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76649117166
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note
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General procedure for the synthesis of 2-substituted 1,2-dihydro-3-phenyl-1-(trichloromethyl)benzo[b]-[1,6]naphthyridines (2) and N-[(1E)-[2-(phenylethynyl)-3-quinolinyl]methylene]benzen-amine (3): To a mixture of 1 (0.1 g, 0.39 mmol) and 3 Å MS (0.3 g) in chloroform (3 mL) the corresponding amine (0.39 mmol) was added. The reaction mixture was refluxed for 24-48 h. After reaction completion as observed by TLC, the solvent was evaporated to leave the crude product, which was purified by basic silica gel column chromatography using a mixture of toluene and ethyl acetate as an eluent to give 2a-f and 3.
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29
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76649115048
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note
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2: C, 86.72; H, 4.85; N, 8.43. Found: C, 86.91; H, 4.77; N, 8.49.
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30
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34547327918
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Godet T., Vaxelaire C., Michel C., Millet A., and Belmont P. Chem. Eur. J. 13 (2007) 5632
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31
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76649085572
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note
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2: C, 78.87; H, 5.23; N, 4.84. Found: C, 79.00; H, 5.25; N, 4.92.
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32
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62249189642
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Formation of 5-endo-dig cyclization product requires the presence of a base. See:
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Formation of 5-endo-dig cyclization product requires the presence of a base. See:. Kanazawa C., Ito A., and Terada M. Synlett (2009) 638
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Kanazawa, C.1
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70549086798
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Cikotiene I., Buksnaitiene R., Rudys S., Morkunas M., and Motiejaitis D. Tetrahedron 66 (2010) 251
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Cikotiene, I.1
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Motiejaitis, D.5
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35
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76649094649
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The more detailed investigation of regioselectivity of acetalisation-cyclization reactions of 2-alkynylquinoline-3-carbaldehydes together with data of NMR and molecular modeling will be published in due course.
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The more detailed investigation of regioselectivity of acetalisation-cyclization reactions of 2-alkynylquinoline-3-carbaldehydes together with data of NMR and molecular modeling will be published in due course.
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33646470553
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Miranda P.O., Padrón J.M., Padrón J.I., Villar J., and Martín V.S. ChemMedChem 1 (2006) 323
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37
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0025775062
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Monks A., Scudiero D.A., Skehan P., Shoemaker R.H., Paull K.D., Vistica D.T., Hose C., Langley J., Cronice P., Vaigro-Wolf M., Gray-Goodrich M., Campbell H., and Mayo M.R. J. Natl. Cancer Inst. 83 (1991) 757
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Mayo, M.R.13
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38
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76649096752
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note
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50 was established as the concentration of compound that inhibited 50% growth when compared to untreated cells.
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