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(1.1), 64 (2.2), 63 (5.2), 62 (2.5), 61 (1.5), 56 (5.1), 55 (9.4),
54 (3.1), 53 (2.3), 52 (2.6), 51 (9.7), 50 (11.7), 49 (1.0), 43
(1.1), 42 (1.7), 41 (1.9), 40 (1.3), 39 (3.6), 38 (2.8), 37 (2.1).
OCH2), 7.10e7.40 (m, 8H, ar-H); 13C NMR (DMSO-d6):
39.8 (imidazolidine-C-5), 53.5 (imidazolidine-C-6), 55.2
(CH3O), 60.8 (CH2O), 136.1 (triazole-C-3), 156.4 (C-7a), ar
C: 114.1, 115.8, 128.5, 130.6, 136.5, 143.7, 157.2, 157.8.
7.1.1.4. 7-(3,4-Dichlorophenyl)-5H-6,7-dihydroimidazo[2,1-c]
[1,2,4]triazole (4). Recrystallized from DMF, yield 65.5%,
m.p. 199e202 ꢀC; IR (KBr) (n, cmꢁ1): 1609 (C]N); 1H
NMR (DMSO-d6, 300 MHz): 4.29 (dd, J ¼ 7.4 Hz,
J0 ¼ 6.2 Hz, 2H, CH2), 4.55 (dd, J ¼ 7.5 Hz, J0 ¼ 6.3 Hz, 2H,
CH2), 7.18e7.95 (m, 3H, ar-H), 8.16 (1H, CH); 13C NMR
(DMSO-d6): 39.7 (imidazolidine-C-5), 53.2 (imidazolidine-
C-6), 140.0 (triazole-C-3), 158.4 (C-7a), ar C: 114.3, 115.6,
121.6, 130.4, 131.3, 136.4; EIMS [70 eV, m/z (%)]: 258
(10.6), 257 (13.0), 256 (64.0), 255 (44.3), 254 (Mþ, 100.0),
253 (57.0), 230 (8.3), 229 (5.9), 228 (23.8), 227 (8.8), 226
(25.0), 219 (6.5), 218 (7.0), 200 (4.2), 198 (4.8), 192 (8.5),
191 (8.0), 187 (9.3), 186 (5.1), 185 (13.8), 175 (5.5), 174
(11.8), 173 (21.2), 172 (18.1), 171 (31.4), 159 (4.4), 147
(10.3), 145 (16.9), 138 (6.4), 137 (4.0), 136 (15.8), 135 (4.0),
111 (10.3), 110 (11.0), 109 (34.2), 101 (4.4), 100 (21.0), 99
(5.8), 97 (4.9), 96 (4.2), 95 (5.9), 85 (4.6), 84 (8.0), 83
(16.0), 76 (4.1), 75 (13.5), 74 (13.2), 73 (7.2), 66 (4.4), 55 (9.1).
7.1.2.3. 3-[(2-Methyl-4-chloro)phenoxymethyl]-7-phenyl-5H-6,
7-dihydroimidazo[2,1-c][1,2,4]triazole
(7). Recrystallized
from DMF, yield 44.2%, m.p. 248e251 ꢀC; IR (KBr) (n,
1
cmꢁ1): 1612 (C]N); H NMR (DMSO-d6, 300 MHz): 2.27
(s, 3H, CH3), 4.25e4.55 (m, 4H, 2CH2), 5.20 (s, 2H,
OCH2), 7.08e7.55 (m, 8H, ar-H); 13C NMR (DMSO-d6):
15.4 (CH3), 39.9 (imidazolidine-C-5), 53.4 (imidazolidine-C-
6), 60.9 (CH2O), 138.4 (triazole-C-3), 159.6 (C-7a), ar C:
113.6, 114.2, 121.6, 124.6, 125.3, 127.9, 129.8, 142.6, 154.5.
7.1.2.4. 3-(4-Chlorophenoxymethyl)-7-(4-methylphenyl)-5H-6,
7-dihydroimidazo[2,1-c][1,2,4]triazole
(8). Recrystallized
from iPrOH, yield 59.3%, m.p. 273e276 ꢀC; IR (KBr) (n,
1
cmꢁ1): 1607 (C]N); H NMR (DMSO-d6, 300 MHz): 2.30
(s, 3H, CH3), 4.20e4.45 (m, 4H, 2CH2), 5.19 (s, 2H, OCH2),
7.08e7.41 (m, 8H, ar-H); 13C NMR (DMSO-d6): 19.8 (CH3),
39.8 (imidazolidine-C-5), 53.3 (imidazolidine-C-6), 60.8
(CH2O), 137.7 (triazole-C-3), 159.9 (C-7a), ar C: 114.2,
116.6, 125.1, 129.0, 129.1, 129.2, 143.6, 156.3; EIMS
[70 eV, m/z (%)]: 342 (2.8), 341 (2.0), 340 (Mþ, 8.5), 215
(1.4), 214 (17.5), 213 (100.0), 211 (1.8), 185 (5.3), 184 (2.5),
183 (2.0), 171 (5.4), 170 (39.5), 169 (15.0), 158 (4.1), 157
(15.8), 155 (1.1), 153 (2.1), 145 (1.3), 144 (3.5), 143 (4.1),
142 (1.9), 131 (1.3), 130 (1.3), 129 (1.4), 128 (1.5), 127
(3.0), 119 (1.3), 118 (5.1), 117 (17.0), 116 (11.5), 115 (1.6),
111 (2.4), 105 (1.1), 101 (2.5), 99 (7.4), 92 (1.3), 91 (12.0),
90 (6.9), 89 (5.6), 77 (2.1), 75 (2.2), 73 (2.5), 68 (1.0), 67
(1.1), 66 (3.3), 65 (6.4), 64 (2.2), 63 (3.0), 54 (1.2), 41 (1.8).
7.1.2. Generalprocedure for synthesis ofthe 3-phenoxymethyl-
7-aryl-5H-6,7-dihydroimidazo[2,1-c][1,2,4]triazole
derivatives (5e13)
The appropriate derivative of 1-aryl-2-hydrazonoimidazoli-
dine (0.05 mol) and adequate phenoxyacetic acid derivative
(0.055 mol) were refluxed in 80 cm3 of DMF for 6 h. Then
the excess of solvent was distilled under reduced pressure.
The product was obtained by neutralizing the content with
aqueous sodium hydroxide (6%) after adding cold water, and
finally purified by recrystallization from DMF, iPrOH, EtOH
or DMFeMeOH mixture in the proportion indicated.
7.1.2.5. 3-[(2-Methyl-4-chloro)phenoxymethyl]-7-(4-methyl-
phenyl)-5H-6,7-dihydroimidazo[2,1-c][1,2,4]triazole (9). Re-
crystallized from EtOH, yield 43.5%, m.p. 245e248 ꢀC; IR
(KBr) (n, cmꢁ1): 1609 (C]N); 1H NMR (DMSO-d6,
300 MHz): 2.11 (s, 3H, CH3), 2.18 (s, 3H, CH3), 3.77e4.10
(m, 4H, 2CH2), 5.18 (s, 2H, OCH2), 6.92e7.40 (m, 7H, ar-
H); 13C NMR (DMSO-d6): 15.3 (CH3), 19.8 (CH3), 39.8 (imi-
dazolidine-C-5), 53.3 (imidazolidine-C-6), 60.9 (CH2O),
137.6 (triazole-C-3), 160.0 (C-7a), ar C: 113.6, 114.2, 124.6,
126.1, 128.5, 129.1, 129.8, 143.7, 154.4; EIMS [70 eV, m/z
(%)]: 356 (1.5), 355 (1.2), 354 (Mþ, 4.7), 215 (1.5), 214
(18.2), 213 (100.0), 211 (1.7), 186 (0.8), 185 (5.1), 184
(2.3), 183 (1.8), 172 (0.7), 171 (4.7), 170 (36.5), 169 (12.9),
159 (0.9), 158 (3.7), 157 (13.4), 155 (1.1), 145 (1.0), 144
(2.9), 143 (4.2), 142 (2.1), 141 (3.6), 131 (1.1), 130 (0.8),
125 (0.8), 120 (1.0), 119 (1.1), 118 (3.9), 117 (13.1), 116
(8.5), 115 (1.5), 113 (1.2), 107 (0.8), 105 (1.0), 104 (0.7),
92 (1.0), 91 (10.3), 90 (5.9), 89 (5.2), 78 (1.9), 77 (9.3), 68
(0.8), 67 (0.8), 66 (1.6), 65 (4.9), 63 (1.4), 51 (1.4), 41 (1.4).
7.1.2.1. 3-Phenoxymethyl-7-phenyl-5H-6,7-dihydroimidazo[2,
1-c][1,2,4]triazole (5). Recrystallized from DMF, yield
68.2%, m.p. 247e250 ꢀC; IR (KBr) (n, cmꢁ1): 1608
(C]N); 1H NMR (DMSO-d6, 300 MHz): 4.33 (dd,
J ¼ 7.8 Hz, J0 ¼ 6.3 Hz, 2H, CH2), 4.59 (dd, J ¼ 7.7 Hz,
J0 ¼ 6.3 Hz, 2H, CH2), 5.33 (s, 2H, OCH2), 7.08e7.59 (m,
10H, ar-H); EIMS [70 eV, m/z (%)]: 292 (Mþ, 4.5), 187
(11.9), 186 (100.0), 185 (55.7), 171 (1.7), 160 (4.8), 159
(7.4), 158 (15.9), 157 (2.0), 132 (1.9), 131 (6.0), 130 (6.1),
129 (1.8), 118 (5.1), 117 (14.7), 116 (2.6), 109 (4.3), 105
(6.2), 104 (28.0), 103 (41.0), 97 (2.6), 95 (2.6), 93 (3.6), 91
(7.1), 90 (2.1), 84 (3.0), 83 (9.3), 82 (2.3), 81 (1.9), 78
(3.3), 77 (26.1), 76 (15.2), 75 (3.3), 74 (1.9), 73 (1.8), 71
(1.9), 70 (1.7), 69 (3.5), 65 (2.6), 64 (1.9), 63 (2.6), 57
(2.3), 56 (2.0), 55 (5.5), 54 (2.1), 52 (2.5), 51 (8.5), 50
(4.1), 43 (2.2), 41 (2.1), 39 (2.7).
7.1.2.2. 3-(4-Chlorophenoxymethyl)-7-(4-methoxyphenyl)-5H-
6,7-dihydroimidazo[2,1-c][1,2,4]triazole (6). Recrystallized
from DMF, yield 59.2%, m.p. 230e233 ꢀC; IR (KBr) (n,
7.1.2.6. 3-(4-Chlorophenoxymethyl)-7-(4-chlorophenyl)-5H-6,
7-dihydroimidazo[2,1-c][1,2,4]triazole (10). Recrystallized from
DMFeMeOH mixture (2:1), yield 69.7%, m.p. 244e246
1
cmꢁ1): 1610 (C]N); H NMR (DMSO-d6, 300 MHz): 3.80
(s, 3H, OCH3), 4.02e4.40 (m, 4H, 2CH2), 5.20 (s, 2H,