10.1002/cbdv.202000290
Chemistry & Biodiversity
Chem. Biodiversity
White solid; Yield: 67%. mp: 176-177 oC. Rf = 0.68 (DCM : MeOH = 14 : 1).IR (KBr, cm-1): 3136, 3063 (CH, arene); 2955 (CH, CH2); 1661 (C=O);
1603, 1454 (C=C).1H-NMR (500 MHz, DMSO-d6, ppm): δ 8.44 (1H, d, J = 8.00 Hz, H-2); 8.11 (1H, d, J = 9.50 Hz, H-6’); 7.93 (1H, d, J = 8.50 Hz,
H-5); 7.43 (1H, d, J = 5.50 Hz, H-8); 7.29-7.21 (6H, m, H-6, H-3”, H-4”, H-5”, H-6”, H-7”); 5.47 (2H, d, J = 2.50 Hz, H-1”a, H-1”b); 5.17 (2H, d, J =
6.50 Hz, H-1’a, H-1’b); 2.37 (3H, s, 7-CH3). 13C NMR (125 MHz, DMSO-d6, ppm): δ 160.21, 148.59, 145.50, 136.29, 129.21, 129.07, 128.64,
128.51, 127.34, 126.40, 124.47, 119.68, 53.38, 41.43, 21.76. ESI-MS m/z: 332.00 [M+H]+ .
3-((1-Benzyl-1H-1,2,3-triazol-4-yl)methyl)-7-methoxyquinazolin-4(3H)-one (4d)
White solid; Yield: 58%. mp: 191-192 oC. Rf = 0.62 (DCM : MeOH = 14 : 1).IR (KBr, cm-1): 3084 (CH, arene); 2972 (CH, CH2); 1674 (C=O); 1609,
1450 (C=C).1H-NMR (500 MHz, DMSO-d6, ppm): δ 8.50 (1H, s, H-2); 8.15 (1H, s, H-6’); 7.95 (1H, d, J = 9.00 Hz, H-5); 7.29-7.22 (6H, m, H-8, H-
3”, H-4”, H-5”, H-6”, H-7”); 7.05 (1H, d, J = 9.00 Hz, H-6); 5.48 (2H, d, J = 3.00 Hz, H-1”a, H-1”b); 5.17 (2H, s, H-1’a, H-1’b); 3.81 (3H, s, 7-
OCH3). 13C NMR (125 MHz, DMSO-d6, ppm): δ 164.51, 129.23, 129.19, 128.92, 128.69, 128.55, 128.22, 117.45, 109.06, 56.35, 54.07, 53.47.ESI-
MS m/z: 348.00 [M+H]+ .
3-((1-Benzyl-1H-1,2,3-triazol-4-yl)methyl)-6,7-dimethoxyquinazolin-4(3H)-one (4e)
White solid; Yield: 54%. mp: 211-212 oC. Rf = 0.59 (DCM : MeOH = 14 : 1).IR (KBr, cm-1): 3061 (CH, arene); 2970 (CH, CH2); 1662 (C=O); 1607,
1499 (C=C).1H-NMR (500 MHz, DMSO-d6, ppm): δ 8.41 (1H, s, H-2); 8.13 (1H, d, J = 5.00 Hz, H-6’); 7.31-7.22 (6H, m, H-5, H-3”, H-4”, H-5”, H-
6”, H-7”); 7.13 (1H, s, H-8); 5.49 (2H, s, H-1”a, H-1”b); 5.18 (2H, s, H-1’a, H-1’b); 3.78 (3H, s, 7-OCH3); 3.76 (3H, s, 6-OCH3). 13C NMR (125 MHz,
DMSO-d6, ppm): δ 159.53, 154.97, 149.33, 147.33, 144.20, 136.24, 129.23, 128.68, 128.56, 124.61, 115.06, 108.50, 105.51, 56.49, 56.18, 53.45,
41.58, 31.16.ESI-MS m/z: 378.10 [M+H]+ .
3-((1-Benzyl-1H-1,2,3-triazol-4-yl)methyl)-6-fluoroquinazolin-4(3H)-one (4f)
White solid; Yield: 63%. mp: 181-182 oC. Rf = 0.65 (DCM : MeOH = 14 : 1).IR (KBr, cm-1): 3061, 3028 (CH, arene); 2922 (CH, CH2); 1689 (C=O);
1605, 1483 (C=C).1H-NMR (500 MHz, DMSO-d6, ppm): δ 8.47 (1H, s, H-2); 8.12 (1H, s, H-6’); 7.74-7.64 (3H, m, H-5, H-7, H-8); 7.29-7.21 (5H, m,
H-3”, H-4”, H-5”, H-6”, H-7”); 5.48 (2H, s, H-1”a, H-1”b); 5.19 (2H, s, H-1’a, H-1’b). 13C NMR (125 MHz, DMSO-d6, ppm): δ 161.74, 159.78,
159.72, 147.91, 145.28, 136.33, 130.71, 130.64, 129.22, 128.65, 128.51, 127.93, 124.42, 123.52, 123.33, 111.30, 111.11, 53.35, 41.65.ESI-
MS m/z: 336.00 [M+H]+ .
3-((1-Benzyl-1H-1,2,3-triazol-4-yl)methyl)-7-fluoroquinazolin-4(3H)-one (4g)
White solid; Yield: 60%. mp: 185-186 oC. Rf = 0.65 (DCM : MeOH = 14 : 1).IR (KBr, cm-1): 3107, 3061 (CH, arene); 2954 (CH, CH2); 1661 (C=O);
1603, 1477 (C=C).1H-NMR (500 MHz, DMSO-d6, ppm): δ 8.53 (1H, s, H-2); 8.13 (1H, s, H-6’); 8.11-8.10 (1H, m, H-5); 7.43 (1H, d, J = 10.00 Hz,
H-6); 7.35-7.21 (6H, m, H-8, H-3”, H-4”, H-5”, H-6”, H-7”); 5.48 (2H, s, H-1”a, H-1”b); 5.18 (2H, s, H-1’a, H-1’b). 13C NMR (125 MHz, DMSO-d6,
ppm): δ 167.08, 165.08, 163.37, 159.69, 150.46, 149.88, 136.29, 129.80, 129.71, 129.22, 128.65, 128.51, 127.93, 124.49, 119.13, 116.38, 116.19,
112.97, 112.80, 53.37, 41.60.ESI-MS m/z: 336.00 [M+H]+ .
3-((1-Benzyl-1H-1,2,3-triazol-4-yl)methyl)-6-chloroquinazolin-4(3H)-one (4h)
White solid; Yield: 67%. mp: 191-192 oC. Rf = 0.64 (DCM : MeOH = 14 : 1).IR (KBr, cm-1): 3107 (CH, arene); 2999, 2953 (CH, CH2); 1665 (C=O);
1605, 1472 (C=C).1H-NMR (500 MHz, DMSO-d6, ppm): δ 8.50 (1H, s, H-2); 8.11 (1H, s, H-6’); 7.99 (1H, d, J = 2.50 Hz, H-5); 7.78 (1H, dd, J =
9.00 Hz, J’ = 2.50 Hz, H-7); 7.64 (1H, d, J = 9.00 Hz, H-8); 7.28-7.21 (5H, m, H-3”, H-4”, H-5”, H-6”, H-7”); 5.47 (2H, s, H-1”a, H-1”b); 5.18 (2H,
s, H-1’a, H-1’b). 13C NMR (125 MHz, DMSO-d6, ppm): δ 159.42, 148.89, 147.13, 142.98, 136.34, 135.07, 131.95, 130.05, 129.22, 128.64, 128.50,
125.52, 124.35, 123.32, 53.33, 41.72.ESI-MS m/z: 352.10 (35Cl), 354.00 (37Cl) [M+H]+ .
3-((1-Benzyl-1H-1,2,3-triazol-4-yl)methyl)-6-bromoquinazolin-4(3H)-one (4i)
White solid; Yield: 63%. mp: 223-124 oC. Rf = 0.66 (DCM : MeOH = 14 : 1).IR (KBr, cm-1): 3127, 3063 (CH, arene); 2945 (CH, CH2); 1676 (C=O);
1615, 1460 (C=C).1H-NMR (500 MHz, DMSO-d6, ppm): δ 8.51 (1H, s, H-2); 8.12 (1H, d, J = 2.00 Hz, H-5); 8.11 (1H, s, H-6’); 7.89 (1H, dd, J =
8.50 Hz, J’ = 2.50 Hz, H-7); 7.56 (1H, d, J = 8.50 Hz, H-8); 7.29-7.21 (5H, m, H-3”, H-4”, H-5”, H-6”, H-7”); 5.48 (2H, s, H-1”a, H-1”b); 5.18 (2H,
s, H-1’a, H-1’b). 13C NMR (125 MHz, DMSO-d6, ppm): δ 159.29, 148.97, 147.40, 142.89, 137.77, 136.36, 130.16, 129.22, 128.64, 128.49, 124.29,
123.66, 120.12, 53.33, 41.73.ESI-MS m/z: 396.00 (79Br), 398.00 (80Br) [M+H]+ .
3-((1-Benzyl-1H-1,2,3-triazol-4-yl)methyl)-6-iodoquinazolin-4(3H)-one (4j)
White solid; Yield: 65%. mp: 231-232 oC. Rf = 0.63 (DCM : MeOH = 14 : 1).IR (KBr, cm-1): 3132, 3059 (CH, arene); 2986, 2930 (CH, CH2); 1665
(C=O); 1605, 1458 (C=C).1H-NMR (500 MHz, DMSO-d6, ppm): δ 8.50 (1H, s, H-2); 8.32 (1H, d, J = 2.00 Hz, H-5); 8.11 (1H, s, H-6’); 8.04 (1H, dd,
J = 8.50 Hz, J’ = 2.00 Hz, H-7); 7.41 (1H, d, J = 8.50 Hz, H-8); 7.29-7.21 (5H, m, H-3”, H-4”, H-5”, H-6”, H-7”); 5.47 (2H, s, H-1”a, H-1”b); 5.17
(2H, s, H-1’a, H-1’b). 13C NMR (125 MHz, DMSO-d6, ppm): δ 159.10, 149.04, 147.68, 143.30, 136.35, 134.81, 129.93, 129.23, 128.65, 128.50,
124.34, 123.85, 92.81, 53.33, 41.74.ESI-MS m/z: 444.00 [M+H]+ .
General procedures for the synthesis of compounds 6a-j
Compounds 6a-j were synthesized via a three-step pathway as illustrated in scheme 2. The first step was similar to that described for
compounds 4a-j, followed by chlorination with thionyl chloride resulting in 4-chloro-quinazoline derivatives 5a-j. A mixture of compounds
2 andthionyl chloride was stirred at 120 C for 5 hours. Then, the resulting mixtures were evaporated under reduced pressure to give the
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