Chem. Pap.
Table 2 Spectral data of compounds 4a–4d and 5a–5k
Compound Spectral data
4a
4b
4c
4d
1H NMR (500 MHz, DMSO-d6) d 7.54 (dd, J = 8.4, 2.0 Hz, 1H, Ph-H), 7.44 (d, J = 2.0 Hz, 1H, Ph-H), 7.16 (d, J = 8.5 Hz, 1H,
Ph-H), 4.42 (s, 2H, SCH2), 3.85 (s, 6H, OCH3), 1.97 (s, 3H, CH3), 1.95 (s, 3H, CH3);
13C NMR (125 MHz, DMSO-d6) d 165.89 (s, C=O), 165.60 (s, Oxadiazole-C), 165.38 (s, C=N), 162.15 (s, Oxadiazole-C), 151.95
(s, Ph-C), 149.11 (s, Ph-C), 120.04 (s, Ph-C), 115.13 (s, Ph-C), 112.04 (s, Ph-C), 109.03 (s, Ph-C), 55.77 (s, OCH3), 55.70 (s,
OCH3), 33.04 (s, SCH2), 21.25 (s, CH3), 16.67 (s, CH3);
MS (ESI, m/z): 352.1 [M?H]?, 374.1 [M?Na]?, 390.0 [M?K]?
1H NMR (500 MHz, DMSO-d6) d 7.23 (s, 2H, Ph-H), 4.44 (s, 2H, SCH2), 3.87 (s, 6H, OCH3), 3.75 (s, 3H, OCH3), 1.97 (s, 3H,
CH3), 1.95 (s, 3H, CH3);
13C NMR (125 MHz, DMSO-d6) d 165.95 (s, C=O), 165.56 (s, Oxadiazole-C), 165.27 (s, C=N), 162.76 (s, Oxadiazole-C), 153.50
(s, Ph-C), 140.59 (s, Ph-C), 118.07 (s, Ph-C), 103.82 (s, Ph-C), 60.27 (s, OCH3), 56.19 (s, OCH3), 33.06 (s, SCH2), 21.25 (s, CH3),
16.68 (s, CH3);
MS (ESI, m/z): 382.0 [M?H]?, 404.1 [M?Na]?, 420.0 [M?K]?
1H NMR (500 MHz, DMSO-d6) d 7.02–6.96 (m, 2H, Ph-H), 6.91–6.85 (m, 2H, Ph-H), 5.31 (s, 2H, OCH2), 4.38 (s, 2H, SCH2), 3.70
(s, 3H, OCH3), 1.97 (s, 3H, CH3), 1.92 (s, 3H, CH3);
13C NMR (125 MHz, DMSO-d6) d 165.83 (s, C=O), 165.39 (s, C=N), 164.09 (s, Oxadiazole-C), 164.01 (s, Oxadiazole-C), 154.27
(s, Ph-C), 151.14 (s, Ph-C), 116.13 (s, Ph-C), 114.68 (s, Ph-C), 60.06 (s, OCH2), 55.38 (s, OCH3), 33.00 (s, SCH2), 21.25 (s, CH3),
16.65 (s, CH3);
MS (ESI, m/z): 352.2 [M?H]?, 374.1 [M?Na]?, 390.1 [M?K]?
1H NMR (500 MHz, DMSO-d6) d 7.71 (d, J = 8.7 Hz, 2H, Ph-H), 7.26 (d, J = 8.6 Hz, 2H, Ph-H), 5.52 (s, 2H, OCH2), 4.39 (s,
2H, SCH2), 1.97 (s, 3H, CH3), 1.92 (s, 3H, CH3);
19F NMR (471 MHz, DMSO-d6) d -59.85 (s, 3F, CF3);
13C NMR (125 MHz, DMSO-d6) d 165.84 (s, C=O), 165.39 (s, C=N), 164.26 (s, Oxadiazole-C), 163.47 (s, Ph-C), 160.03 (s,
Oxadiazole-C), 127.19 (s, J = 3.8 Hz, Ph-C), 122.83 (s, CF3), 122.50 (s, Ph-C), 115.43 (s, Ph-C), 59.55 (s, OCH3), 33.04 (s,
SCH2), 21.25 (s, CH3), 16.65 (s, CH3);
MS (ESI, m/z): 412.0 [M?Na]?, 428.1 [M?K]?
5a
5b
1H NMR (500 MHz, DMSO-d6) d 7.99–7.94 (m, 2H, Ph-H), 7.55–7.49 (m, 3H, Ph-H), 6.23 (s, 2H, NH2), 4.24 (s, 2H, SCH2), 1.97
(s, 3H, CH3), 1.96 (s, 3H, CH3);
13C NMR (125 MHz, DMSO-d6) d 166.31 (s, C=O), 165.43 (s, C=N), 154.28 (s, Triazole-C), 152.90 (s, Triazole-C), 129.73 (s, Ph-
C), 128.57 (s, Ph-C), 127.71 (s, Ph-C), 126.75 (s, Ph-C), 31.96 (s, SCH2), 21.27 (s, CH3), 16.68 (s, CH3);
MS (ESI, m/z): 306.1 [M?H]?, 328.1 [M?Na]?, 344.0 [M?K]?
1H NMR (500 MHz, DMSO-d6) d 8.00–7.94 (m, 2H, Ph-H), 7.56–7.50 (m, 3H, Ph-H), 6.23 (s, 2H, NH2), 4.24 and 4.23 (s, 2H,
SCH2, E-isomer ? Z-isomer), 2.36 and 2.31 (q, J = 7.5 Hz, 2H, CH2, E-isomer ? Z-isomer), 1.96 and 1.94 (s, 3H, CH3,
E-isomer ? Z-isomer), 1.07 and 1.01 (t, J = 7.6 Hz, 3H, CH3CH2, E-isomer ? Z-isomer);
13C NMR (125 MHz, DMSO-d6) d 169.53 and 168.75 (s, C=N, E-isomer ? Z-isomer), 166.39 and 166.29 (s, C=O, E-isomer ? Z-
isomer), 154.27 (s, Triazole-C), 152.90 (s, Triazole-C), 129.72 (s, Ph-C), 128.56 (s, Ph-C), 127.71 (s, Ph-C), 126.74 (s, Ph-C),
32.01 and 31.91 (s, SCH2, E-isomer ? Z-isomer), 28.48 and 23.33 (s, CH2, E-isomer ? Z-isomer), 18.90 and 15.05 (s, CH3,
E-isomer ? Z-isomer), 10.33 and 9.85 (s, CH3, E-isomer ? Z-isomer);
MS (ESI, m/z): 320.1 [M?H]?, 342.1 [M?Na]?, 358.1 [M?K]?
5c
1H NMR (500 MHz, DMSO-d6) d 8.05–7.99 (m, 2H, Ph-H), 7.41–7.35 (m, 2H, Ph-H), 6.23 (s, 2H, NH2), 4.23 (s, 2H, SCH2), 1.97
(s, 3H, CH3), 1.95 (s, 3H, CH3);
19F NMR (471 MHz, DMSO-d6) d -110.98;
13C NMR (125 MHz, DMSO-d6) d 166.29 (s, C=O), 165.43 (s, C=N), 162.90 (s, J = 247.2 Hz, Ph-C), 153.52 (s, Triazole-C),
152.88 (s, Triazole-C), 130.11 (s, Ph-C), 123.31 (s, J = 3.1 Hz, Ph-C), 115.66 (s, Ph-C), 32.01 (s, SCH2), 21.27 (s, CH3), 16.68
(s, CH3);
MS (ESI, m/z): 324.0 [M?H]?, 346.1 [M?Na]?, 362.0 [M?K]?
5d
1H NMR (500 MHz, DMSO-d6) d 8.06–7.99 (m, 2H, Ph-H), 7.41–7.35 (m, 2H, Ph-H), 6.23 (s, 2H, NH2), 4.24 and 4.23 (s, 2H,
SCH2, E-isomer ? Z-isomer), 2.36 and 2.31 (q, J = 7.5 Hz, 2H, CH2, E-isomer ? Z-isomer), 1.96 and 1.94 (s, 3H, CH3,
E-isomer ? Z-isomer), 1.07 and 1.01(t, J = 7.5 Hz, 3H, CH3, E-isomer ? Z-isomer);
19F NMR (471 MHz, DMSO-d6) d -110.96;
13C NMR (125 MHz, DMSO-d6) d 169.57 and 168.79 (s, C=O, E-isomer ? Z-isomer), 166.40 and 163.91 (s, C=N, E-isomer ? Z-
isomer), 161.94 (s, J = 247.6 Hz, Ph-C), 153.53 (s, Triazole-C), 152.91 (s, Triazole-C), 130.12 (s, Ph-C), 123.32 (s, J = 3.1 Hz,
Ph-C), 115.67 (s, Ph-C), 32.08 and 31.98 (s, SCH2, E-isomer ? Z-isomer), 28.49 and 23.34 (s, CH2, E-isomer ? Z-isomer),
18.91 and 15.06 (s, CH3, E-isomer ? Z-isomer), 10.34 and 9.86 (s, CH3, E-isomer ? Z-isomer);
MS (ESI, m/z): 338.1 [M?H]?, 360.1 [M?Na]?, 376.1 [M?K]?
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