Med Chem Res
1
-
4
-Methyl-7-((1-(3-chlorobenzyl)-1H-1,2,3-triazol-4-yl)me-
89 % yield. Mp 195–196 °C. IR (KBr, cm ): tmax 2916
(C–H), 1711 (C=O), 1620 (C=C), 1553 (N–O), 1102 (C–O)
thoxy)-2H-chromen-2-one (4d) The compound 4d was
obtained as a off-white solid via 1,3-dipolar cycloaddition
reaction between azide 1d (84 mg) and alkyne 3a (107 mg)
1
and 1339 (C–N). H NMR (200 MHz, DMSO-d , ppm): d
6
H
5.41 (s, N–CH ), 5.65 (s, O–CH ), 6.15 (s, 1H), 7.32–7.47
2
13
(m, 6H), 7.60–7.74 (m, 2H) and 8.45 (s, 1H). C NMR
2
-
1
in 18 h with 92 % yield. Mp 120–121 °C. IR (KBr, cm ):
tmax 2916 (C–H), 1720 (C=O), 1611 (C=C), 1385 (C–
CH ), 1156 (C–O) and 679 (C–Cl). H NMR (200 MHz,
(50 MHz, DMSO-d , ppm): d 52.1 (N–CH ), 62.7 (O–
CH ), 91.3, 115, 116.4, 122.9, 124.2, 126.4, 128.8, 129.9,
2
6
2
1
3
CDCl , ppm): d 2.38 (s, 3H), 5.23 (s, N–CH ), 5.68 (s, O–
132.8, 134.9, 141.4, 152.8, 161.5 (C=O) and 164.3. HRMS
?
calculated [M ? H] for C H N O : 379.1036, found:
3
H
2
CH ), 6.11 (s, 1H), 6.87–6.96 (m, 2H), 7.19–7.51 (m, 5H)
2
19 15 4 5
1
3
?
and 7.74 (s, 1H). C NMR (50 MHz, CDCl , ppm): d 18.7
379.1032 and [M ? Na] for C H N O Na: 401.0856,
19 14 4 5
3
(
–CH ), 51.6 (N–CH ), 62.3 (O–CH ), 102.1, 112.2, 112.5,
3
found: 401.0853.
2
2
1
1
14, 123.5, 125.7, 127.7, 130, 130.4, 130.5, 132.2, 133.5,
4
-((1-(3-Nitrobenzyl)-1H-1,2,3-triazol-4-yl)methoxy)-2H-
43.2, 152.6, 156.1 and 161 (C=O). HRMS calculated
chromen-2-one (4h) The compound 4h was obtained as a
white solid via 1,3-dipolar cycloaddition reaction between
azide 1b (89 mg) and alkyne 3b (100 mg) in 21 h with
?
M ? H] for C H ClN O : 382.0958, found: 382.0953
[
2
0
17
3 3
?
and [M ? Na] for C H ClN O Na: 404.0778, found:
2
0
16
3 3
4
04.0768.
-
1
87 % yield, Mp 153–154 °C. IR (KBr, cm ): tmax 1703
4
-Methyl-7-((1-(4-bromobenzyl)-1H-1,2,3-triazol-4-yl)me-
(C=O), 1619 (C=C), 1544 (N–O), 1104 (C–O) and 1348
1
(C–N). H NMR (200 MHz, CDCl , ppm): d 5.35 (s, N–
CH ), 5.72 (s, O–CH ), 5.85 (s, 1H), 7.20–7.36 (m, 2H),
2
1
7.50–7.80 (m, 5H), and 8.20–8.27 (m, 2H). C NMR
thoxy)-2H-chromen-2-one (4e) The compound 4e was
obtained as a off-white solid via 1,3-dipolar cycloaddition
reaction between azide 1e (106 mg) and alkyne 3a
3
H
2
3
(
(
107 mg) in 16 h with 95 % yield. Mp 159–160 °C. IR
(50 MHz, CDCl , ppm): d 53.4 (N–CH ), 62.6 (O–CH ),
3
2
2
-1
KBr, cm ): tmax 1697 (C=O), 1606 (C=C), 1386 (C–
91.3, 116.8, 123, 124, 130.5, 132.6, 134, 136.3, 142.4, 150,
154.4, 162.5 (C=O) and 164.9. HRMS calculated
1
CH ), 1156 (C–O) and 752 (C–Br). H NMR (400 MHz,
3
?
[M ? H] for C H N O : 379.1036, found: 379.1032
CDCl , ppm): d 2.40 (s, 3H), 5.25 (s, N–CH ), 5.52 (s,
O–CH ), 6.15 (s, 1H), 6.92–6.96 (m, 2H), 7.15–7.19 (m,
2
3
,
H
2
19 15 4 5
?
and [M ? Na] for C H N O Na: 401.0856, found:
19 14 4 5
1
3
H), 7.28–7.37 (m, 2H) and 7.50–7.54 (m, 3H). C NMR
2
401.0853.
(
50 MHz, CDCl , ppm): d 18.7 (–CH ), 51.7 (N–CH ),
2.3 (O–CH ), 102.1, 112.3, 112.4, 114.1, 125.8, 129.4,
2
3
3
2
4
-((1-(4-Chlorobenzyl)-1H-1,2,3-triazol-4-yl)methoxy)-2H-
6
1
chromen-2-one (4i) The compound 4i was obtained as a
white solid via 1,3-dipolar cycloaddition reaction between
29.5, 132.9, 152.4, 155.1 and 161.1 (C=O). HRMS cal-
?
culated [M ? H] for C H BrN O : 426.0448, found:
2
0
17
3 3
azide 1c (84 mg) and alkyne 3b (100 mg) in 20 h with
-1
8
?
4
26.0428 and [M ? Na] for C H BrN O Na: 448.0268,
20 16 3 3
8 % yield. Mp 194–195 °C. IR (KBr, cm ): tmax 3061
found: 448.0266.
(
C–H), 1720 (C=O), 1619 (C=C), 1137 (C–O) and 751 (C–
1
4
-Methyl-7-((1-benzyl-1H-1,2,3-triazol-4-yl)methoxy)-2H-
Cl). H NMR (200 MHz, CDCl , ppm): d 5.35 (s, N–
3
H
chromen-2-one (4f) The compound 4f was obtained as a
white solid via 1,3-dipolar cycloaddition reaction between
azide 1f (67 mg) and alkyne 3a (107 mg) in 16 h with
CH ), 5.58 (s, O–CH ), 5.88 (s, 1H), 7.21–7.36 (m, 4H),
2 2
1
7.55–7.62 (m, 3H) and 7.78–7.82 (m, 2H). C NMR
3
(50 MHz, CDCl , ppm): d 53.8 (N–CH ), 62.7 (O–CH ),
3
2
2
-
1
9
2 % yield. Mp 134–135 °C. IR (KBr, cm ): tmax 2915
C–H), 1703 (C=O), 1649 (C=C) and 1155 (C–O). H
91.3, 115.5, 116.9, 123.2, 123.4, 124, 129.6, 129.7, 132.7,
132.8, 135.2, 142.1, 153.4, 162.7 (C=O) and 165. HRMS
1
(
?
calculated [M ? H] for C H N O Cl: 368.0796, found:
NMR (400 MHz, CDCl ): dH 2.39 (s, 3H), 5.23 (s, N–
3
19 15 3 3
?
CH ), 5.55 (s, O–CH ), 6.14 (s, 1H), 6.89–6.94 (m, 2H),
2
368.0798 and [M ? Na]
for C H N O Cl Na:
19 14 3 3
2
1
3
7
1
1
1
.37–7.58 (m, 7H). C NMR (100 MHz, CDCl , ppm): d
390.0616, found: 390.0619.
3
8.8 (–CH ), 54.4 (N–CH ), 62.4 (O–CH ), 102.1, 102.2,
3
2
2
4
-((1-(3-Chlorobenzyl)-1H-1,2,3-triazol-4-yl)methoxy)-2H-
12.3, 112.5, 112.8, 114.1, 123, 125.8, 128.3, 129, 129.3,
chromen-2-one (4j) The compound 4j was obtained as a
white solid via 1,3-dipolar cycloaddition reaction between
34.4, 143.5, 152.6, 155.2, 161.2 and 161.3 (C=O). HRMS
?
calculated [M ? H] for C H N O : 348.1343, found:
0 18 3 3
2
azide 1d (84 mg) and alkyne 3b (100 mg) in 22 h with
-1
?
3
48.1346 and [M ? Na] for C H N O Na: 370.1168,
20 17 3 3
8
6 % yield. Mp 166–167 °C. IR (KBr, cm ): t
1720
max
found: 370.1164.
1
C=O), 1620 (C=C), 1138 (C–O) and 748 (C–Cl). H NMR
(
4
-((1-(4-Nitrobenzyl)-1H-1,2,3-triazol-4-yl)methoxy)-2H-
(200 MHz, CDCl , ppm): d 5.36 (s, N–CH ), 5.76 (s, O–
3
H
2
chromen-2-one (4g) The compound 4g was obtained as a
yellow solid via 1,3-dipolar cycloaddition reaction between
azide 1a (89 mg) and alkyne 3b (100 mg) in 20 h with
CH ), 5.89 (s, 1H), 7.21–7.59 (m, 7H) and 7.76–7.83 (d,
2
1
3
2H). C NMR (50 MHz, CDCl , ppm): d 53.9 (N–CH ),
3
2
62.7 (O–CH ), 91.3, 115.5, 116.9, 124, 129.9, 132.5, 132.7,
2
1
23