ACCEPTED MANUSCRIPT
m.p. 142-144 oC; 1H-NMR (300 MHz, CDCl3):
δ
12.55 (s, 1H, 5-OH), 7.95 (m, 2H, Ph-H), 7.55 (m,
3H, Ph-H), 7.43 (m, 5H, Ph-H), 6.67 (s, 1H, Ar-H), 6.49 (s, 1H, Ar-H), 5.17 (s, 2H, ArOCH2), 4.16
(t, 2H, J = 5.7 Hz, O-CH2), 2.84 (t, 2H, J = 5.7 Hz, N-CH2), 2.80 - 2.37 (m, 8H, 4 × N-CH2), 2.2 (s,
3H, N-CH3) ppm. IR: 3464 (OH), 3115 (C-H, aromatic), 2973 (CH3), 2932 (CH2), 2792, 2684, 1655
(C=O), 1613 (C=C), 1585 (C=C), 1503, 1449, 1435, 1372, 1337, 1272, 1201, 1115, 1030, 1009, 816,
695 cm-1. ESI-HRMS m/z calculated for C29H31N2O5 [M + H]+ 487.2227, found 487.2231.
7-(Benzyloxy)-8-(3-(dimethylamino)propoxy)-5-hydroxy-2-phenyl-4H-chromen-4-one
(18c). The mixture of 17c (0.53 g, 1.05 mmol), dimethylamine hydrochloride (1 g), K2CO3 (0.6 g,
4.4 mmol) and anhydrous acetonitrile (25 mL) was heated to reflux under stirring. After the end of
the reaction (monitored by TLC), the mixture was filtered immediately, and the filtrate was
concentrated under reduced pressure and purified by chromatography (EA: MeOH = 10: 1) to give
18c as a yellow solid (0. 25 g, 47.40 %). M.p. 208–210 oC; 1H-NMR (300 MHz, DMSO):
δ 12.65 (s,
1H, 5-OH), 8.09 (m, 2H, Ph-H), 7.83 (m, 3H, Ph-H), 7.53 (m, 5H, Ph-H), 7.05 (s, 1H, Ar-H), 6.82 (s,
1H, Ar-H), 5.30 (s, 2H, ArOCH2 ), 4.23 (t, 2H, J = 5.82 Hz, O-CH2), 3.06 (t, 2H, J = 5.82 Hz,
N-CH2), 2.56 (s, 6H, 2×O-CH3) ppm. IR: 3461 (OH), 3124 (C-H, aromatic), 2943 (CH2), 2677, 1663
(C=O), 1610 (C=C), 1509, 1451, 1397, 1374, 1339, 1273, 1227, 1118, 832, 688 cm-1. ESI-HRMS
m/z calculated for C27H28NO5 [M + H]+ 446.1962, found 446.1969.
7-(Benzyloxy)-8-(3-(diethylamino)propoxy)-5-hydroxy-2-phenyl-4H-chromen-4-one (18d).
The mixture of 17d (0.53 g, 1.1 mmol), diethylamine (0.15 g, 2.2 mmol), K2CO3 (0.3 g, 2.2 mmol)
and anhydrous acetonitrile (25 mL) was heated to reflux under stirring. After the end of the reaction
(monitored by TLC), the mixture was filtered immediately, and the filtrate was concentrated under
reduced pressure and purified by chromatography (EA: MeOH = 20: 1) to give 18d as a yellow solid
o
1
(0. 25 g, 52.32 %). m.p. 172–173 C. H-NMR (300 MHz, CDCl3):
δ 12.6 (s, 1H, 5-OH), 7.89 (m,
2H, Ph-H), 7.58 (m, 3H, Ph-H), 7.46 (m, 5H, Ph-H), 6.67 (s, 1H, Ar-H), 6.54 (s, 1H, Ar-H), 5.11 (s,
2H, ArOCH2), 4.14 (t, 2H, J = 5.01 Hz, O-CH2), 3.13 (m, 6H, 3 × N-CH2), 2.38 (m, 2H,
O-CH2-CH2), 1.45 (t, 6H, J = 2.67 Hz, 2 × CH2-CH3) ppm. IR (KBr): 3416 (OH), 3221, 3061 (C-H,
aromatic), 2976 (CH3), 2943 (CH2), 2737, 2652, 2489, 1656 (C=O), 1616 (C=C), 1506, 1450, 1399,
1374, 1340, 1272, 1221, 1121, 1044, 1010, 809, 770, 694, 640 cm-1. ESI-HRMS m/z calculated for
C29H32NO5 [M + H]+ 474.2275, found 474.2287.
22