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4.3.23. 2-(2-(3-Bromophenoxy)ethyl)-5-(1H-pyrrol-1-yl)-1,3,
4-thiadiazole (8f)
160.00, 140.97, 123.65, 120.21, 113.02, 111.61, 65.39, 21.47; MS
(EI): m/z = found 299 [M+]; calcd. 299.11.
(Yield 60%). mp 98–100 °C; FTIR (KBr): 3159, 3038 (ArAH), 1571
(C@N), 1258 (CAOAC), 820 (CABr); 1H NMR (400 MHz, CDCl3) d
ppm: 3.50 (t, 2H, J = 5.86, CH2), 4.37 (t, 2H, J = 5.84, OCH2), 6.34
(t, 2H, J = 2.18, pyrrole-C3, C4AH), 6.89 (s, 1H, ph-C6AH), 7.11 (s,
1H, ph-C4AH), 7.23–7.37 (m, 4H, ph-C2, C5AH and pyrrole-C2,
4.3.29. 2-(2-(2,5-Dimethylphenoxy)ethyl)-5-(1H-pyrrol-1-yl)-1,3,
4-thiadiazole (8l)
(Yield 55%). mp 100–102 °C; FTIR (KBr): 3171, 2920 (ArAH),
1571 (C@N), 1261 (CAOAC); 1H NMR (400 MHz, CDCl3) d ppm:
2.14 (s, 3H, CH3), 2.26 (s, 3H, CH3), 3.57 (t, 2H, J = 5.78, CH2), 4.31
(t, 2H, J = 5.80, OCH2), 6.35 (t, 2H, J = 2.18, pyrrole-C3, C4AH), 6.64
(d, 1H, J = 6.59, ph-C4AH), 6.72 (d, 1H, J = 7.03, ph-C6AH), 7.04 (d,
1H, J = 7.03, ph-C3AH), 7.28 (t, 2H, J = 2.24, pyrrole-C2, C5AH); 13C
NMR (100 MHz, CDCl3) d ppm: 163.11, 161.09, 156.72, 136.29,
130.67, 123.45, 121.78, 116.06, 111.90, 65.51, 31.13, 21.09,
16.09; MS (EI): m/z = found 299 [M+]; calcd. 299.11.
C5AH); 13C NMR (100 MHz, CDCl3)
d ppm: 163.41, 161.98,
161.52, 131.36, 123.18, 121.06, 120.54, 117.03, 112.56, 112.95,
65.42, 31.19; MS (ESI): m/z = found 351.93 [M++1]; calcd. 350.23.
4.3.24. 2-(2-(2-Bromophenoxy)ethyl)-5-(1H-pyrrol-1-yl)-1,3,
4-thiadiazole (8g)
(Yield 60%). mp 78–80 °C; FTIR (KBr): 3109, 2924 (ArAH), 1525
(C@N), 1246 (CAOAC), 830 (CABr); 1H NMR (400 MHz, CDCl3) d
ppm: 3.51 (t, 2H, J = 5.80, CH2), 4.28 (t, 2H, J = 5.84, OCH2), 6.35
(t, 2H, J = 2.22, pyrrole-C3, C4AH), 6.80, 6.82 (td, 2H, J = 2.22, 1.96,
pyrrole-C2, C6AH), 7.28 (d, 2H, J = 8.23, ph-C2, C5AH), 7.37, 7.39
(td, 2H, J = 2.22, 1.96, ph-C3, C5AH); 13C NMR (100 MHz, CDCl3) d
ppm: 163.15, 161.51, 157.14, 132.49, 120.84, 116.37, 113.81,
112.84, 65.86, 30.84; MS (ESI): m/z = found 349.88 [M+ꢀ1]; calcd.
350.23.
4.3.30. 2-(2-(2,4-Dimethylphenoxy)ethyl)-5-(1H-pyrrol-1-yl)-1,3,
4-thiadiazole (8m)
(Yield 55%). mp 93–95 °C; FTIR (KBr): 3118, 3020 (ArAH), 1535
(C@N), 1239 (CAOAC); 1H NMR (400 MHz, CDCl3) d ppm: 2.22 (s,
3H, CH3), 2.33 (s, 3H, CH3), 3.56 (t, 2H, J = 5.82, CH2), 5.37 (t, 2H,
J = 5.78, OCH2), 6.31 (t, 2H, J = 2.10, pyrrole-C3, C4AH), 6.69–6.98
(m, 3H, ph-C3, C5, C6AH), 7.36 (t, 2H, J = 2.10, pyrrole-C2, C5AH);
13C NMR (100 MHz, CDCl3)
d ppm: 163.22, 161.11, 155.62,
4.3.25. 2-(1H-Pyrrol-1-yl)-5-(2-(4-tolyloxy)ethyl)-1,3,4-thiadiazole
(8h)
131.83, 130.14, 127.11, 126.93, 120.10, 113.13, 111.49, 65.55,
31.21, 21.59, 16.03; MS (EI): m/z = found 299 [M+]; calcd. 299.11.
(Yield 65%). mp 70–72 °C; FTIR (KBr): 3098, 2926 (ArAH), 1588
(C@N), 1234 (CAOAC); 1H NMR (400 MHz, CDCl3) d ppm: 2.29 (s,
3H, CH3), 3.58 (t, 1H, J = 5.80, CH2), 4.29 (t, 2H, J = 5.80, OCH2),
6.35 (t, 2H, J = 2.20, pyrrole-C3, C4AH), 6.82–6.85 (d, 2H, ph-C2,
C5AH), 7.11 (d, 2H, J = 8.40, ph-C2, C5AH), 7.30 (t, 2H, J = 2.20, pyr-
role-C2, C5AH); 13C NMR (100 MHz, CDCl3) d ppm: 163.22, 162.05,
156.20, 130.88, 120.83, 112.84, 108.32, 65.67, 31.03, 20.54; MS
(EI): m/z = found 285 [M+]; calcd. 285.09.
4.3.31. 2-(2-(4-Fluorophenoxy)ethyl)-5-(1H-pyrrol-1-yl)-1,3,
4-thiadiazole (8n)
(Yield 59%). mp 98–100 °C; FTIR (KBr): 3140, 3072 (ArAH), 1565
(C@N), 1253 (CAOAC), 753 (CAF); 1H NMR (400 MHz, CDCl3) d
ppm: 3.59 (t, 2H, J = 5.80, CH2), 5.41 (t, 2H, J = 5.84, OCH2), 6.35
(t, 2H, J = 2.12, pyrrole-C3, C4AH), 6.94–7.05 (m, 4H, ph-C2, C3, C5,
C6AH), 7.32 (t, 2H, J = 2.18, pyrrole-C2, C5AH); 13C NMR
(100 MHz, CDCl3) d ppm: 163.60, 161.89, 155.85, 154.62, 121.01,
116.60, 115.89, 112.33, 65.37, 30.88; MS (EI): m/z = found 289
[M+]; calcd. 289.07.
4.3.26. 2-(1H-Pyrrol-1-yl)-5-(2-(3-tolyloxy)ethyl)-1,3,4-thiadiazole
(8i)
(Yield 59%). mp 90–92 °C; FTIR (KBr): 3033, 2926 (ArAH), 1591
(C@N), 1261 (CAOAC); 1H NMR (400 MHz, CDCl3) d ppm: 2.33 (s,
3H, CH3), 3.53 (t, 2H, J = 5.80, CH2), 4.30 (t, 2H, J = 5.76, OCH2),
6.35 (t, 2H, J = 2.12, pyrrole-C3, C4AH), 6.76 (t, 1H, J = 3.76, ph-
C4AH), 6.81 (d, 1H, J = 7.48, ph-C2AH), 7.18 (d, 1H, J = 7.80, ph-
C6AH), 7.24 (s, 1H, ph-C5AH), 7.30 (t, 2H, J = 2.12, pyrrole-C2,
4.3.32. 2-(2-(4-Iodophenoxy)ethyl)-5-(1H-pyrrol-1-yl)-1,3,
4-thiadiazole (8o)
(Yield 55%). mp 102–104 °C; FTIR (KBr): 3138, 3052 (ArAH),
1565 (C@N), 1249 (CAOAC), 721 (CAI); 1H NMR (400 MHz,
CDCl3) d ppm: 2.95 (t, 2H, J = 5.74, CH2), 4.53 (t, 2H, J = 5.76,
OCH2), 6.34 (t, 2H, J = 2.18, pyrrole-C3, C4AH), 6.85 (d, 2H,
J = 7.76, ph-C2, C6AH), 7.31 (t, 2H, J = 2.22, pyrrole-C2, C5AH),
7.55 (d, 2H, J = 7.76, ph-C3, C5AH); 13C NMR (100 MHz, CDCl3) d
ppm: 163.55, 161.69, 156.20, 138.60, 120.79, 116.08, 113.09,
83.56, 65.30, 31.01; MS (EI): m/z = found 396 [M+]; calcd. 396.97.
C5AH); 13C NMR (100 MHz, CDCl3)
d ppm: 163.29, 162.57,
157.22, 139.90, 130.01, 123.00, 120.83, 115.51, 113.12, 111.60,
65.12, 31.07, 21.50; MS (EI): m/z = found 285 [M+]; calcd. 285.09.
4.3.27. 2-(1H-Pyrrol-1-yl)-5-(2-(2-tolyloxy)ethyl)-1,3,4-thiadiazole
(8j)
(Yield 60%). mp 76–78 °C; FTIR (KBr): 3021, 2923 (ArAH), 1592
(C@N), 1296 (CAOAC); 1H NMR (400 MHz, CDCl3) d ppm: 2.28 (s,
3H, CH3), 3.56 (t, 2H, J = 5.76, CH2), 4.31 (t, 2H, J = 5.76, OCH2),
6.35 (t, 2H, J = 2.16, pyrrole-C3, C4AH), 6.82 (d, 1H, J = 8.40, ph-
C5AH), 6.89 (t, 2H, J = 7.36, ph-C4), 7.15 (t, 2H, J = 7.24, ph-C3,
C6AH), 7.28 (t, 2H, J = 2.16, pyrrole-C2, C5AH); 13C NMR
(100 MHz, CDCl3) d ppm: 163.13, 162.04, 156.20, 130.98, 126.97,
121.17, 120.97, 112.84, 110.85, 65.57, 31.10, 16.57; MS (EI): m/
z = found 285 [M+]; calcd. 285.09.
4.3.33. 2-(2-(Naphthalen-1-yloxy)ethyl)-5-(1H-pyrrol-1-yl)-1,3,
4-thiadiazole (8p)
(Yield 58%). mp 80–82 °C; FTIR (KBr): 3056, 2925 (ArAH), 1597
(C@N), 1264 (CAOAC); 1H NMR (400 MHz, CDCl3) d ppm: 2.92 (t,
2H, J = 5.70, CH2), 4.57 (t, 2H, J = 5.74, OCH2), 6.35 (s, 2H, pyrrole-
C2, C3AH), 6.86 (s, 2H, ph-C2AH), 7.28 (s, 2H, pyrrole-C3, C4AH),
7.54–8.32 (m, 7H, naphthyl-C2, C3, C4, C5, C6, C7, C8AH); 13C NMR
(100 MHz, CDCl3) d ppm: 163.61, 162.42, 155.22, 135.1, 134.18,
129.93, 129.50, 127.64, 127.00, 126.71, 126.82, 123.83, 118.32,
118.27, 113.31, 113.12, 106.91, 63.06, 34.31; MS (EI): m/z = found
321 [M+]; calcd. 321.09.
4.3.28. 2-(2-(3,5-Dimethylphenoxy)ethyl)-5-(1H-pyrrol-1-yl)-1,3,
4-thiadiazole (8k)
(Yield 55%). mp 97–99 °C; FTIR (KBr): 3122, 3008 (ArAH), 1562
(C@N), 1236 (CAOAC); 1H NMR (400 MHz, CDCl3) d ppm: 2.30 (s,
6H, 2CH3), 3.53 (t, 2H, J = 5.80, CH2), 5.44 (t, 2H, J = 5.80, OCH2),
6.32 (t, 2H, J = 2.18, pyrrole-C3, C4AH), 6.66 (m, 2H, ph-C3, C6AH),
6.92–6.95 (m, 1H, ph-C4AH), 7.33 (t, 2H, J = 2.22, pyrrole-C2,
4.3.34. 2-(2-(Naphthalen-2-yloxy)ethyl)-5-(1H-pyrrol-1-yl)-1,3,
4-thiadiazole (8q)
(Yield 55%). mp 86–88 °C; FTIR (KBr): 3140, 2950 (ArAH), 1565
(C@N), 1235 (CAOAC); 1H NMR (400 MHz, CDCl3) d ppm: 2.95 (t,
2H, J = 5.74, CH2), 4.59 (t, 2H, J = 5.74, OCH2), 6.33 (t, 2H, J = 2.24,
pyrrole-C3, C4AH), 6.70–7.80 (m, 7H, naphthyl-C1, C3, C4, C5, C6,
C5AH); 13C NMR (100 MHz, CDCl3)
d ppm: 163.28, 161.19,