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Journal of Combinatorial Chemistry
Volumn 10, Issue 3, 2008, Pages 372-375
Click chemistry approach to assembly proline mimetic libraries containing 1,4-substituted 1,2,3-triazoles
Author keywords

[No Author keywords available]
Indexed keywords

DRUG DERIVATIVE; PROLINE; TRIAZOLE DERIVATIVE;
EID: 45149084105     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc800035z     Document Type: Article
Times cited : (13)
References (51)
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    • (a) Boger, D. L.; Weinreb, S. M. In Hetero Diels-Alder Methodology in Organic Synthesis; Organic Chemistry Monograph 47; Wasserman, H. H., Ed.; Academic Press: New York, 1987.
    • (1987) Organic Chemistry Monograph , vol.47
    • Boger, D.L.1    Weinreb, S.M.2
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    • Trost, B. M, Fleming, I, Paquette, L. A, Eds, Pergamon Press: Oxford, U.K
    • (b) Weinreb, S. M. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I.; Paquette, L. A., Eds.; Pergamon Press: Oxford, U.K, 1991; Vol. 5, pp 401-449.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 401-449
    • Weinreb, S.M.1
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    • Rodriguez-Borges, J. E.; G.-Mera, X.; Fernandez, F.; Lopes, V. H. C.; Magalhães, A. L.; Cordeiro, M. N. D. S. Tetrahedron 2005, 61, 10951-10957, and references therein.
    • (e) Rodriguez-Borges, J. E.; G.-Mera, X.; Fernandez, F.; Lopes, V. H. C.; Magalhães, A. L.; Cordeiro, M. N. D. S. Tetrahedron 2005, 61, 10951-10957, and references therein.
  • 15
    • 13844274936 scopus 로고    scopus 로고
    • Fernandez, F.; G.-Mera, X.; Vale, M. L. C.; Rodriguez-Borges, J. E. Synlett 2005, 2, 319-321, and references therein.
    • (f) Fernandez, F.; G.-Mera, X.; Vale, M. L. C.; Rodriguez-Borges, J. E. Synlett 2005, 2, 319-321, and references therein.
  • 16
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    • For representative examples see: a
    • For representative examples see: (a) Maison, W. Eur. J. Org. Chem. 2007, 2276-2284.
    • (2007) Eur. J. Org. Chem , pp. 2276-2284
    • Maison, W.1
  • 30
    • 45149111034 scopus 로고    scopus 로고
    • General procedure for the synthesis of N-propargyl-2-azabicyclo[2, 2,1]hept-5-ene-2-carboxylates 2a-f: A solution of propargyl amine (3.20 mL, 47 mmol) in dry CH2Cl2 (30 mL) was added under argon to a stirred suspension of glyoxylate/hydrate (47 mmol) and 3 Å molecular sieves (29 g) in dry CH2Cl2 (140 mL) at 0°C. When the addition was complete the reaction mixture was cooled to-78°C and treated successively with trifluoroacetic acid (3.60 mL, 47 mmol, boron trifluoride etherate (5.90 mL, 47 mmol, and freshly distilled cyclopentadiene (7.5 mL, 91 mmol, After 6 h, saturated aqueous NaHCO3 solution (120 mL) and then solid NaHCO3 (12 g) were added. The reaction mixture was allowed to reach room temperature and filtered through a pad of Celite, and the organic layer of the resulting mixture was separated. The aqueous layer was extracted with CH2Cl2 3 x 100 mL, The pooled
    • 4. Removal of the solvent on a rotary evaporator left an oily residue that upon chromatography on silica gel using a (19:1) hexane/EtOAc mixture as eluent afforded pure exo-adduct in the early fractions and the endo-adduct in the latter ones, both as colourless oils.
  • 31
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    • Complete description of the spectroscopic and analytical data of all compounds described is included in the Supporting Information
    • Complete description of the spectroscopic and analytical data of all compounds described is included in the Supporting Information.
  • 51
    • 45149109646 scopus 로고    scopus 로고
    • General procedure for the Cu-catalyzed Huisgen cycloaddition between N-propargyl-2-azabicyclo[2,2,1]-5-ene-2-carboxylates (2a-f) and azides (3a-c, To a Kimble vial containing a solution of the N-propargyl-2-azabicyclo[2,2,1]hept-5-ene-2-carboxylates 2a-e (0.38 mmol) in 3 mL of a THF/H2O (5:1, a mixture of the corresponding azide (3a-c, 0.38 mmol, sodium ascorbate (0.08 mmol, and CuSO4·5H2O (0.04 mmol) were added. The reaction mixture was orbitally stirred, at 40°C, until reactions reached completion (2-5 h, filtered through a Celite pad, and successively washed (5 mL) with THF, CH2Cl2, MeOH, and AcOEt. Evaporation of the solvents afforded an oily residue that was diluted with CH2Cl2 (10 mL, treated with PS-TMG 500 mg, and stirred for 0.5 h to remove the copper salts. Isolation of the desired 1,2,3-triazoles 4a-r was accomplished by preparativ
    • 2 (10 mL), treated with PS-TMG (500 mg), and stirred for 0.5 h to remove the copper salts. Isolation of the desired 1,2,3-triazoles 4a-r was accomplished by preparative chromatography.

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