Kamal et al.
phenylboronic acid 15e (0.062 g, 0.39 mmol)) to give 16l as
yellow solid; 0.113 g; 70% yield; Mp: 154–159 °C; FT‒IR
(cmꢀ1) 3454, 1650, 1573, 1478, 1297, 1030, 788; 1H NMR
(500 MHz, CDCl3): d = 7.66 (d, J = 15.41 Hz, 1H), 7.58 (d,
J = 8.39 Hz, 1H), 7.56 (s, 1H), 7.35 (d, J = 4.73 Hz, 2H),
7.32–7.29 (m, 2H), 7.27 (s, 1H), 7.16 (d, J = 5.64 Hz, 1H),
6.97 (d, J = 8.24 Hz, 1H), 6.81 (s, 1H), 6.07 (s, 2H), 3.95 (s,
3H); 13C NMR (125 MHz, CDCl3): 188.40, 150.20, 149.30,
147.81, 146.79, 142.20, 141.59, 137.57, 134.98, 134.20,
130.88, 129.72, 129.45, 128.26, 127.67, 127.21, 123.51,
121.28, 113.65, 110.40, 110.25, 105.85, 101.78, 56.03;
MS–ESIMS: m/z 409 (M + H)+. HR ESIMS: m/z calcd for
(E)-1-(4-methoxyphenyl)-3-(6-(4-methoxyphenyl)
benzo[d][1,3]dioxol-5-yl)prop-2-en-1-one 16o
The compound 16o was prepared according to the
method described for compound 16a employing (E)-3-(6-
bromobenzo[d][1,3]dioxol-5-yl)-1-(4-methoxyphenyl)prop-2-
en-1-one 14c (0.15 g, 0.41 mmol)) and 4-meth-
oxyphenylboronic acid 15a (0.063 g, 0.41 mmol)) to give
16o as yellow solid; 0.116 g; 72% yield; Mp: 154–159 °C;
FT‒IR (cmꢀ1) 2921, 1653, 1604, 1481, 1168, 1028, 826; 1H
NMR (300 MHz, CDCl3): d = 7.98 (d, J = 9.06 Hz, 2H),
7.77 (d, J = 15.108 Hz, 1H), 7.33 (d, J = 15.864 Hz, 1H),
7.29 (s, 1H), 7.20 (d, J = 9.06 Hz, 2H), 6.95 (d,
J = 8.30 Hz, 4H), 6.83 (s, 1H), 6.05 (s, 2H), 3.88 (s, 3H),
3.85 (s, 3H); 13C NMR (75 MHz, CDCl3): 188.51, 163.14,
159.07, 149.18, 147.14, 143.13, 140.25, 139.08, 132.07,
131.13, 130.97, 130.62, 127.07, 124.68, 120.64, 113.71,
113.66, 110.37, 105.72, 101.56, 55.39, 55.24; MS–ESIMS:
m/z 389 (M + H)+. HR ESIMS: m/z calcd for C24H21O5:
389.1383; found: 389.1391.
C
23H18ClO5: 409.0848; found: 409.0842.
(E)-3-(6-(2-fluoro-5-methylphenyl)benzo[d][1,3]
dioxol-5-yl)-1-(4-hydroxy-3-methoxyphenyl)prop-2-
en-1-one 16m
The compound 16m was prepared according to the method
described for compound 16a employing (E)-3-(6-bro-
mobenzo[d][1,3]dioxol-5-yl)-1-(4-hydroxy-3-methoxy-
phenyl)prop-2-en-1-one 14b (0.15 g, 0.39 mmol)) and
(E)-1-(4-methoxyphenyl)-3-(6-(3,4,5-
2-fluoro-5-methylphenylboronic
acid
15f
(0.061 g,
trimethoxyphenyl)benzo[d][1,3]dioxol-5-yl)prop-2-
en-1-one 16p
0.39 mmol)) to give 16m as yellow solid; 0.109 g; 68% yield;
Mp: 164–169 °C; FT‒IR (cmꢀ1) 3280, 1649, 1577, 1480,
1168, 1034, 815; 1H NMR (300 MHz, CDCl3): d = 7.59 (dd,
J = 7.55, 1.13 Hz, 1H), 7.54 (s, 2H), 7.35–7.27 (m, 2H),
7.14 (m, 1H), 7.05–6.97 (m, 2H), 6.94 (d, J = 8.12 Hz, 1H),
6.80 (s, 1H), 6.13 (s, 1H), 6.06 (s, 2H), 3.93 (s, 3H), 2.34 (s,
3H); 13C NMR (125 MHz, CDCl3): 188.63, 150.13, 149.20,
147.93, 146.74, 142.08, 133.50, 132.76, 132.32, 130.97,
130.27, 130.21, 127.94, 126.21, 123.53, 121.04, 115.52,
115.35, 113.66, 110.85, 110.44, 105.48, 101.74, 56.01,
20.61; MS–ESIMS: m/z 407 (M + H)+. HR ESIMS: m/z calcd
for C24H20FO5: 407.1289; found: 407.1288.
The compound 16p was prepared according to the
method described for compound 16a employing (E)-3-(6-
bromobenzo[d][1,3]dioxol-5-yl)-1-(4-methoxyphenyl) prop-
2-en-1-one 14c (0.15 g, 0.41 mmol)) and 3,4,5-trim-
ethoxyphenylboronic acid 15b (0.088 g, 0.41 mmol)) to
give 16p as yellow solid; 0.148 g; 80% yield; Mp: 179–
183 °C; FT‒IR (cmꢀ1) 2925, 1659, 1585, 1482, 1136,
1030, 822; 1H NMR (300 MHz, CDCl3): d = 7.97 (d,
J = 9.065 Hz, 2H), 7.83 (d, J = 15.108 Hz, 1H), 7.34 (d,
J = 15.108 Hz, 1H), 7.29 (s, 1H), 6.96 (d, J = 9.065 Hz,
2H), 6.88 (s, 1H), 6.49 (s, 2H), 6.07 (s, 2H), 3.91 (s, 3H),
3.88 (s, 3H), 3.85 (s, 6H); 13C NMR (75 MHz, CDCl3):
188.54, 163.20, 152.81, 149.08, 147.40, 142.92, 139.04,
135.27, 131.0, 130.58, 127.08, 120.96, 113.69, 110.19,
107.26, 105.74, 101.64, 60.88, 56.14, 55.39; MS–ESIMS:
m/z 449 (M + H)+. HR ESIMS: m/z calcd for C26H25O7:
449.1594; found: 449.1589.
(E)-3-(6-(2,4-dichlorophenyl)benzo[d][1,3]dioxol-5-
yl)-1-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one
16n
The compound 16n was prepared according to the
method described for compound 16a employing (E)-3-(6-
bromobenzo[d][1,3]dioxol-5-yl)-1-(4-hydroxy-3-methoxy-
phenyl)prop-2-en-1-one 14b (0.15 g, 0.39 mmol)) and
2,4-dichlorophenylboronic acid 15g (0.075 g, 0.39 mmol))
to give 16n as yellow solid; 0.124 g; 71% yield; Mp: 137–
142 °C; FT‒IR (cmꢀ1) 3417, 1644, 1573, 1471, 1300,
1037; 1H NMR (300 MHz, CDCl3): d = 7.53 (dd, J = 6.56,
1.83 Hz, 2H), 7.49 (d, J = 1.98 Hz, 1H), 7.39 (d,
J = 15.41 Hz, 1H), 7.31 (d, J = 1.67 Hz, 2H), 7.29 (t,
J = 2.59 Hz, 1H), 7.16 (d, J = 8.24 Hz, 1H), 6.94 (d,
J = 8.69 Hz, 1H), 6.71 (s, 1H), 6.08 (s, 2H), 3.93 (s, 3H);
13C NMR (125 MHz, CDCl3): 188.16, 150.31, 149.15,
148.16, 146.79, 141.18, 136.87, 134.84, 134.49, 132.60,
129.57, 127.83, 127.07, 123.52, 121.08, 119.59, 113.72,
110.46, 110.37, 105.51, 101.88, 56.02; MS–ESIMS: m/z
443 (M + H)+. HR ESIMS: m/z calcd for C23H17Cl2O5:
443.0447; found: 443.0453.
(E)-3-(5,50-bibenzo[d][1,3]dioxol-5-yl)-1-(4-
methoxyphenyl)prop-2-en-1-one 16q
The compound 16q was prepared according to the method
described for compound 16a employing (E)-3-(6-bro-
mobenzo[d][1,3]dioxol-5-yl)-1-(4-methoxyphenyl)prop-2-en-
1-one 14c (0.15 g, 0.41 mmol)) and benzo[d][1,3]dioxol-5-
ylboronic acid 15c (0.068 g, 0.41 mmol)) to give 16q as yel-
low solid; 0.11 g; 66% yield; Mp: 196–201 °C; FT‒IR (cmꢀ1
)
2898, 1651, 1604, 1484, 1168, 1026, 824; 1H NMR
(300 MHz, CDCl3): d = 8.13 (d, J = 8.68 Hz, 2H), 7.78 (d,
J = 10.38 Hz, 2H), 7.59 (d, J = 55.29 Hz, 1H), 7.06 (d,
J = 8.87 Hz, 2H), 7.0 (d, J = 7.73 Hz, 1H), 6.88 (d,
J = 12.46 Hz, 2H), 6.72 (d, J = 9.25 Hz, 1H), 6.14 (s, 2H),
6.10 (s, 2H), 3.86 (s, 3H); 13C NMR (75 MHz, CDCl3):
185.36, 161.13, 147.11, 145.36, 144.88, 139.5, 136.67,
1272
Chem Biol Drug Des 2015; 86: 1267–1284