8
Synthesis of 1,2,3-Triazole Derivatives of 4,4’-Dihydroxybenzophenone
J. Braz. Chem. Soc.
7.12 (d, 4H, J 8.1 Hz), 7.17 (d, 4H, J 8.6 Hz), 7.67 (d, 4H,
J 8.6 Hz), 7.74 (d, 4H, J 8.1 Hz), 8.32 (s, 2H); C NMR
(75 MHz, DMSO-d6) d 52.7, 61.8, 94.9, 114.9, 125.4, 130.6,
130.7, 132.2, 136.2, 138.0, 142.9, 161.7, 193.6; HRMS
[M + Na]+ calculated for C33H27I2N6O3: 809.0228, found:
809.0202.
acetate:dichoromethane:hexane 3:1:3 v/v); IR (ATR)
νmax / cm-1 3101, 2351, 1976, 1642, 1599, 1528, 1246;
1H NMR (300 MHz, CDCl3) d 5.30 (s, 4H), 5.66 (s, 4H),
7.03 (d, 4H, J 8.7 Hz), 7.56-7.61 (m, 4H), 7.67 (s, 2H),
7.76 (d, 4H, J 8.7 Hz), 8.17 (s, 2H), 8.24 (d, 4H, J 7.2 Hz);
13C NMR (75 MHz, CDCl3) d 53.3, 62.0, 114.3, 122.9,
123.9, 130.4, 131.2, 132.2, 133.9, 136.4, 144.5, 148.6,
161.4, 194.3; HRMS [M + H]+ calculated for C33H27N8O7:
647.1997, found: 647.1995.
13
Bis(4-(1-(2-methylbenzyl)-1H-1,2,3-triazol-4-yl)methoxy)
benzophenone (9)
Yield: 55% (0.165 g, 0.282 mmol); white
solid; mp 186-187 °C; TLC: Rf = 0.32 (ethyl
acetate:dichoromethane:hexane 3:1:3 v/v); IR (ATR)
Bis(4-(1-(2,4-difluorobenzyl)-1H-1,2,3-triazol-4-yl)methoxy)
benzophenone (13)
ν
max / cm-1 3099, 2921, 1970, 1639, 1601, 1258; 1H NMR
Yield: 57% (0.185 g, 0.294 mmol); white solid; mp 180-
181°C;TLC:Rf=0.10(ethylacetate:dichoromethane:hexane
3:1:3 v/v); IR (ATR) νmax / cm-1 3140, 2886, 2009, 1978,
1638, 1600, 1259; 1H NMR (300 MHz, CDCl3) d 5.26 (s,
4H), 5.56 (s, 4H), 6.85-6.92 (m, 4H), 7.03 (d, 4H, J 8.7 Hz),
7.26-7.36 (m, 2H), 7.70 (s, 2H), 7.76 (d, 4H, J 8.7 Hz);
13C NMR (75 MHz, CDCl3) d 47.3 (d, J 3.8 Hz), 62.0, 104.5
(t, J 25.2 Hz), 112.2 (dd, J 21.5, 3.8 Hz), 114.2, 117.8 (dd,
J 14.9, 3.8 Hz), 122.8, 131.1, 131.8 (dd, J 9.9, 4.8 Hz),
132.2, 144.0, 161.4, 162.1 (dd, J 52.1, 12.0 Hz), 194.3.
HRMS [M + H]+ calculated for C33H25F4N6O3: 629.1919,
found: 629.1911.
(300 MHz, CDCl3) d 2.28 (s, 6H), 5.24 (s, 4H), 5.56 (s,
4H), 7.02 (d, 4H, J 8.4 Hz), 7.20-7.33 (m, 8H), 7.44 (s,
2H), 7.75 (d, 4H, J 8.4 Hz); 13C NMR (75 MHz, CDCl3) d
18.9, 52.5, 62.1, 114.3, 122.6, 126.7, 129.3, 129.5, 131.0,
131.1, 132.2, 136.9, 143.7, 161.4, 194.3; HRMS [M + H]+
calculated for C35H33N6O3: 585.2609, found: 585.2609.
Bis(4-(1-(3-methylbenzyl)-1H-1,2,3-triazol-4-yl)methoxy)
benzophenone (10)
Yield: 42% (0.126 g, 0.215 mmol); white
solid; mp 130-131 °C; TLC Rf = 0.25 (ethyl
acetate:dichoromethane:hexane 3:1:3 v/v); IR (ATR)
νmax / cm-1 3122, 2944, 2165, 1976, 1640, 1596, 1236;
1H NMR (300 MHz, CDCl3) d 2.34 (s, 6H), 5.25 (s, 4H),
5.50 (s, 4H), 7.02 (d, 4H, J 8.7 Hz), 7.06-7.09 (m, 4H),
7.17 (d, 2H, J 7.5 Hz), 7.26 (t, 2H, J 8.4 Hz), 7.56 (s, 2H),
7.75 (d, 4H, J 8.7 Hz); 13C NMR (75 MHz, CDCl3) d 21.3,
54.3, 62.1, 114.2, 122.7, 125.2, 128.9, 129.0, 129.6, 131.1,
132.2, 134.2, 139.0, 143.8, 161.4, 194.3; HRMS [M + H]+
calculated for C35H33N6O3: 585.2609, found: 585.2600.
Bis(4-(1-(2-chlorobenzyl)-1H-1,2,3-triazol-4-yl)methoxy)
benzophenone (14)
Yield: 60% (0.193 g, 0.310 mmol); white
solid; mp 176-177 °C; TLC: Rf = 0.21 (ethyl
acetate:dichoromethane:hexane 3:1:3 v/v); IR (ATR)
ν
max / cm-1 3098, 2943, 1970, 1640, 1599, 1257; 1H NMR
(300 MHz, CDCl3) d 5.27 (s, 4H), 5.68 (s, 4H), 7.03 (d,
4H, J 8.7 Hz), 7.21-7.34 (m, 6H), 7.43 (d, 2H, J 8.7 Hz),
7.67 (s, 2H), 7.75 (d, 4H, J 8.7 Hz); 13C NMR (75 MHz,
CDCl3) d 51.5, 62.0, 114.3, 123.1, 127.6, 129.9, 130.4,
130.5, 131.1, 132.2, 132.2, 133.5, 143.8, 161.4, 194.3;
HRMS [M + H]+ calculated for C33H27Cl2N6O3: 625.1516,
found: 625.1505.
Bis(4-(1-(4-methylbenzyl)-1H-1,2,3-triazol-4-yl)methoxy)
benzophenone (11)
Yield: 59% (0.177 g, 0.302 mmol); white
solid; mp 134-135 °C; TLC Rf = 0.18 (ethyl
acetate:dichoromethane:hexane 3:1:3 v/v); IR (ATR)
νmax / cm-1 3031, 2917, 2364, 2022, 1976, 1640, 1599,
Bis(4-(1-(2,6-dichlorobenzyl)-1H-1,2,3-triazol-4-yl)methoxy)
benzophenone (15)
1
1246; H NMR (300 MHz, CDCl3) d 2.35 (s, 6H), 5.24
(s, 4H), 5.49 (s, 4H), 7.02 (d, 4H, J 8.1 Hz), 7.20 (s, 4H),
7.53 (s, 2H), 7.75 (d, 4H, J 8.1 Hz); 13C NMR (75 MHz,
CDCl3) d 21.2, 54.1, 62.1, 114.2, 122.7, 128.2, 129.8, 131.0,
131.3, 132.2, 138.9, 143.8, 161.4, 194.3; HRMS [M + H]+
calculated for C35H33N6O3: 585.2609, found: 585.2604.
Yield: 57% (0.204 g, 0.294 mmol); white
solid; mp 187-188 °C; TLC: Rf = 0.33 (ethyl
acetate:dichoromethane:hexane 3:1:3 v/v); IR (ATR)
ν
max / cm-1 3094, 2354, 1976, 1642, 1600, 1256; 1H NMR
(300 MHz, CDCl3) d 5.24 (s, 4H), 5.87 (s, 4H), 7.03 (d,
4H, J 8.7 Hz), 7.25-7.33 (m, 2H), 7.41 (d, J 8.1 Hz), 7.62
(s, 2H), 7.75 (d, 4H, J 8.7 Hz); 13C NMR (75 MHz, CDCl3)
d 49.1, 62.1, 114.3, 122.7, 128.9, 129.9, 131.1, 131.2, 132.2,
136.8, 143.4, 161.4, 194.3; HRMS [M + H]+ calculated for
C33H24Cl4N6NaO3: 717.3833, found: 717.0584.
Bis(4-(1-(3-nitrobenzyl)-1H-1,2,3-triazol-4-yl)methoxy)
benzophenone (12)
Yield: 54% (0.181 g, 0.280 mmol); white
solid; mp 171-172 °C; TLC: Rf = 0.10 (ethyl