M. M. El-bendary et al.
4.7.2 Ethyl 2-(4-phenyl-1H-1,2,3-triazol-1-yl)acetate (3b)
DMSO): δH 1.22 (t, 3H, J = 7.08 Hz, CH3), 4.19 (q, 2H,
J = 7.08 Hz, CH2) 5.31 (s, 2H, CH2), 5.42 (s, 2H, CH2),
7.22 (d, 2H, J=8.8 Hz, ArH), 7.54–7.71 (m, 5H, ArH), 7.76
(d, 2H, J=8.8 Hz, ArH), 8.28 (s, 1H, triazol H), 13CNMR
(100 MHz, DMSO): δC 14.39, 50.86, 61.69, 62.00, 115.09,
126.71, 128.92, 129.70, 130.100, 132.59, 138.13, 142.64,
162.14, 167.64, 182.92, 194.92. MS (m/z): 365 (M+). Anal.
Calcd. for C20H19N3O4: C, 65.74; H, 5.24; N, 11.50. Found:
C, 65.89; H, 5.21; N, 11.38.
mp: 93–95 °C. IR (KBr) (νmax, cm−1): 1736 (C=O ester),
1494 (N=N), 1452 (C=C). 1HNMR (400 MHz, DMSO): δH
1.24 (t, 3H, J=7 Hz, CH3), 4.21 (q, 2H, J=7 Hz, CH2) 5.45
(s, 2H, CH2), 7.35–7.87 (m, 5H, ArH), 8.56 (s, 1H, triazol
H), 13CNMR (100 MHz, DMSO): δC 14.43, 51.01, 62.06,
123.22, 125.63, 128.46, 129.23, 130.95, 146.86, 167.69. MS
(m/z): 231 (M+). Anal. Calcd. for C12H13N3O2: C, 62.33; H,
5.67; N, 18.17. Found: C, 62.56; H, 5.60; N, 18.01.
4.7.7 2-(4-((4-Benzoylphenoxy)
methyl)-1H-1,2,3-triazol-1-yl)acetonitrile (3g)
4.7.3 2-(4-Phenyl-1H-1,2,3-triazol-1-yl)acetonitrile (3c)
mp: 70–72 °C. IR (KBr) (νmax, cm−1): 2210 (C≡N), 1495
mp: 162–164 °C. IR (KBr) (νmax, cm−1): 2212 (C≡N), 1679
1
(C=O), 1493 (N=N), 1442 (C=C). HNMR (400 MHz,
1
(N=N), 1450 (C=C). HNMR (400 MHz, DMSO): δH
DMSO): δH 5.36 (s, 2H, CH2), 5.56 (s, 2H, CH2), 7.13 (d,
2H, J=8.8 Hz), 7.39–7.81 (m, 7H, ArH), 8.29 (s, 1H, triazol
H), 13CNMR (100 MHz, DMSO): δC 45.13, 62.13, 115.43,
117.12, 126.53, 128.69, 129.18, 130.57, 131.15, 132.34,
138.92, 143.15, 162.01, 194.34. MS (m/z): 318 (M+). Anal.
Calcd. for C18H14N4O2: C, 67.91; H, 4.43; N, 17.60. Found:
C, 68.09; H, 4.38; N, 17.47.
5.74 (s, 2H, CH2), 7.32–7.83 (m, 5H, ArH), 8.51 (s, 1H,
triazol H), 13CNMR (100 MHz, DMSO): δC 47.22, 114.33,
126.59, 128.01, 129.49, 130.24, 130.47, 149.53. MS (m/z):
184 (M+). Anal. Calcd. for C10H8N4: C, 65.21; H, 4.38; N,
30.42. Found: C, 65.34; H, 4.33; N, 30.33.
4.7.4 2-(4-Phenyl-1H-1,2,3-triazol-1-yl)ethanol (3d)
4.7.8 (4-((1-(2-Hydroxyethyl)-1H-1,2,3-triazol-4-yl)
mp: 87–89 °C. IR (KBr) (νmax, cm−1): 3412 (OH), 1495
(N=N), 1448 (C=C). 1HNMR (400 MHz, DMSO): δH 3.22
(br s, 1H, OH, D2O exchangeable), 4.16 (t, 2H, J = 5 Hz,
CH2), 4.53 (t, 2H, J=5 Hz, CH2), 7.25–7.76 (m, 5H, ArH),
8.66 (s, 1H, triazol H), 13CNMR (100 MHz, DMSO): δC
54.63, 60.31, 126.34, 128.43, 129.31, 130.23, 130.64,
148.13. MS (m/z): 189 (M+). Anal. Calcd. for C10H11N3O:
C, 63.48; H, 5.86; N, 22.21. Found: C, 63.67; H, 5.80; N,
22.08.
methoxy)phenyl)(phenyl)methanone (3h)
mp: 213–215 °C. IR (KBr) (νmax, cm−1): 3409 (OH), 1678
1
(C=O), 1492 (N=N), 1451 (C=C). HNMR (400 MHz,
DMSO): δH 3.31 (br s, 1H, OH, D2O exchangeable), 4.14 (t,
2H, J=5.6 Hz, CH2), 4.46 (t, 2H, J=5.6 Hz, CH2), 5.59 (s,
2H, CH2), 7.09 (d, 2H, J=8.6 Hz), 7.21–7.86 (m, 7H, ArH),
8.69 (s, 1H, triazol H), 13CNMR (100 MHz, DMSO): δC
52.59, 61.39, 62.91, 115.14, 126.07, 128.98, 129.43, 130.02,
130.63, 132.16, 138.74, 142.50, 163.10, 194.06. MS (m/z):
323 (M+). Anal. Calcd. for C18H17N3O3: C, 66.86; H, 5.30;
N, 13.00. Found: C, 67.02; H, 5.26; N, 12.88.
4.7.5 (4-((1-(4-Fluorobenzyl)-1H-1,2,3-triazol-4-yl)
methoxy)phenyl)(phenyl)methanone (3e)
4.7.9 4,4′-(((Sulfonylbis(4,1-phenylene))
bis(oxy))bis(methylene))
mp: 205–207 °C. IR (KBr) (νmax, cm−1): 1676 (C=O), 1493
1
(N=N), 1459 (C=C). HNMR (400 MHz, DMSO): δH
bis(1-(4-fluorobenzyl)-1H-1,2,3-triazole) (3i)
5.23 (s, 2H, CH2), 5.52 (s, 2H, CH2), 6.79–7.67 (m, 13H,
ArH), 8.35 (s, 1H, triazol H), 13CNMR (100 MHz, DMSO):
δC 51.75, 61.27, 114.63, 115.73, 115.98, 122.47, 128.87,
129.67, 130.25, 130.47, 130.56, 132.36, 137.98, 144.69,
161.14, 161.43, 194.80, 19FNMR (DMSO): δF −112.02. MS
(m/z): 387 (M+). Anal. Calcd. for C23H18FN3O2: C, 71.31;
H, 4.68; N, 10.85. Found: C, 71.47; H, 4.65; N, 10.72.
mp: 293–295 °C. IR (KBr) (νmax, cm−1): 1496 (N=N), 1452
1
(C=C), 1305, 1124 (SO2). HNMR (400 MHz, DMSO):
δH 5.23 (s, 4H, 2CH2), 5.45 (s, 4H, 2CH2), 7.21 (d, 4H,
J=8.8 Hz, ArH), 7.81 (d, 4H, J=8.8 Hz, ArH), 8.41 (s, 2H,
2triazol H), 13CNMR (100 MHz, DMSO): δC 53.15, 62.13,
115.10, 116.26, 126.24, 129.42, 129.96, 132.17, 133.68,
142.01, 162.38, 166.58. (m/z): 628 (M+). Anal. Calcd.
for C32H26 F2N6O4S: C, 61.14; H, 4.17; N, 13.37; S, 5.10.
Found: C, 61.38; H, 4.13; N, 13.25; S, 5.02.
4.7.6 Ethyl 2-(4-((4-benzoylphenoxy)
methyl)-1H-1,2,3-triazol-1-yl)acetate (3f)
mp: 178–180 °C. IR (KBr) (νmax, cm−1): 1721 (C=O ester),
1692 (C=O), 1492 (N=N), 1451 (C=C). 1HNMR (400 MHz,
1 3