Organic & Biomolecular Chemistry
Paper
+
5
2
.88; N, 14.42; O, 21.97%; found C, 57.91; H, 5.99; N, 14.62; O, LCMS: (ESI, m/z): [M + H] calcd for C24
1.77%.
4-(((7-Chloroquinolin-4-yl)oxy)methyl)-1H-1,2,3-triazol-1-yl) 21.36%; found C, 64.34; H, 5.36; N, 9.55; O, 21.16%.
phenyl)-methanone (Tr6). Snow white solid, yield = 66% (R 7-((1-(7-Chloroquinolin-4-yl)-1H-1,2,3-triazol-4-yl)methoxy)-
.35 in 100% ethylacetate); m.p. 192–194 °C; H NMR 4-methyl-2H-chromen-2-one (Tr10). Light chocolate coloured
300 MHz, CDCl ) δ 7.86–7.78 (m, 5H), 7.53 (s, 1H), 7.51 (d, J = solid, yield 68% (R 0.4 in 100% ethylacetate);
.12 Hz, 1H), 7.45 (d, J = 7.8 Hz, 4H), 7.42 (s, 1H), 6.25 (s, 1H), m.p. 190–192 °C; H NMR (300 MHz, CDCl ) δ 9.08 (d, J =
.85 (s, 2H). H NMR (300 MHz, Chloroform-d) δ 7.89–7.73 (m, 4.8 Hz, 1H), 8.26 (d, J = 1.8 Hz, 1H), 8.17 (s, 1H), 7.99 (d, J =
H
23
N
3
O
6
; 450.1; found
450.0; anal. calcd for C H N O ; C, 64.14; H, 5.16; N, 9.35; O,
2
4
23 3 6
(
(
0
(
0
1
5
f
=
1
3
=
f
=
1
3
1
1
3
H), 7.53 (s, 1H), 7.51–7.43 (m, 5H), 6.25 (s, 2H). C NMR 9.0 Hz, 1H), 7.62 (dd, J = 9.3, 2.1 Hz, 1H), 7.55–7.51 (m, 1H),
) δ 169.67, 133.42, 132.93, 131.98, 130.62, 7.27 (s, 1H), 7.03 (d, J = 2.4 Hz, 1H), 7.00 (s, 1H), 6.17 (s,
28.62, 127.35, 123.31, 115.34, 113.39, 109.50, 107.58, 103.40, 1H), 5.44 (s, 2H), 2.42 (s, 3H). C NMR (75 MHz, CDCl ) δ
(75 MHz, CDCl
3
1
3
1
9
3
+
7.61, 95.13, 85.75, 73.49. LCMS: (ESI, m/z): [M + H] calcd for 161.03, 160.91, 157.02, 155.19, 152.36, 151.37, 150.24,
C
19
H
13ClN
4
O
2
365.0; found 365.1; anal. calcd for 144.03, 140.79, 137.09, 129.63, 129.08, 125.86, 124.76,
C H ClN O ; C, 62.56; H, 3.59; Cl, 9.72; N, 15.36; O, 8.77%; 124.44, 120.18, 116.09, 112.52, 112.39, 102.14, 62.10, 18.67.
1
9
13
4 2
+
found C, 62.76; H, 3.80; Cl, 9.92; N, 15.56; O, 8.57%.
-(4-(((2,7a-Dihydrobenzo[d]thiazol-2-yl)thio)methyl)-1H-1,2,3- found 418.9; anal. calcd for C22
triazol-1-yl)-1-(3,4-dimethoxyphenyl)propan-1-one (Tr7). Off Cl, 8.46; N, 13.38; O, 11.46%; found C, 63.29; H, 3.41; Cl,
white solid, yield = 61% (R = 0.75 in 100% ethylacetate); 8.26; N, 13.59; O, 11.68%.
m.p. 200–202 °C; H NMR (300 MHz, CDCl ) δ 7.89 (d, J = 8.1 1-((1-(7-Chloroquinolin-4-yl)-1H-1,2,3-triazol-4-yl)methyl)-1H-
Hz, 1H), 7.77 (s, 1H), 7.74 (d, J = 7.8 Hz, 1H), 7.50 (dd, J = 8.4, indole-3-carbaldehyde (Tr11). Light brown solid, yield = 69%
LCMS: (ESI, m/z): [M + H] calcd for C22
4 3
H15ClN O 419.0
3
H
15ClN ; C, 63.09; H, 3.61;
4 3
O
f
1
3
1
1
1
2
2
1
1
3
.8 Hz, 2H), 7.42 (dd, J = 5.1, 2.1 Hz, 2H), 7.31 (d, J = 7.8 Hz, (R
H), 7.26 (s, 1H), 6.85 (d, J = 8.4 Hz, 1H), 4.76 (t, J = 6.3 Hz, (300 MHz, CDCl
H), 4.67 (s, 2H), 3.94 (s, 3H), 3.90 (s, 3H), 3.58 (t, J = 6.6 Hz, (d, J = 6.9 Hz, 1H), 8.24 (s, 1H), 7.94 (s, 1H), 7.90–7.81 (m, 2H),
H). C NMR (75 MHz, CDCl
53.04, 149.17, 143.60, 135.46, 129.23, 126.06, 124.34, 124.21, 7.26 (s, 1H), 5.67 (s, 2H). C NMR (75 MHz, CDCl
22.90, 121.55, 121.06, 110.13, 109.94, 56.12, 56.00, 45.15, 153.64, 151.27, 150.19, 146.46, 143.72, 139.89, 137.89, 136.93,
f
= 0.35 in 100% ethylacetate); m.p. 188–190 °C; H NMR
3
) δ 10.05 (s, 1H), 9.02 (d, J = 4.5 Hz, 1H), 8.34
1
3
3
) δ 194.97, 165.79, 153.89, 7.55 (dd, J = 16.2, 9.0 Hz, 2H), 7.38 (dd, J = 12.9, 5.1 Hz, 2H),
1
3
3
) δ 184.59,
−
8.16, 27.77. LCMS: (ESI, m/z): [M
441.1; found 440.8; anal. calcd for 119.08, 116.00, 109.94, 42.49. LCMS: (ESI, m/z): [M + H] calcd
C H N O S ; C, 56.99; H, 5.01; N, 12.66; O, 10.85; S, 14.49%; for C H ClN O 388.0; found 387.9; anal. calcd for
− H] calcd For 134.91, 129.66, 129.08, 124.52, 124.24, 123.85, 123.38, 122.47,
+
C
21
H
22
22
N
4
O
3
S
2
2
1
4
3
2
21 14
5
found C, 56.76; H, 5.21; N, 12.88; O, 10.98; S, 14.69%.
-(3,4-Dimethoxyphenyl)-3-(4-(((5-methoxy-3a,7a-dihydro-1H-
benzo[d]imidazol-2-yl)thio)methyl)-1H-1,2,3-triazol-1-yl)propan-
-one (Tr8). Brown solid, yield = 66% (R
21 5
C H14ClN O; C, 65.04; H, 3.64; Cl, 9.14; N, 18.06; O, 4.13%;
found C, 65.25; H, 3.87; Cl, 9.35; N, 18.00; O, 4.02%.
2-(((1-(7-Chloroquinolin-4-yl)-1H-1,2,3-triazol-4-yl)methyl)thio)
1
1
f
= 0.45 in 100% ethyla- benzo[d]thiazole (Tr12). White solid, yield = 70% (R
f
= 0.4 in
1
1
cetate); m.p. 199–201 °C; H NMR (300 MHz, CDCl
3
) δ 10.34 (s, 100% ethylacetate); m.p. 155–157 °C; H NMR (300 MHz,
1
=
4
3
2
1
1
4
H), 7.69 (s, 1H), 7.40 (s, 1H), 7.36 (d, J = 5.1 Hz, 1H), 7.32 (d, J CDCl ) δ 9.02 (s, 1H), 8.18 (d, J = 20.1 Hz, 2H), 7.91–7.84 (m,
3
9.0 Hz, 1H), 6.91 (d, J = 1.5 Hz, 1H), 6.76 (d, J = 8.4 Hz, 1H), 1H), 7.84–7.74 (m, 2H), 7.45 (d, J = 7.5 Hz, 2H), 7.38–7.19 (m,
1
3
.62 (t, J = 6.3 Hz, 2H), 4.33 (s, 1H), 3.82 (d, J = 8.4 Hz, 6H), 2H), 4.83 (s, 2H). C NMR (75 MHz, CDCl
3
) δ 152.93, 151.38,
.69 (s, 2H), 3.62 (s, 1H), 3.43 (t, J = 6.3 Hz, 2H), 2.21 (s, 1H), 150.17, 145.10, 140.83, 137.60, 136.86, 135.58, 129.42, 129.02,
1
3
.00 (s, 3H). C NMR (75 MHz, CDCl
56.67, 153.92, 149.11, 147.62, 143.79, 129.00, 124.20, 123.01, 27.42. LCMS: (ESI, m/z): [M + 2] calcd for C19
15.07, 112.70, 110.16, 109.95, 96.82, 56.05, 55.93, 55.70, found 411.8; anal. calcd for C H ClN S ; C, 55.67; H, 2.95;
3
) δ 194.94, 176.73, 126.23, 125.03, 124.64, 124.35, 121.48, 121.26, 120.49, 116.05,
+
H
5 2
12ClN S 411.0;
1
9
12
5 2
−
5.43, 37.82, 27.07, 20.91. LCMS: (ESI, m/z): [M − H] calcd for Cl, 8.65; N, 17.09; S, 15.64%; found C, 55.88; H, 2.74; Cl, 8.85;
S 454.1; found 454.0; anal. calcd for C22 S; N, 17.28; S, 15.81%.
C
22
H
25
N
5
O
4
25 5 4
H N O
C, 58.01; H, 5.53; N, 15.37; O, 14.05; S, 7.04%; found C, 58.21;
H, 5.68; N, 15.57; O, 14.25; S, 7.34%.
7-Chloro-4-(4-(((5-methoxy-1H-benzo[d]imidazol-2-yl)thio)
methyl)-1H-1,2,3-triazol-1-yl)quinoline (Tr13). Yellow solid,
7
-((1-(3-(3,4-Dimethoxyphenyl)-3-oxopropyl)-1H-1,2,3-triazol- yield = 61% (R
f
= 0.6 in 100% ethylacetate); m.p. 210–212 °C;
H NMR (300 MHz, chloroform-d) δ 8.96 (s, 1H), 8.11 (s, 3H),
= 0.7 in 100% ethylacetate); 7.69 (d, J = 9.3 Hz, 1H), 7.45–7.31 (m, 3H), 6.92 (s, 1H), 6.75 (d,
1
4
-yl)methoxy)-4-methyl-2H-chromen-2-one (Tr9). Pale yellow
solid, yield 72% (R
m.p. 182–184 °C; H NMR (300 MHz, CDCl
=
f
1
13
3
) δ 7.85 (s, 1H), J = 8.7 Hz, 1H), 4.63 (s, 2H), 3.76 (s, 3H). C NMR (75 MHz,
.56 (dd, J = 9.6, 1.8 Hz, 1H), 7.51 (s, 1H), 7.48 (s, 1H), 7.27 (s, CDCl ) δ 184.66, 179.29, 155.88, 151.34, 149.86, 145.28, 140.59,
7
3
1
1
3
H), 6.96 (d, J = 2.4 Hz, 1H), 6.91 (d, J = 4.8 Hz, 1H), 6.14 (s, 138.08, 136.36, 129.07, 128.63, 124.96, 124.34, 121.73, 120.26,
+
H), 5.23 (s, 2H), 4.84 (t, J = 6.3 Hz, 2H), 3.95 (s, 3H), 3.93 (s, 116.02, 111.39, 111.00, 55.64, 26.67. LCMS: (ESI, m/z): [M + H]
1
3
H), 3.64 (t, J = 6.0 Hz, 2H), 2.39 (s, 3H). C NMR (75 MHz, calcd for C H ClN OS 423.0; found 422.9; anal. calcd for
20 15 6
CDCl
3
) δ 194.94, 161.14, 155.01, 153.86, 152.57, 149.09, 142.59,
C
20
H
15ClN
6
OS; C, 56.80; H, 3.58; Cl, 8.38; N, 19.87; O, 3.78; S,
1
1
29.09, 125.67, 124.62, 122.94, 113.91, 112.48, 112.07, 110.18, 7.58%; found C, 56.98; H, 3.79; Cl, 8.58; N, 19.57; O, 3.58; S,
09.88, 101.95, 62.13, 56.11, 55.96, 45.15, 38.10, 29.65, 18.60. 7.77%.
This journal is © The Royal Society of Chemistry 2021
Org. Biomol. Chem., 2021, 19, 1589–1603 | 1599