Simple and convenient conversion of acridones into 9-unsubstituted acridines via acridanes using borane tetrahydrofuran complex

Tetrahedron Letters

Volumn 50, Issue 49, 2009, Pages 6894-6896

  Desbois, Nicolas ^a   Szollosi, Anna ^b   Maisonial, Aurélie ^c,d   Weber, Valérie ^c,d   Moreau, Emmanuel ^c,d   Teulade, Jean Claude ^c,d   Chavignon, Olivier ^c,d   Blache, Yves ^e   Chezal, Jean Michel ^c,d  

^a Chu   (France)

^b UNIVERSITÉ DE BOURGOGNE   (France)

^c UNIVERSITÉ CLERMONT AUVERGNE   (France)

^d CENTRE JEAN PERRIN   (France)

^e UNIVERSITÉ DE TOULON   (France)

Author keywords

Acridine; Acridone; Borane complex; Reduction

Indexed keywords

ACRIDINE DERIVATIVE; ACRIDONE DERIVATIVE; BORANE DERIVATIVE; BORANE TETRAHYDROFURAN; FURAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; COLUMN CHROMATOGRAPHY; OXIDATION; REDUCTION KINETICS; SYNTHESIS;

EID: 70350015573     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.09.141     Document Type: Article

References (30)

1. Biwersi J., Tulk B., and Verkman A.S. Anal. Biochem. 219 (1994) 139
2. Mccapra F. In: Acheson R.M. (Ed). The Chemistry of Heterocyclic Compounds: Acridines Vol. 9 (1973), John Wiley & Sons 615-630
3. Wainwright M. J. Antimicrob. Chemother. 47 (2001) 1
4. Guetzoyan L., Ramiandrasoa F., Dorizon H., Desprez C., Bridoux A., Rogier C., Pradines B., and Perree-Fauvet M. Bioorg. Med. Chem. 15 (2007) 3278
5. Denny W. Curr. Med. Chem. 9 (2002) 1655
6. Belmont P., Bosson J., Godet T., and Tiano M. Anti-Cancer Agents Med. Chem. 7 (2007) 139
7. Atwell G.J., Rewcastle G.W., Baguley B.C., and Denny W.A. J. Med. Chem. 30 (1987) 664
8. Csuk R., Barthel A., and Raschke C. Tetrahedron 60 (2004) 5737
9. Bernthsen A. Justus Liebigs Ann. Chem. 224 (1884) 1-56
10. Baum J.S., Condon M.E., and Shook D.A. J. Org. Chem. 52 (1987) 2983
11. Desbois N., Gardette M., Papon J., Labarre P., Maisonial A., Auzeloux P., Lartigue C., Bouchon B., Debiton E., Blache Y., Chavignon O., Teulade J.C., Maublant J., Madelmont J.C., Moins N., and Chezal J.M. Bioorg. Med. Chem. 16 (2008) 7671
12. Madelmont, J. C.; Chezal, J. M.; Moins, N.; Teulade, J. C.; Chavignon, O. Patent WO2008012782, 2008.
13. Martin R.F., and Kelly D.P. Aust. J. Chem. 32 (1979) 2637
14. Kinsey B.M., Fayad F., Venkateshan C.N., Adelstein S.J., and Kassis A.I. Int. J. Radiat. Appl. Instrum., B Nucl. Med. Biol. 17 (1990) 341
15. Khurana J.M., Bansal G., Kukreja G., and Pandey R.R. Monatsh. Chem. 134 (2003) 1365
16. Tamano M., and Koketsu J. Bull. Chem. Soc. Jpn. 58 (1985) 2577
17. Albert A., and Goldacre R. J. Chem. Soc. (1946) 706
18. 2CO) δ 4.02 (s, 3H), 7.66 (m, 1H), 7.90 (d, 1H, J = 9 Hz), 8.06 (m, 2H), 8.26 (d, 1H, J = 9 Hz), 8.36 (s, 1H), 9.02 (s, 1H).
19. Gopinath V.S., Thimmaiah P., and Thimmaiah K.N. Bioorg. Med. Chem. 16 (2008) 474
20. Consonni R., Croce P.D., Ferraccioli R., and La Rosa C. J. Chem. Soc., Perkin Trans. 1 15 (1996) 1809
21. Mayur Y.C., Padma T., Parimala B.H., Chandramouli K.H., Jagadeesh S., Made Gowda N.M., and Thimmaiah K.N. Med. Chem. 2 (2006) 63
22. Acheson R.M., Hoult T.G., and Barnard K.A. J. Chem. Soc. (1954) 4142
23. Singh S., and Singh M. J. Sci. Ind. Res. 10 (1951) 298
24. Sahu S.K., Kortylewicz Z.P., Baranowska-Kotylewicz J., Taube R.A., Adelstein S.J., and Kassis A.I. Radiat. Res. 147 (1997) 401
25. Ngadi L., Brouant P., Galy A.M., Galy J.P., Soyfer J.C., and Barbe J. Eur. J. Med. Chem. 25 (1990) 21
26. Graboyes H., Anderson E.L., Levinson S.H., and Resnick T.M. J. Heterocycl. Chem. 12 (1975) 1225
27. Chen J., Zhang J., Zhuang Q., Chen J., and Lin X. Electroanalysis 19 (2007) 1765
28. Stefanska B., Bontemps-Gracz M.M., Antonini I., Martelli S., Arciemiuk M., Piwkowska A., Rogacka D., and Borowski E. Bioorg. Med. Chem. 13 (2005) 1969
29. 3, 300 MHz) δ 5.26 (s, 2H), 7.55 (m, 2H), 7.67 (m, 1H), 7.79 (m, 1H), 8.02 (d, 1H, J = 8.5 Hz), 8.15 (d, 1H, J = 9 Hz), 8.21 (d, 1H, J = 9 Hz), 9.10 (s, 1H).
30. 3, 200 MHz) δ 3.99 (s, 3H), 7.40 (t, 1H, J = 7.8 Hz), 7.90 (m, 2H), 8,27 (br s, 1H), 8.45 (dd, 1H, J = 7.6, 1.6 Hz), 8.53 (d, 1H, J = 7.8 Hz), 11.67 (s, 1H).