Molecular Diversity
+
2
H), 4.33 (s, 2H), 4.88 (m, 1H), 7.00 (t, J=7.8 Hz, 1H),7.10
136.2, 136.5, 162.7, 167.3. EI-MS: m/z (%) 321 (M , 61),
(
t, J = 7.8 Hz, 1H), 7.32 (s, 1H), 7.38 (d, J = 8.4 Hz, 1H),
156 (35), 130 (100), 91 (53), 77 (8), 44 (8). Anal.Calcd for
C H N OS: C, 67.27; H, 4.70; N, 13.07; S, 9.98; Found:
1
3
7
.50 (d, J=8.4 Hz, 1H), 11.05 (s, 1H). CNMR(150 MHz,
1
8
15
3
DMSO-d ): δ 21.3, 21.4, 33.9, 69.2, 106.5, 111.6, 118.1,
C, 67.37; H, 4.69; N, 12.93; S, 9.93.
6
1
18.7, 121.3, 124.1, 126.5, 136.2, 162.4, 167.0, 167.2.
+
EI-MS: m/z (%) 331 (M , 48), 130 (100). Anal.Calcd for
2‑((1H‑indol‑3‑yl)methyl)‑5‑((2‑methylbenzyl)thio)‑1,3,4‑oxa-
1
C H N O S: C, 57.99; H, 5.17; N, 12.68; S, 9.68; Found:
diazole (10k) Yield, 80%. mp, 129–131 °C. H NMR
1
6
17
3
3
C, 57.88; H, 5.05; N, 12.56; S, 9.66.
(600 MHz, DMSO-d ): δ 2.31 (s, 3H), 4.34 (s, 2H), 4.42
6
(
s, 2H), 7.01 (m, 2H),7.12 (d, J=7.2 Hz, 1H), 7.15 (m, 3H),
tert‑butyl 2‑((5‑((1H‑indol‑3‑yl)methyl)‑1,3,4‑oxadiazol‑2‑yl)
thio)acetate (10g) Yield, 89%. mp, 100–102 °C. H NMR
7.34 (s, 1H), 7.40 (d, J=7.8 Hz, 1H), 7.51 (d, J=7.8 Hz,
1
13
1H),11.08 (s, 1H). CNMR(150 MHz, DMSO-d ): δ 18.6,
6
(
600 MHz, DMSO-d ): δ1.33 (s, 9H),4.03 (s, 2H), 4.33 (s,
21.5, 34.4, 106.5, 111.6, 118.2, 118.8, 121.3, 124.2, 126.0,
6
2
H), 7.00 (t, J=7.2 Hz, 1H),7.10 (t, J=7.8 Hz, 1H), 7.33
126.6, 128.1, 129.8, 130.4, 133.7, 136.2, 136.6, 162.5,
+
(
s, 1H), 7.38 (d, J=7.8 Hz, 1H), 7.51 (d, J=7.8 Hz, 1H),
167.3. EI-MS: m/z (%) 335 (M , 53), 320 (4), 231 (9), 205
13
1
3
1
2
1.05 (s, 1H). C NMR (150 MHz, DMSO-d ): δ 21.4, 27.4,
(6), 156 (39), 130 (21), 105 (100), 77 (16), 44 (19). Anal.
Calcd for C H N OS: C, 68.03; H, 5.11; N, 12.53; S, 9.56;
6
4.6, 81.9, 106.5, 111.6, 118.1, 118.7, 121.3, 124.1, 126.5,
19
17
3
+
36.2, 162.5, 166.5, 167.1. EI-MS: m/z (%) 345 (M , 45),
Found: C, 67.92; H, 5.30; N, 12.37; S, 9.31.
89 (25), 130 (100). Anal.Calcd for C H N O S: C, 59.11;
17
19
3
3
H, 5.54; N, 12.17; S, 9.28; Found: C, 59.15; H, 5.53; N,
2‑((1H‑indol‑3‑yl)methyl)‑5‑((2‑ꢀuorobenzyl)thio)‑1,3,4‑oxa-
1
1
2.07; S, 9.47.
diazole (10l) Yield, 88%. mp, 101–103 °C. H NMR
(
600 MHz, DMSO-d ): δ 4.33 (s, 2H), 4.43 (s, 2H), 7.01
6
ethyl 2‑((5‑((1H‑indol‑3‑yl)methyl)‑1,3,4‑oxadiazol‑2‑yl)
(m, 2H),7.14 (m, 2H), 7.31 (m, 3H), 7.39 (d, J=7.8 Hz, 1H),
1
3
thio)‑2‑methylpropanoate (10h) Yield, 32%. mp, 126-
7.49 (d, J=7.2 Hz, 1H), 11.07 (s, 1H). CNMR(150 MHz,
1
1
28 °C. H NMR (600 MHz, DMSO-d ): δ0.98 (t, J=7.2 Hz,
DMSO-d ): δ21.4, 29.7, 106.5, 111.6, 115.3, 115.5,
6
6
3
H), 1.53 (m, 6H),3.91 (q, J=7.2 Hz, 2H), 4.37 (s, 2H), 7.00
118.1, 118.7, 121.3, 123.4 (d, J = 13.5 Hz, 1C), 124.3
C–F
(
t, J = 7.8 Hz, 1H),7.10 (t, J = 7.8 Hz, 1H), 7.33 (s, 1H),
(d, J = 27.6 Hz, 1C), 126.6, 130.1 (d, J = 8.1 Hz,
C–F
C–F
7
1
5
1
5
.38 (d, J=7.8 Hz, 1H), 7.50 (d, J=7.8 Hz, 1H), 11.06 (s,
1C), 131.2 (d, J = 2.3 Hz, 1C), 136.2, 159.4, 161.1,
C–F
1
3
+
H). C NMR (150 MHz, DMSO-d ): δ 13.5, 21.6, 25.7,
162.2, 167.5. EI-MS: m/z (%) 339 (M , 48), 238 (11), 156
6
3.2, 61.4, 106.4, 111.5, 118.1, 118.7, 121.3, 124.1, 126.5,
(25), 130 (21), 109 (34), 86 (18), 77 (5). Anal.Calcd for
C H FN OS: C, 63.70; H, 4.16; N, 12.38; S, 9.45; Found:
36.2, 160.2, 168.6, 171.4. Anal.Calcd for C H N O S: C,
17
19
3
3
18 14
3
9.11; H, 5.54; N, 12.17; S, 9.28; Found: C, 59.34; H, 5.46;
C, 63.83; H, 4.02; N, 12.16; S, 9.66.
N, 12.41; S, 9.44.
2
‑((1H‑indol‑3‑yl)methyl)‑5‑((3‑ꢀuorobenzyl)thio)‑1,3,4‑oxadi-
1
(
E)‑ethyl 4‑((5‑((1H‑indol‑3‑yl)methyl)‑1,3,4‑oxadiazol‑2‑yl)
azole (10m) Yield, 65%. mp, 85–87 °C. H NMR (600 MHz,
1
thio)but‑2‑enoate (10i) Yield, 30%. mp, 86–88 °C. H NMR
DMSO-d ): δ4.33 (s, 2H), 4.43 (s, 2H), 7.00 (m, 1H),7.08
6
(
600 MHz, DMSO-d ): δ1.20 (s, 3H),4.01 (d, J = 6.0 Hz,
(m, 3H), 7.24 (m, 2H), 7.26 (s, 1H),7.38 (m, 1H), 7.49 (d,
6
1
3
2
H), 4.11 (d, J = 6.6 Hz, 2H), 4.34 (s, 2H), 6.02 (d,
J=7.8 Hz, 1H), 11.08 (s, 1H). CNMR(150 MHz, DMSO-
d ): δ 21.5, 35.1, 106.5, 111.6, 114.6 (d, J =23.7 Hz, 1C),
J=15.0 Hz, 1H), 6.88 (t, J=7.8 Hz, 1H),7.01 (d, J=6.6 Hz,
6
C–F
1
7
H), 7.10 (s, 1H), 7.34 (s, 1H), 7.38 (d, J = 7.8 Hz, 1H),
115.7 (d, J = 22.2 Hz, 1C), 118.2, 118.8, 121.4, 124.2,
C–F
1
3
.50 (d, J=6.6 Hz, 1H), 11.05 (s, 1H). CNMR(150 MHz,
125.0 (d, J =2.25 Hz, 1C), 126.6, 130.4(d, J =8.1 Hz,
C–F
C–F
DMSO-d ): δ 14.0, 21.4, 32.3, 60.1, 106.5, 111.6, 118.1,
1C), 136.2, 139.5 (d, J = 8.1 Hz, 1C), 161.1, 162.6 (d,
6
C–F
+
1
1
18.7, 121.3, 124.0, 124.2, 126.5, 136.2, 141.9, 162.2,
J
=27.6 Hz, 1C), 167.4. EI-MS: m/z (%) 339 (M , 56),
C–F
+
65.0, 167.4. EI-MS: m/z (%) 343 (M , 20), 230 (79), 130
238 (8), 156 (17), 130 (100), 109 (28), 77 (5). Anal.Calcd for
(
100). Anal.Calcd for C H N O S: C, 59.46; H, 4.99; N,
C H FN OS: C, 63.70; H, 4.16; N, 12.38; S, 9.45; Found:
1
7
17
3
3
18 14
3
1
2.24; S, 9.34; Found: C, 59.39; H, 5.08; N, 12.12; S, 9.57.
C, 63.74; H, 4.33; N, 12.33; S, 9.59.
2
‑((1H‑indol‑3‑yl)methyl)‑5‑(benzylthio)‑1,3,4‑oxadiazole
2‑((1H‑indol‑3‑yl)methyl)‑5‑((3‑methylbenzyl)thio)‑1,3,4‑oxa-
1
1
(
10j) Yield, 92%. mp, 117–119 °C. H NMR (600 MHz,
diazole (10n) Yield, 50%. mp, 97–99 °C. H NMR
DMSO-d ): δ4.34 (s, 2H), 4.40 (s, 2H), 7.01 (m, 1H),7.11
(600 MHz, DMSO-d ): δ2.50 (s, 3H), 4.33 (s, 2H), 4.37 (s,
6
6
(
m, 1H), 7.22 (s, 3H), 7.27 (s, 2H),7.34 (s, 1H), 7.40
2H), 7.01 (t, J=7.8 Hz, 1H),7.04 (d, J=7.8 Hz, 1H), 7.06 (s,
(
d, J = 8.4 Hz, 1H), 7.50 (d, J = 7.2 Hz, 1H), 11.09 (s,
1H), 7.10 (m, 3H), 7.33 (s, 1H), 7.39 (d, J=7.8 Hz, 1H),7.51
1
3
13
1
1
H). CNMR(150 MHz, DMSO-d ): δ21.5, 35.8, 106.6,
(d, J = 7.8 Hz, 1H), 11.06 (s, 1H). CNMR(150 MHz,
6
11.6, 118.8, 121.4, 124.3, 126.6, 128.7, 128.5, 128.9,
DMSO-d ): δ20.8, 21.4, 35.8, 106.6, 111.6, 118.1, 118.8,
6
1
3