Tetrabutylammonium hydrogen sulfate catalyzed eco-friendly and efficient synthesis of glycosyl 1,4-dihydropyridines

Tetrahedron Letters

Volumn 45, Issue 49, 2004, Pages 9011-9014

  Tewari, Neetu ^a   Dwivedi, Namrata ^a   Tripathi, Rama P ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

1,4 dihydropyridines; Ammonium acetate; Enamines; Glycosyl dihydropyridines; Tetrabutylammonium hydrogen sulfate

Indexed keywords

DIETHYLENE GLYCOL; ENAMINE; ESTER DERIVATIVE; KETONE DERIVATIVE; PYRIDINE DERIVATIVE; TETRABUTYLAMMONIUM;

ARTICLE; CATALYSIS; CATALYST; INFRARED SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 8744244554     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.10.057     Document Type: Article

References (27)

1. U. Eisner, and J. Kuthan Chem. Rev. 72 1972 1 42
2. R.J. Kill, and D.A. Widdowson E.E. Van Tamelen Bioorg. Chem. Series 4 1978 Academic New York 239 275
3. J.P. Kutney Heterocycles 7 1977 593 614
4. D.M. Stout, and A.I. Meyers Chem. Rev. 82 1982 223 243
5. F. Bossert, H. Meyer, and E. Wehinger Angew Chem., Int. Ed. Engl. 20 1981 762 769
6. H. Nakayama, and Y. Kasoka Heterocycles 42 1996 901 909
7. A. Saushins, and G. Duburs Heterocycles 27 1988 269 289
8. P.P. Mager, R.A. Coburn, A.J. Solo, D.J. Triggle, and H. Rothe Drug Des. Discov. 8 1992 273 289
9. R. Manhold, B. Jablonka, W. Voigdt, K.F. Schoenfinger, and K. Schravan Eur. J. Med. Chem. 27 1992 229 235
10. V. Klusa Drugs Future 20 1995 135 138
11. R.G. Bretzel, C.C. Bollen, E. Maeser, and K.F. Federlin Am. J. Kidney Dis. 21 1993 53 64
12. R. Boer, and V. Gekker Drugs Future 20 1995 499 509
13. R.G. Bretzel, C.C. Bollen, E. Maeser, and K.F. Fedrlin Am. J. Kidney Dis. 17 1992 465 468
14. R.P. Tripathi, R. Tripathi, V.K. Tiwari, L. Bala, S. Sinha, A. Srivastava, R. Srivastava, and B.S. Srivastava Eur. J. Med. Chem. 37 2002 773 781
15. N. Tewari, V.K. Tiwari, R.C. Mishra, R.P. Tripathi, A.K. Srivastava, R. Ahmad, R. Srivastava, and B.S. Srivastava Bioorg. Med. Chem. 11 2003 2911 2923
16. A. Shah, H. Gaveriya, N. Motohashi, S.M. Kawase, S. Saito, H. Sakagami, Y. Satoh, A. Solymosi, K. Walfard, and J. Molnar Anticanc. Res. 20 2000 373 377
17. P.S. Kharkar, B. Desai, H. Gaveria, B. Varu, R. Loria, Y. Maliapara, A. Shah, and V.M. Kulkarni J. Med. Chem. 45 2002 4858 4867
18. A. Shah, H. Gaveriya, N. Motohashi, S. Kawase, S. Farkas, G. Gyorgyi, and J. Molnar Int. J. Antimicrob. Agents 20 2002 227 235
19. A. Shah, V. Vora, B. Desai, and H. Gaveriya Heterocycl. Commun. 7 2001 481 486
20. A. Dondoni, A. Massi, and E. Minghini Synlett 2002 89 92
21. M.A. Zolfigol, and M. Safaiee Synlett 2004 827 830
22. K. Freudberg, W. Dum, and H. Hochstetter Von Ber. Dtsch. Chem. Ges. 61 1928 1732 1734
23. N. Tewari, D. Katiyar, V.K. Tiwari, and R.P. Tripathi Tetrahedron Lett. 44 2003 6639 6642
24. N. Tewari, R.C. Mishra, V.K. Tiwari, and R.P. Tripathi Synlett 2002 1779 1782
25. M.L. Wolform, and S. Hanessian J. Org. Chem. 27 1962 1800 1804
26. D. Katiyar, R.C. Mishra, and R.P. Tripathi J. Carbohydr. Chem. 23 2004 49 70
27. General Procedure: A mixture of glycosyl aldehyde 1a (1.0 g, 4.95 mmol), enamine 2a (0.49 mL, 4.95 mmol), acetylacetone (0.49 mL, 4.95 mmol) and TBAHS (0.2 g) was magnetically stirred at 80°C in diethylene glycol (2 mL) for 1.5 h. After cooling the reaction mixture it was poured onto crushed ice. The crude product, thus obtained, was purified by column chromatography on silica gel using chloroform:methanol (98:2) as eluent to afford the desired product 3 Physical Data