ꢀꢀꢀꢁ
322ꢀ ꢀS.M. Somagond et al.: 1,2,4-Triazole hybrids of 2-(aryloxy)quinolines
[4-{(6-Methoxy-2-(p-tolyloxy)quinolin-3-yl)methyl}]-2-phe- [4-{(2-(4-Chlorophenoxy)-6-methylquinolin-3-yl)methyl}]-
nyl-2H-1,2,4-triazol-3(4H)-one (11)ꢀThis compound was obtained 2-phenyl-2H-1,2,4-triazol-3(4H)-one (17)ꢀThis compound was
from 3a and 7j; buff solid; yield 89%; mp 188–190°C; IR: ν 1710 (C=O), obtained from 3a and 7p; yellow solid; yield 78%; mp 168–170°C; IR:
1627 (C=N) cm−1; 1H NMR: δ 8.32 (s, 1H, ArH), 8.26 (s, 1H, C5H), 7.81–8.23 ν 1706 (C=O), 1628 (C=N) cm−1; 1H NMR: δ 8.34 (s, 1H, ArH), 8.22–8.25
(m, 12H, ArH), 5.12 (s, 2H, CH2), 3.83 (s, 3H, OCH3 ), 2.47 (s, 3H, CH3); 13C (s, 1H, C5H ), 7.21–7.91 (m, 12H, ArH), 5.12 (s, 2H, CH2), 2.43 (s, 3H, CH3);
NMR: δ 159.0, 152.0, 149.0, 144.0, 141.5, 139.1, 138.6, 138.3, 135.9, 134.4, 13C NMR: δ 158.2, 151.1, 150.7, 145.7, 143.2, 138.3, 137.7, 134.6, 132.1, 131.1,
132.0, 131.0, 129.6, 128.7, 126.7, 124.5, 123.6, 122.0, 121.5, 119.4, 41.2, 20.4; 129.3, 129.0, 126.7, 126.4, 125.1, 123.7, 123.6, 119.8, 117.8, 41.4, 20.8; MS:
+
+
MS: m/z 438 [M ]. Anal. Calcd for C26H22N4O3: C, 71.22; H, 5.06; N, 12.78. m/z 444 [Mꢁ+ꢁ2], 442 [M ]. Anal. Calcd for C25H19N4ClO2: C, 67.80; H,
Found: C, 71.40; H, 5.20; N, 12.82. 4.32; N, 12.65. Found: C, 67.92; H, 4.40; N, 12.80.
[4-{(2-(2-Methoxyphenoxy)quinolin-3-yl)methyl}]-2-phe- [4-{(6-Chloro-2-(4-chlorophenoxy)quinolin-3-yl)methyl}]-2-phe-
nyl-2H-1,2,4-triazol-3(4H)-one (12)ꢀThis compound was obtained nyl-2H-1,2,4-triazol-3(4H)-one (18)ꢀThis compound was obtained
from 3a and 7k; yellow solid; yield 97%; mp 178–180°C; IR: ν 1706 from 3a and 7q; pale brown solid; yield 90%; mp 134–136°C; IR: ν
1
(C=O), 1623 (C=N) cm−1; 1H NMR: δ 8.36 (s, 1H, ArH), 8.33 (s, 1H, C5H), 1712 (C=O), 1630 (C=N) cm−1; H NMR δ 8.37 (s, 1H, ArH), 8.32 (s, 1H,
7.21–7.99 (m, 13H, ArH), 5.14 (s, 2H, CH2), 2.40 (s, 3H, OCH3); 13C NMR: C5H), 7.12–8.15 (m, 12, ArH), 5.16 (s, 2H, CH2); 13C NMR: δ 159.9, 151.6,
δ 159.2, 153.0, 150.9, 147.0, 143.5, 140.1, 139.6, 139.3, 137.9, 136.4, 135.0, 144.0, 143.3, 138.8, 135.0, 134.7, 130.8, 129.9, 129.1, 128.7, 127.1, 126.7,
132.0, 130.0, 129.7, 127.6, 125.9, 125.6, 125.0, 123.5, 120.9, 119.4, 42.5, 20.7; 125.6, 124.4, 122.1, 121.8, 121.5, 118.4, 41.9; MS: m/z 466 [Mꢁ+ꢁ4], 464
+
+
MS: m/z 424 [M ]. Anal. Calcd for C25H20N4O3: C, 70.74; H, 4.75; N, 13.20. [Mꢁ+ꢁ2], 463 [Mꢁ+ꢁ1], 462 [M ]. Anal. Calcd for C24H16N4Cl2O2: C, 62.22; H,
Found: C, 70.80; H, 5.01; N, 13.54. 3.48; N, 12.09. Found to be C, 62.50; H, 3.52; N, 12.12.
[4-{(2-(2-Methoxyphenoxy)-6-methylquinolin-3-yl)methyl}]- [4-{(2-(4-Chlorophenoxy)-6-methoxyquinolin-3-yl)methyl}]-
2-phenyl-2H-1,2,4-triazol-3(4H)-one (13)ꢀThis compound was 2-phenyl-2H-1,2,4-triazol-3(4H)-one (19)ꢀThis compound was
obtained from 3a and 7l; buff solid; yield 65%; mp 132–134°C; IR: obtained from 3a and 7r; pale yellow solid; yield 79%; mp 175–177°C;
1
1
ν 1715 (C=O), 1620 (C=N) cm−1; H NMR: δ 8.33 (s, 1H, ArH), 8.31 (s, IR: ν 1707 (C=O), 1625 (C=N) cm−1; H NMR: δ 8.34 (s, 1H, ArH), 8.31
1H, C5H), 7.19–7.75 (m, 12H, ArH), 5.12 (s, 2H, CH2), 2.39 (s, 3H, OCH3), (s, 1H, C5H), 7.85–8.08 (m, 12H, ArH ), 4.93 (s, 2H, CH2), 3.83 (s, 3H,
2.44 (s, 3H, CH3); 13C NMR: δ 158.0, 152.0, 149.0, 145.0, 144.0, 143.0, OCH3 ); 13C NMR: δ 159.2, 155.7, 153.9, 147.9 145.7, 144.0, 142.0, 140.0,
138.3, 138.0, 136.6, 135.2, 134.0, 131.0, 129.3, 129.0, 128.4, 124.1, 124.0, 137.1, 135.7, 132.0, 129.5, 128.6, 127.8, 123.6, 119.2, 118.0, 116.0, 115.0,
+
+
123.8, 123.0, 119.3, 119.0, 42.4, 20.0; MS: m/z 438 [M ]. Anal. Calcd 114.0, 113.0, 55.9, 43.9; MS: m/z 460 [Mꢁ+ꢁ2], 458 [M ]. Anal. Calcd for
for C26H22N4O3: C, 71.22; H, 5.06; N, 12.78. Found: C, 71.47; H, 5.12; N, C25H19N4ClO3: C, 65.43; H, 4.17; N, 12.21. Found: C, 65.52; H, 4.22; N, 12.5.
12.82.
[2-{(4-Methoxyphenyl)-4-((2-(p-tolyloxy)quinolin-3-yl)
[4-{(6-Chloro-2-(2-methoxyphenoxy)quinolin-3-yl)methyl}]- methyl}]-2H-1,2,4-triazol-3(4H)-one (20)ꢀThis compound was
2-phenyl-2H-1,2,4-triazol-3(4H)-one (14)ꢀThis compound was obtained from one 3b and 7g; light brown solid; yield 87%; mp 126–
obtained from 3a and 7m; pale yellow solid; yield 71%; mp 192–194°C; 128°C; IR: ν 1719 (C=O), 1623 (C=N) cm−1; 1H NMR: δ 8.54 (s, 1H, ArH),
IR: 1708 (C=O), 1624 (C=N) cm−1; 1H NMR: δ 8.56 (s, 1H, ArH), 8.48 (s, 8.29 (s, 1H, C5H), 7.20–8.12 (m, 12H, ArH), 5.06 (s, 2H, CH2), 3.81 (s, 3H,
1H, C5H), 7.21–8.32 (m, 12H, ArH), 5.28 (s, 2H, CH2), 2.39 (s, 3H, OCH3); OCH3), 2.43 (s, 3H, CH3); 13C NMR: δ 156.1, 142.0, 139.0, 136.0, 134.0,
13C NMR: δ 160.0, 156.0, 152.0, 147.0, 146.0, 145.0, 139.6, 139.0, 137.0, 131.0, 130.0, 129.0, 128.1, 128.0, 127.0, 124.7, 123.0, 122.0, 121.0, 119.0,
+
136.1, 135.0, 133.0, 131.0, 130.0, 129.0, 125.4, 125.0, 124.2, 124.0, 120.5, 118.7, 118.0, 116.0, 41.0, 55.9, 20.7; MS: m/z 438 [M ]. Anal. Calcd for
+
120.0, 42.5; MS: m/z 460 [Mꢁ+ꢁ2], 458 [M ]. Anal. Calcd for C25H19N4ClO3: C26H22N4O3: C, 71.22; H, 5.06; N, 12.78. Found: C, 71.43; H, 5.20; N, 12.91.
C, 65.43; H, 4.17; N, 12.21. Found: C, 65.63; H, 4.23; N, 12.48.
2-{(4-Methoxyphenyl)-4-[(6-methyl-2-(p-tolyloxy)quinolin-3-yl)
[4-{(6-Methoxy-2-(2-methoxyphenoxy)quinolin-3-yl)methyl}]- methyl}]-2H-1,2,4-triazol-3(4H)-one (21)ꢀThis compound was
2-phenyl-2H-1,2,4-triazol-3(4H)-one (15)ꢀThis compound was obtained from 3b and 7h; beige solid; yield 90%; mp 144–146°C; IR:
obtained from 3a and 7n; buff solid; yield 65%; mp 132–134°C; IR: ν ν 1711 (C=O), 1620 (C=N) cm−1; H NMR: δ 8.63 (s, 1H, ArH), 8.31 (s,
1
1701 (C=O), 1620 (C=N) cm−1; 1H NMR: δ 8.35 (s, 1H, ArH), 8.33 (s, 1H, 1H, C5H ), 7.21–8.19 (m, 11H, ArH), 5.09 (s, 2H, CH2) 3.82 (s, 3H, OCH3),
C5H), 7.21–7.87 (m, 12H, ArH), 5.18 (s, 2H, CH2), 2.39 (s, 3H, OCH3), 2.44 2.44 (s, 3H, CH3); 13C NMR: δ 156.0, 141.0, 138.0, 135.0, 133.0, 130.0,
(s, 3H, OCH3); 13C NMR: δ 159.0, 154.0, 150.0, 146.0, 145.0, 144.0, 139.0, 129.1, 129.5, 128.2, 128.1, 126.0, 123.7, 123.0, 121.9, 120.6, 118.1, 118.9,
+
138.5, 137.3, 136.2, 135.0, 132.0, 130.0, 129.9, 129.7, 125.4, 125, 124.6, 124.0, 117.3, 117.0, 41.1, 55.0, 20.9, 20.6; MS: m/z 452 [M ]. Anal. Calcd for
+
121.0, 120.8, 42.5, 41.7; MS: m/z 454 [M ]. Anal. Calcd for C26H22N4O4: C, C27H24N4O3: C, 71.67; H, 5.35; N, 12.38. Found: C, 71.92; H, 5.43; N, 12.45.
68.71; H, 4.88; N, 12.33. Found: C, 68.82; H, 4.91; N, 12.76.
[4-(6-Chloro-2-(p-tolyloxy)quinolin-3-yl)methyl]-2-(4-
[4-{(2-(4-Chlorophenoxy)quinolin-3-yl)methyl}]-2-phe- methoxyphenyl)-2H-1,2,4-triazol-3(4H)-one (22)ꢀThis compound
nyl-2H-1,2,4-triazol-3(4H)-one (16)ꢀThis compound was obtained was obtained from 3b and 7i; pale yellow solid; yield 78%; mp 128–
from 3a and 7o; brown crystalline solid; yield 72%; mp 120–122°C; IR: 130°C; IR: ν 1717 (C=O), 1621 (C=N) cm−1; 1H NMR: δ 8.50 (s, 1H, ArH),
ν 1713 (C=O), 1622 (C=N) cm−1; 1H NMR: δ 8.39 (s, 1H, ArH), 8.37 (s, 1H, 8.47 (s, 1H, C5H), 6.9–8.11 (m, 11H, ArH), 5.15 (s, 2H, CH2), 3.78 (s, 3H,
C5H), 7.30–8.23 (m, 10H, ArH), 5.16 (s, 2H, CH2), 2.43 (s, 3H, CH3); 13C OCH3), 2.36 (s, 3H, CH3); 13C NMR: δ 162.3, 159.9, 157.2, 151.1, 144.3,
NMR: δ 166.0, 167.0, 162.0, 157.0, 145.5, 138.3, 135.9, 135.7, 133.0, 132.7, 138.3, 137.9, 135.0, 134.7, 131.5, 130.8, 129.8, 127.0, 126.7, 123.5, 122.1,
129.8, 127.7, 126.2, 125.3, 124.1, 123.9, 122.0, 121.0, 43.5, 21.0; MS: m/z 430 121.9, 120.4, 114.6, 55.8, 41.8, 20.9; MS: m/z 475 [Mꢁ+ꢁ2], 473 [Mꢁ+ꢁ1], 472
+
+
[Mꢁ+ꢁ2], 428 [M ]. Anal. Calcd for C24H17N4ClO2: C, 67.21; H, 4; N, 13.06. [M ]. Anal. Calcd for C26H21N4ClO3: C, 66.03; H, 4.48; N, 11.85. Found:
Found: C, 67.52; H, 4.3; N, 13.4. C, 66.72; H, 4.6; N, 12.2.
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