Multifunctional catalysis of a ruthenium-grafted hydrotalcite: One-pot synthesis of quinolines from 2-aminobenzyl alcohol and various carbonyl compounds via aerobic oxidation and aldol reaction

Tetrahedron Letters

Volumn 45, Issue 31, 2004, Pages 6029-6032

  Motokura, Ken ^a   Mizugaki, Tomoo ^a   Ebitani, Kohki ^a   Kaneda, Kiyotomi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

2 Aminobenzyl alcohol; Heterogeneous catalyst; Hydrotalcite; Molecular oxygen; Quinoline synthesis; Ruthenium

Indexed keywords

2 AMINOBENZYL ALCOHOL; ALCOHOL; CARBONYL DERIVATIVE; HYDROTALCITE; QUINOLINE DERIVATIVE; RUTHENIUM; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; OXIDATION; SYNTHESIS;

EID: 3142700696     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.06.023     Document Type: Article

References (34)

1. Hall N. Science. 266:1994;32
2. For excellent reports of one-pot syntheses, see: Koeller K.M., Wong C.-H. Chem. Rev. 100:2000;4465
3. McCarroll A.J., Walton J.C. Angew. Chem., Int. Ed. 40:2001;2224
4. Kawasaki T., Yamamoto Y. J. Org. Chem. 67:2002;5138
5. Gelman F., Blum J., Avnir D. J. Am. Chem. Soc. 124:2002;14460
6. Balme G., Bossharth E., Monterio N. Eur. J. Org. Chem. 2003;4101
7. For one-pot syntheses using multifunctional heterogeneous catalysts, see: Chen Y.Z., Hwang C.M., Liaw C.W. Appl. Catal. A: General. 169:1998;207
8. Choudary B.M., Chowdari N.S., Madhi S., Kantam M.L. J. Org. Chem. 68:2003;1736
9. A recent review of hydrotalcite catalysts, see: Sels B.F., De Vos D.E., Jacobs P.A. Catal. Rev. 43:2001;443
10. For transition metal-exchanged HT catalysts, see: Kaneda K., Yamashita T., Matsushita T., Ebitani K. J. Org. Chem. 63:1998;1750
11. Matsushita T., Ebitani K., Kaneda K. Chem. Commun. 1999;265
12. Choudary B.M., Madhi S., Chowdari N.S., Kantam M.L., Sreedhar B. J. Am. Chem. Soc. 124:2002;14127
13. For catalyses of basic HTs, see: Choudary B.M., Kantam M.L., Kavita B., Reddy C.V., Rao K.K., Figueras F. Tetrahedron Lett. 39:1998;3555
14. Kantam M.L., Choudary B.M., Reddy C.V., Rao K.K., Figueras F. Chem. Commun. 1998;1033
15. Yamaguchi K., Mori K., Mizugaki T., Ebitani K., Kaneda K. J. Org. Chem. 65:2000;6897
16. Honma T., Nakajo M., Mizugaki T., Ebitani K., Kaneda K. Tetrahedron Lett. 43:2002;6229
17. Motokura K., Nishimura D., Mori K., Mizugaki T., Ebitani K., Kaneda K. J. Am. Chem. Soc. 126:2004;5662
18. Jones G. Katritzky A.R., Rees A.R. Comprehensive Heterocyclic Chemistry. Vol. 2:1984;395 Pergamon, New York
19. Cho C.-S., Kim B.-T., Kim T.-J., Shim S.-C. Chem. Commun. 2001;2576
20. Use of alcohols instead of ketones, see: Cho C.S., Kim B.T., Choi H.-J., Kim T.-J., Shim S.C. Tetrahedron. 59:2003;7997
21. Friedlaender P. Chem. Ber. 15:1882;2572
22. For a review, see: Cheng C.-C., Yan S.-J. Org. React. 28:1982;37
23. Hydrotalcite was available from TOMITA Pharmaceutical Co., Ltd
24. The preparation of the Ru/HT and other Ru catalysts: see Ref. 7
25. We think that the role of triethylamine is neutralization of HCl generated by the chemical absorption of the Ru species onto the HT surface
26. 2 atmosphere. After 20 h, the catalyst was separated by filtration. The filtrate was evaporated, and the crude product was purified by column chromatography (silica gel, ethyl acetate-hexane (1:9) mixture), which afforded the desired product, 2-phenylquinoline (1.82 g, 89% yield)
27. Recycling experiment of the Ru/HT-N is as follows. The reaction of 2-aminobenzyl alcohol (1.0 mmol) and acetophenone (1.2 mmol) in toluene (8 mL) with Ru/HT-N (0.30 g, Ru: 0.03 mmol) and MS4A (0.3 g) was carried out under reflux. After 20 h, the Ru/HT-N was removed by filtration and GC analysis of the filtrate showed an 84% yield of 2-phenylquinoline. The recovered Ru/HT-N was washed with toluene, acetone, and water successively, and then dried in vacuo before reuse. The recycling reaction using the spent Ru/HT-N catalyst afforded the quinoline in 81% GC yield under same reaction conditions
28. For aerobic oxidation of alcohols to carbonyl compounds using supported Ru catalysts, see: Yamaguchi K., Mori K., Mizugaki T., Ebitani K., Kaneda K. J. Am. Chem. Soc. 122:2000;7144
29. Yamaguchi K., Mizuno N. Angew. Chem., Int. Ed. 41:2002;4538
30. Both oxidation and aldol reaction occurred on the Ru/HT surface, because the reactions completely stopped when the solid catalyst was removed by simple filtration
31. A review of transition metal-catalyzed hydrogen transfer reactions, see: Zassinovich G., Mestronl G., Gladiali S. Chem. Rev. 92:1992;1051
32. Stephane C., Desfosses S., Dionne R., Theberge N., Burnell R.H. J. Nat. Prod. 56:1993;138
33. Fournet A., Mahieux R., Fakhfakh M.A., Franck X., Hocquemiller R., Figadére B. Bioorg. Med. Chem. Lett. 13:2003;891
34. Wang W.-B., Lu S.-M., Yang P.-Y., Han X.-W., Zhou Y.-G. J. Am. Chem. Soc. 125:2003;10536