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CDCl 3 ): 1.41 (t, J ¼ 7.1 Hz, 6H, -O-CH 2 -CH 3 ), 4.41 (q, J ¼ 7.1 Hz, 4H, -O-CH 2 -CH 3, p.61 ,
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CDCl 3 ): 0.99 (t, J ¼ 7.3 Hz, 6H, -O-CH 2 -CH 2 -CH 2 -CH 3 ), 1.48 (m, 4H, -O-CH 2 -CH 2 -CH 2 -CH 3, 4H, -O-CH 2 -CH 2 -CH 2 -CH 3 Hz, 4H, -O-CH 2 -CH 2 - CH 2 -CH 3 ), pp.77-90 ,
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Packard 5971A electron impact (70eV) mass spectrometer, equipped with a Hewlett Packard 5890 series II gas chromatograph. 1 H and 13 C nmr spectra were recorded on a Bruker-AC 250-M Hz spectrometer with CDCl 3 or DMSO-d 6 as both solvent and internal reference. The chemical shifts () are expressed in ppm and coupling constants (J) in Hz. Compounds 1-3 were prepared as described in the literature, -Oxo-2H-benzo[h]chromen-4-yl)-acetic acid ,
(2-Oxo-2H-benzo[h]chromen-4-yl)-N-(2-propyn-yl)- acetamide (8) To a solution of (2-oxo-2H-benzo[h]- chromen-4-yl)acetic acid (1 g, 3.93 mmol) in dry dimethylformamide (5 mL) were added N-hydroxysuccinimide (0.476 g, 4.13 mmol) and N,N'-dicyclohexylcarbodiimide (1.7 g, 8.28 mmol) in dimethylformamide (5 mL) The mixture was stirred at room temperature for 24 h, then propargylamine (0.276 mL, 4.02 mmol) was added and left to stir overnight at the same temperature. The formed precipitate was filtered. The obtained filtrate was poured into water, filtrated, washed with water and dried at room temperature until constant weight. Pure product was obtained by cristallisation from diethyl ether. (0.65 g), 57 %, dark beige solid General procedure for the preparation of compounds 9 (ad ) The mixture was refluxed for 4 h, 1H, NH, J=5.3 Hz), 8.38-8.34 (m, 1H), 8.05-8.00 (m, 1H), 7.84 (d, 1H, J=8.7 Hz) Thionyl chloride excess was evaporated in vacuo. To the obtained acid chloride was added toluene (2.13 mL mL), and aluminium chloride, pp.20-22 ,
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31 (s, 2H16 (s, 2H33 (s, 3H, CH 3 ) 13 C nmr (DMSO-d 6 ): 177 General procedure for the preparation of compounds 15 (a-d) Compounds 15a-d were obtained from 2-(2-Oxo-2H- benzo[h]chromen-4-yl)-N-(2-propyn-yl)acetamide 8, using the same procedure as for 12a-d. N-{[1-(4-Benzoylbenzyl)-1H-1, 2H, J=3.9, 1.1 Hz) (t, 1H, NH, J=5.3 Hz), pp.93-100 ,
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