Synthesis of 3-quinolinecarboxylic acid esters from the Baylis-Hillman adducts of 2-halobenzaldehyde N-tosylimines

Tetrahedron Letters

Volumn 42, Issue 22, 2001, Pages 3737-3740

  Kim, Jae Nyoung ^a   Lee, Hong Jung ^a   Lee, Ka Young ^a   Kim, Hyoung Shik ^a  

^a Chonnam National University   (South Korea)

Author keywords

3 quinolinecarboxylic acid ethyl esters; Baylis Hillman adducts

Indexed keywords

2 HALOBENZALDEHYDE N TOSYLIMINE DERIVATIVE; 3 QUINOLINECARBOXYLIC ACID ESTER DERIVATIVE; IMINE; O HALOBENZALDEHYDE N TOSYLIMINE DERIVATIVE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; COMPLEX FORMATION; DERIVATIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0000984929     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(01)00552-4     Document Type: Article

References (35)

1. Ciganek E. Organic Reactions. 51:1997;201-350 John Wiley & Sons, New York.
2. Drewes S.E., Roos G.H.P. Tetrahedron. 44:1988;4653.
3. Basavaiah D., Rao P.D., Hyma R.S. Tetrahedron. 52:1996;8001.
4. Brezezinski L.J., Rafel S., Leahy J.W. J. Am. Chem. Soc. 119:1997;4317.
5. Rafel S., Leahy J.W. J. Org. Chem. 62:1997;1521.
6. Kim H.S., Kim T.Y., Lee K.Y., Chung Y.M., Lee H.J., Kim J.N. Tetrahedron Lett. 41:2000;2613.
7. Lee H.J., Seong M.R., Kim J.N. Tetrahedron Lett. 39:1998;6223.
8. Lee H.J., Kim H.S., Kim J.N. Tetrahedron Lett. 40:1999;4363.
9. Basavaiah D., Sarma P.K.S. J. Chem. Soc., Chem. Commun. 1992;955.
10. Charette A.B., Cote B., Monroc S., Prescott S. J. Org. Chem. 60:1995;6888.
11. Basavaiah D., Krishnamacharyulu M., Hyma R.S., Pandiaraju S. Tetrahedron Lett. 38:1997;2141.
12. Chavan S.P., Ethiraj K.S., Kamat S.K. Tetrahedron Lett. 38:1997;7415.
13. Perlmutter P., Tabone M. Tetrahedron Lett. 29:1988;949.
14. Lawrence R.M., Perlmutter P. Chem. Lett. 1992;305.
15. Foucaud A., El Guemmout F. Bull. Soc. Chim. Fr. 1989;403.
16. Kim J.N., Lee K.Y., Kim H.S., Kim T.Y. Org. Lett. 2:2000;343.
17. Familoni O.B., Kaye P.T., Klaas P.J. J. Chem. Soc., Chem. Commun. 1998;2563.
18. Bode M.L., Kaye P.T. J. Chem. Soc., Perkin Trans. 1. 1993;1809.
19. Bode M.L., Kaye P.T. J. Chem. Soc., Perkin Trans. 1. 1990;2612.
20. Amri H., El Gaied M.M., Ben Ayed T., Villieras J. Tetrahedron Lett. 33:1992;6159.
21. Amri H., El Gaied M.M., Ben Ayed T., Villieras J. Tetrahedron Lett. 33:1992;7345.
22. Jungheim L.N. Tetrahedron Lett. 30:1989;1889.
23. Michael J.P. Nat. Prod. Rep. 14:1997;605.
24. Balasubramanian M., Keay J.G. Katritzky A.R., Rees C.W., Scriven E.F.V. Comprehensive Heterocyclic Chemistry II. 5:1996;245-300 Pergamon Press, Oxford.
25. Jones G. Katritzky A.R., Rees C.W., Scriven E.F.V. Comprehensive Heterocyclic Chemistry II. 5:1996;167-243 Pergamon Press, Oxford.
26. Ranu B.C., Hajra A., Jana U. Tetrahedron Lett. 41:2000;531.
27. Cho C.S., Oh B.H., Shim S.C. Tetrahedron Lett. 40:1999;1499.
28. Cacchi S., Fabrizi G., Marinelli F. Synlett. 1999;401.
29. Suginome M., Fukuda T., Ito Y. Org. Lett. 1:1999;1977.
30. Katritzky A.R., Arend M. J. Org. Chem. 63:1998;9989.
31. Ruhland T., Kunzer H. Tetrahedron Lett. 37:1996;2757.
32. Radl S., Bouzard D. Heterocycles. 34:1992;2143.
33. Qiang L.G., Baine N.H. J. Org. Chem. 53:1988;4218.
34. ++2, 20).
35. For the preparation of the Baylis-Hillman adducts 1a-h, see Refs. 2b and 2c.