The Journal of Organic Chemistry
Page 6 of 9
1
2
3
4
5
6
7
8
NMR (CDCl3, 300 MHz): = 1.24 (d, 3J = 7.6 Hz, 6 H), 2.96
(CDCl3, 300 MHz): = 3.85 (s, 3 H), 4.23 (s, 3 H), 5.25 (s, 2 H),
6.78 (s, 1 H), 7.31 (t, 3J = 7.3 Hz, 1 H), 7.41 (t, 3J = 7.4 Hz, 1 H),
7.82 (d, 3J = 7.1 Hz, 2 H), 7.91 (s, 1 H). 13C NMR (CDCl3,
75 MHz): = 39.0 (CH3), 50.9 (CH2), 53.4 (CH3), 103.0 (CH),
123.2 (CH), 125.7 (CH), 127.9 (CH), 128.8 (CH), 133.2 (Cquat),
134.3 (Cquat), 139.5 (Cquat), 150.7 (Cquat), 166.6 (Cquat). MS (EI)
m/z (%): 297 ([M]+, 100), 240 (35), 226 (33), 210 (18), 196 (69),
184 (67), 171 (21), 153 (10), 139 (21), 126 (10), 77 (13). IR
(sep, 3J = 6.9 Hz, 1 H), 4.09 (s, 3 H), 5.57 (s, 2 H), 6.21 (s, 1 H),
7.28–7.41 (m, 5 H), 7.58 (s, 1 H). 13C NMR (CDCl3, 75 MHz):
= 23.1 (CH3), 27.8 (CH), 38.5 (CH3), 54.4 (CH2), 102.3 (CH),
121.5 (CH), 128.3 (CH), 129.1 (CH), 129.4 (CH), 133.4 (Cquat),
134.4 (Cquat), 139.7 (Cquat), 158.5 (Cquat). MS (GC-MS) m/z (%):
281 ([M]+, 25), 253 (19), 238 (23), 210 (40), 183 (20), 162 (28),
9
105 (17), 91 (100), 77 (30), 65 (22), 51 (33). IR (ATR): ̃ = 3123
cm-1, 3067, 3032, 2960, 2928, 2868, 1605, 1514, 1496, 1456,
1433, 1383, 1362, 881, 792, 743. Anal. Calcd. for C16H19N5
(281.16): C 68.30, H 6.81, N 24.89; Found: C 68.41, H 6.93, N
24.75.
(ATR): ̃
= 3140 cm-1, 3076, 2949, 2853, 1763, 1601, 1477, 1436,
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
1406, 1364, 831, 793, 772, 741. Anal. Calcd. for C15H15N5O2
(297.12): C 60.60, H 5.09, N 23.56; Found: C 60.79, H 5.05, N
23.73.
1-Benzyl-4-(1-benzyl-3-phenyl-1H-pyrazol-5-yl)-1H-1,2,3-
triazole (1h). According to GP2 94 mg (44%) of 1h was obtained
as a colorless solid after purification by flash chromatography (n-
hexane/acetone 3:1), Mp 133-134 °C. 1H NMR (CDCl3,
300 MHz):= 5.52 (s, 2 H), 5.81 (s, 2 H), 6.77 (s, 1 H), 7.16–
7.42 (m, 13 H), 7.44 (s, 1 H), 7.84 (d, 3J = 7.0 Hz, 2 H). 13C NMR
(CDCl3, 75 MHz): = 54.4 (CH2), 54.5 (CH2), 103.4 (CH), 121.9
(CH), 125.8 (CH), 127.3 (CH), 127.5 (CH), 128.0 (CH), 128.3
(CH), 128.6 (CH), 128.8 (CH), 129.1 (CH), 129.4 (CH), 133.1
(Cquat), 134.3 (Cquat), 134.5 (Cquat), 137.5 (Cquat), 138.9 (Cquat),
151.0 (Cquat). MS (EI) m/z (%): 391 ([M]+, 75), 314 (16), 272
(100), 259 (10), 245 (29), 169 (18), 142 (13), 115 (13), 91 (76),
4-(1-Methyl-3-phenyl-1H-pyrazol-5-yl)-1-phenyl-1H-1,2,3-
triazole (1l). According to GP2 86 mg (57%) of 1l was obtained
as a colorless solid after purification by flash chromatography (n-
hexane/acetone 3:1), Mp 115-116 °C. 1H NMR (CDCl3,
3
300 MHz): = 4.33 (s, 3 H), 6.86 (s, 1 H), 7.34 (t, J = 7.3 Hz, 1
H), 7.44 (t, 3J = 7.4 Hz, 2 H), 7.51 (t, 3J = 7.3 Hz, 1 H), 7.59 (t, 3J
= 7.5 Hz, 2 H), 7.81 (d, 3J = 7.1 Hz, 2 H), 7.86 (d, 3J = 7.1 Hz, 2
H), 8.22 (s, 1 H). 13C NMR (CDCl3, 75 MHz): = 39.1 (CH3),
103.0 (CH), 120.1 (CH), 120.8 (CH), 125.8 (CH), 128.2 (CH),
129.4 (CH), 130.1 (CH), 132.5 (Cquat), 134.5 (Cquat), 136.8 (Cquat),
139.4 (Cquat), 150.5 (Cquat). MS (EI) m/z (%): 301 ([M]+, 29), 273
(100), 230 (71), 202 (13), 196 (10), 169 (17), 142 (16), 127 (16),
65 (11). IR (ATR):
̃
= 3127 cm-1, 3109, 3086, 3030, 2934, 1605,
77 (23), 51 (11). IR (ATR): ̃
= 3111 cm-1, 3063, 2941, 2860,
1892, 1599, 1495, 1450, 1439, 1368, 808, 758, 738. Anal. Calcd.
for C18H15N5 (301.13): C 71.74, H 5.02, N 23.24; Found: C 71.69,
H 5.00, N 23.25.
1495, 1454, 1423, 1362 845, 822, 797, 766, 729. Anal. Calcd. for
C25H21N5 (391.18): C 76.70, H 5.41, N 17.89; Found: C 76.70, H
5.44, N 17.62.
1-(4-Chlorobenzyl)-4-(1-methyl-3-phenyl-1H-pyrazol-5-yl)-
1H-1,2,3-triazole (1i). According to GP2 104 mg (58%) of 1i was
obtained as a colorless solid after purification by flash chromatog-
1-(4-Methoxyphenyl)-4-(1-methyl-3-phenyl-1H-pyrazol-5-yl)-
1H-1,2,3-triazole (1m). According to the GP2 101 mg (54%) of
1m was obtained as a colorless solid after purification by flash
chromatography (n-hexane/acetone 3:1), Mp 158-159 °C. 1H
NMR (CDCl3, 300 MHz): = 3.88 (s, 3 H), 4.27 (s, 3 H), 6.81 (s,
1 H), 7.05 (d, 3J = 9.0 Hz, 2 H), 7.31 (t, 3J = 7.3 Hz, 1 H), 7.41 (t,
3J = 7.4 Hz, 2 H), 7.68 (d, 3J = 9.1 Hz, 2 H), 7.83 (d, 3J = 7.0 Hz,
2 H), 8.10 (s, 1 H). 13C NMR (CDCl3, 75 MHz): = 39.1 (CH3),
55.8 (CH3), 102.9 (CH), 115.0 (CH), 120.1 (CH), 122.4 (CH),
125.7 (CH), 127.9 (CH), 128.8 (CH), 130.1 (Cquat), 133.2 (Cquat),
134.3 (Cquat), 139.4 (Cquat), 150.7 (Cquat), 160.3 (Cquat). MS (EI)
m/z (%): 331 ([M]+, 8), 303 (100), 288 (26), 260 (20), 217 (11),
1
raphy (n-hexane/acetone 3:1), Mp 136-137 °C. H NMR (CDCl3,
300 MHz): = 4.21 (s, 3 H), 5.56 (s, 2 H), 6.70 (s, 1 H), 7.25–
7.42 (m, 7 H), 7.65 (s, 1 H), 7.79 (d, 3J = 7.0 Hz, 2 H). 13C NMR
(CDCl3, 75 MHz): = 39.1 (CH3), 53.7 (CH2), 102.8 (CH), 121.6
(CH), 125.6 (CH), 127.9 (CH), 128.8 (CH), 129.6 (CH), 132.8
(Cquat), 133.2 (Cquat), 134.3 (Cquat), 134.3 (Cquat), 135.3 (Cquat),
150.6 (Cquat). MS (EI) m/z (%): 349 ([M]+, 100), 321 (57), 293
(33), 286 (11), 258 (14), 217 (53), 196 (50), 183 (67), 169 (12),
154 (10), 125 (64), 89 (25), 77 (13), 66 (17). IR (ATR): ̃ = 3156
cm-1, 3105, 3034, 2990, 2970, 2945, 2924, 2884, 1599, 1493,
1456, 1410 812, 791, 764, 740. Anal. Calcd. for C19H16ClN5
(349.11): C 65.24, H 4.61, N 20.02; Found C 64.98, H 4.56, N
20.12.
169 (12), 127 (19), 77 (11). IR (ATR): ̃
= 3123 cm-1, 3080, 3061,
2976, 2938, 2901, 2841, 1609, 1516, 1447, 1418, 1358, 821, 800,
768, 741. Anal. Calcd. for C19H17N5O (331.14): C 68.87, H 5.17,
N 21.13; Found: C 68.82, H 5.12, N 21.12.
4-(1-methyl-3-phenyl-1H-pyrazol-5-yl)-1-phenethyl-1H-1,2,3-
triazole (1j). According to GP2 82 mg (48%) of 1j was obtained
as a colorless solid after purification by flash chromatography (n-
hexane/acetone 3:1), Mp 135-136 °C. 1H NMR (CDCl3,
600 MHz): = 3.27 (t, 3J = 7.1 Hz, 2 H), 4.15 (s, 3 H), 4.67 (t,
1-(4-Bromophenyl)-4-(1-methyl-3-phenyl-1H-pyrazol-5-yl)-
1H-1,2,3-triazole (1n). According to GP2 110 mg (52%) of 1n
was obtained as a colorless solid after purification by flash chro-
matography (n-hexane/acetone 3:1), Mp 144-145 °C. 1H NMR
3
(CDCl3, 300 MHz): = 4.27 (s, 3 H), 6.82 (s, 1H), 7.32 (t, J =
3J = 7.1 Hz, 2 H), 6.67 (s, 1 H), 7.12 (d, J = 7.0 Hz, 2 H), 7.27–
7.3 Hz, 1 H), 7.42 (t, 3J = 7.4 Hz, 2 H), 7.68–7.72 (m, 4 H), 7.83
3
3
7.43 (m, 6 H), 7.80 (d, 3J = 7.1 Hz, 2 H). 13C NMR (CDCl3,
75 MHz): = 36.8 (CH2), 38.9 (CH3), 52.0 (CH2), 102.7 (CH),
122.2 (CH), 125.6 (CH), 127.4 (CH), 127.8 (CH), 128.7 (CH),
128.8 (CH), 129.0 (CH), 133.2 (Cquat), 134.6 (Cquat), 136.9 (Cquat),
138.5 (Cquat), 150.6 (Cquat). MS (EI) m/z (%): 329 ([M]+, 100), 300
(16), 273 (24), 210 (45), 182 (24), 171 (9), 139 (15), 105 (26), 91
(d, J = 7.1 Hz, 2 H), 8.16 (s, 1 H). 13C NMR (CDCl3, 75 MHz):
= 39.2 (CH3), 103.1 (CH), 119.7 (CH), 122.1 (CH), 123.1 (CH),
125.7 (CH), 128.0 (CH), 128.8 (CH), 133.1 (Cquat), 133.2 (Cquat),
133.9 (Cquat), 135.7 (Cquat), 139.9 (Cquat), 150.8 (Cquat); MS (EI)
m/z (%): 381 ([81Br-M]+, 7), 379 ([79Br-M]+, 7), 353 (9), 351 (9),
332 (18), 272 (100), 229 (10), 169 (13), 127 (13), 77 (8). IR
(14), 79 (20), 77 (21). IR (ATR):
̃
= 3105 cm-1, 3076, 3030,
(ATR): ̃
= 2961 cm-1, 2934, 2862, 1603, 1510, 1456, 1427, 1366,
2945, 2841, 1950, 1614, 1603, 1493, 1449, 1431, 1362 854, 810,
770, 746. Anal. Calcd. for C20H19N5 (329.16): C 72.92, H 5.81, N
21.26; Found: C 72.95, H 5.81, N 21.23.
827, 816, 800, 779, 756, 725. Anal. Calcd. for C18H14BrN5
(379.04): C 56.86, H 3.71, N 18.42; Found: C 56.91, H 3.85, N
18.40.
Methyl
2-(4-(1-Methyl-3-phenyl-1H-pyrazol-5-yl)-1H-1,2,3-
3-(4-(1-Methyl-3-phenyl-1H-pyrazol-5-yl)-1H-1,2,3-triazol-1-
yl)pyridine (1o). According to GP2 110 mg (52%) of 1o was
obtained as a colorless solid after purification by flash chromatog-
triazol-1-yl)acetate (1k). According to GP2 103 mg (49%) of 1k
was obtained as a colorless solid after purification by flash chro-
matography (n-hexane/acetone 3:1), Mp 151-152 °C. 1H NMR
1
raphy (n-hexane/acetone 2:1), Mp 140-142 °C. H NMR (CDCl3,
6
ACS Paragon Plus Environment