Molecular Diversity
+
uct was purified by silica gel column chromatography using
dichloromethane/methyl alcohol (40:1) as eluent to give the
pure product compounds 12k–3m. Yield: 80–85%.
186.27 HRMS(ESI) m/z: 434.1960 [M+H] . Purity: 98.2%
by HPLC (MeOH/0.1% TEA 85:15 (v/v)).
(
E)-3-(3-(4-(2-(dimethylamino)ethoxy)-3,5-dimethoxyph
(
E)-3-(3-(4-(2-(dimethylamino)ethoxy)-3-methoxyphenyl)
enyl)acryloyl)-2-chromen-2-one (13k)
acryloyl)-2H-chromen-2-one (12k)
◦
1
Yellow solid, yield: 80.2%, mp: 183.9–185.6 C; H NMR
Brownish yellow solid, yield: 85.6%, mp: 124.9–126.3
(
400 MHz, DCCl3): δ (ppm) 2.62 (6H, s, 2×NCH ), 3.14
3
◦
1
C; H NMR (400 MHz, DCCl3): δ (ppm) 2.62 (6H, s,
(
2H, s, J = 8 Hz, OCH2CH ), 3.82 (6H, s, 2×OCH ), 4.33
2
3
2
×NCH ), 3.15 (2H, t, J = 8 Hz, OCH2CH ), 3.92 (3H,
3
2
(2H, t, J = 8 Hz, OCH CH ), 6.83 (2H, s, H phenyl),
2
2
2,6
s, OCH ), 4.34 (2H, t, J = 8 Hz, OCH CH2), 6.92 (1H, d,
3
2
,8 5,7
7.36–7.43 (2H, m, H6 coumarin), 7.65–7.70 (2H, m, H
J = 8 Hz, H phenyl), 7.20(1H, s, H2 phenyl), 7.25 (1H, d,
5
coumarin), 7.77 (1H, d, J = 16 Hz, Hα), 7.85(1H, d, J =
J = 8 Hz, H6 phenyl), 7.35–7.42 (2H, m, H6,8 coumarin),
13
1
6 Hz, H ), 8.65 (1H, s, H4 coumarin) C NMR (100MHz,
β
7.65–7.69 (2H, m, H5 coumarin), 7.78–7.86 (2H, m, Hα
,7
CDCl3) δ:45.67, 52.46, 56.12, 67.93, 105.68, 116.79, 118.54,
23.71, 125.08, 125.87, 128.73, 130.09, 134.35, 139.91,
42.35, 144.78, 148.18, 153.28, 155.29, 159.44, 186.29
HRMS(ESI) m/z: 424.1759 [M+H] . Purity: 98.8% by
1
3
and H ), 8.59 (1H, s, H4 coumarin) C NMR (100MHz,
β
1
CDCl3) δ:45.46, 55.98, 57.46, 65.77, 110.75, 112.83, 116.67,
1
1
1
1
18.59, 122.03, 123.88, 124.99, 125.47, 128.31, 130.00,
+
34.15, 145.17, 147.85, 149.46, 150.63, 155.15, 159.41,
HPLC (MeOH/0.1% TEA 85:15 (v/v)).
+
86.25. HRMS(ESI) m/z: 394.1651 [M+H] . Purity: 98.5%
by HPLC (MeOH/0.1% TEA 85:15 (v/v)).
(E)-3-(3-(3,5-dimethoxy-4-(2-(pyrrolidin-1-yl)ethoxy)phe
nyl)acryloyl)-2H-chromen-2-one (13l)
(E)-3-(3-(3-methoxy-4-(2-(pyrrolidin-1-yl)ethoxy)
phenyl)acryloyl)-2H-chromen-2-one (12l)
Brownish yellow solid, yield: 80.3%, mp: 274.1–276.4
◦
1
C; H NMR (400 MHz, DCCl3): δ (ppm) 2.22–2.26 (4H,
Brownish yellow solid, yield: 75.2%, mp: 158.9–160.7
◦
1
m, pyrrolidine-H), 3.12–3.20 (4H, m, pyrrolidine-H), 3.62
C; H NMR (400 MHz, DCCl3): δ (ppm) 2.22–2.26 (4H, m,
(
(
7
2H, s, J = 8 Hz, OCH2CH ), 3.90 (6H, s, 2×OCH ), 4.62
pyrrolidine-H), 3.15–3.20 (4H, m, pyrrolidine-H), 3.62 (2H,
2
3
2H, t, J = 8 Hz, OCH CH2), 6.88 (2H, s, H2,6 phenyl),
s, OCH2CH ), 3.92 (3H, s, OCH ), 4.65 (2H, s, OCH CH2),
2
2
3
2
.35–7.41 (2H, m, H6,8 coumarin),7.65–7.74 (2H, m, H
5,7
6
.94 (1H, d, J = 8 Hz, H phenyl), 7.20–7.24 (1H, m,
5
coumarin), 7.77 (1H, d, J = 16 Hz, Hα), 7.85(1H, d, J =
H2,6 phenyl), 7.35–7.41 (2H, m, H6,8 coumarin), 7.65–
1
3
1
6 Hz, H ), 8.57 (1H, s, H4 coumarin) CNMR(100MHz,
β
7
.70 (2H, m, H5,7 coumarin), 7.81 (2H, m, Hα and H ),
β
1
3
CDCl3) δ:23.75, 52.46, 56.05, 67.93, 105.35, 116.75, 118.54,
8.59 (1H, s, H4 coumarin) C NMR (100MHz, CDCl3)
123.71, 125.08, 125.87, 128.75, 130.09, 134.35, 139.91,
δ:23.29, 53.78, 54.60, 55.98, 64.37, 110.80, 114.18, 116.70,
1
42.35, 144.76, 148.18, 153.28, 155.20, 159.35, 186.25
1
1
1
18.57, 122.74, 123.66, 125.05, 125.34, 129.67, 130.07,
34.25, 144.69, 148.03, 149.06, 149.71, 155.18, 159.44,
86.30. HRMS(ESI) m/z: 420.1808 [M+H] . Purity: 98.9%
+
HRMS(ESI) m/z: 450.1915 [M+H] . Purity: 98.2% by
+
HPLC (MeOH/0.1% TEA 85:15 (v/v)).
by HPLC (MeOH/0.1% TEA 85:15 (v/v)).
(E)-3-(3-(3,5-dimethoxy-4-(2-(piperidin-1-yl)ethoxy)phenyl)
(E)-3-(3-(3-methoxy-4-(2-(piperidin-1-yl)ethoxy)
acryloyl)-2H-chromen-2-one (13m)
phenyl)acryloyl)-2H-chromen-2-one (12m)
◦
1
Yellow solid, yield: 78.3%, mp: 214.9–216.7 C; H NMR
◦
1
Yellow solid, yield: 80.6%, mp: 270.9–272.1 C; H NMR
(400 MHz, DCCl3): δ (ppm) 1.26 (6H, s, piperidine-H),
1.63 (4H, s, piperidine-H), 2.33 (2H, s, OCH2CH ), 3.88
(
400 MHz, DCCl3): δ (ppm) 1.26–1.52 (6H, m, piperidine-
2
H),1.74 (4H, s, piperidine-H), 3.01 (2H, t, J = 8 Hz ,
OCH2CH ), 3.92 (3H, s, OCH ), 4.31 (2H, t, J = 8 Hz,
(6H, s, 2×OCH ), 4.36 (2H, s, OCH CH2), 6.87 (2H, s,
3
2
H2,6 phenyl), 7.35–7.41 (2H, m, H6,8 coumarin), 7.65–7.70
(2H, m, H5,7 coumarin), 7.77(1H, d, J = 16 Hz, Hα),
2
3
OCH CH2), 6.91 (1H, d, J = 8 Hz, H phenyl), 7.19
2
5
(
7
1H, s, H2 phenyl), 7.25 (1H, d, J = 8 Hz, H6 phenyl),
7.85(1H, d, J = 16 Hz, H ), 8.59(1H, s, H4 coumarin)
β
1
3
.34–7.40 (2H, m, H6,8 coumarin), 7.64–7.69 (2H, m, H5
C NMR (100MHz, CDCl3) δ:21.33, 23.34, 29.70, 54.00,
,7
coumarin), 7.77–7.85 (2H, m, Hα and H ), 8.57 (1H, s,
56.11, 57.14, 67.93, 105.66, 116.71, 118.54, 123.71, 125.08,
125.87, 128.75, 130.09, 134.35, 139.91, 142.35, 144.76,
148.18, 153.28, 155.20, 159.44, 186.26. HRMS(ESI) m/z:
464.2076 [M+H] . Purity: 99.1% by HPLC (MeOH/0.1%
TEA 85:15 (v/v)).
β
H4 coumarin) 13C NMR (100MHz, CDCl3) δ:23.55, 25.01,
29.70, 54.68, 55.98, 57.12, 65.77, 110.76, 112.80, 116.67,
118.59, 122.03, 123.88, 124.99, 125.47, 128.31, 130.00,
134.15, 145.17, 147.85, 149.46, 150.60, 155.14, 159.41,
+
1
23