MedChemComm
Research Article
+
2
91.31 ([M + H] ). Anal. calc. for C H N O: C, 65.97; H, 4.50;
2H), 5.65 (s, 2H), 7.57–7.60 (m, 1H), 7.83–7.86 (m, 2H), 8.04–
8.07 (m, 2H), 8.14–8.21(m, 3H). MS (ESI): 336.30 ([M + H] ).
16
13 5
+
N, 24.04ꢀ; found: C, 65.60; H, 4.52; N, 24.03ꢀ.
.1.6 2-((1H-Benzoijd]ij1,2,3]triazol-1-yl)methyl)-5-(3-bromo-
benzyl)-1,3,4-oxadiazole (5b). White powder, yield 54ꢀ, m. p.
42 °C. H-NMR (300 MHz, DMSO-d , δ ppm): 4.27 (s, 2H),
.37 (s, 2H), 7.28–7.29 (m, 2H), 7.44–7.45 (m, 1H), 7.46–7.84
m, 2H), 7.57–7.59 (m, 2H), 8.07–8.10 (d, J = 8.37 Hz, 1H) MS
ESI): 370.20 ([M + H] ). Anal. calc. for C H BrN O: C, 51.91;
H, 3.27; N, 18.92ꢀ; found: C, 51.94; H, 3.31; N, 18.89.
.1.7 2-((1H-Benzoijd]ij1,2,3]triazol-1-yl)methyl)-5-(4-bromo-
benzyl)-1,3,4-oxadiazole (5c). White powder, yield 66ꢀ, m. p.
30–232 °C. H-NMR (300 MHz, DMSO-d
H); 6.39 (s, 2H), 7.25–7.31 (m, 2H), 7.44–7.45 (m, 2H), 7.48–
.50 (d, J = 7.27 Hz, 2H), 8.06–8.10 (m, 2H). MS (ESI): 370.20
[M + H] ). Anal. calc. for C16
8.92ꢀ; found: C, 51.90; H, 3.28; N, 18.91ꢀ.
.1.8 2-((1H-Benzoijd]ij1,2,3]triazol-1-yl)methyl)-5-(3-chloro-
benzyl)-1,3,4-oxadiazole (5d). White powder, yield 62ꢀ, m. p.
35–237 °C. H-NMR (300 MHz, DMSO-d , δ ppm): 4.67(s,
H), 6.08 (s, 2H), 7.38–7.45 (m, 2H), 7.54–7.59 (m, 3H), 7.66–
4
12 6 3
Anal. calc. for C16H N O : C, 57.14; H, 3.60; N, 24.99; O,
14.27ꢀ; found: C, 57.18; H, 3.58; N, 25.01ꢀ.
1
2
6
(
(
4.1.14
2-((1H-Benzoijd]ij1,2,3]triazol-1-yl)methyl)-5-(3-
6
bromophenyl)-1,3,4-oxadiazole (5j). White powder, yield 70ꢀ,
1
m. p. 235–237 °C. H-NMR (300 MHz, DMSO-d , δ ppm): 5.57
6
+
(s, 2H), 7.28–7.41 (m, 2H), 7.44–7.48 (m, 2H), 7.49–7.50 (m,
16
12
5
+
3H); 8.09–8.10 (m, 1H). MS (ESI): 356.18 ([M + H] ). Anal.
4
calc. for C H BrN O: C, 50.58; H, 2.83; N, 19.66ꢀ; found: C,
15
10
5
50.56; H, 2.80; N, 19.69ꢀ.
1
2
2
7
(
1
6
, δ ppm): 4.65 (s,
4.1.15
2-((1H-Benzoijd]ij1,2,3]triazol-1-yl)methyl)-5-(4-
bromophenyl)-1,3,4-oxadiazole (5k). White powder, yield
1
71ꢀ, m. p. 240–242 °C. H-NMR (300 MHz, DMSO-d , δ
6
+
5
H12BrN O: C, 51.91; H, 3.27; N,
ppm): 5.56 (s, 2H), 7.42–7.81 (m, 3H), 7.81–7.86 (m, 4H),
+
8.80–8.81(m, 1H). MS (ESI): 366.01 ([M + H] ). Anal. calc. For
4
C H BrN O: C, 55.90; H, 3.13; N, 26.08ꢀ; found: C, 55.92;
15
10
5
H, 3.15; N, 26.30ꢀ.
1
2
2
7
4.1.16 2-((1H-Benzoijd]ij1,2,3]triazol-1-yl)methyl)-5-(3-chloro-
6
phenyl)-1,3,4-oxadiazole (5l). White powder, yield 65ꢀ, m. p.
+
1
.70 (m, 1H), 8.04–8.07 (m, 2H). MS (ESI): 325.75 ([M + H] ).
240–242 °C. H-NMR (300 MHz, DMSO-d
6
, δ ppm): 6.09 (s,
Anal. calc. For C H ClN O: C, 58.99; H, 3.71; N, 21.50ꢀ;
2H), 7.09–7.15 (m, 3H), 7.17–7.44 (m, 1H), 7.65 (d, J = 7.64
Hz, 2H), 7.82 (d, J = 8.14, 2H). MS (ESI): 332.05 ([M + H] ).
Anal. calc. for C16H13NO S: C, 58.00; H, 3.95; N, 4.23ꢀ;
5
found: C, 58.02; H, 3.97; N, 4.26ꢀ.
16
12
5
+
found: C, 56.01; H, 3.73; N, 21.48ꢀ.
.1.9 2-((1H-Benzoijd]ij1,2,3]triazol-1-yl)methyl)-5-(3-fluoro-
benzyl)-1,3,4-oxadiazole (5e). White powder, yield 67ꢀ, m. p.
4
1
2
2
7
40–242 °C. H-NMR (300 MHz, DMSO-d
6
, δ ppm): 4.38(s,
4.1.17 2-((1H-Benzoijd]ij1,2,3]triazol-1-yl)methyl)-5-(3-fluoro-
H), 5.79 (s, 2H), 7.22–7.38 (m, 5H), 7.43–7.52 (m, 1H), 7.55–
.58(m, 1H), 8.03–8.06 (m, 1H). MS (ESI): 309.30 ([M + H] ).
phenyl)-1,3,4-oxadiazole (5m). White powder, yield 56ꢀ, m.
+
1
p. 230–232 °C. H-NMR (300 MHz, DMSO-d , δ ppm): 5.63 (s,
6
Anal. calc. for C16
found: C, 62.14; H, 3.90; N, 22.66ꢀ.
.1.10 2-((1H-Benzoijd]ij1,2,3]triazol-1-yl)methyl)-5-(3-
methoxybenzyl)-1,3,4-oxadiazole (5f). White powder, yield
H
12FN
5
O: C, 62.13; H, 3.91; N, 22.64ꢀ;
2H), 7.39–7.46 (m, 2H), 7.54–7.62 (m, 3H), 7.70–7.73 (m, 1H),
8.04–8.07 (m, 2H). MS (ESI): 346.37 ([M + H] ). Anal. calc. for
+
4
C H FN O, C, 61.02; H, 3.41; N, 23.72; O, 5.42ꢀ, found: C,
15
10
5
61.04; H, 3.39; N, 23.74ꢀ.
1
6
0ꢀ, m. p. 240–242 °C. H-NMR (300 MHz, DMSO-d
ppm): 4.38(s, 2H), 4.56 (s, 3H), 5.79 (s, 2H), 6.83–6.86 (m,
H), 7.17–7.20 (m, 3H), 7.38–7.40 (m, 1H), 7.43–7.54 (m, 1H).
6
, δ
4.1.18
2-((1H-Benzoijd]ij1,2,3]triazol-1-yl)methyl)-5-(3-
methoxyphenyl)-1,3,4-oxadiazole (5n). White powder, yield
1
3
62ꢀ, m. p. 235–237 °C. H-NMR (300 MHz, DMSO-d
6
, δ
+
MS (ESI): 321.33 ([M + H] ). Anal. calc. for C17
H N O
15 5 2
: C,
3.54; H, 4.71; N, 21.79ꢀ; found: C, 63.50; H, 4.73; N,
1.80ꢀ.
.1.11
methoxybenzyl)-1,3,4-oxadiazole (5g). White powder, yield
ppm): 3.45 (s, 2H), 5.43 (s, 2H), 7.16–7.21(m, 1H), 7.21–7.52
6
2
(m, 2H), 7.71–7.80 (m, 3H), 8.07–8.14 (m, 2H). MS (ESI):
+
307.31 ([M + H] ). Anal. calc. for C16
13 5 2
H N O : C, 62.53; H,
4
2-((1H-Benzoijd]ij1,2,3]triazol-1-yl)methyl)-5-(4-
4.26; N, 22.79ꢀ; found: C, 62.54; H, 4.24; N, 22.80ꢀ.
4.1.19 2-((1H-Benzoijd]ij1,2,3]triazol-1-yl)methyl)-5-(4-
methoxyphenyl)-1,3,4-oxadiazole (5o). White powder, yield
1
5
9ꢀ, m. p. 169–170 °C. H-NMR (300 MHz, DMSO-d
ppm): 4.51(s, 2H), 4.72 (s, 3H), 5.26 (s, 2H), 6.81–6.84 (m,
H), 7.06–7.09 (m, 3H), 7.42–7.45 (m, 3H). MS (ESI): 321.33
6
, δ
1
6
70ꢀ, m. p. 230–232 °C. H-NMR (300 MHz, DMSO-d , δ
2
ppm): 3.81 (s, 3H), 5.08 (s, 2H), 7.23–7.55 (m, 3H), 7.65–7.78
+
(
2
[M + H] ). Anal. calc. for C17
H N O
15 5 2
:C, 63.54; H, 4.71; N,
1.79ꢀ; found: C, 63.51; H, 4.73; N, 21.80ꢀ.
.1.12 2-((1H-Benzoijd]ij1,2,3]triazol-1-yl)methyl)-5-(2-
methoxybenzyl)-1,3,4-oxadiazole (5h). White powder, yield
(m, 2H), 7.90–8.07 (m, 1H), 8.15–8.34(m, 2H). MS (ESI):
+
307.31 ([M + H] ). Anal. calc. for C16
13 5 2
H N O : C, 62.53; H,
4
4.26; N, 22.79ꢀ; found: C, 62.52; H, 4.29; N, 22.80ꢀ.
4.1.20 2-((1H-Benzoijd]ij1,2,3]triazol-1-yl)methyl)-5-(2-
1
5
4ꢀ, m. p. 170–172 °C. H-NMR (300 MHz, DMSO-d
ppm): 4.78(s, 2H), 4.91 (s, 3H), 5.23 (s, 2H), 6.42–6.44 (m,
H), 7.09–7.14 (m, 4H), 7.46–7.54 (m, 3H), 8.01–8.20 (m, 1H).
6
, δ
methoxyphenyl)-1,3,4-oxadiazole (5p). White powder, yield
1
64ꢀ, m. p. 230–232 °C. H-NMR (300 MHz, DMSO-d , δ
6
2
ppm): 3.89 (s, 3H), 5.23 (s, 2H), 7.12–7.23 (m, 1H), 7.23–7.44
(m, 3H), 7.55–7.75 (m, 2H), 7.77–7.96 (m, 1H), 8.10–8.12 (m,
+
MS (ESI): 307.11([M + H] ). Anal. calc. for C16
H N O
13 5 2
: C,
2.53; H, 4.26; N, 22.79ꢀ; found: C, 62.56; H, 4.28; N,
2.77ꢀ.
.1.13 2-((1H-Benzoijd]ij1,2,3]triazol-1-yl)methyl)-5-(4-nitro-
benzyl)-1,3,4-oxadiazole (5i). White powder, yield 50ꢀ, m. p.
+
6
2
2H). MS (ESI): 307.31 ([M + H] ). Anal. calc. for C H N O : C
1
6
13 5 2
62.53; H, 4.26; N, 22.79ꢀ; found: C, 62.55; H, 4.28; N,
22.80ꢀ.
4.1.21 2-((1H-Benzoijd]ij1,2,3]triazol-1-yl)methyl)-5-(4-nitro-
phenyl)-1,3,4-oxadiazole (5q). White powder, yield 63ꢀ, m. p.
4
1
2
6
35–237 °C. H-NMR (300 MHz, DMSO-d , δ ppm): 4.76 (s,
This journal is © The Royal Society of Chemistry 2015
Med. Chem. Commun.