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Organic & Biomolecular Chemistry
Journal Name
COMMUNICATION
Yield: 85%, Yellow solid, m.p: 119-120°C; 1H NMR (400 MHz, CDCl3)
δ 8.29 (d, J = 7.6 Hz, 2H), 7.59 (t, J = 7.2 Hz, 1H), 7.49 (t, J = 7.2 Hz, 5-Methyl-1-(1-phenylvinyl)-N-(o-tolyl)-1H-1,D2O,3I-:t1r0ia.1z0o3l9e/-C49-OB00686A
2H), 7.31 – 7.25(m, 5H), 7.15 – 7.02 (m, 2H), 6.92 (t, J = 8.4 Hz, 2H), carboxamide (4ad)
5.82 (s, 1H), 5.59 (s, 1H). 13C NMR (101 MHz, CDCl3) δ 186.57, Yield: 70%, Pale yellow oil liquid; 1H NMR (400 MHz, CDCl3) δ 9.02 (s,
164.35(d, JC-F = 249 Hz), 143.30, 142.01, 141.47, 137.16, 133.28, 1H), 8.10 (d, J = 8.0 Hz, 1H), 7.39 (d, J = 6.4 Hz, 3H), 7.26 (m, 2H),
130.95(d, JC-F = 3 Hz), 129.93, 129.70, 128.34 (d, JC-F = 7.5 Hz), 7.18 (d, J = 6.4 Hz, 2H), 7.10 (t, J = 7.4 Hz, 1H), 6.05 (s, 1H), 5.62 (s,
128.00, 127.91, 125.95, 115.83 (d, JC-F = 21 Hz), 115.60. 19F NMR 1H), 2.43 (d, J = 5.6 Hz, 6H). 13C NMR (101 MHz, CDCl3) δ 159.29,
(376 MHz, CDCl3) δ -110.79 (s, 1F). IR (KBr): 2925, 1660, 1492, 1449, 142.00, 138.67, 137.97, 135.68, 134.19, 130.65, 130.12, 129.21,
1417, 1256, 1199, 1178, 1009, 920, 834, 772, 695, 530 cm-1. HRMS 128.68, 126.90, 125.75, 124.98, 122.21, 115.24, 17.87, 9.54. IR
(ESI): Calcd. for C23H16FN3NaO [M+Na]+: 392.1170; found: 392.1174. (KBr): 2924, 1685, 1611, 1588, 1529, 1456, 1331, 1254, 1160, 887,
775, 755, 696, 627 cm-1. HRMS (ESI): Calcd. for C19H18N4NaO
(1-(1-(4-Chlorophenyl)vinyl)-5-phenyl-1H-1,2,3-triazol-4-
yl)(phenyl)methanone (4ib)
[M+Na]+: 341.1373; found: 341.1377.
Yield: 82%, Pale yellow oil liquid; 1H NMR (400 MHz, CDCl3) δ 8.29 N-(3-chlorophenyl)-5-methyl-1-(1-phenylvinyl)-1H-1,2,3-triazole-4-
(d, J = 7.2 Hz, 2H), 7.58 (t, J = 6.8 Hz, 1H), 7.48 (t, J = 7.2 Hz, 2H), carboxamide (4ae)
7.35 – 7.24 (m, 5H), 7.20 (d, J = 8.4 Hz, 2H), 7.02 (d, J = 8.4 Hz, 2H), Yield: 73%, Pale yellow oil liquid; 1H NMR (400 MHz, CDCl3) δ 9.08 (s,
5.86 (s, 1H), 5.60 (s, 1H). 13C NMR (101 MHz, CDCl3) δ 186.51, 1H), 7.90 (s, 1H), 7.49 (d, J = 8.0 Hz, 1H), 7.40 (d, J = 7.2 Hz, 3H), 7.29
143.26, 142.03, 141.36, 137.13, 135.66, 133.27, 133.17, 130.76, (t, J = 8.0 Hz, 1H), 7.18 – 7.12 (m, 3H), 6.06 (s, 1H), 5.62 (s, 1H), 2.44
129.97, 129.69, 128.96, 128.36, 128.33, 127.20, 125.84, 116.23. IR (s, 3H). 13C NMR (101 MHz, CDCl3) δ 159.30, 141.91, 138.92, 138.33,
(KBr): 2926, 1660, 1601, 1509, 1449, 1257, 1199, 1179, 1009, 919, 138.18, 134.90, 134.08, 130.18, 130.16, 129.24, 125.71, 124.49,
841, 773, 746, 695, 542 cm-1. HRMS (ESI): Calcd. for C23H16ClN3NaO 120.00, 117.84, 115.36, 9.56. IR (KBr): 2926, 1683, 1593, 1522,
[M+Na]+: 408.0874; found: 408.0879.
1483, 1426, 1274, 1159, 1099, 912, 774, 695, 441 cm-1. HRMS (ESI):
Calcd. for C18H15ClN4NaO [M+Na]+: 361.0827; found: 361.0828.
(1-(1-(2-Chlorophenyl)vinyl)-5-phenyl-1H-1,2,3-triazol-4-
yl)(phenyl)methanone (4jb)
N-(4-chlorophenyl)-5-methyl-1-(1-phenylvinyl)-1H-1,2,3-triazole-4-
Yield: 81%, Pale yellow oil liquid; 1H NMR (400 MHz, CDCl3) δ 8.27 carboxamide (4af)
1
(d, J = 7.2 Hz, 2H), 7.57 (t, J = 7.2 Hz, 1H), 7.47 (t, J = 7.6 Hz, 2H), Yield: 83%, Pale yellow solid, m.p: 136-137°C; H NMR (400 MHz,
7.28 – 7.21 (m, 5H), 7.18 (d, J = 8.0 Hz, 2H) , 7.14 – 7.10 (m, 1H), CDCl3) δ 9.10 (s, 1H), 7.67 (d, J = 8.4 Hz, 2H), 7.39 (d, J = 6.8 Hz, 3H),
7.06 – 7.01 (m, 5H), 5.99 (s, 1H), 5.69 (s, 1H). 13C NMR (101 MHz, 7.33 (d, J = 8.4 Hz, 2H), 7.16 (d, J = 7.2 Hz, 2H), 6.05 (s, 1H), 5.61 (s,
CDCl3) δ 186.54, 143.64, 141.26, 140.32, 137.27, 133.33, 133.16, 1H), 2.43 (s, 3H). 13C NMR (101 MHz, CDCl3) δ 159.25, 141.90,
132.53, 131.24, 130.81, 130.74, 130.45, 130.21, 129.69, 128.33, 138.24, 136.37, 134.08, 130.17, 129.41, 129.23, 129.21, 125.70,
128.19, 126.84, 126.27, 118.19. IR (KBr): 2926, 1657, 1503, 1448, 121.14, 115.43, 115.33, 100.08, 9.55. IR (KBr): 2924, 1681, 1593,
1255, 1201, 1179, 1009, 921, 772, 695 cm-1. HRMS (ESI): Calcd. for 1519, 1492, 1401, 1304, 1278, 1239, 1239, 1159, 1091, 1011, 828,
C23H16ClN3NaO [M+Na]+: 408.0874; found: 408.0879.
774, 693, 654, 505, 435 cm-1. HRMS (ESI): Calcd. for C18H15ClN4NaO
[M+Na]+: 361.0827; found: 361.0831.
(1-(1-(3-Chlorophenyl)vinyl)-5-phenyl-1H-1,2,3-triazol-4-
yl)(phenyl)methanone (4kb)
N-(2-chlorophenyl)-5-methyl-1-(1-phenylvinyl)-1H-1,2,3-triazole-4-
Yield: 86%, White solid, m.p: 133-134°C; 1H NMR (400 MHz, CDCl3) δ carboxamide (4ag)
8.29 (d, J = 7.8 Hz, 2H), 7.58 (t, J = 7.2 Hz, 1H), 7.48 (t, J = 7.6 Hz, Yield: 80%, Brown solid, m.p: 88-89°C; 1H NMR (400 MHz, CDCl3) δ
2H), 7.35 – 7.20 (m, 6H), 7.16 (t, J = 7.8 Hz, 1H), 7.09 (s, 1H), 6.94 (d, 9.68 (s, 1H), 8.52 (d, J = 8.2 Hz, 1H), 7.47 – 7.35 (m, 4H), 7.31 (t, J =
J = 7.6 Hz, 1H), 5.88 (s, 1H), 5.64 (s, 1H). 13C NMR (101 MHz, CDCl3) 7.8 Hz, 1H), 7.22 – 7.15 (m, 2H), 7.08 (t, J = 8.0 Hz, 1H), 6.05 (s, 1H),
δ 186.57, 143.36, 142.14, 141.23, 137.21, 136.48, 134.87, 133.34, 5.63 (s, 1H), 2.44 (s, 3H). 13C NMR (101 MHz, CDCl3) δ 159.35,
130.85, 130.07, 130.04, 129.79, 129.73, 128.44,128.40, 126.20, 141.94, 138.42, 138.23, 134.68, 134.14, 130.13, 129.38, 129.21,
125.93, 124.21, 116.94. IR (KBr): 2925, 1658, 1597, 1483, 1449, 127.72, 125.74, 124.79, 123.54, 121.48, 115.33, 9.56. IR (KBr): 2924,
1420, 1255, 1200, 1179, 1009, 921, 771, 694 cm-1. HRMS (ESI): 2852, 1692, 1590, 1529, 1441, 1304, 1243, 1160, 1050, 1034, 980,
Calcd. for C23H16ClN3NaO [M+Na]+: 408.0874; found: 408.0873.
886, 774, 753, 696, 631, 441 cm-1. HRMS (ESI): Calcd. for
C18H15ClN4NaO [M+Na]+: 361.0827; found: 361.0834.
5-Methyl-N-phenyl-1-(1-phenylvinyl)-1H-1,2,3-triazole-4-
carboxamide (4ac)
2-Methoxy-N-(1-(5-methyl-1-(1-phenylvinyl)-1H-1,2,3-triazol-4-
Yield: 74%, Pale yellow solid, m.p: 79-80°C; 1H NMR (400 MHz, yl)vinyl)aniline (4ah)
CDCl3) δ 9.08 (s, 1H), 7.71 (d, J = 8.0 Hz, 2H), 7.40 – 7.36 (m, 5H), Yield: 78%, Brown oil liquid; 1H NMR (400 MHz, CDCl3) δ 9.69 (s, 1H),
7.18 – 7.16 (m, 3H), 6.05 (s, 1H), 5.62 (s, 1H), 2.44 (s, 3H). 13C NMR 8.50 (d, J = 7.6 Hz, 1H), 7.38 (d, J = 6.8 Hz, 3H), 7.17 (d, J = 6.8 Hz,
(101 MHz, CDCl3) δ 159.29, 141.96, 138.48, 138.10, 137.77, 134.15, 2H), 7.08 (d, J = 7.6 Hz, 1H), 7.00 (t, J = 7.6 Hz, 1H), 6.94 (d, J = 8.0
130.15, 129.22, 125.73, 124.50, 119.96, 115.29, 9.57. IR (KBr): 3058, Hz, 1H), 6.04 (s, 1H), 5.61 (s, 1H), 3.95 (s, 3H), 2.44 (s, 3H). 13C NMR
2926, 1681, 1598, 1528, 1443, 1312, 1247, 1160, 1057, 980, 913, (101 MHz, CDCl3) δ 159.24, 148.61, 142.00, 138.90, 137.86, 134.25,
883, 774, 755, 693, 587, 509 cm-1. HRMS (ESI): Calcd. for 130.06, 129.18, 127.63, 125.74, 124.01, 121.05, 119.87, 115.17,
C18H16N4NaO [M+Na]+: 327.1216; found: 327.1217.
110.23, 55.90, 9.55. IR (KBr): 2929, 2839, 1681, 1602, 1578, 1462,
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Org. Biomol. Chem.
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