Organic & Biomolecular Chemistry
DOI: 10.1039/C6OB00013D
6
4
1
.51ꢀ6.48 (m, 1H), 6.33 (d, J = 8.5 Hz, 1H), 3.44 (t, J = 6.5 Hz,
(125 MHz, CDCl ) δ 160.8, 151.2, 138.9, 129.8, 128.5 (2C),
3
1
3
H), 2.00ꢀ1.98 (m, 4H). C NMR (125 MHz, CDCl ) δ 157.2,
126.8, 126.7 (2C), 105.6, 101.4, 99.0, 56.6, 55.0, 38.5.
Compound 7e: pale yellow liquid (148.0 mg, 88%). H NMR
3
1
48.1, 136.7, 110.9, 106.4, 46.5 (2C), 25.4 (2C).
Compound 6a : pale yellow liquid (103.3 mg, 92%). H NMR
8a
1
(500 MHz, CDCl , TMS) δ 7.29ꢀ7.19 (m, 5H), 7.07 (t, J = 8.5 Hz,
3
5
0
5
0
5
0
5
0
5
0
5
0
5
(500 MHz, CDCl , TMS) δ 7.24 (t, J = 8.0 Hz, 2H), 6.93 (d, J = 70 1H), 6.20ꢀ6.15 (m, 2H), 6.10 (t, J = 2.0 Hz, 1H), 4.49 (s, 2H),
3
13
8
1
.0 Hz, 2H), 6.81 (t, J = 8.0 Hz, 1H), 3.14 (t, J = 5.0 Hz, 4H),
.72ꢀ1.68 (m, 4H), 1.59ꢀ1.54 (m, 2H). C NMR (125 MHz,
2.98 (s, 3H), 2.87 (s, 6H). C NMR (125 MHz, CDCl ) δ 151.8,
3
1
3
150.9, 139.5, 129.6, 128.4 (2C), 126.8 (2C), 126.7, 102.3, 102.2,
97.5, 56.9, 40.7, 38.5. IR (neat) ν 2920, 2862, 2802, 2386, 2352,
1602, 1574, 1506, 1447, 1180, 1157, 1121, 1008, 983, 969, 805,
CDCl ) δ 152.2, 128.9 (2C), 119.1, 116.5 (2C), 50.6 (2C), 25.8
3
(2C), 24.3.
11
1
ꢀ1
+
1
1
2
2
3
3
4
4
5
5
6
6
Compound 6b : pale yellow liquid (119.1 mg, 97%). H NMR 75 732 cm . MS (DART Positive): 240 (M ). HRMS (DART
500 MHz, CDCl , TMS) δ 7.12 (t, J = 7.5 Hz, 1H), 6.75ꢀ6.73 (m,
Positive): Calcd. for C H N : 241.1699; found: 241.1697.
(
3
16 21
2
8b
1
2
3
H), 6.64 (d, J = 7.5 Hz, 1H), 3.12 (t, J = 5.5 Hz, 4H), 2.30 (s,
Compound 7f : colorless liquid (141.8 mg, 96%). H NMR
1
3
H), 1.71ꢀ1.66 (m, 4H), 1.57ꢀ1.53 (m, 2H). C NMR (125 MHz,
(500 MHz, CDCl , TMS) δ 7.38 (d, J = 7.5 Hz, 2H), 7.32 (t, J =
3
CDCl ) δ 152.3, 138.5, 128.8, 120.1, 117.4, 113.6, 50.7 (2C),
7.5 Hz, 2H), 7.25 (d, J = 7.0 Hz, 1H), 7.19 (t, J = 7.5 Hz, 1H),
80 7.16 (t, J = 8.0 Hz, 1H), 7.08 (d, J = 8.0 Hz, 1H), 6.98 (t, J = 7.5
Hz, 1H), 4.03 (s, 2H), 2.58 (s, 3H), 2.40 (s, 3H). C NMR (125
3
25.9 (2C), 24.3, 21.7.
8a
1
13
Compound 6c : pale yellow liquid (108.7 mg, 89%). H NMR
(
500 MHz, CDCl , TMS) δ 7.04 (d, J = 8.5 Hz, 2H), 6.85 (d, J =
MHz, CDCl ) δ 152.4, 139.1, 132.9, 131.1, 128.3 (2C), 128.2
3
3
8
4
.5 Hz, 2H), 3.07 (t, J = 5.5 Hz, 4H), 2.25 (s, 3H), 1.72ꢀ1.67 (m,
(2C), 126.9, 126.4, 123.0, 120.1, 60.8, 40.9, 18.4.
Compound 7g : pale yellow liquid (102.6 mg, 74%). H NMR
1
3
7c
1
H), 1.56ꢀ1.52 (m, 2H). C NMR (125 MHz, CDCl ) δ 150.2,
3
129.5, 128.6, 116.9, 51.2 (2C), 25.9 (2C), 24.3, 20.3.
Compound 6d : pale yellow liquid (127.5 mg, 95%). H NMR
85 (500 MHz, CDCl , TMS) δ 7.41 (d, J = 2.0 Hz, 1H), 7.40ꢀ7.38
3
8a
1
(m, 1H), 7.28 (t, J = 7.5 Hz, 2H), 7.23ꢀ7.20 (m, 3H), 6.54 (dd, J =
7.0, 5.0 Hz, 1H), 6.48 (d, J = 8.5 Hz, 1H), 4.78 (s, 2H), 3.04 (s,
(
500 MHz, CDCl , TMS) δ 7.14 (t, J = 8.0 Hz, 1H), 6.54 (d, J =
3
13
8
3
.0 Hz, 1H), 6.47 (s, 1H), 6.37 (d, J = 8.0 Hz, 1H), 3.77 (s, 3H),
.14 (t, J = 5.0 Hz, 4H), 1.70ꢀ1.66 (m, 4H), 1.58ꢀ1.53 (m, 2H).
3H). C NMR (125 MHz, CDCl ) δ 158.8, 147.9, 138.6, 137.21,
3
137.20, 128.4 (2C), 126.9, 126.8, 111.7, 105.6, 53.1, 36.0.
1
3
8a
1
C NMR (125 MHz, CDCl ) δ 160.5, 153.5, 129.5, 109.2, 103.9,
90
Compound 8a : pale yellow liquid (124.4 mg, 97%). H NMR
3
1
02.7, 55.0, 50.5 (2C), 25.7 (2C), 24.3.
(500 MHz, CDCl , TMS) δ 7.25ꢀ7.22 (m, 4H), 7.00 (dd, J = 8.0,
1.0 Hz, 4H), 6.92 (td, J = 7.5, 1.0 Hz, 2H), 3.27 (s, 3H). C NMR
3
12
1
13
Compound 6e : colorless liquid (115.2 mg, 94%). H NMR
500 MHz, CDCl , TMS) δ 7.16ꢀ7.12 (m, 2H), 6.99 (d, J = 8.0
(
(125 MHz, CDCl ) δ 149.1 (2C), 129.2 (4C), 121.3 (2C), 120.5
3
3
Hz, 1H), 6.93 (t, J = 7.5 Hz, 1H), 2.83 (t, J = 5.0 Hz, 4H), 2.30 (s,
3H), 1.72ꢀ1.68 (m, 4H), 1.58ꢀ1.53 (m, 2H). C NMR (125 MHz,
(4C), 40.2.
1
3
8a
1
95
Compound 8b : colorless liquid (131.9 mg, 96%). H NMR
CDCl ) δ 152.9, 132.7, 130.9, 126.4, 122.6, 119.0, 53.4 (2C),
(500 MHz, CDCl , TMS) δ 7.25 (t, J = 8.0 Hz, 2H), 7.16 (t, J =
3
3
2
6.6 (2C), 24.4, 17.8.
8.0 Hz, 1H), 6.99 (d, J = 8.0 Hz, 2H), 6.93 (t, J = 7.5 Hz, 1H),
6.85ꢀ6.82 (m, 2H), 6.78 (d, J = 7.5 Hz, 1H), 3.29 (s, 3H), 2.30 (s,
7c
1
Compound 6f : pale yellow liquid (85.1 mg, 75%). H NMR
500 MHz, CDCl , TMS) δ 8.17 (dd, J = 5.0, 1.5 Hz, 1H), 7.45ꢀ
13
(
3H). C NMR (125 MHz, CDCl ) δ 149.2, 149.1, 139.0, 129.1
3
3
7.41 (m, 1H), 6.64 (d, J = 8.5 Hz, 1H), 6.55 (dd, J = 7.5, 5.0 Hz, 100 (2C), 129.0, 122.4, 121.5, 120.9, 120.1 (2C), 117.9, 40.2, 21.5.
1
3
8a
1
1
H), 3.52 (t, J = 4.5 Hz, 4H), 1.64 (s, 6H). C NMR (125 MHz,
Compound 8c : pale yellow liquid (126.4 mg, 85%). H NMR
CDCl ) δ 159.7, 147.8, 137.2, 112.3, 107.0, 46.2 (2C), 25.4 (2C),
(500 MHz, CDCl , TMS) δ 7.28 (t, J = 8.0 Hz, 2H), 7.15 (t, J =
3
3
2
4.7.
Compound 6g : pale yellow liquid (90.7 mg, 80%). H NMR
8.0 Hz, 1H), 7.06 (d, J = 8.0 Hz, 2H), 6.99 (t, J = 7.5 Hz, 1H),
6.57 (dd, J = 8.0, 1.5 Hz, 1H), 6.53 (t, J = 2.0 Hz, 1H), 6.48 (dd, J
7c
1
13
(500 MHz, CDCl , TMS) δ 8.30 (d, J = 3.0 Hz, 1H), 8.04 (d, J = 105 = 8.0, 2.0 Hz, 1H), 3.75 (s, 3H), 3.30 (s, 3H). C NMR (125
3
4
1
1
.5 Hz, 1H), 7.18ꢀ7.11 (m, 2H), 3.18 (t, J = 5.5 Hz, 4H), 1.73ꢀ
MHz, CDCl ) δ 160.5, 150.4, 148.9, 129.7, 129.2 (2C), 121.9,
3
1
3
.68 (m, 4H), 1.61ꢀ1.57 (m, 2H). C NMR (125 MHz, CDCl ) δ
121.6 (2C), 112.2, 105.9, 105.6, 55.2, 40.3.
Compound 9a : colorless liquid (135.1 mg, 98%). H NMR
3
13
1
47.6, 139.8, 138.8, 123.3, 122.4, 49.7 (2C), 25.4 (2C), 23.9.
8a
1
Compound 7a : pale yellow liquid (136.5 mg, 99%). H NMR
(500 MHz, CDCl , TMS) δ 7.18 (d, J = 8.0 Hz, 2H), 7.10 (t, J =
3
(500 MHz, CDCl , TMS) δ 7.32ꢀ7.29 (m, 2H), 7.24ꢀ7.19 (m, 5H), 110 7.5 Hz, 2H), 6.97 (d, J = 8.0 Hz, 2H), 6.89 (t, J = 7.5 Hz, 2H),
3
1
3
6
3
(
.75 (d, J = 8.0 Hz, 2H), 6.70 (t, J = 7.5 Hz, 1H), 4.52 (s, 2H),
.00 (s, 3H). C NMR (125 MHz, CDCl ) δ 149.8, 139.0, 129.1
5.12 (s, 1H), 2.25 (s, 6H). C NMR (125 MHz, CDCl ) δ 142.0
3
13
3
(2C), 130.8 (2C), 127.5 (2C), 126.8 (2C), 121.4 (2C), 118.4 (2C),
17.7.
Compound 9b : yellow liquid (132.8 mg, 96%). H NMR (500
2C), 128.5 (2C), 126.8, 126.7 (2C), 116.6, 112.4 (2C), 56.6,
8.4.
Compound 7b : pale yellow liquid (135.0 mg, 91%). H NMR 115 MHz, CDCl , TMS) δ 7.17ꢀ7.14 (m, 2H), 7.11ꢀ7.05 (m, 3H),
13
1
3
8a
1
3
1
3
(
500 MHz, CDCl , TMS) δ 7.29ꢀ7.26 (m, 2H), 7.21ꢀ7.19 (m, 3H),
6.90ꢀ6.85 (m, 3H), 5.27 (s, 1H), 2.29 (s, 3H), 2.23 (s, 3H).
C
3
7
3
1
.08 (t, J = 7.5 Hz, 1H), 6.57ꢀ6.52 (m, 3H), 4.47 (s, 2H), 2.95 (s,
NMR (125 MHz, CDCl ) δ 142.1, 141.1, 130.8, 130.4, 129.8
3
13
H), 2.27 (s, 3H). C NMR (125 MHz, CDCl ) δ 149.9, 139.1,
(2C), 127.1, 126.7, 121.1, 118.6 (2C), 117.4, 20.6, 17.8.
3
14
1
38.7, 129.0 (2C), 128.5 (2C), 126.8 (2C), 117.6, 113.1, 109.7,
Compound 9c : pale yellow liquid (146.2 mg, 99%). H NMR
56.6, 38.3, 21.9.
Compound 7c : pale yellow liquid (133.6 mg, 90%). H NMR
120 (500 MHz, CDCl , TMS) δ 7.16ꢀ7.14 (m, 1H), 7.06 (t, J = 7.5 Hz,
3
8
a
1
1H), 7.02 (s, 1H), 6.93 (d, J = 1.5 Hz, 2H), 6.82 (t, J = 7.5 Hz,
1
3
(500 MHz, CDCl , TMS) δ 7.28 (t, J = 7.5 Hz, 2H), 7.22ꢀ7.19 (m,
2H), 5.03 (s, 1H), 2.28 (s, 3H), 2.24 (s, 3H), 2.20 (s, 3H).
C
3
3
2
H), 7.01 (d, J = 8.0 Hz, 2H), 6.66 (d, J = 8.0 Hz, 2H), 4.45 (s,
NMR (125 MHz, CDCl ) δ 143.0, 138.9, 131.7, 131.6, 130.6,
129.2, 127.3, 126.8, 125.9, 120.5, 120.3, 116.5, 20.7, 17.69,
3
1
3
H), 2.93 (s, 3H), 2.23 (s, 3H). C NMR (125 MHz, CDCl ) δ
3
147.9, 139.2, 129.7 (2C), 128.5 (2C), 126.9 (2C), 126.8, 125.8, 125 17.68.
8c
1
1
12.8 (2C), 57.0, 38.6, 20.2.
Compound 9d : white solid (141.7 mg, 90%). H NMR (500
MHz, CDCl , TMS) δ 7.11 (d, J = 7.5 Hz, 1H), 6.95 (d, J = 8.0
Hz, 1H), 6.94 (s, 2H), 6.67 (t, J = 7.5 Hz, 1H), 6.13 (d, J = 8.0
8b
1
Compound 7d : pale yellow liquid (147.8 mg, 93%). H NMR
500 MHz, CDCl , TMS) δ 7.28 (t, J = 7.5 Hz, 2H), 7.21ꢀ7.19 (m,
3
(
3
1
3
3
H), 7.10 (t, J = 8.0 Hz, 1H), 6.36 (dd, J = 8.0, 2.0 Hz, 1H), 6.29ꢀ
Hz, 1H), 4.85 (s, 1H), 2.31 (s, 3H), 2.30 (s, 3H), 2.14 (s, 6H). C
13
6.26 (m, 2H), 4.48 (s, 2H), 3.72 (s, 3H), 2.97 (s, 3H). C NMR
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