Bifunctional acid-base ionic liquid for the one-pot synthesis of fine chemicals: Thioethers, 2H-chromenes and 2H-quinoline derivatives

Applied Catalysis A: General

Volumn 481, Issue , 2014, Pages 27-38

  Climent, Maria J ^a   Iborra, Sara ^a   Sabater, Maria J ^a   Vidal, Juan D ^a  

^a CSIC   (Spain)

Author keywords

Acid base; Bifunctional; Chromenes; Condensation; Fine chemicals; Michael addition; One pot; Organocatalysis; Quinolines

Indexed keywords

ADDITION REACTIONS; CATALYSTS; CONDENSATION; REACTION KINETICS;

ACID BASE; BI-FUNCTIONAL; CHROMENES; FINE CHEMICALS; MICHAEL ADDITIONS; ONE POT; ORGANOCATALYSIS; QUINOLINES;

IONIC LIQUIDS;

EID: 84901427330     PISSN: 0926860X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.apcata.2014.05.004     Document Type: Article

References (72)

1. S. Huh, H.T. Chen, J.W. Wiench, M. Pruski, and V.S.Y. Lin Angew. Chem. Int. Ed. 44 2005 1826 1830
2. R.K. Zeidan, S.J. Hwang, and M.E. Davis Angew. Chem. Int. Ed. 45 2006 6332 6335
3. C. Kwong, R. Huang, M. Zhang, M. Shi, and P. Toy Chem. Eur. J. 13 2007 2369 2376
4. M. Martin, F. Manea, R. Fiammengo, L. Prins, L. Pasquato, and P. Scrimin J. Am. Chem. Soc. 129 2007 6982 6983
5. J.K. Lee, M.C. Kung, and H.H. Kung Top. Catal. 49 2008 136 144
6. T. Weil, M. Kotke, C.M. Kleiner, and P.R. Schreiner Org. Lett. 10 2008 1513 1516
7. M.J. Climent, A. Corma, I. Dominguez, S. Iborra, M.J. Sabater, and G. Sastre J. Catal. 246 2007 136 146
8. M. Boronat, M.J. Climent, A. Corma, S. Iborra, R. Monton, and M.J. Sabater Chem. Eur. J. 16 2010 1221 1231
9. M. Boronat, M.J. Climent, A. Corma, S. Iborra, R. Montón, and M.J. Sabater PCCP 13 2011 17255 17261
10. M.J. Climent, A. Corma, and S. Iborra Chem. Rev. 111 2011 1072 1133
11. A. Corma, J. Navas, and M.J. Sabater Chem. Eur. J. 18 2012 14150 14156
12. A. Corma, T. Ródenas, and M.J. Sabater J. Catal. 279 2011 319 327
13. A. Corma, T. Ródenas, and M.J. Sabater Chem. Eur. J. 16 2010 254 260
14. H. Wynberg Top. Stereochem. 16 16 1986 87 129
15. A. Kamimura J. Synth. Org. Chem. Jpn. 62 62 2004 705 715
16. A. Berkessel, and H. Gröger Asymmetric Organocatalysis 2005 Wiley-VCH Weinheim
17. R. Okazaki Organosulfur Chemistry vol. 1 1995 Academic Press London 225
18. D. Enders, K. Lütgen, and A.A. Narine Synthesis 7 2007 959 980
19. O.M. Berner, L. Tesdechi, and D. Eriders J. Org. Chem. 2002 1877 1894
20. V.A. Ashwood, R.E. Buckingham, F. Cassidy, J.M. Evans, E.A. Faruk, T.C. Hamilton, and D.J. Nash J. Med. Chem. 29 1986 2194 2201
21. J.N. Kim, and K.Y. Lee Curr. Org. Chem. 6 2002 627 645
22. J.M. Evans, C.S. Fake, and T.C. Hamilton J. Med. Chem. 26 1983 1582 1589
23. G.P. Ellis, and G.P. Chromenes Chromanones and Chromones 1977 Wiley Interscience New York
24. J.D. Hepworth A.R. Katrizky, C.W. Rees, A.J. Boulton, A. McKillop, Comprehensive Heterocyclic Chemistry vol. 3 1984 Pergamon Press Oxford
25. B.W. Fravel, and N.A. Nedolya A.R. Katrizky, C.A. Ramsden, E.F.V. Scriven, R.J.K. Taylor, Comprehensive Heterocyclic Chemistry III 2008 Elsevier, Ltd.
26. K.Y. Lee, D.H. Nam, C.S. Moon, S.H. Seo, J.Y. Lee, and Y.S. Lee Eur. J. Med. Chem. 41 2006 991 996
27. S. Sang, J.D. Lambert, S. Tian, J. Hong, J. Hou, J. Ryu, R.E. Stark, R.T. Rosen, M. Huang, C.S. Yang, and C. Ho Bioorg. Med. Chem. 12 2004 459 467
28. M. Sirafianpour, O. Kayser, J. Christensen, M. Asfa, M.W. Stark, and J.W. Jarozewski J. Nat. Prod. 65 2002 1754 1758
29. K.M. Dawood, and T. Fuchigami J. Org. Chem. 66 2001 7691 7695
30. A. Fournet, M.E. Ferreira, A. Rojas De Arias, S. Torres De Ortiz, S. Fuentes, H. Nakayama, A. Schinini, and R. Hocquemiller Antimicrob. Agents Chemother. 40 1996 2447 2451
31. M.A. Fakhfakh, A. Fournet, E. Prina, J.-F. Mouscadet, X. Franck, and B. Figadère Bioorg. Med. Chem. 11 2003 5013 5240
32. M. Henry, S. Alibert, C. Rogier, J. Barbe, and B. Pradines Curr. Top. Med. Chem. 8 2008 563 578
33. B. Heiniger, G. Gakhar, K. Prasain, D.H. Hua, and T.A. Nguyen Anticancer Res. 30 2010 3927 3932
34. D.A. Marble, and J.A. Bosso Drug Intell. Clin. Pharm. 20 1986 261 266
35. R. Musiol, M. Serda, S. Hensel-Bielowka, and J. Polanski Curr. Med. Chem. 17 2010 1960 1973
36. O. Bilker, V. Lindo, M. Panico, A.E. Etiene, T. Paxton, A. Dell, M. Rogers, R.E. Sinden, and H.R. Morris Nature 392 1988 289 292
37. P.A. Winstanley Parasitol. Today 16 2000 146 153
38. L.Y. Vargas, M.V. Castelli, V.V. Kouznetsov, J.M. Urbina, S.N. Lopez, M. Sortino, R.D. Enriz, J.C. Ribas, and S. Sacchino Bioorg. Med. Chem. 11 2003 1531 1550
39. L. Dassonneville, A. Lansiaux, A. Wattelet, N. Wattez, C. Mahieu, S. Van Miert, L. Pieters, and C. Bailly Eur. J. Pharmacol. 409 2000 9 18
40. Y.-L. Shi, and M. Shi Org. Biomol. Chem. 5 2007 1499 1504
41. G. Sartori, G. Casiraghi, L. Bolzoni, and G. Castani J. Org. Chem. 44 1979 803 805
42. J.J. Talley Synthesis 1983 845
43. B.A. Chauder, C.C. Lopes, R.S.C. Lopes, A.J.M. da Silva, and V. Snieckus Synthesis 1998 279
44. J.Y. Goujon, F. Zammatio, S. Pagnoncelli, Y. Boursereau, and B. Kirschleger Synthesis 2002 322
45. V.V. Kouznetsov, L.Y. Vargas Mendez, and C.M. Melendez Gómez Curr. Org. Chem. 9 2005 141 161
46. C.R. Brindaban, H. Alakananda, and J. Umasish Tetrahedron Lett. 41 2000 531 533
47. S. Madapa, Z. Tusi, and S. Batra Curr. Org. Chem. 12 2008 1116 1183
48. J. Wiesner, R. Ortmann, H. Jomaa, and M. Schlitzer Angew. Chem. Int. Ed. 43 2003 5274 5293
49. M.-C. Yan, Y.-J. Jang, and C.-F. Yao Tetrahedron Lett. 42 42 2001 2717 2721
50. M.-C. Yan, Y.-J. Jang, W.-Y. Kuo, Z. Tu, K.-H. Shen, T.-S. Cuo, C.-H. Ueng, and C.-F. Yao Heterocycles 57 2002 1033 1048
51. B.C. Das, S. Mohapatra, P.D. Campbell, S. Nayak, S.M. Mahalingam, and T. Evans Tetrahedron Lett. 51 2010 2567 2570
52. S. Bonollo, D. Lanari, T. Angelini, F. Pizzo, A. Marrocchi, and L. Vaccaro J. Catal. 285 2012 216 222
53. R.S. Varma, and G.W. Kabalka Heterocycles 23 1985 139 141
54. R. Ballini, G. Bosica, D. Fiorini, and A. Palmieri Green Chem. 7 2005 825 827
55. I. Ibrahem, H. Sundén, R. Rios, G.-L. Zhao, and A. Córdova Chimia 61 2007 219 223
56. M.C. Yan, Z. Tu, C. Lin, S. Ko, J. Hsu, and C.F. Yao J. Org. Chem. 69 2004 1565 1570
57. S.-H. Zhao, and Z.-B. Chen Synth. Commun. 35 2005 3045 3053
58. P. Kotrusz, and Š. Toma Molecules 11 2006 197 205
59. S. Matsubara, M. Yoshioka, and K. Utimoto Chem. Lett. 1994 827
60. M. Pérez, and R. Pleixats Tetrahedron 51 1995 8355 8362
61. G. Cardillo, L. Gentilucci, M. Gianotti, and P.A. Tolomelli J. Org. Chem. 66 2001 8657 8660
62. K. Nakama, S. Seki, and S. Kanemasa Tetrahedron Lett. 42 2001 6719 6722
63. T.-P. Loh, and L.-L. Wei Synlett 1998 975
64. G. Bartoli, M. Bosco, E. Marcantoni, M. Petrini, L.L. Sambri, and E. Torregiani J. Org. Chem. 66 2001 9052 9055
65. M. Kawatsura, and J.F. Hartwig Organometallics 20 2001 1960 1964
66. N. Srivastava, and B.K. Banik J. Org. Chem. 68 2003 2109 2114
67. G.V.M. Sharma, V.G. Reddy, A.S. Chander, and K.R. Reddy Tetrahedron Asymm. 13 2002 21 24
68. R. Ballini, G. Bosica, M.V. Gil, E. Roman, and J.A. Serrano Tetrahedron Asymm. 13 2002 1773 1789
69. K. Albrecht, M. Moeller, and J. Groll Adv. Polym. Sci. 2010 69
70. B. Movassagh, and P. Shaygan Arkivoc XII 2006 130 137
71. B.D. Foy, R.A. Smudde, and W.F. Wood J. Chem. Ed. 70 4 1993 322 323
72. A.R. Katritzky, S. Rachwal, and B. Rachwal Tetrahedron 52 1996 15031 15070