Job/Unit: O30343
/KAP1
Date: 05-06-13 10:06:03
Pages: 8
Magnetically Recoverable CuFe2O4 Nanoparticles
1-(3,4-Dimethoxyphenyl)-4-p-tolyl-1H-1,2,3-triazole (4c): Table 4,
2925, 2856, 1605, 1521, 1452, 1243, 1166, 1028, 808 cm–1. 1H NMR
(300 MHz, CDCl3): δ = 3.96 (s, 3 H), 3.98 (s, 3 H), 6.98 (d, J =
9.0 Hz, 1 H), 7.17–7.25 (m, 1 H), 7.39 (s, 1 H), 7.50–7.60 (m, 1 H),
entry 3. White solid; m.p. 130–132 °C. IR (KBr): ν = 2927, 2849,
˜
1601, 1518, 1465, 1261, 1170, 1019, 812 cm–1. 1H NMR (300 MHz,
CDCl3): δ = 2.38 (s, 3 H), 3.90 (s, 3 H), 3.95 (s, 3 H), 6.89 (d, J = 7.67–7.75 (m, 1 H), 7.87 (d, J = 7.5 Hz, 1 H), 8.13 (d, J = 9.0 Hz,
9.0 Hz, 1 H), 7.11–7.15 (m, 1 H), 7.19 (d, J = 8.0 Hz, 2 H), 7.37
1 H), 8.17 (s, 1 H) ppm. 13C NMR (75 MHz, CDCl3): δ = 56.0,
(s, 1 H), 7.73 (d, J = 8.0 Hz, 2 H), 8.02 (s, 1 H) ppm. 13C NMR 56.1, 104.7, 111.0, 112.1, 121.0, 123.9, 128.9, 129.4, 130.0, 130.9,
(75 MHz, CDCl3): δ = 21.2, 55.9 (2 C), 104.7, 111.0, 111.9, 117.1,
132.3, 142.4, 148.0, 149.3, 149.5 ppm. MS (ESI): m/z = 327 [M +
125.6, 127.4, 129.4, 129.5, 130.6, 148.1, 149.1, 149.6 ppm. MS
H]+. HRMS (EI, 70 eV): calcd. for C16H15O4N4 327.10878; found
(ESI): m/z = 296 [M + H]+. HRMS (EI, 70 eV): calcd. for 327.10868.
C17H18O2N3 296.13935; found 296.13930.
4-(2-Nitrophenyl)-1-(3,4,5-trimethoxyphenyl)-1H-1,2,3-triazole (4j):
4-p-Tolyl-1-(3,4,5-trimethoxyphenyl)-1H-1,2,3-triazole (4d): Table 4,
entry 4. Pale-yellow solid; m.p. 103–105 °C. IR (KBr): ν = 2924,
(Table 4, entry 10). Pale-yellow solid; m.p. 163–165 °C. IR (KBr):
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ν = 2925, 2856, 1603, 1511, 1464, 1233, 1123, 825 cm–1. H NMR
˜
˜
2855, 1602, 1507, 1463, 1237, 1127, 1031, 824 cm–1 1H NMR
.
(300 MHz, CDCl3): δ = 3.88 (s, 3 H), 3.93 (s, 6 H), 6.95 (s, 2 H),
7.52 (t, J = 7.0 Hz, 1 H), 7.68 (t, J = 7.0 Hz, 1 H), 7.85 (d, J =
8.0 Hz, 1 H), 8.10 (d, J = 8.0 Hz, 1 H), 8.16 (s, 1 H) ppm. 13C
NMR (75 MHz, CDCl3): δ = 56.3, 60.9, 98.5, 121.2, 124.1, 124.2,
129.0, 131.0, 132.4, 132.5, 138.3, 142.5, 148.0, 153.8 ppm. MS
(ESI): m/z = 357 [M + H]+. HRMS (EI, 70 eV): calcd. for
C17H17O5N4 357.11935; found 357.11963.
(300 MHz, CDCl3): δ = 2.40 (s, 3 H), 3.86 (s, 3 H), 3.94 (s, 6 H),
6.96 (s, 2 H), 7.22 (d, J = 7.5 Hz, 2 H), 7.75 (d, J = 7.5 Hz, 2 H),
8.05 (s, 1 H) ppm. 13C NMR (75 MHz, CDCl3): δ = 21.3, 56.2,
60.8, 98.1, 117.2, 125.6, 127.3, 129.4, 129.5, 132.8, 137.9, 148.2,
153.8 ppm. MS (ESI): m/z = 326 [M + H]+. HRMS (EI, 70 eV):
calcd. for C18H20O3N3 326.14992; found 326.15033.
1-(3,4-Dimethoxyphenyl)-4-(4-fluorophenyl)-1H-1,2,3-triazole (4e):
2-[1-(3,4-Dimethoxyphenyl)-1H-1,2,3-triazol-4-yl]pyridine (4k):
Table 4, entry 5. White solid; m.p. 138–140 °C. IR (KBr): ν = 2930,
˜
Table 4, entry 11. Pale-brown solid; m.p. 73–75 °C. IR (KBr): ν =
˜
2846, 1602, 1518, 1446, 1236, 1163, 1022, 836 cm–1 1H NMR
.
2925, 2855, 1604, 1517, 1461, 1252, 1168, 1036, 832 cm–1. 1H NMR
(300 MHz, [D6]DMSO): δ = 3.83 (s, 3 H), 3.89 (s, 3 H), 7.15 (d, J
= 8.5 Hz, 1 H), 7.35–7.44 (m, 1 H), 7.53–7.61 (m, 2 H), 7.89–7.98
(m, 1 H), 8.11 (d, J = 7.9 Hz, 1 H), 8.65 (d, J = 4.3 Hz, 1 H), 9.32
(s, 1 H) ppm. 13C NMR (75 MHz, [D6]DMSO): δ = 55.7, 55.8,
104.4, 111.8, 112.0, 119.6, 121.1, 123.1, 129.8, 137.2, 147.9, 148.8,
149.2, 149.5 (2 C) ppm. MS (ESI): m/z = 305 [M + Na]+. HRMS
(EI, 70 eV): calcd. for C15H14O2N4Na 305.10090; found 305.10029.
(300 MHz, [D6]DMSO): δ = 3.84 (s, 3 H), 3.88 (s, 3 H), 7.17 (d, J
= 8.5 Hz, 1 H), 7.31–7.39 (m, 2 H), 7.43–7.52 (m, 2 H), 7.93–8.00
(m, 2 H), 9.22 (s, 1 H) ppm. 13C NMR (75 MHz, [D6]DMSO): δ =
55.7, 55.8, 104.4, 111.9 (d, J = 5.1 Hz), 115.7, 116.0, 119.5, 126.9,
127.2 (d, J = 8.1 Hz), 129.9 (d, J = 2.9 Hz), 146.1, 148.8, 149.2,
161.8 (d, J = 244.7 Hz) ppm. MS (ESI): m/z = 300 [M + H]+.
HRMS (EI, 70 eV): calcd. for C16H15O2N3F 300.11428; found
300.11490.
2-[1-(3,4,5-Trimethoxyphenyl)-1H-1,2,3-triazol-4-yl]pyridine (4l):
4-(4-Fluorophenyl)-1-(3,4,5-trimethoxyphenyl)-1H-1,2,3-triazole
Table 4, entry 12. Pale-brown solid; m.p. 80–82 °C. IR (KBr): ν =
˜
(4f): Table 4, entry 6. Pale-yellow solid; m.p. 143–145 °C. IR (KBr):
2927, 2858, 1604, 1511, 1468, 1250, 1123, 1035, 829 cm–1. 1H NMR
(300 MHz, [D6]DMSO): δ = 3.72 (s, 3 H), 3.91 (s, 6 H), 7.30–7.45
(m, 3 H), 7.95 (td, J = 1.6, 7.6 Hz, 1 H), 8.12 (d, J = 7.9 Hz, 1 H),
8.65 (d, J = 3.2 Hz, 1 H), 9.42 (s, 1 H) ppm. 13C NMR (75 MHz,
[D6]DMSO): δ = 56.2, 60.1, 97.8, 119.6, 121.4, 123.2, 132.3, 137.2
(2 C), 148.0, 149.4, 149.5, 153.4 ppm. MS (ESI): m/z = 335 [M +
Na]+. HRMS (EI, 70 eV): calcd. for C16H16O3N4Na 335.11146;
found 335.11080.
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ν = 2930, 1601, 1506, 1458, 1231, 1127, 1032, 829 cm–1. H NMR
˜
(300 MHz, [D6]DMSO): δ = 3.73 (s, 3 H), 3.90 (s, 6 H), 7.26 (s, 2
H), 7.31–7.41 (m, 2 H), 7.91–8.02 (m, 2 H), 9.28 (s, 1 H) ppm. 13C
NMR (75 MHz, [D6]DMSO): δ = 56.1, 60.1, 97.7, 115.8 (d, J =
22.1 Hz), 119.6, 126.7 (d, J = 2.9 Hz), 127.2 (d, J = 8.1 Hz), 132.3,
137.2, 146.2, 153.4, 161.8 (d, J = 244.7 Hz) ppm. MS (ESI): m/z =
330 [M + H]+. HRMS (EI, 70 eV): calcd. for C17H17O3N3F
330.12485; found 330.12549.
4-(3-Chlorophenyl)-1-(3,4-dimethoxyphenyl)-1H-1,2,3-triazole (4g):
1-(3,4-Dimethoxyphenyl)-4-(6-methoxynaphthalen-2-yl)-1H-1,2,3-tri-
azole (4m): Table 4, entry 13. White solid; m.p. 176–178 °C. IR
Table 4, entry 7. Pale-yellow solid; m.p. 133–136 °C. IR (KBr): ν =
˜
2930, 2831, 1599, 1515, 1466, 1229, 1167, 1019, 809 cm–1. 1H NMR
(300 MHz, CDCl3): δ = 3.93 (s, 3 H), 3.97 (s, 3 H), 6.92 (d, J =
9.0 Hz, 1 H), 7.13–7.20 (m, 1 H), 7.28–7.41 (m, 3 H), 7.78 (d, J =
8.0 Hz, 1 H), 7.84 (s, 1 H), 8.10 (s, 1 H) ppm. 13C NMR (75 MHz,
CDCl3): δ = 56.0, 56.1, 104.8, 111.2, 112.2, 118.0, 123.7, 125.7,
128.2, 130.0, 130.4, 132.0, 134.8, 146.8, 149.5, 149.8 ppm. MS
(ESI): m/z = 316 [M + H]+. HRMS (EI, 70 eV): calcd. for
C16H15O2N3Cl 316.08473; found 316.08484.
(KBr): ν = 2828, 2845, 1604, 1516, 1471, 1236, 1165, 1025,
˜
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818 cm–1. H NMR (300 MHz, CDCl3): δ = 3.94 (s, 3 H), 3.96 (s,
3 H), 4.00 (s, 3 H), 6.98 (d, J = 8.3 Hz, 1 H), 7.14–7.26 (m, 3 H),
7.40–7.48 (m, 1 H), 7.76–7.48 (m, 2 H), 7.97 (d, J = 8.3 Hz, 1 H),
8.20 (s, 1 H), 8.34 (s, 1 H) ppm. 13C NMR (75 MHz, CDCl3): δ =
55.2, 56.0, 56.1, 104.7, 105.6, 111.1, 112.2, 115.6, 117.6, 119.2,
124.3, 127.3, 128.8, 129.6, 130.5, 131.9, 134.4, 148.2, 149.2, 149.6,
157.8 ppm. MS (ESI): m/z = 362 [M + H]+. HRMS (EI, 70 eV):
calcd. for C21H20O3N3 362.14992; found 362.15022.
4-(3-Chlorophenyl)-1-(3,4,5-trimethoxyphenyl)-1H-1,2,3-triazole
(4h): Table 4, entry 8. Pale-yellow solid; m.p. 152–154 °C. IR (KBr):
˜
4-(6-Methoxynaphthalen-2-yl)-1-(3,4,5-trimethoxyphenyl)-1H-1,2,3-
triazole (4n): Table 4, entry 14. Pale-yellow solid; m.p. 148–150 °C.
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ν = 2928, 1602, 1510, 1464, 1241, 1121, 1036, 828 cm–1. H NMR
(300 MHz, CDCl3): δ = 3.84 (s, 3 H), 3.92 (s, 6 H), 6.93 (s, 2 H),
7.29 (d, J = 7.8 Hz, 1 H), 7.34 (t, J = 7.8 Hz, 1 H), 7.77 (d, J =
7.8 Hz, 1 H), 7.82 (s, 1 H), 8.09 (s, 1 H) ppm. 13C NMR (75 MHz,
CDCl3): δ = 56.3, 60.8, 98.3, 117.9, 123.7, 125.7, 128.2, 130.0,
132.0, 132.6, 134.8, 138.5, 146.8, 153.9 ppm. MS (ESI): m/z = 346
[M + H]+. HRMS (EI, 70 eV): calcd. for C17H17O3N3Cl 346.09530;
found 346.09569.
IR (KBr): ν = 2928, 2845, 1604, 1516, 1471, 1236, 1165, 1025,
˜
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818 cm–1. H NMR (300 MHz, CDCl3): δ = 3.87 (s, 3 H), 3.92 (s,
3 H), 3.94 (s, 6 H), 6.96 (s, 2 H), 7.04–7.16 (m, 2 H), 7.73 (d, J =
8.3 Hz, 2 H), 7.90 (d, J = 8.3 Hz, 1 H), 8.13 (s, 1 H), 8.25 (s, 1
H) ppm. 13C NMR (75 MHz, CDCl3): δ = 55.2, 56.3, 60.9, 98.3,
105.7, 114.1, 117.6, 119.2, 124.3, 125.2, 127.3, 128.8, 129.5, 132.8,
134.3, 138.2, 148.3, 153.8, 157.9 ppm. MS (ESI): m/z = 392 [M +
1-(3,4-Dimethoxyphenyl)-4-(2-nitrophenyl)-1H-1,2,3-triazole (4i): H]+. HRMS (EI, 70 eV): calcd. for C22H22O4N3 392.16048; found
Table 4, entry 9. Pale-yellow solid; m.p. 132–134 °C. IR (KBr): ν = 392.16079.
˜
Eur. J. Org. Chem. 0000, 0–0
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