Heterogeneous metallo-organocatalysis for the selective one-pot synthesis of 2-benzylidene-indoxyl and 2-phenyl-4-quinolone

Tetrahedron

Volumn 67, Issue 5, 2011, Pages 976-981

  Genelot, Marie ^a   Dufaud, Véronique ^a   Djakovitch, Laurent ^a  

^a UNIVERSITÉ DE LYON   (France)

Author keywords

4 Quinolones; Heterogeneous catalysis; Indoxyls; Mesoporous supports; Metallo organocatalysis; One pot synthesis

Indexed keywords

2 BENZYLIDENE INDOXYL; 2 PHENYL 4 QUINOLONE; AMINE; BENZYLIDENE DERIVATIVE; PALLADIUM; PHOSPHINE; QUINOLONE DERIVATIVE; SILICON DIOXIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; HYBRID; ONE POT SYNTHESIS; PRIORITY JOURNAL; QUANTUM YIELD; SOLID STATE;

EID: 78651374508     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.11.112     Document Type: Article

References (30)

1. H. Grohe Chem. Brit. 1992 34 36
2. M.P. Wentland, and J.B. Cornett Annu. Rep. Med. Chem. 20 1985 145 154
3. F.E. Ward, D.L. Garling, R.T. Bickler, D.M. Lawer, and D.P. Cummings J. Med. Chem. 24 1981 1073 1077
4. A. Aimi, M. Nishimura, A. Miwa, H. Hoshino, S. Sakai, and J. Higiniwa Tetrahedron Lett. 30 1989 4991 4994
5. N.J. Leonard, F.-F. Herbrandson, and E.M. van Heyningen J. Am. Chem. Soc. 68 1946 1279 1281
6. R.H. Reitsema Chem. Rev. 43 1948 43 68
7. B. Chen, X. Huang, and J. Wang Synthesis 1987 482 483
8. A. Kasahara, T. Izumi, H. Watabe, and S. Takahashi Chem. Ind. 1981 121
9. K. Okuro, and H. Alper J. Org. Chem. 62 1997 1566 1567
10. R. Grigg, A. Liu, D. Shaw, S. Suganthan, D.E. Woodall, and G. Yoganathan Tetrahedron Lett. 41 2000 7125 7128
11. S. Torii, H. Okumoto, and L.H. Xu Tetrahedron Lett. 32 1991 237 240
12. S. Torii, H. Okumoto, L.H. Xu, M. Sadakane, M.V. Shostakovsky, A.B. Ponomaryov, and V.N. Kalinin Tetrahedron 49 1993 6773 6784
13. V.N. Kalinin, M.V. Shostakovskii, and A.B. Ponomarev Tetrahedron Lett. 33 1992 373 376
14. N. Haddad, J. Tan, and V. Farina J. Org. Chem. 71 2006 5031 5034
15. B. Gerby, A. Boumendjel, M. Blanc, P.P. Bringuier, P. Champelovier, A. Fortuné, X. Ronot, and J. Boutonnat Bioorg. Med. Chem. Lett. 17 2007 208 213
16. R.A. Abramovitch, and A.M. Marko Can. J. Chem. 38 1960 131 135
17. F.M. Dean, and C. Patamapongse J. Chem. Soc., Perkin Trans. 1 1974 952 955
18. E. Wu, K. Komolpis, and H.Y. Wang Biotechnol. Tech. 13 1999 567 569
19. E. Braudeau, S. David, and J.C. Fischer Tetrahedron 30 1974 1445 1455
20. M.C. Hewitt, and L. Shao ARKIVOC 2006 37 46
21. M. Hooper, and W.N. Pitkethly J. Chem. Soc., Perkin Trans. 1 1972 1607 1613
22. Z.W. An, M. Catellani, and G.P. Chiusoli J. Organomet. Chem. 397 1990 C31 C32
23. M. Genelot, A. Bendjeriou, V. Dufaud, and L. Djakovitch Appl. Catal., A 369 2009 125 132
24. In TANDEM catalysis all catalysts are introduced in the reactor from the start of the reaction; in MULTI-CATALYSIS, the catalysts are introduced in the reactor step by step. See: D.E. Fogg, and E.N. dos Santos Coord. Chem. Rev. 248 2004 2365 2379
25. Following the European Medicines Agency, in: E.M. Agency (Ed.) 2008 p. 34, acceptable residual palladium content for drugs administered by oral and parental routes should be below 1 ppm and 10 ppm [often <5 ppm in drug testing], respectively.
26. MS m/z (relative intensity): 207(49), 206 (30), 130 (100), 102 (16), 77 (15).1H NMR (250 MHz, DMSO) δ 10.97 (s, 1H), 7.40 (d, J=7.5 Hz, 1H), 7.33-7.11 (m, 6H), 6.95 (m, 2H), 6.13 (s, 1H), 4.05 (s, 2H) in agreement with I. Ambrogio, S. Cacchi, G. Fabrizi, and A. Prastaro Tetrahedron 65 2009 8916 8929
27. Y. Coquerel, P. Bremond, and J. Rodriguez J. Organomet. Chem. 692 2007 4805 4808
28. L. Djakovitch, K. Koehler, and J.G. De Vries D. Astruc, Nanoparticles and Catalysis 2008 Wiley-VCH Weinheim 303 348
29. L. Djakovitch, M. Wagner, C.G. Hartung, M. Beller, and K. Koehler J. Mol. Catal. A: Chem. 219 2004 121 130
30. N. Batail, A. Bendjeriou, L. Djakovitch, and V. Dufaud Appl. Catal., A 388 2010 179 187