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HETEROCYCLES, Vol. 81, No. 7, 2010
1
White powder; mp 219 °C; H-NMR (300 MHz, CDCl3) ꢀ 1.68 (brs, 1H, OH), 4.40 (s, 2H, CH2),
7.10-7.15 (m, 6H, TrH), 7.28-7.33 (m, 9H, TrH), 7.50 (d, J = 0.4 Hz, 1H, pyrazole-H), 7.72 (s, J = 0.4 Hz,
1H, pyrazole-H); 13C-NMR (75 MHz, CDCl3) ꢀ 51.8, 77.2, 79.1, 88.1, 101.0, 127.4, 127.5, 129.6, 135.1,
141.7, 142.1; EI-MS m/z 364 (M+), HRMS m/z 364.1576, Calcd. for C25H20N2O: 364.1576; IR (vmax)
(KBr) 3399 (OH), 3055, 3032, 2233 (CꢀC), 1596, 1490, 1445, 1372 cm-1.
4-Trimethylsilylethynyl-1-tritylpyrazole (3b)
1
White powder; mp 144 °C; H-NMR (300 MHz, CDCl3) ꢀ 0.20 (s, 9H, CH3Si), 7.09-7.13 (m, 6H, TrH),
7.29-7.31 (m, 9H, TrH), 7.53 (d, J = 0.7 Hz, 1H, pyrazole-H), 7.75 (d, J = 0.7 Hz, 1H, pyrazole-H);
13C-NMR (75 MHz, CDCl3) ꢀ 0.5, 79.1, 95.02, 96.34, 101.8, 127.4, 127.5, 129.7, 135.3, 142.1, 142.6;
EI-MS m/z 406 (M+), HRMS m/z 406.1871, Calcd for C27H26N2Si: 406.1865; IR (vmax) (KBr) 3056, 2165
(CꢀC), 1596, 1489, 1445, 1398 (Si-CH3), 1352 (Si-CH3)cm-1.
4-Octyn-1-yl-1-tritylpyrazole (3c)
1
White powder; mp 110 °C; H-NMR (300 MHz, CDCl3) ꢀ 0.88 (t, J = 6.9 Hz, 3H, CH3), 1.26-1.44 (m,
6H, CH2), 1.56 (quint, J = 7.3 Hz, 2H, CH2), 2.33 (t, J = 7.1 Hz, 2H, CH2), 7.09-7.15 (m, 6H, TrH),
7.29-7.35 (m, 9H, TrH), 7.44 (d, J = 0.6 Hz, pyrazole-H), 7.68 (d, J = 0.6 Hz, pyrazole-H); 13C-NMR (75
MHz, CDCl3) ꢀ 14.5, 19.8, 22.9, 29.0, 29.1, 31.7, 71.4, 78.9, 90.8, 102.3, 127.4, 127.4, 129.7, 134.3,
141.6, 142.3; EI-MS m/z 418 (M+), HRMS m/z 418.2400, Calcd for C30H30N2: 418.2409; IR (vmax) (KBr)
3032, 3058, 2928, 2856, 2241(CꢀC), 1596, 1486, 1444 cm-1.
4-Phenylethynyl-1-tritylpyrazole (3d)
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White powder; mp 212 °C; H-NMR (300 MHz, CDCl3); ꢀ 7.14-7.19 (m, 6H, TrH), 7.29-7.34 (m, 12H,
Ph and Tr), 7.59 (s, 1H, pyrazole-H), 7.82 (s, 1H, pyrazole-H); 13C-NMR (75 MHz, CDCl3) ꢀ 79.1, 80.8,
90.0, 101.8, 123.0, 127.4, 127.48, 127.53, 127.9, 129.7, 130.8, 134.7, 141.6, 142.1; EI-MS m/z 410 (M+),
HRMS m/z 410.1780, Calcd for C30H22N2: 410.1783; IR (vmax) (KBr) 3059, 3032, 2224 (CꢀC), 1595,
1489, 1445 cm-1.
4-(4-Fluorophenyl)ethynyl-1-tritylpyrazole (3e)
White powder; mp 220 °C; 1H-NMR (300 MHz, CDCl3) ꢀ 7.00 (dd, J = 8.7, 8.7 Hz, 2H, ArH), 7.12-7.18
(m, 6H, TrH), 7.28-7.35 (m, 9H, TrH), 7.41 (dd, J = 5.4, J = 8.7 Hz, 2H, ArH), 7.59 (s, 1H, pyrazole-H),
7.81 (s, 1H, pyrazole-H); 13C-NMR (75 MHz, CDCl3) ꢀ 79.1, 80.5, 89.0, 101.6, 115.3 (d, 2JC-F = 21.6 Hz),
119.1 (d, 4JC-F = 3.4 Hz), 127.4, 127.5, 129.7, 132.7 (d, 3JC-F = 8.0 Hz), 134.7, 141.6, 142.1, 161.6 (d, 1JC-F
= 245.2 Hz); EI-MS m/z 428 (M+), HRMS m/z 428.1692, Calcd for C30H21FN2: 428.1689; IR (vmax) (KBr)
3058, 3033, 2224 (CꢀC), 1599, 1503, 1445, 1227 (C-F) cm-1.
4-(4-Methoxyphenylethynyl)-1-tritylpyrazole (3f)
1
White powder; mp 201 °C; H-NMR (300 MHz, CDCl3) ꢀ 3.80 (s, 3H, OCH3), 6.83 (d, J = 8.9 Hz, 2H,
ArH), 7.13-7.33 (m, 15H, TrH), 7.37 (d, J = 8.9 Hz, 2H, Ar-H), 7.56 (s, 1H, pyrazole-H), 7.79 (s, 1H,