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aromatic), 7.80 (d, J = 8.6 Hz, 1H, aromatic), 7.74 (ddd, J = 6.9, 5.9,
1.4 Hz, 1H, aromatic), 7.70 (dd, J = 7.7, 1.4 Hz, 1H, aromatic),
7.57–7.52 (m, 1H, aromatic), 7.48 (d, J = 16.5 Hz, 1H, vinyl), 7.22–
7.15 (m, 1H, aromatic), 6.96–6.91 (m, 1H, aromatic), 6.87 (t,
J = 7.5 Hz, 1H, aromatic); 13C NMR (101 MHz, DMSO) d 156.63,
156.30, 148.19, 136.89, 131.22, 130.24, 130.04, 129.09, 128.47,
128.24, 127.87, 127.40, 126.41, 123.48, 120.51, 119.90, 116.52;
EI-HRMS: found 247.09938 (calc. for C17H13NO: 247.09971).
4.2.1.2.3. 2-[2-(4-Ethoxyphenyl)vinyl]quinoline (3). Method A,
an yellow solid, yield 17%, mp 143–145 °C, HPLC purity 98.94%;
128.46, 123.86, 120.23, 119.37, 118.58, 117.78, 114.58; EI-HRMS:
found 263.09391 (calc. for C17H13NO2: 263.09463).
4.2.1.2.8.
Method B, a brick-red solid, yield 58.6%, mp 273 °C, m/z = 301.45
[M+Na]+, HPLC purity 99.65%; UV (nm), kmax/log : 361.9/3.58; 1H
2-[2-(2,4-Dihydroxyphenyl)vinyl]quinolin-8-ol
(8).
e
NMR (400 MHz, DMSO) d 11.89 (bs, 1H, OH), 10.66 (s, 1H, OH),
10.32 (bs, 1H, OH), 8.78 (d, J = 9.1 Hz, 1H, aromatic), 8.42 (d,
J = 9.1 Hz, 1H, aromatic), 8.23 (d, J = 16.2 Hz, 1H, vinyl), 7.95 (d,
J = 16.1 Hz, 1H, vinyl), 7.59 (t, J = 6.6 Hz, 2H, aromatic), 7.46 (t,
J = 7.4 Hz, 2H, aromatic), 6.55 (d, J = 2.1 Hz, 1H, aromatic), 6.42
(dd, J = 8.6, 2.0 Hz, 1H, aromatic); 13C NMR (101 MHz, DMSO) d
162.80, 160.31, 154.19, 148.37, 143.88, 141.52, 131.84, 129.27,
128.53, 127.84, 118.75, 116.81, 115.54, 114.33, 109.04, 103.33;
EI-HRMS: found 279.08949 (calc. for C17H13NO3: 279.08954).
4.2.1.2.9. 2-[2-(2-Ethoxyphenyl)vinyl]quinolin-8-ol (9). Method
B, an yellow solid, yield 57.5%, mp 100 °C, m/z = 313.92
UV (nm), kmax/loge
: 346.2/3.62; 1H NMR (400 MHz, DMSO) d
8.32 (d, J = 8.6 Hz, 1H, aromatic), 7.98 (d, J = 8.5 Hz, 1H, aromatic),
7.93 (d, J = 8.0 Hz, 1H, aromatic), 7.84 (d, J = 8.6 Hz, 1H, aromatic),
7.79 (d, J = 16.3 Hz, 1H, vinyl), 7.73 (dd, J = 11.2, 4.2 Hz, 1H,
aromatic), 7.68 (d, J = 8.7 Hz, 2H, aromatic), 7.58 – 7.51 (m, 1H,
aromatic), 7.33 (d, J = 16.4 Hz, 1H, vinyl), 6.99 (d, J = 8.7 Hz, 2H,
aromatic), 4.08 (q, J = 6.9 Hz, 2H, CH2-ethoxy), 1.35 (t, J = 7.0 Hz,
3H, CH3-ethoxy); 13C NMR (101 MHz, DMSO) d 159.60, 158.92,
157.11, 156.46, 148.17, 136.06, 134.35, 131.16, 130.22, 129.24,
128.25, 127.35, 126.81, 122.51, 120.25, 115.27, 114.59, 64.20,
[MÀH+Na]|+, HPLC purity 90.83%; UV (nm), kmax/log
e: 303.5/3.53;
1H NMR (400 MHz, DMSO) d 9.53 (s, 1H, OH), 8.28 (d, J = 8.6 Hz,
1H, aromatic), 8.12 (d, J = 16.5 Hz, 1H, vinyl), 7.78 (d, J = 8.6 Hz,
1H, aromatic), 7.72 (t, J = 4.1, 2.1 Hz, 1H, aromatic), 7.52 (d,
J = 16.5 Hz, 1H, vinyl), 7.42–7.30 (m, 3H, aromatic), 7.12–7.06 (m,
2H, aromatic), 7.02 (t, J = 7.5 Hz, 1H, aromatic), 4.17 (q, J = 6.9 Hz,
2H, CH2-ethoxy), 1.46 (t, J = 7.0 Hz, 3H, CH3-ethoxy); 13C NMR
15.10; EI-HRMS: found 275.13145 (calc. for
C
19H17NO:
275.13101).
4.2.1.2.4.
Method A, an white crystals, yield 37%, mp 120 °C, HPLC purity
99.72%; UV (nm), kmax/log
: 335.4/3.54; 1H NMR (400 MHz, DMSO)
8-Chloro-2-[2-(2-chlorophenyl)vinyl]quinoline (4).
(101 MHz, DMSO)
d 157.12, 154.48, 153.38, 138.69, 136.92,
e
130.37, 130.13, 129.53, 128.50, 128.14, 127.41, 125.44, 121.13,
120.94, 118.09, 113.02, 111.79, 64.15, 15.13; EI-HRMS: found
291.12606 (calc. for C19H17NO2: 291.12593).
d 8.48 (d, J = 8.5 Hz, 1H, aromatic), 8.24 (d, J = 16.1 Hz, 1H, vinyl),
8.05 (dd, J = 7.5, 1.9 Hz, 1H, aromatic), 8.00–7.92 (m, 3H, aromatic),
7.64–7.53 (m, 3H, aromatic), 7.48–7.38 (m, 2H, aromatic); 13C
NMR: 101 MHz, DMSO d ppm 156.08, 143.93, 138.03, 134.28,
133.56, 132.62, 131.66, 130.83, 130.61, 130.53, 130.39, 129.14,
128.19, 128.02, 127.82, 127.08, 122.03; EI-HRMS: found
299.02606 (calc. for C17H11Cl2N: 299.02685).
4.2.1.2.10.
2-[2-(4-Ethoxyphenyl)vinyl]quinolin-8-ol
(10).
Method B, an yellow solid, yield 20.5%, mp 130 °C, m/z = 313.77
[MÀH+Na]|+, HPLC purity 97.18%; UV (nm), kmax/log
e: 306.8/3.51;
1H NMR (400 MHz, DMSO) d 8.37 (d, J = 8.7 Hz, 1H, aromatic),
7.87–7.82 (m, 2H, aromatic), 7.77 (d, J = 16.3 Hz, 1H, vinyl), 7.68
(d, J = 8.7 Hz, 2H, aromatic), 7.57–7.47 (m, 2H, aromatic), 7.30 (d,
J = 16.3 Hz, 1H, vinyl), 6.99 (d, J = 8.7 Hz, 2H, aromatic), 4.13–4.04
(q, 2H, CH2-ethoxy), 1.35 (t, J = 7.0 Hz, 3H, CH3-ethoxy); 13C NMR
4.2.1.2.5. 2-[2-(2-Chlorophenyl)vinyl]quinolin-8-ol (5). Method
B, an yellow solid, yield 91%, mp 125 °C, m/z = 283.33 [M+2H]+,
HPLC purity 97.04%; UV (nm), kmax/loge
: 309.8/3.56; 1H NMR
(400 MHz, DMSO) d 8.45 (d, J = 8.6 Hz, 1H, aromatic), 8.22 (d,
J = 16.0 Hz, 1H, vinyl), 8.04 (dd, J = 7.6, 1.8 Hz, 1H, aromatic), 7.88
(dd, J = 7.9, 1.7 Hz, 1H, aromatic), 7.81 (d, J = 8.5 Hz, 1H, aromatic),
7.62–7.53 (m, 4H, aromatic), 7.47–7.37 (m, 2H, aromatic); 13C NMR
(101 MHz, DMSO) d 169.73, 154.89, 147.65, 140.71, 137.52, 134.11,
133.59, 131.16, 130.75, 130.40, 129.79, 128.90, 128.14, 127.74,
126.64, 126.14, 122.41, 122.15; EI-HRMS: found 281.06112 (calc.
for C17H12ClNO: 281.06074).
(101 MHz, DMSO) d 191.71, 159.52, 154.28, 153.28, 138.60,
136.83, 134.61, 132.28, 129.44, 129.11, 127.96, 127.31, 126.06,
121.25, 118.02, 115.29, 111.56, 64.20, 15.10; EI-HRMS: found
291.12481 (calc. for C19H17NO2: 291.12593).
4.2.1.2.11. 5,7-Dichloro-2-[2-(2-chlorophenyl)vinyl]quinolin-8-ol
(11). Method A, a beige crystals, yield 47.0%, mp 205–210 °C, m/
z = 348.27 [M]À; HPLC purity 98.74%; UV (nm), kmax/log
e: 319.9/
3.61; 1H NMR (400 MHz, DMSO) d 8.48 (d, J = 8.7 Hz, 1H, aromatic),
8.36 (d, J = 16.2 Hz, 1H, vinyl), 7.98 (d, J = 8.8 Hz, 1H, aromatic),
7.94 (dd, J = 7.6; 2.0 Hz, 1H, aromatic); 7.77 (s, 1H, aromatic);
7.58–7.50 (m, 2H, aromatic); 7.47–7.36 (m, 2H, aromatic); 13C
NMR: 101 MHz, DMSO d ppm 155.17, 149.33, 139.39, 134.81,
133.99, 133.57, 132.06, 131.14, 130.83, 130.44, 128.27, 128.17,
127.85, 124.37, 123.01, 119.63, 116.28; EI-HRMS: found
348.98262 (calc. for C17H10Cl3NO: 348.98280).
4.2.1.2.6.
Method B, an orange solid, yield 30%, mp 316 °C, m/z = 264.55
[M+2H]+, HPLC purity 99.63%; UV (nm), kmax/log
: 292.6/3.52;
2-[2-(2-Hydroxyphenyl)vinyl]quinolin-8-ol
(6).
e
1H NMR (400 MHz, DMSO) d 11.72 (bs, 1H, OH), 10.61 (s, 1H,
OH), 8.82 (d, J = 9.0 Hz, 1H, aromatic), 8.43 (d, J = 7.4 Hz, 1H, aro-
matic), 8.29 (d, J = 16.4 Hz, 1H, vinyl), 8.09 (d, J = 16.6 Hz, 1H, vi-
nyl), 7.62 (d, J = 5.0 Hz, 3H aromatic), 7.47 (s, 1H, aromatic), 7.30
(t, J = 7.6 Hz, 1H, aromatic), 7.07 (d, J = 8.2 Hz, 1H, aromatic), 6.94
(t, J = 7.5 Hz, 1H, aromatic); 13C NMR (101 MHz, DMSO) d 158.06,
153.50, 149.07, 144.18, 139.91, 132.63, 129.77, 128.44, 122.25,
120.46, 120.01, 119.15, 118.70, 117.16, 116.60; EI-HRMS: found
263.09370 (calc. for C17H13NO2: 263.09463).
4.2.1.2.12. 5,7-Dichloro-2-[2-(2-hydroxyphenyl)vinyl]quinolin-8-
ol (12). Yield 87% of a beige crystalline compound; mp. 141 °C;
Anal. Calcd: C, 61.47; H, 3.34; N, 4.22. Found: C, 61.87; H, 3.05;
N, 4.12%; HPLC purity 98.10%; UV (nm), kmax/loge
: 309.9/3.61.22
4.2.1.2.13. 5,7-Dichloro-2-[2-(4-hydroxyphenyl)vinyl]quinolin-8-
ol (13). Yield 86% of a beige crystalline compound; mp. 198 °C;
Anal. Calcd: C, 61.47; H, 3.34; N, 4.22. Found: C, 61.54; H, 3.32;
4.2.1.2.7.
Method B, an orange solid, yield 50%, mp 215 °C, m/z = 264.45
[M+2H]+, HPLC purity 99.91%; UV (nm), kmax/log
: 296.9/3.55;
2-[2-(3-Hydroxyphenyl)vinyl]quinolin-8-ol
(7).
e
N, 4.28; HPLC purity 98.52%; UV (nm), kmax/loge
: 309.9/3.58.22
1H NMR (400 MHz, DMSO) d 10.93 (bs, 1H, OH), 9.73 (bs, 1H,
OH), 8.68 (s, 1H, aromatic), 8.24 (s, 1H, aromatic), 8.14 (d,
J = 16.3 Hz, 1H, vinyl), 7.72 (d, J = 16.3 Hz, 1H, vinyl), 7.62–7.50
(m, 2H, aromatic), 7.31 (t, J = 7.8 Hz, 2H, aromatic), 7.17 (d,
J = 7.7 Hz, 1H, aromatic), 7.14 (d, J = 18.3 Hz, 1H, aromatic), 6.86
(dd, J = 8.0, 1.8 Hz, 1H, aromatic); 13C NMR (101 MHz, DMSO) d
158.33, 153.17, 150.63, 141.76, 140.68, 137.34, 130.58, 129.06,
4.2.1.2.14. 5,7-Dichloro-2-[2-(2,4-dihydroxyphenyl)vinyl]quinolin-
8-ol (14). Yield 83% of a beige crystalline compound; mp. 102–
1030 °C; HPLC purity 98.96%; UV (nm), kmax/loge
: 321.9/3.65.22
4.2.1.2.15. 5,7-Dichloro-2-[2-(3,4-dihydroxyphenyl)vinyl]quinolin-
8-ol (15). Yield 44% of an ocher crystals, mp 250–252 °C.52
4.2.1.2.16. 5,7-Dichloro-2-[2-(3,5-dihydroxyphenyl)vinyl]quinolin-
8-ol (16). Yield 93% of a beige crystalline compound, mp. 206 °C;
HPLC purity 98.59%; UV (nm), kmax/loge
: 314.5/3.68.22