European Journal of Organic Chemistry
10.1002/ejoc.201900480
FULL PAPER
(
E)-ethyl
yl)phenoxy)ethyl)phenyl)acrylate (3aa) Yellow oil; yield: 43.4 mg (56%);
1H NMR (400 MHz, CDCl
) δ 9.13 (s, 1H), 8.70 (s, 2H), 7.65 (d, J=16.0 Hz,
H), 7.49-7.44 (m, 2H), 7.40-7.36 (m, 2H), 7.35-731 (m, 2H), 7.22-7.17 (m,
H), 6.44 (d, J=16.0 Hz, 1H), 4.27 (q, J=7.1 Hz, 2H), 3.72 (s, 2H), 1.34 (t,
) δ 169.2, 166.8, 157.6, 156.3,
47.8, 144.0, 135.1, 133.3, 131.1, 130.9, 130.6, 130.4, 129.4, 128.8, 127.8,
3-(3-(2-oxo-2-(2-(pyrimidin-5-
(E)-ethyl
3-(3-methyl-5-(2-oxo-2-(2-(pyrimidin-5-
yl)phenoxy)ethyl)phenyl)acrylate (3ea) Yellow oil; yield: 64.3 mg (80%);
1H NMR (400 MHz, CDCl
) δ 9.14 (s, 1H), 8.71 (s, 2H), 7.62 (d, J=16.0 Hz,
1H), 7.49-7.44 (m, 1H), 7.40-7.35 (m, 2H), 7.25 (s, 1H), 7.21 (d, J=8.0 Hz,
1H), 7.14 (s, 1H), 6.98 (s, 1H), 6.42 (d, J=16.0 Hz, 1H), 4.26 (q, J=7.1 Hz,
2H), 3.68 (s, 2H), 2.34 (s, 3H), 1.34 (t, J=7.1 Hz, 3H). 13C NMR (100 MHz,
CDCl ) δ 169.3, 166.9, 157.6, 156.3, 147.9, 144.2, 139.2, 135.0, 133.1,
3
131.8, 131.1, 130.6, 130.4, 128.0, 127.8, 127.0, 126.0, 123.2, 118.7, 60.5,
40.9, 21.2, 14.3. HRMS (ESI): calcd for C24
3
3
1
2
J=7.1 Hz, 3H). 13C NMR (100 MHz, CDCl
3
1
1
C
27.2, 127.0, 123.1, 118.9, 60.6, 40.9, 14.3. HRMS (ESI): calcd for
+
+
H N O
23 20 2 4
([M+H] ) 389.1496, found 389.1493.
H N O
22 2 4
([M+H] ) 403.1652,
found 403.1658.
3,3'-(5-(2-oxo-2-(2-(pyrimidin-5-yl)phenoxy)ethyl)-1,3-
phenylene)diacrylate(3aa') Yellow solid; m.p. 61 °C; yield: 19.0 mg
(E)-ethyl
yl)phenoxy)ethyl)phenyl)acrylate (3fa) Orange oil; yield: 62.7 mg (75%);
1H NMR (400 MHz, CDCl
) δ 9.13 (s, 1H), 8.70 (s, 2H), 7.61 (d, J=16.0 Hz,
1H), 7.50-7.46 (m, 1H), 7.41-7.36 (m, 2H), 7.22-7.19 (m, 1H), 6.97 (t, J=1.6
Hz, 1H), 6.93 (s, 1H), 6.72 (t, J=1.6 Hz, 1H), 6.42 (d, J=16.0 Hz, 1H), 4.27
(q, J=7.2 Hz, 2H), 3.82 (s, 3H), 3.68 (s, 2H), 1.35 (t, J=7.2 Hz, 3H). 13
C
3-(3-methoxy-5-(2-oxo-2-(2-(pyrimidin-5-
1
(
19%); H NMR (400 MHz, CDCl
3
) δ 9.13 (s, 1H), 8.71 (s, 2H), 7.64 (d,
J=16.0 Hz, 2H), 7.58 (s, 1H), 7.51-7.47 (m, 1H), 7.40-7.37 (m, 2H), 7.33
d, J=1.2 Hz, 2H), 7.21 (d, J=8.0 Hz, 1H), 6.47 (d, J=16.0 Hz, 2H), 4.28 (q,
J=7.1 Hz, 4H), 3.74 (s, 2H), 1.71 (s, 2H), 1.35 (t, J=7.1 Hz, 6H). 13C NMR
3
(
(
100 MHz, CDCl
3
) δ 168.9, 166.6, 157.6, 156.3, 147.8, 143.1, 135.8, 134.0,
1
1
4
31.1, 130.6, 130.4, 130.1, 127.8, 127.1, 126.7, 123.1, 119.9, 60.7, 40.8,
4.3. HRMS (ESI): calcd for C28H N O ([M+H] ) 487.1864, found
26 2 6
87.1873.
NMR (100 MHz, CDCl
136.3, 134.5, 131.1, 130.6, 130.4, 127.9, 127.0, 123.1, 121.5, 119.2, 116.7,
112.2, 60.6, 55.4, 41.0, 14.3. HRMS (ESI): calcd for C24
([M+H]+)
19.1601, found 419.1610.
3
) δ 169.1, 166.8, 160.2, 157.6, 156.3, 147.8, 144.0,
+
22 2 5
H N O
4
(
E)-ethyl
yl)phenoxy)ethyl)phenyl)acrylate (3ba) Yellow oil; yield: 56.3 mg (70%);
1H NMR (400 MHz, CDCl
) δ 9.13 (s, 1H), 8.70 (s, 2H), 7.93 (d, J=15.9 Hz,
H), 7.49-7.44 (m, 1H), 7.40-7.36 (m, 2H), 7.35-7.34 (m, 1H), 7.20 (d,
J=7.8 Hz, 1H), 7.14 (d, J=7.8 Hz, 1H), 7.06 (dd, J=7.8, 1.7 Hz, 1H), 6.34
3-(4-methyl-3-(2-oxo-2-(2-(pyrimidin-5-
(E)-ethyl
3-(3-fluoro-5-(2-oxo-2-(2-(pyrimidin-5-
3
yl)phenoxy)ethyl)phenyl)acrylate (3ga) White solid; m.p. 79-80 °C;
1
1
yield: 66.6 mg (82%); H NMR (400 MHz, CDCl
3
) δ 9.15 (s, 1H), 8.71 (s,
2H), 7.59 (d, J=16.0 Hz, 1H), 7.51-7.47 (m, 1H), 7.42-7.37 (m, 2H), 7.24-
7.20 (m, 1H), 7.15 (dt, J=8.8, 2.0 Hz, 1H), 7.09 (s, 1H), 6.90 (dt, J=8.8, 2.0
Hz, 1H), 6.43 (d, J=16.0 Hz, 1H), 4.28 (q, J=7.2 Hz, 2H), 3.71 (s, 2H), 1.35
(
(
1
1
C
d, J=15.9 Hz, 1H), 4.28 (q, J=7.1 Hz, 2H), 3.68 (s, 2H), 2.43 (s, 3H), 1.35
t, J=7.1 Hz, 3H). 13C NMR (100 MHz, CDCl
) δ 169.4, 166.9, 157.5, 156.3,
47.9, 141.8, 136.9, 133.9, 131.3, 131.1, 130.6, 130.5, 130.3, 127.9, 127.1,
3
(t, J=7.2 Hz, 3H). 13C NMR (100 MHz, CDCl
3
) δ 168.6, 166.4, 163.0 (d,
27.0, 123.2, 119.9, 60.5, 40.7, 19.5, 14.3. HRMS (ESI): calcd for
J=246.3 Hz), 157.7, 156.3, 147.7, 142.6 (d, J=2.7 Hz), 137.1 (d, J=8.2 Hz),
135.3 (d, J=8.1 Hz), 131.0, 130.6, 130.4, 127.8, 127.1, 124.8 (d, J=2.6 Hz),
+
H N O
24 22 2 4
([M+H] ) 403.1652, found 403.1663.
1
23.1, 120.3, 117.8 (d, J=22.2 Hz), 113.6 (d, J=21.9 Hz), 60.7, 40.7, 14.3.
+
HRMS (ESI): calcd for C23
H19FN O
2 4
([M+H] ) 407.1402, found 407.1417.
(
E)-ethyl
yl)phenoxy)ethyl)phenyl)acrylate (3ca) Yellow oil; yield: 59.4 mg (71%);
1H NMR (400 MHz, CDCl
) δ 9.19 (s, 1H), 8.75 (s, 2H), 7.61 (d, J=16.0 Hz,
H), 7.49-7.43 (m, 2H), 7.39-7.36 (m, 2H), 7.32 (d, J=2.0 Hz, 1H), 7.23 (d,
3-(4-methoxy-3-(2-oxo-2-(2-(pyrimidin-5-
3
(E)-ethyl
3-(3-chloro-5-(2-oxo-2-(2-(pyrimidin-5-
1
yl)phenoxy)ethyl)phenyl)acrylate (3ha) White solid; m.p. 81-82 °C;
1
J=7.9 Hz, 1H), 6.86 (d, J=8.5 Hz, 1H), 6.31 (d, J=16.0 Hz, 1H), 4.25 (q,
J=7.1 Hz, 2H), 3.81 (s, 3H), 3.73 (s, 2H), 1.33 (t, J=7.1 Hz, 3H). 13C NMR
yield: 66.0 mg (78%); H NMR (400 MHz, CDCl
3
) δ 9.16 (s, 1H), 8.71 (s,
2H), 7.57 (d, J=16.0 Hz, 1H), 7.51-7.47 (m, 1H), 7.44 (t, J=1.6 Hz, 1H),
7.40-7.36 (m, 2H), 7.23-7.20 (m, 1H), 7.19 (s, 1H), 7.16 (t, J=1.6 Hz, 1H),
6.44 (d, J=16.0 Hz, 1H), 4.27 (q, J=7.2 Hz, 2H), 3.69 (s, 2H), 1.34 (t, J=7.2
Hz, 3H). 13C NMR (100 MHz, CDCl
142.4, 136.7, 135.2, 134.9, 131.0, 130.7, 130.6, 130.4, 127.8, 127.2, 127.1,
(
100 MHz, CDCl
3
) δ 169.4, 167.2, 159.1, 157.5, 156.4, 148.0, 143.9, 131.3,
1
6
4
30.5, 130.4, 130.3, 129.6, 127.7, 127.2, 126.8, 123.3, 122.4, 116.2, 110.8,
0.4, 55.7, 36.0, 14.4. HRMS (ESI): calcd for C24
H N O
22 2 5
([M+H]+)
3
) δ 168.6, 166.4, 157.7, 156.3, 147.7,
19.1601, found 419.1614.
1
27.0, 123.1, 120.4, 60.8, 40.5, 14.3. HRMS (ESI): calcd for C23
H19ClN O
2 4
+
([M+H] ) 423.1106, found 423.1113.
(
E)-ethyl
yl)phenoxy)ethyl)phenyl)acrylate (3da) Yellow oil; yield: 60.0 mg (64%);
1H NMR (400 MHz, CDCl
) δ 9.19 (s, 1H), 8.74 (s, 2H), 7.59 (d, J = 7.9 Hz,
H), 7.57 (s, 1H), 7.51-7.47 (m, 1H), 7.42-7.37 (m, 2H), 7.34-7.31 (m, 3H),
.44 (d, J=16.0 Hz, 1H), 4.27 (q, J=7.1 Hz, 2H), 3.90 (s, 2H), 1.34 (t, J=7.1
) δ 168.1, 166.6, 157.7, 156.4, 147.8,
42.7, 134.3, 133.7, 133.6, 131.2, 130.9, 130.6, 130.4, 128.4, 127.8, 127.0,
3-(4-bromo-3-(2-oxo-2-(2-(pyrimidin-5-
3
(E)-ethyl
3-(3-bromo-5-(2-oxo-2-(2-(pyrimidin-5-
1
6
yl)phenoxy)ethyl)phenyl)acrylate (3ia) White solid; m.p. 83-84 °C; yield:
1
66.3 mg (71%); H NMR (400 MHz, CDCl
3
) δ 9.16 (s, 1H), 8.71 (s, 2H),
Hz, 3H). 13C NMR (101 MHz, CDCl
7.60 (t, J=1.6 Hz, 1H), 7.56 (d, J=16.0 Hz, 1H), 7.51-7.47 (m, 1H), 7.42-
7.36 (m, 2H), 7.31 (t, J=1.6 Hz, 1H), 7.23 (t, J=2.0 Hz, 1H), 7.22-7.20 (m,
1H), 6.43 (d, J = 16.0 Hz, 1H), 4.27 (q, J = 7.2 Hz, 2H), 3.69 (s, 2H), 1.34
3
1
1
26.7, 123.2, 119.6, 60.7, 41.5, 14.3. HRMS (ESI): calcd for C23
H19BrN O
2 4
+
(t, J = 7.2 Hz, 3H). 13C NMR (100 MHz, CDCl
([M+H] ) 467.0601, found 467.0609.
3
) δ 168.5, 166.4, 157.7, 156.2,
1
1
C
47.7, 142.3, 136.9, 135.1, 133.5, 131.0, 130.6, 130.4, 129.9, 127.8, 127.5,
27.1, 123.3, 123.1, 120.4, 60.7, 40.5, 14.3. HRMS (ESI): calcd for
(
2E,2'E)-diethyl
3,3'-(4-bromo-5-(2-oxo-2-(2-(pyrimidin-5-
+
H19BrN O
23 2 4
([M+H] ) 467.0601, found 467.0602.
yl)phenoxy)ethyl)-1,3-phenylene)diacrylate (3da´) White solid; m.p. 84-
8
1
5 °C; yield: 12.3 mg (11%); H NMR (400 MHz, CDCl
3
) δ 9.19 (s, 1H), 8.73
(s, 2H), 8.02 (d, J=15.9 Hz, 1H), 7.64 (d, J=2.0 Hz, 1H), 7.60 (d, J=16.0
(E)-ethyl
3-(3-(2-oxo-2-(2-(pyrimidin-5-yl)phenoxy)ethyl)-5-
Hz, 1H), 7.51-7.46 (m, 1H), 7.40-7.36 (m, 3H), 7.28-7.26 (m, 1H), 6.49 (d,
J=16.0 Hz, 1H), 6.40 (d, J=15.9 Hz, 1H), 4.33-4.25 (m, 4H), 3.96 (s, 2H),
(trifluoromethyl)phenyl)acrylate (3ja) White solid; m.p. 113-114 °C;
1
yield: 61.3 mg (67%); H NMR (400 MHz, CDCl
3
) δ 9.14 (s, 1H), 8.71 (s,
1
1
1
1
5
.38-1.33 (m, 6H). 13C NMR (100 MHz, CDCl
57.7, 156.4, 147.8, 142.8, 142.1, 136.7, 135.2, 134.1, 131.4, 131.2, 130.6,
30.4, 129.0, 127.8, 127.1, 126.5, 123.2, 122.6, 120.4, 60.9, 60.8, 42.3,
3
) δ 168.0, 166.4, 166.0,
2H), 7.70 (s, 1H), 7.66 (d, J=16.0 Hz, 1H), 7.52-7.47 (m, 2H), 7.45 (s, 1H),
7.43-7.38 (m, 2H), 7.23-7.21 (m, 1H), 6.51 (d, J=16.0 Hz, 1H), 4.29 (q,
J=7.2 Hz, 2H), 3.79 (s, 2H), 1.35 (t, J=7.2 Hz, 3H). 13C NMR (100 MHz,
+
2
4.3. HRMS (ESI): calcd for C28H25BrN O
6
([M+H] ) 565.0969, found
CDCl
3
) δ 168.5, 166.3, 157.7, 156.3, 147.7, 142.2, 136.0, 134.3, 132.0 (q,
65.0973.
J=32.4 Hz), 131.9, 131.0, 130.6, 130.5, 127.8, 127.3 (q, J=3.5 Hz), 127.2,
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