Parallel synthesis of substituted imidazoles from 1,2-aminoalcohols

Tetrahedron Letters

Volumn 43, Issue 43, 2002, Pages 7687-7690

  Bleicher, Konrad H ^a   Gerber, Fernand ^a   Wüthrich, Yves ^a   Alanine, Alexander ^a   Capretta, Alfredo ^b  

^a F HOFFMANN LA ROCHE LTD   (Switzerland)

^b BROCK UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; AMINE; AMINOALCOHOL; AZEPINE DERIVATIVE; IMIDAZOLE DERIVATIVE; IMINE;

ACYLATION; ALCOHOL OXIDATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CYCLIZATION; MASS SPECTROMETRY; METHODOLOGY; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0037152291     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01839-7     Document Type: Article

References (15)

1. For a review on imidazoles, see: (a) Grimmet, M. R. In Comprehensive Hetereocyclic Chemistry, Potts, K. T., Ed.; Pergamon Press: Oxford, 1984; Vol. 4, pp. 345-498; (b) Grimmet, M. R. In Comprehensive Hetereocyclic Chemistry II, Shinkai, I., Ed.; Pergamon Press: Oxford, 1996; Vol. 3, pp. 77-220.
2. For a review on imidazoles, see: (a) Grimmet, M. R. In Comprehensive Hetereocyclic Chemistry, Potts, K. T., Ed.; Pergamon Press: Oxford, 1984; Vol. 4, pp. 345-498; (b) Grimmet, M. R. In Comprehensive Hetereocyclic Chemistry II, Shinkai, I., Ed.; Pergamon Press: Oxford, 1996; Vol. 3, pp. 77-220.
3. For examples, see Ref. 1 and (a) Gordon, T. D.; Singh, J.; Hansen, P. E.; Morgan, B. A. Tetrahedron Lett. 1993, 34, 1901-1904; (b) Bilodeau, M. T.; Cunnigham, A. M. J. Org. Chem. 1998, 63, 2800-2801; (c) Njar, V. C. O. Synthesis 2000, 2019-2028; (d) Jetter, M. C.; Reitz, A. B. Synthesis 1998, 829-831.
4. For examples, see Ref. 1 and (a) Gordon, T. D.; Singh, J.; Hansen, P. E.; Morgan, B. A. Tetrahedron Lett. 1993, 34, 1901-1904; (b) Bilodeau, M. T.; Cunnigham, A. M. J. Org. Chem. 1998, 63, 2800-2801; (c) Njar, V. C. O. Synthesis 2000, 2019-2028; (d) Jetter, M. C.; Reitz, A. B. Synthesis 1998, 829-831.
5. For examples, see Ref. 1 and (a) Gordon, T. D.; Singh, J.; Hansen, P. E.; Morgan, B. A. Tetrahedron Lett. 1993, 34, 1901-1904; (b) Bilodeau, M. T.; Cunnigham, A. M. J. Org. Chem. 1998, 63, 2800-2801; (c) Njar, V. C. O. Synthesis 2000, 2019-2028; (d) Jetter, M. C.; Reitz, A. B. Synthesis 1998, 829-831.
6. For examples, see Ref. 1 and (a) Gordon, T. D.; Singh, J.; Hansen, P. E.; Morgan, B. A. Tetrahedron Lett. 1993, 34, 1901-1904; (b) Bilodeau, M. T.; Cunnigham, A. M. J. Org. Chem. 1998, 63, 2800-2801; (c) Njar, V. C. O. Synthesis 2000, 2019-2028; (d) Jetter, M. C.; Reitz, A. B. Synthesis 1998, 829-831.
7. Engel N., Steglich W. Liebigs Ann. Chem. 1978;1916-1927.
8. For examples, see: (a) Andersson, M. A.; Epple, R.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 2002, 41, 472-475; (b) Schaus, S. E.; Larrow, J. F.; Jacobsen, E. N. J. Org. Chem. 1997, 62, 4197.
9. For examples, see: (a) Andersson, M. A.; Epple, R.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 2002, 41, 472-475; (b) Schaus, S. E.; Larrow, J. F.; Jacobsen, E. N. J. Org. Chem. 1997, 62, 4197.
10. General procedure for amide formation. The aminoalcohol (1 mmol), carboxylic acid (1.1 mmol) and EDCI (210 mg, 1.1 mmol) were suspended in acetonitrile (25 ml) and sufficient water was added dropwise to allow for complete dissolution of all the reagents. The reaction mixture was stirred at room temperature for 18 h at which time the solvent was evaporated under a reduced pressure and material used directly in the following step. Alternatively, the residue could be purified by column chromatography using silica gel.
11. 2 (4×40 ml) in a separatory funnel and washed with 0.1N HCl (3×40 ml). The organic layer was then dried with sodium sulphate and evaporated under a reduced pressure. The residue could be purified by column chromatography using silica gel or used directly in the following step.
12. 5 (833 mg, 4 mmol) was added. The mixture was allowed to stir for a further 5 h. The solvent was evaporated under a reduced pressure and the residue suspended in ethyl acetate (3×20 ml) and then washed with 0.1N NaOH (3×20 ml). The organic layer was then dried over sodium sulphate, evaporated under a reduced pressure and the residue purified by column chromatography using silica gel.
13. Love B.E., Ren J. J. Org. Chem. 58:1993;5556-5557.
14. 5 (833 mg, 4 mmol). The mixture was allowed to stir for a further 5 h. The solvent was evaporated under a reduced pressure and the residue suspended in ethyl acetate (3×20 ml) then washed with 0.1N NaOH (3×20 ml). The organic layer was then dried over sodium sulphate, evaporated under a reduced pressure and the residue purified by column chromatography using silica gel.
15. 2: calculated 254.1783, observed 254.1790.