3.3. Spectral Analysis
3.3.1. (E)-2-(Benzo[d]oxazol-2-ylthio)-1-(3-nitrophenyl)-N-(5-(4-nitrophenyl)-1,3,4-oxadiazol-2-yl)ethan-1-imine (1)
Yield: 63%; brown solid; m.p.: 192–193 °C; 1H-NMR (600 MHz, DMSO-d6): δ 8.83 (s, 1H, Ar-H), 8.72 (d, J = 8.2 Hz, 2H, Ar-H), 8.65 (dd, J = 8.6, 1.3 Hz, 1H, Ar-H), 8.54 (d, J = 8.5 Hz, 2H, Ar-H), 8.41 (dd, J = 8.0, 1.8 Hz, 1H, Ar-H), 8.06 (t, J = 8.7 Hz, 1H, Ar-H), 8.03 (dd, J = 7.0, 1.4 Hz, 1H, Benzoxazole-H), 7.99 (dd, J = 7.2, 1.6 Hz, 1H, Benzoxazole-H), 7.67 (t, J = 7.6, 1.2 Hz, 1H, Benzoxazole-H), 7.64 (t, J = 7.6, 1.2 Hz, 1H, Benzoxazole-H), 3.82 (s, 2H, -SCH2); 13C-NMR (150 MHz, DMSO-d6): δ 179.1, 174.4, 174.2, 170.8, 163.0, 160.9, 157.7, 150.3, 150.2, 147.7, 146.3, 146.0, 144.6, 144.3, 141.5, 141.2, 139.3, 138.7, 136.0, 132.9, 127.8, 115.6, 43.8. HR EI-MS: m/z calcd for C23H14N6O6S [M]+ 502.0954; Found: 502.0930.
3.3.2. (E)-2-(Benzo[d]oxazol-2-ylthio)-1-(3-nitrophenyl)-N-(5-(3-nitrophenyl)-1,3,4-oxadiazol-2-yl)ethan-1-imine (2)
Yield: 59%; brown solid; m.p.: 188–189 °C; 1H-NMR (600 MHz, DMSO-d6): δ 8.82 (s, 1H, Ar-H), 8.72 (s, 1H, Ar-H), 8.75 (dd, J = 8.4, 2.3 Hz, 1H, Ar-H), 8.66 (dd, J = 8.8, 1.5 Hz, 1H, Ar-H), 8.57 (dd, J = 8.3, 2.5 Hz, 1H, Ar-H), 8.42 (dd, J = 8.5, 1.9 Hz, 1H, Ar-H), 8.08 (t, J = 8.5 Hz, 1H, Ar-H), 8.00 (t, J = 7.9 Hz, 1H, Ar-H), 8.05 (dd, J = 7.2, 1.8 Hz, 1H, Benzoxazole-H), 7.95 (dd, J = 7.3, 1.8 Hz, 1H, Benzoxazole-H), 7.72 (t, J = 7.8 Hz, 1H, Benzoxazole-H), 7.69 (t, J = 7.6 Hz, 1H, Benzoxazole-H), 3.85 (s, 2H, -SCH2); 13C-NMR (150 MHz, DMSO-d6): δ 181.5, 175.7, 175.4, 172.8, 167.0, 163.9, 159.7, 156.8, 156.5, 155.7, 154.3, 154.2, 150.6, 150.4, 147.8, 147.4, 142.3, 140.2, 137.5, 135.2, 129.4, 122.6, 44.7. HR EI-MS: m/z calcd for C23H14N6O6S[M]+ 502.3250; Found: 502.3211.
3.3.3. (E)-2-(Benzo[d]oxazol-2-ylthio)-N-(5-(2,4-dichlorophenyl)-1,3,4-oxadiazol-2-yl)-1-(3-nitrophenyl)ethan-1-imine (3)
Yield: 62%; black solid; m.p.: 197–198 °C; 1H-NMR (600 MHz, DMSO-d6): δ 8.79 (s, 1H, Ar-H), 8.68 (dd, J = 8.8, 2.0 Hz, 1H, Ar-H), 8.64 (dd, J = 8.4, 1.8 Hz, 1H, Ar-H), 8.56 (t, J = 8.5 Hz, 1H, Ar-H), 8.23 (s, 1H, Ar-H), 8.17 (d, J = 8.0 Hz, 1H, Ar-H), 8.10 (dd, J = 7.6, 2.0 Hz, 1H, Benzoxazole-H), 8.05 (dd, J = 7.7, 2.8 Hz, 1H, Benzoxazole-H), 8.02 (d, J = 8.7 Hz, 1H, Ar-H), 7.92 (t, J = 7.4 Hz, 1H, Benzoxazole-H), 7.89 (t, J = 7.3 Hz, 1H, Benzoxazole-H), 3.80 (s, 2H, -SCH2); 13C-NMR (150 MHz, DMSO-d6): δ 182.3, 170.4, 170.0, 168.2, 167.3, 165.6, 159.1, 157.8, 157.3, 156.2, 154.8, 154.6, 152.8, 152.5, 149.8, 149.4, 145.3, 143.2, 139.4, 137.2, 128.4, 126.6, 44.2. HR EI-MS: m/z calcd for C23H13N5Cl2O4S [M]+ 526.4753; Found: 526.4719.
3.3.4. (E)-2-(Benzo[d]oxazol-2-ylthio)-N-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl)-1-(3-nitrophenyl)ethan-1-imine (4)
Yield: 64%; white solid; m.p.: 203–204 °C; 1H-NMR (600 MHz, DMSO-d6): δ 8.80 (s, 1H, Ar-H), 8.71 (dd, J = 8.6, 1.3 Hz, 1H, Ar-H), 8.66 (dd, J = 8.3, 2.8 Hz, 1H, Ar-H), 8.61 (d, J = 8.3 Hz, 2H, Ar-H), 8.56 (t, J = 8.2 Hz, 1H, Ar-H), 8.54 (d, J = 8.5 Hz, 2H, Ar-H), 8.37 (dd, J = 7.5, 2.0 Hz, 1H, Benzoxazole-H), 8.15 (dd, J = 7.6, 1.9 Hz, 1H, Benzoxazole-H), 7.97 (t, J = 7.7, 2.2 Hz, 1H, Benzoxazole-H), 7.94 (t, J = 7.9, 1.8 Hz, 1H, Benzoxazole-H), 3.72 (s, 2H, -SCH2); 13C-NMR (150 MHz, DMSO-d6): δ 186.8, 176.4, 176.0, 172.8, 168.0, 164.9, 159.7, 157.4, 157.1, 152.7, 151.3, 148.5, 143.6, 141.3, 140.8, 140.4, 139.7, 138.4, 136.9, 135.9, 127.4, 118.6, 42.8. HR EI-MS: m/z calcd for C23H14ClN5O4S [M]+ 491.1987; Found: 491.1923.
3.3.5. (E)-4-(5-((2-(Benzo[d]oxazol-2-ylthio)-1-(3-nitrophenyl)ethylidene)amino)-1,3,4-oxadiazol-2-yl)-N,N-dimethylaniline (5)
Yield: 66%; white solid; m.p.: 201–202 °C; 1H-NMR (600 MHz, DMSO-d6): δ 8.77 (s, 1H, Ar-H), 8.68 (dd, J = 8.2, 2.3 Hz, 1H, Ar-H), 8.61 (dd, J = 8.0, 2.1 Hz, 1H, Ar-H), 8.54 (t, J = 8.4 Hz, 1H, Ar-H), 8.47 (d, J = 8.0 Hz, 2H, Ar-H), 8.38 (dd, J = 7.4, 2.8 Hz, 1H, Benzoxazole-H), 8.26 (dd, J = 7.7, 2.0 Hz, 1H, Benzoxazole-H), 8.07 (t, J = 7.2 Hz, 1H, Benzoxazole-H), 7.95 (t, J = 7.0 Hz, 1H, Benzoxazole-H), 7.34 (d, J = 8.0 Hz, 2H, Ar-H), 3.70 (s, 2H, -SCH2), 3.10 (s, 6H, -N(CH3)2); 13C-NMR (150 MHz, DMSO-d6): δ 178.3, 176.7, 176.2, 175.9, 170.0, 169.9, 165.1, 162.4, 162.1, 159.4, 157.3, 157.2, 145.6, 145.2, 142.8, 142.4, 140.7, 139.4, 133.9, 131.9, 126.4, 122.8, 43.9, 43.5, 40.2. HR-EI-MS: m/z calcd for C25H20N6O4S [M]+ 500.2289; Found: 500.2243.
3.3.6. (E)-2-(Benzo[d]oxazol-2-ylthio)-N-(5-(4-(benzyloxy)phenyl)-1,3,4-oxadiazol-2-yl)-1-(p-tolyl)ethan-1-imine (6) (Figures S1 and S2)
Yield: 56%; black solid; m.p.: 191–192 °C; 1H-NMR (600 MHz, DMSO-d6): δ 8.18 (d, J = 8.2 Hz, 1H, Ar-H), 7.97 (dd, J = 7.5, 2.3 Hz, 1H, Benzoxazole-H),7.78 (dd, J = 7.8, 2.3 Hz, 1H, Benzoxazole-H), 7.58 (d, J = 8.3 Hz, 2H, Ar-H), 7.51 (t, J = 8.9 Hz, 1H, Ar-H), 7.43 (d, J = 7.4 Hz, 2H, Ar-H), 7.18 (d, J = 7.6 Hz, 2H, Ar-H), 7.17 (m, J = 8.3 Hz, 3H, Ar-H), 7.16 (t, J = 7.8, Hz, 1H, Benzoxazole-H), 7.15 (t, J = 7.3 Hz, 1H, Benzoxazole-H), 7.09 (d, J = 8.0 Hz, 1H, Ar-H),7.08 (d, J = 7.6 Hz, 1H, Ar-H),3.77 (s, 2H, OCH2), 3.72 (s, 2H, -SCH2), 1.68 (s, 3H, Ar-CH3). 13C-NMR (150 MHz, DMSO-d6): δ 193.7, 174.0, 168.1, 166.4, 158.5, 155.8, 142.0, 141.8, 135.2, 132.7, 131.0, 130.9, 130.7, 130.5, 129.3, 129.0, 128.8, 127.8, 122.0, 121.9, 121.5, 121.4, 120.2, 118.5, 114.4, 113.9, 109.5, 100.4, 63.0, 39.9, 24.6; HR EI-MS: m/z calcd for C31H24N4O3S [M]+ 532.7332; Found: 532.7287.
3.3.7. (E)-2-(Benzo[d]oxazol-2-ylthio)-N-(5-(3-nitrophenyl)-1,3,4-oxadiazol-2-yl)-1-(p-tolyl)ethan-1-imine (7)
Yield: 73%; yellow solid; m.p.: 186–188 °C; 1H-NMR (600 MHz, DMSO-d6): δ 8.75 (s, 1H, Ar-H), 8.65 (dd, J = 8.0, 2.9 Hz, 1H, Ar-H), 8.63 (dd, J = 8.1, 2.0 Hz, 1H, Ar-H), 8.55 (t, J = 8.0 Hz, 1H, Ar-H), 8.51 (d, J = 8.3 Hz, 2H, Ar-H), 8.31 (dd, J = 7.5, 1.8 Hz, 1H, Benzoxazole-H), 8.26 (dd, J = 7.4, 2.3 Hz, 1H, Benzoxazole-H), 8.09 (t, J = 7.3 Hz, 1H, Benzoxazole-H), 8.02 (t, J = 7.4 Hz, 1H, Benzoxazole-H), 7.77 (d, J = 6.7 Hz, 2H, Ar-H), 3.72 (s, 2H, -SCH2), 2.63 (s, 3H, Ar-CH3); 13C-NMR (150 MHz, DMSO-d6): δ 188.5, 177.7, 177.4, 176.1, 172.0, 170.9, 168.1, 166.3, 165.1, 158.4, 156.3, 157.2, 150.6, 148.2, 147.4, 143.4, 142.7, 142.4, 133.5, 133.2, 129.3, 128.8, 43.9, 24.4. HR EI-MS: m/z calcd for C24H17N5O4S [M]+ 471.6381; Found: 471.6323.
3.3.8. (E)-4-(5-((2-(Benzo[d]oxazol-2-ylthio)-1-(p-tolyl)ethylidene)amino)-1,3,4-oxadiazol-2-yl)-N,N-dimethylaniline (8) (Figures S3 and S4)
Yield: 60%; white solid; m.p.: 195–196 °C; 1H-NMR (600 MHz, DMSO-d6): δ 8.61 (dd, J = 7.9, 1.9 Hz, 1H, Benzoxazole-H), 8.26 (d, J = 8.0 Hz, 2H, Ar-H), 7.84 (dd, J = 7.7, 2.0 Hz, 1H, Benzoxazole-H), 7.70 (t, J = 7.6 Hz, 1H, Benzoxazole-H), 7.59 (t, J = 7.8 Hz, 1H, Benzoxazole-H), 7.48 (d, J = 8.2 Hz, 2H, Ar-H), 7.24–6.92 (m, J = 6.7 Hz, 4H, Ar-H), 3.74 (s, 2H, -SCH2), 3.17 (s, 6H, N(CH3)2), 1.50 (s, 3H, Ar-CH3); 13C-NMR (150 MHz, DMSO-d6): δ 195.4, 188.4, 147.6, 144.8, 144.2, 132.6, 132.2, 132.1, 131.9, 131.8, 131.6, 131.5, 131.4, 131.3, 131.2, 131.1, 129.7, 128.5, 127.2, 123.3, 123.2, 121.1, 45.6, 40.2, 40.0, 20.1; HR EI-MS: m/z calcd for C26H23N5O2S [M]+ 469.1398; Found: 469.1321.
3.3.9. (E)-2-(Benzo[d]oxazol-2-ylthio)-N-(5-(2,4-dichlorophenyl)-1,3,4-oxadiazol-2-yl)-1-(p-tolyl)ethan-1-imine (9) (Figures S5 and S6)
Yield: 75%; white solid; m.p.: 205–206 °C; 1H-NMR (600 MHz, DMSO-d6): δ 8.52 (s, 1H, Ar-H), 7.69 (dd, J = 7.1, 2.9 Hz, 1H, Benzoxazole-H), 7.54 (d, J = 8.0 Hz, 2H, Ar-H), 7.44 (d, J = 6.7 Hz, 2H, Ar-H),7.30 (d, J = 6.7 Hz, 2H, Ar-H),7.16 (dd, J = 7.4, 2.1 Hz, 1H, Benzoxazole-H), 6.83 (t, J = 7.1 Hz, 1H, Benzoxazole-H), 6.11 (t, J = 7.6 Hz, 1H, Benzoxazole-H), 3.81 (s, 2H, -SCH2), 3.73 (s, 3H, Ar-CH3); 13C-NMR (150 MHz, DMSO-d6): δ 185.9, 169.0, 168.6, 168.1, 168.0, 150.3, 149.5, 145.6, 143.1, 140.6, 140.1, 132.2, 132.0, 127.8, 127.5, 125.2, 124.0, 123.9, 122.3, 122.1, 119.1, 109.4, 45.6, 21.6; HR EI-MS: m/z calcd for C24H16Cl2N4O2S [M]+ 495.1579; Found: 495.1542.
3.3.10. (E)-2-(Benzo[d]oxazol-2-ylthio)-N-(5-(4-nitrophenyl)-1,3,4-oxadiazol-2-yl)-1-(p-tolyl)ethan-1-imine (10)
Yield: 72%; yellow solid; m.p.: 197–198 °C; 1H-NMR (600 MHz, DMSO-d6): δ 8.69 (d, J = 8.3 Hz, 2H, Ar-H), 8.57 (d, J = 7.9 Hz, 2H, Ar-H), 8.41 (d, J = 8.8 Hz, 2H, Ar-H), 8.33 (dd, J = 7.4, 1.5 Hz, 1H, Benzoxazole-H), 8.25 (dd, J = 7.8, 2.2 Hz, 1H, Benzoxazole-H) 8.17 (t, J = 7.4 Hz, 1H, Benzoxazole-H), 8.04 (t, J = 7.5 Hz, 1H, Benzoxazole-H), 7.84 (d, J = 6.1 Hz, 2H, Ar-H), 3.62 (s, 2H, -SCH2), 2.68 (s, 3H, Ar-CH3); 13C-NMR (150 MHz, DMSO-d6): δ 189.1, 178.6, 178.3, 177.1, 175.2, 173.2, 169.7, 168.6, 165.9, 163.4, 157.3, 153.2, 153.0, 151.0, 149.4, 146.4, 144.6, 143.2, 139.5, 136.2, 129.3, 127.8, 45.8, 24.7. HR EI-MS: m/z calcd for C24H17N5O4S [M]+ 471.3642; Found: 471.3603.
3.3.11. (E)-2-(Benzo[d]oxazol-2-ylthio)-N-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl)-1-(p-tolyl)ethan-1-imine (11)
Yield: 74%; white solid; m.p.: 193–194 °C; 1H-NMR (600 MHz, DMSO-d6): δ 8.65 (d, J = 8.0 Hz, 2H, Ar-H), 8.59 (d, J = 7.7 Hz, 2H, Ar-H), 8.47 (d, J = 8.3 Hz, 2H, Ar-H), 8.35 (dd, J = 7.7, 1.8 Hz, 1H, Benzoxazole-H), 8.23 (dd, J = 7.4, 2.6 Hz, 1H, Benzoxazole-H), 8.19 (t, J = 7.6 Hz, 1H, Benzoxazole-H), 8.08 (t, J = 7.3 Hz, 1H, Benzoxazole-H), 7.89 (d, J = 6.9 Hz, 2H, Ar-H), 3.68 (s, 2H, -SCH2), 2.60 (s, 3H, Ar-CH3); 13C-NMR (150 MHz, DMSO-d6): δ 188.2, 177.1, 177., 176.6, 174.4, 172.5, 167.4, 165.7, 163.4, 161.2, 158.3, 156.5, 154.2, 153.8, 149.7, 147.1, 145.3, 143.8, 137.2, 135.2, 128.3, 122.5, 42.4, 24.6; HR EI-MS: m/z calcd for C24H17ClN4O2S [M]+ 460.3872; Found: 471.3812.
3.3.12. (E)-4-(5-((2-(Benzo[d]oxazol-2-ylthio)-1-(p-tolyl)ethylidene)amino)-1,3,4-oxadiazol-2-yl)benzaldehyde (12)
Yield: 64%; brown solid; m.p.: 187–189 °C; 1H-NMR (600 MHz, DMSO-d6): δ 9.80 (s, 1H, CHO), 8.63 (d, J = 8.2 Hz, 2H, Ar-H), 8.60 (d, J = 7.8 Hz, 2H, Ar-H), 8.50 (d, J = 8.0 Hz, 2H, Ar-H), 8.39 (dd, J = 7.7, 1.8 Hz, 1H, Benzoxazole-H), 8.24 (dd, J = 7.5, 2.8 Hz, 1H, Benzoxazole-H), 8.13 (t, J = 7.9 Hz, 1H, Benzoxazole-H), 8.06 (t, J = 7.4 Hz, 1H, Benzoxazole-H), 7.86 (d, J = 7.9 Hz, 2H, Ar-H), 3.69 (s, 2H, -SCH2), 2.51 (s, 3H, Ar-CH3); 13C-NMR (150 MHz, DMSO-d6): δ 190.5, 180.6, 177.4, 177.2, 176.0, 174.1, 172.8, 169.3, 167.2, 163.7, 161.6, 158.8, 157.5, 155.2, 153.8, 149.9, 147.7, 146.3, 144.8, 139.2, 138.2, 126.3, 124.5, 43.4, 24.9; HR EI-MS: m/z calcd for C25H18N4O3S [M]+ 460.3872; Found: 471.3812.
3.3.13. (E)-2-(Benzo[d]oxazol-2-ylthio)-N-(5-(4-(benzyloxy)phenyl)-1,3,4-oxadiazol-2-yl)-1-(m-tolyl)ethan-1-imine (13)
Yield: 57%; black solid; m.p.: 201–203 °C; 1H-NMR (600 MHz, DMSO-d6): δ 8.82 (d, J = 8.0 Hz, 2H, Ar-H), 8.77 (s, 1H, Ar-H), 8.58 (dd, J = 8.2, 2.5 Hz, 1H, Ar-H), 8.49 (dd, J = 7.1, 2.4 Hz, 1H, Benzoxazole-H), 8.42 (dd, J = 7.6, 2.6 Hz, 1H, Benzoxazole-H), 8.34 (dd, J = 7.0, 2.4 Hz, 1H, Ar-H), 8.23 (t, J = 7.0 Hz, 1H, Ar-H), 8.17 (dd, J = 8.9, 1.7 Hz, 2H, Ar-H), 8.11 (t, J = 7.3, Hz, 1H, Benzoxazole-H), 8.04 (t, J = 7.3 Hz, 1H, Benzoxazole-H), 7.96 (d, J = 8.1 Hz, 2H, Ar-H), 7.90 (t, J = 8.3 Hz, 1H, Ar-H), 7.86 (t, J = 8.0 Hz, 1H, Ar-H), 7.76 (m, J = 8.3 Hz, 1H, Ar-H), 5.67 (s, 2H, OCH2), 3.79 (s, 2H, -SCH2), 2.50 (s, 3H, Ar-CH3). 13C-NMR (150 MHz, DMSO-d6): δ 187.9, 176.8, 176.5, 175.9, 174.1, 171.9, 169.4, 167.2, 167.0, 164.9, 162.4, 161.8, 160.8, 159.9, 158.3, 153.5, 152.8, 150.5, 147.5, 144.2, 143.4, 143.0, 142.4, 140.7, 138.9, 137.9, 128.5, 126.7, 72.9, 45.5, 28.6; HR EI-MS: m/z calcd for C31H24N4O3S [M]+ 532.7332; Found: 532.7287.
3.3.14. (E)-2-(Benzo[d]oxazol-2-ylthio)-N-(5-(naphthalen-2-yl)-1,3,4-oxadiazol-2-yl)-1-(p-tolyl)ethan-1-imine (14)
Yield: 55%; black solid; m.p.: 205–207 °C; 1H-NMR (600 MHz, DMSO-d6): δ 8.56 (s, 1H, Naphthalene-H), 8.51 (dd, J = 6.9, 1.6 Hz, Naphthalene-H), 8.47 (dd, J = 6.8, 1.8 Hz, Naphthalene-H), 8.43 (d, J = 8.2 Hz, 1H, Naphthalene-H), 8.39 (d, J = 8.0 Hz, 1H, Naphthalene-H), 8.34 (dd, J = 7.1, 2.6 Hz, 1H, Benzoxazole-H), 8.27 (dd, J = 7.4, 2.8 Hz, 1H, Benzoxazole-H), 8.19 (t, J = 8.2 Hz, 1H, Naphthalene-H), 8.10 (t, J = 8.5 Hz, 1H, Naphthalene-H), 8.01 (d, J = 8.7 Hz, 2H, Ar-H), 7.97 (d, J = 8.4 Hz, 2H, Ar-H), 8.01 (t, J = 7.1 Hz, 1H, Benzoxazole-H), 7.98 (t, J = 7.6 Hz, 1H, Benzoxazole-H), 3.79 (s, 2H, -SCH2), 2.58 (s, 3H, Ar-CH3); 13C-NMR (150 MHz, DMSO-d6): δ 192.8, 181.4, 181.2, 180.2, 178.2, 175.4, 171.7, 169.8, 167.5, 165.0, 163.9, 161.3, 159.5, 157.6, 150.8, 150.6, 148.7, 148.2, 145.2, 141.8, 138.1, 129.3, 43.8, 21.9. HR EI-MS: m/z calcd for C28H20N4O2S [M]+ 476.1739; Found: 476.1702.
3.3.15. (E)-2-(Benzo[d]oxazol-2-ylthio)-1-(3,4-dichlorophenyl)-N-(5-(3,4-dichlorophenyl)-1,3,4-oxadiazol-2-yl)ethan-1-imine (15)
Yield: 76%; white solid; m.p.: 198–200 °C; 1H-NMR (600 MHz, DMSO-d6): δ 8.46 (s, 1H, Ar-H), 8.41 (s, 1H, Ar-H), 8.40 (d, J = 8.2 Hz, 1H, Ar-H), 8.33 (d, J = 7.8 Hz, 1H, Ar-H), 8.25 (d, J = 7.2 Hz, 1H, Ar-H), 8.18 (dd, J = 7.2, 2.0 Hz, 1H, Benzoxazole-H), 8.13 (dd, J = 7.0, 2.0 Hz, 1H, Benzoxazole-H), 8.06 (d, J = 7.3 Hz, 1H, Ar-H), 7.91 (t, J = 7.02 Hz, 1H, Benzoxazole-H), 7.80 (t, J = 7.05 Hz, 1H, Benzoxazole-H), 3.77 (s, 2H, -SCH2); 13C-NMR (150 MHz, DMSO-d6): δ 190.4, 179.4, 179.1, 178.5, 177.2, 174.9, 171.8, 169.2, 166.7, 165.9, 160.3, 150.2, 155.6, 151.2, 149.8, 148.4, 145.7, 144.2, 137.6, 136.6, 124.3, 121.8, 40.8;HR EI-MS: m/z calcd for C23H12Cl4N4O2S [M]+ 550.1269; Found: 550.1230.
3.3.16. (E)-2-(Benzo[d]oxazol-2-ylthio)-1-(3,4-dichlorophenyl)-N-(5-(3-nitrophenyl)-1,3,4-oxadiazol-2-yl)ethan-1-imine (16)
Yield: 68%; white solid; m.p.: 191–193 °C; 1H-NMR (600 MHz, DMSO-d6): δ 8.84 (s, 1H, Ar-H), 8.78 (dd, J = 7.8, 2.3 Hz, 1H, Ar-H), 8.71 (dd, J = 7.9, 1.7 Hz, 1H, Ar-H), 8.63 (t, J = 7.5 Hz, 1H, Ar-H), 8.52 (s, 1H, Ar-H), 8.47 (d, J = 7.9 Hz, 1H, Ar-H), 8.40 (dd, J = 7.8, 2.1 Hz, 1H, Benzoxazole-H), 8.32 (dd, J = 7.0, 2.3 Hz, 1H, Benzoxazole-H), 7.92 (d, J = 8.7 Hz, 1H, Ar-H), 7.83 (t, J = 7.4 Hz, 1H, Benzoxazole-H), 7.74 (t, J = 7.0 Hz, 1H, Benzoxazole-H), 3.86 (s, 2H, -SCH2); 13C-NMR (150 MHz, DMSO-d6): δ 182.8, 170.6, 170.8, 167.9, 167.7, 165.1, 158.1, 157.2, 157.0, 156.9, 154.2, 154.3, 152.4, 152.7, 148.8, 148.4, 144.3, 142.2, 138.4, 137.9, 128.1, 125.6, 44.0. HR EI-MS: m/z calcd for C23H13N5Cl2O4S [M]+ 526.1759; Found: 526.1703.
3.3.17. (E)-2-(Benzo[d]oxazol-2-ylthio)-N-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl)-1-(3,4-dichlorophenyl)ethan-1-imine (17)
Yield: 67%; white solid; m.p.: 183–186 °C; 1H-NMR (600 MHz, DMSO-d6): δ 8.81 (s, 1H, Ar-H), 8.78 (d, J = 7.9 Hz, 1H, Ar-H), 8.72 (d, J = 7.7 Hz, 1H, Ar-H), 8.61 (d, J = 7.1 Hz, 2H, Ar-H), 8.47 (dd, J = 7.0, 2.3 Hz, 1H, Benzoxazole-H), 8.39 (dd, J = 7.9, 2.0 Hz, 1H, Benzoxazole-H), 8.22 (d, J = 8.0 Hz, 2H, Ar-H), 8.08 (t, J = 7.5 Hz, 1H, Benzoxazole-H), 7.94 (t, J = 7.4 Hz, 1H, Benzoxazole-H), 3.62 (s, 2H, -SCH2); 13C-NMR (150 MHz, DMSO-d6): δ 185.8, 173.6, 173.4, 170.3, 169.7, 169.1, 165.3, 165.2, 162.7, 161.9, 159.2, 153.3, 151.8, 150.7, 148.6, 148.2, 145.3, 144.2, 137.0, 135.9, 129.2, 126.9, 44.7. HR EI-MS: m/z calcd for C23H13N4Cl3O2S [M]+ 515.3750; Found: 515.3701.
3.3.18. (E)-4-(5-((2-(Benzo[d]oxazol-2-ylthio)-1-(3,4-dichlorophenyl)ethylidene)amino)-1,3,4-oxadiazol-2-yl)-N,N-dimethylaniline (18)
Yield: 69%; white solid; m.p.: 193–194 °C; 1H-NMR (600 MHz, DMSO-d6): δ 8.87 (s, 1H, Ar-H), 8.81 (d, J = 7.3 Hz, 1H, Ar-H), 8.77 (d, J = 7.2 Hz, 1H, Ar-H), 8.62 (dd, J = 7.9, 2.0 Hz, 1H, Benzoxazole-H), 8.56 (dd, J = 7.2, 2.3 Hz, 1H, Benzoxazole-H), 8.51 (d, J = 7.1 Hz, 2H, Ar-H), 8.38 (t, J = 7.2 Hz, 1H, Benzoxazole-H), 8.30 (t, J = 7.5 Hz, 1H, Benzoxazole-H), 7.68 (d, J = 8.1 Hz, 2H, Ar-H), 3.57 (s, 2H, -SCH2), 3.23 (s, 6H, N(CH3)2); 13C-NMR (150 MHz, DMSO-d6): δ 185.2, 174.6, 174.2, 172.3, 170.6, 170.2, 169.3, 168.2, 167.7, 164.4, 160.2, 158.3, 157.8, 155.2, 151.6, 149.4, 146.3, 143.2, 138.0, 131.2, 129.8, 123.9, 45.4, 45.0, 40.6; HR EI-MS: m/z calcd for C25H19N5Cl2O2S [M]+ 524.3920; Found: 524.3861.
3.3.19. (E)-2-(Benzo[d]oxazol-2-ylthio)-1-(3,4-dichlorophenyl)-N-(5-(4-nitrophenyl)-1,3,4-oxadiazol-2-yl)ethan-1-imine (19)
Yield: 71%; yellow solid; m.p.: 193–194 °C; 1H-NMR (600 MHz, DMSO-d6): δ 8.81 (d, J = 7.2 Hz, 2H, Ar-H), 8.68 (d, J = 7.1 Hz, 2H, Ar-H), 8.87 (s, 1H, Ar-H), 8.82 (d, J = 7.8 Hz, 1H, Ar-H), 8.72 (d, J = 7.09 Hz, 1H, Ar-H), 8.32 (dd, J = 7.7, 2.4 Hz, 1H, Benzoxazole-H), 8.18 (dd, J = 7.2, 2.7 Hz, 1H, Benzoxazole-H), 7.98 (t, J = 7.7 Hz, 1H, Benzoxazole-H), 7.67 (t, J = 7.0 Hz, 1H, Benzoxazole-H), 3.41 (s, 2H, -SCH2); 13C-NMR (150 MHz, DMSO-d6): δ 188.2, 177.6, 177.1, 175.0, 173.0, 171.9, 169.8, 168.9, 167.2, 164.6, 163.2, 159.3, 158.8, 156.7, 154.5, 149.8, 145.3, 144.3, 134.0, 132.2, 126.8, 113.7, 39.8; HR EI-MS: m/z calcd for C23H13N5Cl2O4S [M]+ 526.3650; Found: 526.3611.