1440, 1377, 1356, 1128, 980, 960, 815 cm−1. 1H NMR (CDCl3,
300 MHz) 2.40 (s, 3H), 7.27 (d, 2H, J = 8.6), 7.82 (s, 1H), 7.91
(d, 2H, J = 8.6). 13C NMR (CDCl3, 75 MHz) 21.2, 91.2, 118.8
(2C), 130.0 (2C), 140.8, 141.5, 142.3. HRMS (ESI): calcd for
C9H9IN3 [M + H]+ 285.9841, found 285.9841.
142.4, 158.1. HRMS (ESI): calcd for C9H8I2N3O [M + H]+
427.8757, found 427.8748.
2-(3-Chloro-2-iodophenyl)-4-iodo-2H-[1,2,3]triazole (3e).
Yellow solid (mp = 84 °C). IR (ATR): 2924, 2849, 1594, 1483,
1
1455, 1432, 1371, 1353, 1128, 982, 963, 779 cm−1. H NMR
4-Iodo-2-(4-isopropylphenyl)-2H-[1,2,3]triazole (2c). Yellow
liquid. IR (ATR): 2959, 2926, 2870, 1513, 1445, 1420, 1374,
(CDCl3, 300 MHz) 7.31 (dd, 1H, J = 1.5 and 7.9), 7.42 (dd, 1H,
J = 7.9 and 8.0), 7.61 (dd, 1H, J = 1.5 and 8.0), 7.92 (s, 1H).
13C NMR (CDCl3, 75 MHz) 91.8, 99.6, 126.0, 129.7, 130.7,
141.0, 142.8, 145.0. HRMS (ESI): calcd for C8H535ClI2N3
[M + H]+ 431.8261, found 431.8262.
1356, 1128, 1052, 980, 960, 834 cm−1 1H NMR (CDCl3,
.
300 MHz) 1.28 (d, 6H, J = 6.9), 2.96 (m, 1H), 7.32 (d, 2H, J =
8.6), 7.82 (s, 1H), 7.94 (d, 2H, J = 8.6). 13C NMR (CDCl3,
75 MHz) 24.1 (2C), 33.9, 91.2, 118.8 (2C), 127.4 (2C), 137.6,
142.3, 149.1. HRMS (ESI): calcd for C11H13IN3 [M + H]+
314.0154, found 314.0150.
2-(5-Chloro-2-iodophenyl)-4-iodo-2H-[1,2,3]triazole (3′e).
Yellow solid (mp = 102 °C). IR (ATR): 3127, 3086, 2926, 1577,
1561, 1472, 1442, 1414, 1352, 1099, 1019, 981, 961, 874,
1
2-(3-Chlorophenyl)-4-iodo-2H-[1,2,3]triazole (2e). Yellow
solid (mp = 98 °C). IR (ATR): 3132, 3074, 2921, 2851, 1566,
815 cm−1. H NMR (CDCl3, 300 MHz) 7.19 (dd, 1H, J = 2.4
and 8.5), 7.51 (d, 1H, J = 2.4), 7.91 (d, 1H, J = 8.5), 7.92 (s,
1H). 13C NMR (CDCl3, 75 MHz) 89.2, 82.2, 127.8, 131.3,
135.1, 141.5, 143.0, 143.3. HRMS (ESI): calcd for
C8H535ClI2N3 [M + H]+ 431.8261, found 431.8270.
1455, 1414, 1352, 1261, 1219, 1126, 1023, 980, 962, 840 cm−1
.
1H NMR (CDCl3, 300 MHz) 7.34 (ddd, 1H, J = 1.2, 1.9 and
8.0), 7.41 (dd, 1H, J = 8.0 and 8.0), 7.85 (s, 1H), 7.94 (ddd, 1H,
J = 1.2, 2.1 and 8.0), 8.09 (dd, 1H, J = 1.9 and 2.1). 13C NMR
(CDCl3, 75 MHz) 92.3, 116.8, 119.1, 128.2, 130.6, 135.4,
140.2, 143.0. HRMS (ESI): calcd for C8H635ClIN3 [M + H]+
305.9295, found 305.9295.
2-(2-Iodo-4-methylphenyl)-2H-[1,2,3]triazole (4b). Brown
solid (mp = 124 °C). IR (ATR): 3139, 2956, 2922, 1514, 1498,
1
1411, 1251, 1150, 1024, 962, 951, 819 cm−1. H NMR (CDCl3,
300 MHz) 2.40 (s, 3H), 7.27 (m, 1H), 7.35 (d, 1H, J = 8.1), 7.82
(m, 1H), 7.87 (s, 2H). 13C NMR (CDCl3, 75 MHz) 20.8, 92.8,
127.4, 129.7, 135.5 (2C), 140.8, 141.0, 141.5. HRMS (ESI):
calcd for C9H9IN3 [M + H]+ 285.9841, found 285.9838.
2-(2-Iodo-4-methoxyphenyl)-2H-[1,2,3]triazole (4d). Orange
solid (mp = 92 °C) which rapidly decomposes by loss of iodine.
1H NMR (CDCl3, 300 MHz) 3.86 (s, 3H), 6.84 (dd, 1H, J = 2.7
and 8.8), 7.36 (d, 1H, J = 8.8), 7.48 (d, 1H, J = 2.7), 7.86
(s, 2H).
4-Iodo-2-(2-iodophenyl)-2H-[1,2,3]triazole (3a). Yellow
liquid. IR (ATR): 3052, 2930, 1501, 1479, 1437, 1382, 1264,
1
1023, 981, 960, 843 cm−1. H NMR (CDCl3, 300 MHz) 7.20
(m, 1H), 7.48 (m, 2H), 7.92 (s, 1H), 8.00 (m, 1H). 13C NMR
(CDCl3, 75 MHz) 91.6, 92.6, 127.8, 129.1, 131.3, 140.7, 141.2,
142.7. HRMS (ESI): calcd for C8H6I2N3 [M + H]+ 397.8651,
found 397.8650.
4-Iodo-2-(2-iodo-4-methylphenyl)-2H-[1,2,3]triazole (3b).
Yellow solid (mp = 108 °C). IR (ATR): 3132, 2922, 2853, 2431,
2-(2,5-Diiodo-4-methoxyphenyl)-4-iodo-2H-[1,2,3]triazole
(5d). Yellow liquid. IR (ATR): 3120, 2968, 2936, 2841, 1485,
1
1493, 1431, 1260, 1125, 1027, 979, 962, 839, 821 cm−1. H
1
NMR (CDCl3, 300 MHz) 2.39 (s, 3H), 7.26 (m, 1H), 7.34 (d,
1H, J = 8.1), 7.81 (m, 1H), 7.90 (s, 1H). 13C NMR (CDCl3,
75 MHz) 20.9, 91.3, 92.5, 127.3, 129.7, 140.5, 140.8, 141.9,
142.5. HRMS (ESI): calcd for C9H8I2N3 [M + H]+ 411.8808,
found 411.8811.
1437, 1333, 1241, 1043, 1019, 981, 961, 838, 820 cm−1. H
NMR (CDCl3, 300 MHz) 3.95 (s, 3H), 7.28 (s, 1H), 7.82 (s,
1H), 7.89 (s, 1H). 13C NMR (CDCl3, 75 MHz) 57.2, 85.3, 91.6,
92.9, 121.2, 137.1, 137.5, 142.7, 159.5. HRMS (ESI): calcd for
C9H6I3NaN3O [M + Na]+ 575.7543, found 575.7545.
4-Iodo-2-(2-iodo-4-isopropylphenyl)-2H-[1,2,3]triazole (3c).
Yellow liquid. IR (ATR): 3003, 2960, 2932, 1709, 1421, 1359,
1221, 1092, 982, 962, 902 cm−1. H NMR (CDCl3, 300 MHz)
1
Crystallography
1.27 (d, 6H, J = 6.9), 2.94 (m, 1H), 7.31 (dd, 1H, J = 1.8 and
8.1), 7.37 (d, 1H, J = 8.1), 7.82 (d, 1H, J = 1.8), 7.90 (s, 1H).
13C NMR (CDCl3, 75 MHz) 23.9 (2C), 33.8, 91.3, 92.8, 127.2,
127.5, 138.5, 140.6, 142.5, 152.8. HRMS (ESI): calcd for
C11H12I2N3 [M + H]+ 439.9121, found 439.9105.
Single crystals suitable for X-ray diffraction were grown after
slow evaporation of solutions of 2a, 2e, 3b, 3d, 3′d, 3e, 3′e and
4b in dichloromethane at room temperature.
The samples were studied with graphite monochromatized
Mo-Kα radiation (λ = 0.71073 Å). X-ray diffraction data were
collected at T = 150(2) K using APEXII Bruker-AXS diffracto-
meter. The structure was solved by direct methods using the
SIR97 program,38 and then refined with full-matrix least-square
methods based on F2 (SHELX-97)39 with the aid of the WINGX
program.40 All non-hydrogen atoms were refined with anisotro-
pic thermal parameters. H atoms were finally included in their
calculated positions. Except N-linked hydrogen that was intro-
duced in the structural model through Fourier difference maps
analysis, H atoms were finally included in their calculated posi-
tions. Molecular diagrams were generated by ORTEP-3 (version
2.02).41
4-Iodo-2-(2-iodo-4-methoxyphenyl)-2H-[1,2,3]triazole (3d).
Yellow solid (mp = 58 °C). IR (ATR): 2968, 2935, 2839, 1593,
1569, 1495, 1439, 1295, 1264, 1239, 1227, 1029, 1018, 980,
1
960, 841 cm−1. H NMR (CDCl3, 300 MHz) 3.85 (s, 3H), 6.97
(dd, 1H, J = 2.7 and 8.8), 7.35 (d, 1H, J = 8.8), 7.46 (d, 1H, J =
2.7), 7.89 (s, 1H). 13C NMR (CDCl3, 75 MHz) 56.0, 91.2, 93.7,
114.6, 125.1, 128.3, 136.3, 142.4, 160.7. HRMS (ESI): calcd for
C9H7I2NaN3O [M + Na]+ 449.8576, found 449.8570.
4-Iodo-2-(3-iodo-4-methoxyphenyl)-2H-[1,2,3]triazole (3′d).
Yellow solid (mp = 140 °C). IR (ATR): 2939, 2841, 1493, 1440,
1269, 1245, 1043, 1017, 981, 965, 809 cm−1. 1H NMR (CDCl3,
300 MHz) 3.93 (s, 3H), 6.88 (d, 1H, J = 8.9), 7.81 (s, 1H), 7.98
(dd, 1H, J = 2.6 and 8.9), 8.47 (d, 1H, J = 2.6). 13C NMR
(CDCl3, 75 MHz) 56.9, 85.9, 91.4, 110.6, 120.0, 129.9, 133.9,
Crystal data for 2a. C8H6IN3, Mr = 271.06, orthorhombic,
Pc21n, a = 4.3176(3), b = 13.3505(10), c = 15.2661(12) Å, V =
This journal is © The Royal Society of Chemistry 2012
Org. Biomol. Chem., 2012, 10, 4878–4885 | 4883