A novel TMSI-mediated synthesis of Hantzsch 1,4-dihydropyridines at ambient temperature

Tetrahedron Letters

Volumn 44, Issue 21, 2003, Pages 4129-4131

  Sabitha, Gowravaram ^a   Reddy, G S Kiran Kumar ^a   Reddy, Ch Srinivas ^a   Yadav, J S ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Ambient temperature; Hantzsch 1,4 dihydropyridines; One pot condensation; TMSI

Indexed keywords

1,4 DIHYDROPYRIDINE DERIVATIVE; BENZALDEHYDE DERIVATIVE; IODOTRIMETHYLSILANE; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; DRUG SYNTHESIS; ENVIRONMENTAL TEMPERATURE; INFRARED SPECTROSCOPY; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE;

EID: 0038327797     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00813-X     Document Type: Article

References (25)

1. Bossert F., Meyer H., Wehinger E. Angew. Chem., Int. Ed. Engl. 20:1981;762-769.
2. Nakayama H., Kasoaka Y. Heterocycles. 42:1996;901-909.
3. Godfraid T., Miller R., Wibo M. Pharmocol. Rev. 38:1986;321-416.
4. Sausins A., Duburs G. Heterocycles. 27:1988;269-289.
5. Mager P.P., Coburn R.A., Solo A.J., Triggle D.J., Rothe H. Drug Design Discovery. 8:1992;273.
6. Mannhold R., Jablonka B., Voigdt W., Schoenafinger K., Schravan K. Eur. J. Med. Chem. 27:1992;229-235.
7. Klusa V. Drugs Fut. 20:1995;135-138.
8. Bretzel R.G., Bollen C.C., Maeser E., Federlin K.F. Am. J. Kidney. Dis. 21:1993;53-64.
9. Bretzel R.G., Bollen C.C., Maeser E., Federlin K.F. Drugs Fut. 17:1992;465-468.
10. Boer R., Gekeler V. Drugs Fut. 20:1995;499-509.
11. Anniyappan M., Muralidhran D., Perumal P.T. Synth. Commun. 32:2002;659-663.
12. Yadav J.S., Reddy B.V.S., Reddy P.T. Synth. Commun. 31:2001;425-430.
13. Alajarin R., Vaquero J.J., Navio J.L.G., Alvarez-Builla J. Synlett. 1992;297-298.
14. Cotterill I.C., Usyatinsky A.Y., Arnold J.M., Clark D.S., Dordick J.S., Michels P.C., Khmelnitsky Y.L. Tetrahedron Lett. 39:1998;1117-1120.
15. Hantzsch A. Justus Liebigs Ann. Chem. 1:1882;215.
16. Gordeev M.F., Patel D.V., Gordon E.M. J. Org. Chem. 61:1996;924-928.
17. Breitenbucher J.G., Figliozzi G. Tetrahedron Lett. 41:2000;4311-4315.
18. Ohberg L., Westman J. Synlett. 2001;1296-1298.
19. Anderson A.G. Jr., Berkelhammer G. J. Am. Chem. Soc. 80:1958;992-999.
20. Phillips A.P. J. Am. Chem. Soc. 71:1949;4003-4007.
21. Maquestiau A., Maeyence A., Eynde J.-J.V. Tetrahedron Lett. 32:1991;3839-3840.
22. For a review, see: Olah G.A., Narang S.C. Tetrahedron. 38:1982;2225-2277.
23. Sabitha G., Yadav J.S. Synth. Commun. 28:1998;3065-3071.
24. Sabitha G., Abraham S., Reddy B.V.S., Yadav J.S. Tetrahedron Lett. 40:1999;1569-1570.
25. 3): δ 1.20 (t, 6H, J=8.5 Hz), 2.30 (s, 6H), 4.10 (q, 4H, J=8.2 Hz), 4.90 (s, 1H), 5.75 (brs, 1H), 7.15-7.23 (m, 4H).