Synthesis of fused tetrahydro-β-carbolinequinoxalinones in 1-n-butyl-2,3-dimethylimidazolium bis(trifluoromethylsulfonyl)imide ([bdmim][Tf2N]) and 1-n-butyl-2,3-dimethylimidazolium perfluorobutylsulfonate ([bdmim][PFBuSO3]) ionic liquids

Tetrahedron Letters

Volumn 46, Issue 36, 2005, Pages 6131-6136

  Tseng, Ming Chung ^a   Liang, Yang Min ^a   Chu, Yen Ho ^a  

^a NATIONAL CHUNG CHENG UNIVERSITY   (Taiwan)

Author keywords

Ionic liquid; Organic synthesis; Tetrahydro carbolinequinoxalinone

Indexed keywords

1 BUTYL 2,3 DIMETHYLIMIDAZOLIUM BIS(TRIFLUOROMETHYLSULFONYL)IMIDE; 1 BUTYL 2,3 DIMETHYLIMIDAZOLIUM PERFLUOROBUTYLSULFONATE; ANION; IMIDAZOLE DERIVATIVE; QUINOXALINE DERIVATIVE; SULFONIC ACID DERIVATIVE; TRYPTOLINE DERIVATIVE; TRYPTOPHAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; COMMERCIAL PHENOMENA; HYDROLYSIS; LIQUID; MASS SPECTROMETRY; MATERIALS; MOLECULAR STABILITY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 23244463060     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.06.153     Document Type: Article

References (48)

1. For recent reviews, see: C.E. Song Chem. Commun. 2004 1033 1043
2. J. Dupont, R.F. de Souza, and P.A. Suarez Chem. Rev. 102 2002 3667 3692
3. H. Oliver-Bourbigou, and L. Magna J. Mol. Catal. A: Chem. 182-183 2002 419 437
4. H. Zhao, and S.V. Malhotra Aldrichim. Acta 35 2002 75 83
5. R. Sheldon Chem. Commun. 2001 2399 2407
6. R. Hagiwara, and Y. Ito J. Fluorine Chem. 105 2000 221 227
7. T. Welton Chem. Rev. 99 1999 2071 2083
8. R.D. Rogers, and K.R. Seddon Science 302 2003 792 793
9. J. Fraga-Dubreuil, and J.P. Bazureau Tetrahedron Lett. 41 2000 7351 7355
10. For recent studies on reaction selectivity in ionic liquids, see: S.H. Schofer, N. Kaftzik, P. Wasserscheid, and U. Kragl Chem. Commun. 2001 425 426
11. K.-W. Kim, B. Song, M.-Y. Choi, and M.-J. Kim Org. Lett. 3 2001 1507 1509
12. T. Fischer, A. Sethi, T. Welton, and J. Woolf Tetrahedron Lett. 40 1999 793 796
13. M.J. Earle, P.B. McCormac, and K.R. Seddon Chem. Commun. 1998 2245 2246
14. P. Formentin, H. Garcia, and A. Leyva J. Mol. Catal. A 214 2004 137 142
15. R.P. Swatloski, J.D. Holbrey, and R.D. Rogers Green Chem. 5 2003 361 363
16. C.B. Murray, G. Sanford, and S.R. Korn J. Fluorine Chem. 123 2003 81 84
17. N.E. Leadbeater, H.M. Torenius, and H. Tye Tetrahedron 59 2003 2253 2258
18. N.M.T. Lourenco, and C.A.M. Afonso Tetrahedron 59 2003 789 794
19. J.G. Huddleston, A.E. Visser, W.M. Reichert, H.D. Willauer, G.A. Broker, and R.D. Rogers Green Chem. 3 2001 156 164
20. A.E. Visser, R.P. Swatloski, W.M. Reichert, S.T. Griffin, and R.D. Rogers Ind. Eng. Chem. Res. 39 2000 3596 3604
21. Y.-H. Yen, and Y.-H. Chu Tetrahedron Lett. 45 2004 8137 8140
22. J.-C. Hsu, Y.-H. Yen, and Y.-H. Chu Tetrahedron Lett. 45 2004 4673 4676
23. L. Gubicza, N. Nemestothy, T. Frater, and K. Belafi-Bako Green Chem. 5 2003 236 239
24. J.H. Davis, and P.A. Fox Chem. Commun. 2003 1209 1212
25. P. Wasserscheid, R. van Hall, and A. Bosmann Green Chem. 4 2002 400 404
26. L. Cammarata, S.G. Kazarian, P.A. Salter, and T. Welton Phys. Chem. Chem. Phys. 3 2001 5192 5200
27. S.I. Lall, D. Mancheno, S. Castro, V. Behaj, J.I. Cohen, and R. Engel Chem. Commun. 2000 2413 2414
28. M.J. Earle, S.P. Katdare, and K.R. Seddon Org. Lett. 6 2004 707 710
29. 7d
30. + calcd = 153.1386, obsd = 153.1390.
31. D.W. Morrison, D.C. Forbes, and J.H. Davis Jr. Tetrahedron Lett. 42 2001 6053 6055
32. P. Bonhote, A.-P. Dias, N. Papageorgiou, K. Kalyanasundaram, and M. Gratzel Inorg. Chem. 35 1996 1168 1178
33. R.D. Chambers Fluorine in Organic Chemistry 1973 Wiley-Interscience New York
34. V.R. Koch, C. Nanjundiah, Battista, G. Appetecchi, and B. Scrosati J. Electrochem. Soc. 142 1995 L116 L118
35. 3] ionic liquid and found that it is, as expected, a liquid at ambient temperature.
36. E.D. Cox, and J.M. Cook Chem. Rev. 95 1995 1797 1842
37. R. Chicharro, S. de Castro, J.L. Reino, and V.J. Aran Eur. J. Org. Chem. 2003 2314 2326
38. J.A. Willardsen, D.A. Dudley, W.L. Cody, L. Chi, T.B. McClanahan, T.E. Mertz, R.E. Potoczak, L.S. Narasimhan, D.R. Holland, S.T. Rapundalo, and J.J. Edmunds J. Med. Chem. 47 2004 4089 4099
39. 2 (4 equiv) to carry out the final cyclization-upon-reduction reaction at 70°C (for reaction time, see Table 1). The reaction was allowed to proceed until the nitro compounds were completely consumed and cyclized as monitored by TLC. Upon completion of the total three-step synthesis, the solution mixture containing the desired tetrahydro-β- carbolinequinoxalinones was concentrated under reduced pressure and purified by silica gel flash chromatography (ethyl acetate/hexane = 2:3). The final tetrahydro-β-carbolinequinoxalinone products were afforded as a colorless solid with overall isolated yields of 34-55%.
40. For the synthesis of quinoxalin-2-ones in solution, see: J.A. Willardsen, D.A. Dudley, W.L. Cody, L. Chi, T.B. McClanahan, T.E. Mertz, R.E. Potoczak, L.S. Narasimhan, D.R. Holland, S.T. Rapundalo, and J.J. Edmunds J. Med. Chem. 47 2004 4089 4099
41. B.-C. Chen, R. Zhao, M.S. Bednarz, B. Wang, J.E. Sundeen, and J.C. Barrish J. Org. Chem. 69 2004 977 979
42. For the solid-phase synthesis of quinoxalin-2-ones, see: J. Lee, W.V. Murray, and R.A. Rivero J. Org. Chem. 62 1997 3874 3879
43. G.A. Morales, J.W. Gorbett, and W.F. DeGrado J. Org. Chem. 63 1998 1172 1177
44. A. Mazurov Tetrahedron Lett. 41 2000 7 10
45. J. Lee, W.V. Murray, and R.A. Rivero J. Org. Chem. 62 1997 3874 3879
46. Y.H. Cho, and J.C. Park Tetrahedron Lett. 38 1997 8331 8334
47. G.R. Brown, A.J. Foubister, and P.D. Ratcliffe Tetrahedron Lett. 40 1999 1219 1222
48. J.S. Yadav, B.V.S. Reddy, A.K. Basak, and A.V. Narsaiah Tetrahedron Lett. 44 2003 2217 2220