Onium salt supported organic synthesis in water: application to Grieco's multicomponent reaction

Tetrahedron

Volumn 64, Issue 8, 2008, Pages 1962-1970

  Ouach, Aziz ^a   Gmouh, Said ^a   Pucheault, Mathieu ^a   Vaultier, Michel ^a  

^a UNIVERSITÉ DE RENNES 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

3 [(4 FORMYLPHENOXY)PROPYL]TRIMETHYLAMMONIUM CHLORIDE; [3 (4 AMINOBENZOYLOXY)PROPYL]TRIMETHYLAMMONIUM CHLORIDE; [3 (4 FORMYLBENZOYLOXY)PROPYL]TRIMETHYLAMMONIUM CHLORIDE; [3 [4 (2 CHLORO) 6,6A,7,11B TETRAHYDRO 6H INDENO[2,1 C]QUINOLIN 6 YL BENZOYLOXY]PROPYL]TRIMETHYLAMMONIUM CHLORIDE; [3 [4 (2 NITRO) 6,6A,7,11B TETRAHYDRO 6H INDENO[2,1 C]QUINOLIN 6 YL BENZOYLOXY]PROPYL]TRIMETHYLAMMONIUM CHLORIDE; [3 [4 (3A,4,5,9B TETRAHYDRO 3H CYCLOPENTA[C]QUINOLIN 4 YL)BENZOYLOXY]PROPYL]TRIMETHYLAMMONIUM CHLORIDE; [3 [4 (4 CHLOROPHENYL) 3A,4,5,9B TETRAHYDRO 3H CYCLOPENTA[C]QUINOLINE 8 CARBONYLOXY]PROPYL]TRIMETHYLAMMONIUM CHLORIDE; [3 [4 (4 FLUOROPHENYL) 3A,4,5,9B TETRAHYDRO 3H CYCLOPENTA[C]QUINOLINE 8 CARBONYLOXY]PROPYL]TRIMETHYLAMMONIUM CHLORIDE; [3 [4 (4 NITROPHENYL) 3A,4,5,9B TETRAHYDRO 3H CYCLOPENTA[C]QUINOLINE 8 CARBONYLOXY]PROPYL]TRIMETHYLAMMONIUM CHLORIDE; [3 [4 (8 CHLORO) 3A,4,5,9B TETRAHYDRO 3H CYCLOPENTA[C]QUINOLIN 4 YL BENZOYLOXY]PROPYL]TRIMETHYLAMMONIUM CHLORIDE; [3 [4 (8 METHYL) 3A,4,5,9B TETRAHYDRO 3H CYCLOPENTA[C]QUINOLIN 4 YL BENZOYLOXY]PROPYL]TRIMETHYLAMMONIUM CHLORIDE; [3 [4 (8 NITRO) 3A,4,5,9B TETRAHYDRO 3H CYCLOPENTA[C]QUINOLIN 4 YL BENZOYLOXY]PROPYL]TRIMETHYLAMMONIUM CHLORIDE; [3 [6 (4 NITROPHENYL) 5,6A,7,11B TETRAHYDRO 6H INDENO[2,1 C]QUINOLINE 2 CARBONYLOXY]PROPYL]TRIMETHYLAMMONIUM CHLORIDE; AMMONIUM CHLORIDE; ANILINE DERIVATIVE; BENZALDEHYDE DERIVATIVE; CATION; QUINOLINE DERIVATIVE; SOLVENT; UNCLASSIFIED DRUG; WATER;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; MOLECULAR WEIGHT; PRIORITY JOURNAL; SOLUBILITY; SYNTHESIS;

EID: 38149088875     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.11.060     Document Type: Article

References (26)

1. Vaultier, M.; Gmouh, S., CNRS; 1, U.R. FR2845084, WO2004029004, 2004; p 129.
2. Vaultier, M.; Gmouh, S.; Hassine, F., CNRS; Rennes1, U. WO2005005345, 2005; p 190.
3. Wasserscheid P., and Welton T. Ionic Liquids in Synthesis (2007), Wiley-VCH, Weinheim
4. Miao W., and Chan T.H. Acc. Chem. Res. 39 (2006) 897-908
5. Merrifield R.B. J. Am. Chem. Soc. 85 (1963) 2149-2154
6. Toy P.H., and Janda K.D. Acc. Chem. Res. 33 (2000) 546-554
7. Vaultier, M.; Roche, C.; Gmouh, S.; Commercon, A., Aventis Pharma SA, F.; CNRS. PCT FR2006001597, 2006; p 67.
8. Hassine F., Gmouh S., Pucheault M., and Vaultier M. Monatsh. Chem. 138 (2007) 1167-1174
9. Lee S.-G. Chem. Commun. (2006) 1049-1063
10. Dondoni A., Massi A., Minghini E., and Bertolasi V. Tetrahedron 60 (2004) 2311-2326
11. Verron J., Joerger J.-M., Pucheault M., and Vaultier M. Tetrahedron Lett. 48 (2007) 4055-4058
12. In: Zhu J., and Bienayme H. (Eds). Multicomponent Reactions (2005), Wiley-VCH, Weinheim
13. Demaude T., Knerr L., and Pasau P. J. Comb. Chem. 6 (2004) 768-775
14. Basso A., Banfi L., Riva R., Piaggio P., and Guanti G. Tetrahedron Lett. 44 (2003) 2367-2370
15. Grieco P.A., and Bahsas A. Tetrahedron Lett. 29 (1988) 5855-5858
16. Carranco I., Díaz J.L., Jiménez O., Vendrell M., Albericio F., Royo M., and Lavilla R. J. Comb. Chem. 7 (2005) 33-41
17. Kiselyov A.S., Smith L., and Armstrong R.W. Tetrahedron 54 (1998) 5089-5096
18. Dubois P., Marchand G., Fouillet Y., Berthier J., Douki T., Hassine F., Gmouh S., and Vaultier M. Anal. Chem. 78 (2006) 4909-4917
19. Chao-Jun Li T.-H.C. Comprehensive Organic Reactions in Aqueous Media. 2nd ed. (2007), Wiley-VCH, Weinheim pp i-xvi
20. Cornils B., and Herrmann W.A. In: Cornils B., and Herrmann W.A. (Eds). Aqueous-Phase Organometallic Catalysis. 2nd ed. (2005), Wiley-VCH, Weinheim
21. Lubineau A., and Augé J. Modern Solvents in Organic Synthesis (1999), Wiley-VCH, Weinheim p 1
22. Herrerias C.I., Yao X., Li Z., and Li C.J. Chem. Rev. 107 (2007) 2546-2562
23. Pirrung M.C., and Sarma K.D. J. Am. Chem. Soc. 126 (2004) 444-445
24. Sartori G., Bigi F., Maggi R., Mazzacani A., and Oppici G. Eur. J. Org. Chem. (2001) 2513-2518
25. Borrione E., Prato M., Scorrano G., Stivanello M., and Lucchini V. J. Heterocycl. Chem. 25 (1988) 1831-1835
26. Kouznetsov V.V., Puentes C.O., Bohorquez A.R.R., Zacchino S.A., Sortino M., Gupta M., Vazquez Y., Bahsas A., and Amaro-Luis J. Lett. Org. Chem. 3 (2006) 300-304