMISSION ELECTRON MICROSCOPY;

EID: 70449130739     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.09.137     Document Type: Article

References (32)

1. The term 'privileged scaffolds or structures' was originally introduced by Merck researchers in their work on benzodiazepines:. Evans B.E., et al. J. Med. Chem. 31 (1988) 2235-2246
2. Patchett A.A., and Nargund R.P. Ann. Rep. Med. Chem. 35 (2000) 289-298
3. Chen, H.; Zhang, W.; Tam, R.; Raney, A. K. PCT Int. Appl. WO 2005058315 A1 20050630, 2005.
4. Perrier V., Wallace A.C., Kaneko K., Safar J., Prusiner S.B., and Cohen F.E. Proc. Natl. Acad. Sci. U.S.A. 97 (2000) 6073-6078
5. Levy, S. B.; Alekshun, M. N.; Podlogar, B. L.; Ohemeng, K.; Verma, A. K.; Warchol, T.; Bhatia, B.; Bowser, T.; Grier, M. U.S. Patent Appl., 2,005,124,678 A1 20,050,609, 2005.
6. Cocco M.T., Congiu C., Lilliu V., and Onnis V. Eur. J. Med. Chem. 40 (2005) 1365
7. Anderson, D. R.; Stehle, N. W.; Kolodziej, S. A.; Reinhard, E. J. PCT Int. Appl. WO 2004055015 A1 20040701, 2004.
8. Harada, H.; Watanuki, S.; Takuwa, T.; Kawaguchi, K.; Okazaki, T.; Hirano, Y.; Saitoh, C. PCT Int. Appl. WO 2002006237 A1 20020124, 2002.
9. Fredholm B.B., Ijzerman A.P., Jacobson K.A., Klotz K.-N., and Linden J. Pharmacol. Rev. 53 (2001) 527-552
10. Fletcher M.D., Hurst T.E., Miles T.J., and Moody C.J. Tetrahedron 62 (2006) 5454-5463
11. Movassaghi M., and Hill M.D. J. Am. Chem. Soc. 128 (2006) 4592-4593
12. Winter A., and Risch N. Synthesis (2003) 2667-2670
13. Thomas A.D., and Asokan C.V. Tetrahedron Lett. 43 (2002) 2273-2275
14. Tanaka K., Mori H., Yamamoto M., and Katsumara S. J. Org. Chem. 66 (2001) 3099-3110
15. Mashraqui S.H., and Karnik M.A. Tetrahedron Lett. 39 (1998) 4895-4898
16. Singh K., Singh J., and Singh H. Tetrahedron 54 (1998) 935-942
17. Renslo A.R., and Danheiser R.L. J. Org. Chem. 63 (1998) 7840-7850
18. Vijn R.J., Arts H.J., Green R., and Castelijns A.M. Synthesis (1994) 573-578
19. Ahmed S., and Baruah R.C. Tetrahedron Lett. 37 (1996) 8231-8232
20. Komatsu M., Ohgishi H., Takamatsu S., Ohshiro Y., and Agawa T. Angew. Chem., Int. Ed. Engl. 21 (1982) 213-214
21. Attia A.M.E., and Ismail A.E.-H.A.A. Tetrahedron 59 (2003) 1749-1752
22. Anabha E.R., Nirmala K.N., Thomas A., and Asokan C.V. Synthesis (2007) 428-432
23. Evdokimov N.M., Kireev A.S., Yakovenko A.A., Antipin M.Y., Magedov I.V., and Kornienko A. J. Org. Chem. 72 (2007) 3443-3453
24. Evdokimov N.M., Magedov I.V., Kireev A.S., and Konienko A. Org. Lett. 8 (2006) 899-902
25. Ranu B.C., Jana R., and Sowmiah S. J. Org. Chem. 72 (2007) 3152-3154
26. Guo K., Thompson M.J., Reddy T.R.K., Mutter R., and Chen B. Tetrahedron 63 (2007) 5300-5311
27. Sridhar M., Ramanaiah B.C., Narsaiah C., Mahesh B., Kumaraswamy M., Mallu K.K.R., Ankathi V.M., and Rao S.P. Tetrahedron Lett. 50 (2009) 3897-3900
28. Banerjee S., Das J., and Santra S. Tetrahedron Lett. 50 (2009) 124-127
29. Banerjee S., and Santra S. Tetrahedron Lett. 50 (2009) 2037-2040
30. Bagwe R.P., Hilliard L.R., and Tan W. Langmuir 22 (2006) 4357-4362
31. 9cThis procedure was followed for the synthesis of all the substituted pyridines listed in Table 2. The recovered catalyst was washed with ethanol and reused for subsequent reactions.
32. Chang L.C.W., Kunzel J., Mulder-Krieger T., Spanjersberg R.F., Roerink S.F., Van den Hout G., Beukers M.W., Brussee J., and Ijzerman A.P. J. Med. Chem. 48 (2005) 2045-2053