A general synthesis of quinolinones and benzothiazine 1,1-dioxides via ring closing metathesis

Tetrahedron Letters

Volumn 49, Issue 22, 2008, Pages 3677-3681

  Minville, Joannie ^a   Poulin, Jason ^a   Dufresne, Claude ^a   Sturino, Claudio F ^a  

^a MERCK FROSST CENTRE FOR THERAPEUTIC RESEARCH   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLAMIDE DERIVATIVE; BENZOTHIAZINE 1,1 DIOXIDE DERIVATIVE; BENZOTHIAZINE DERIVATIVE; BETA 2 ADRENERGIC RECEPTOR STIMULATING AGENT; IMMUNOMODULATING AGENT; N PHENYLACRYLAMIDE DERIVATIVE; N PHENYLETHYLENESULFONAMIDE DERIVATIVE; PROTEIN FARNESYLTRANSFERASE INHIBITOR; QUINOLINE DERIVATIVE; QUINOLINONE DERIVATIVE; SEROTONIN 2 ANTAGONIST; SEROTONIN 2A ANTAGONIST; SULFONAMIDE;

ARTICLE; CATALYST; DRUG SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; RING CLOSING METATHESIS;

EID: 43049092241     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.03.144     Document Type: Article

References (51)

1. Forbis R.M., and Rinehart Jr. K.L. J. Am. Chem. Soc. 95 (1973) 5003
2. Nadzan A.M., and Rinehart Jr. K.L. J. Antibiot. (1977) 523
3. Strelitz F., Flon H., and Asheshov I.N. Proc. Natl. Acad. Sci. U.S.A. (1955) 620
4. Rinehart Jr. K.L., Leadbetter G., Larson R.A., and Forbis R.M. J. Am. Chem. Soc. 92 (1970) 6994
5. Naganawa H., Wakashiro T., Yagi A., Kondo S., Takita T., Hamada M., Maeda K., and Umezawa H. J. Antibiot. 23 (1970) 365
6. Matera M.G., and Cazzola M. Drugs 67 (2007) 503
7. Caraglia M., Marra M., Viscomi C., D'Alessandro A.M., Budillon A., Meo G., Arra C., Barbieri A., Rapp U.R., Baldi A., Tassone P., Venuta S., Abbruzzese A., and Tagliaferri P. Int. J. Cancer 121 (2007) 2317
8. Norman P. Curr. Opin. Investig. Drugs 3 (2002) 313
9. Kieseier B.C., and Wiendl H. CNS Drugs 21 (2007) 483
10. McCort G., Hoornaert C., Aletru M., Denys C., Duclos O., Cadilhac C., Guilpain E., Dellac G., Janiak P., Galzin A.-M., Delahaye M., Guilbert F., and O'Connor S. Bioorg. Med. Chem. 9 (2001) 2129
11. For representative methods for the synthesis of quinolinones see:. Sim M.M., Lee C.L., and Ganesan A. Tetrahedron Lett. 39 (1998) 6399
12. Kondo Y., Inamoto K., and Sakamoto T. J. Comb. Chem. 2 (2000) 232
13. Miura Y., Takaku S., Nawata Y., and Hamana M. Heterocycles 32 (1991) 1579
14. Bashir M., Kingston D.G.I., Carman R.J., Van Tassell R.L., and Wilkins T.D. Heterocycles 29 (1989) 1127
15. Gesto C., De La Cuesta E., and Avendano C. Synth. Commun. 19 (1989) 3523
16. Robl J.A. Synthesis (1991) 56
17. Lee H., and Anderson W.K. Tetrahedron Lett. 31 (1990) 4405
18. Yamaguchi S., Yokoi T., Yamada M., Arai H., Uchiuzo Y., and Kawase Y. J. Heterocycl. Chem. 27 (1990) 1003
19. Jaroszewski J.W. J. Heterocycl. Chem. 27 (1990) 1227
20. Kitahara Y., Shimizu M., and Kubo A. Heterocycles 31 (1990) 2085
21. Balasubramaniyan V., and Argade N.P. Synth. Commun. 19 (1989) 3103
22. Yamaguchi S., Yoshimoto Y., Murai R., Ohama E., and Kawase Y. J. Heterocycl. Chem. 27 (1990) 999
23. For representative examples of the use of cyclic sulfonamides in medicinal chemistry see:. Hanson P.R., Probst D.A., Robinson R.E., and Yau M. Tetrahedron Lett. 40 (1999) 4761 and references cited within
24. For recent reviews on ring-closing metathesis see:. Trnka T.M., and Grubbs R.H. Acc. Chem. Res. 34 (2001) 18
25. Furstner A. Angew. Chem., Int. Ed. 39 (2000) 3012
26. Grubbs R.H. Tetrahedron 60 (2004) 7117
27. For leading references in the use of RCM for the synthesis of lactams see:. Ma S., and Ni B. Org. Lett. 4 (2002) 639
28. Huwe C.M., Kiehl O.C., and Blechert S. Synlett (1996) 65
29. Lim S.H., Ma S., and Beak P. J. Org. Chem. 66 (2001) 9056
30. Greenwood E.S., Parsons P.J., and Young M.J. Synth. Commun. 33 (2003) 223
31. Veerman J.J.N., van Maarseveen J.H., Visser G.M., Kruse C.G., Schoemaker H.E., Hiemstra H., and Rutjes F.P.J.T. Eur. J. Org. Chem. 11 (1998) 2583
32. Schuster M., Pernerstorfer J., and Blechert S. Angew. Chem., Int. Ed. 35 (1996) 1979
33. Rodriguez S., Castillo E., Carda M., and Marco J.A. Tetrahedron 58 (2002) 1185
34. Rutjes F.P.J.T., and Schoemaker H.E. Tetrahedron Lett. 38 (1997) 677
35. Gille S., Ferry A., Billard T., and Langlois B.R. J. Org. Chem. 68 (2003) 8932
36. Chen Y., Zhang H., and Nan F. J. Comb. Chem. 6 (2004) 684
37. Donohoe T.J., Fishlock L.P., and Procopiou P.A. Org. Lett. 10 (2008) 285
38. Hanson P.R., Probst D.A., Robinson R.E., and Yau M. Tetrahedron Lett. 40 (1999) 4761
39. Freitag D., Schwab P., and Metz P. Tetrahedron Lett. 45 (2004) 3589
40. Brown R.C.D., Castro J.L., and Moriggi J.-D. Tetrahedron Lett. 41 (2000) 3681
41. Chatterjee A.K., Morgan J.P., Scholl M., and Grubbs R.H. J. Am. Chem. Soc. 122 (2000) 3783
42. Chao W., Meketa M.L., and Weinreb S.M. Synthesis 12 (2004) 2058
43. For representative literature reports of vinyl chlorides participating in ring-closing metathesis see:. Chao W., and Weinreb S.M. Org. Lett. 5 (2003) 2505
44. De Matteis V., van Delft F.L., de Gelder R., Tiebes J., and Rutjes F.P.J.T. Tetrahedron Lett. 45 (2004) 959
45. For a discussion of the effects of olefin substitution on the RCM of a series of α,β-unsaturated amides see Ref. 6g.
46. Loev B., Kormendy M.F., and Snader K.M. J. Org. Chem. 31 (1966) 3531
47. Hwang K.-J., and Lee T.-S. Korean J. Med. Chem. 9 (1999) 75
48. Blondet D., and Pascal J.-C. Tetrahedron Lett. 35 (1994) 2911
49. Makara G.M., and Ma Y. Tetrahedron Lett. 42 (2001) 4123
50. Li M., Wu R.S., Tsai J.S.C., and Salamone S.J. Bioorg. Med. Chem. Lett. 13 (2003) 383
51. 2), and olefination sequence. For a representative example of this sequence see:. Bennasar M.-L., Zulaica E., and Tummers S. Tetrahedron Lett. 45 (2004) 6283