SEYİTDANLIOĞLU et al/Turk J Chem
J = 7.4 Hz, 2H), 6.97 (t, J = 7.4 Hz, 1H), 7.06 (t, J = 7.0 Hz, 1H), 7.16 (bs, 1H), 7.32 (d, J = 8.0 Hz, 1H),
13
7.49–7.56 (m, 3H), 7.63 (t, J = 6.8 Hz, 1H), 8.00 (d, J = 7.8 Hz, 2H), 10.78 (s, 1H); C NMR (100 MHz,
DMSO) δ = 19.9, 39.2, 111.8, 114.1, 118.7, 118.8, 121.4, 122.8, 127.5, 128.4, 129.2, 133.5, 136.7, 137.2, 200.2;
+
HRMS (ESI): m/z calculated for C17 H16 NO [M+H] : 250.1226; found: 250.1235.
1-(Furan-2-yl)-3-(1H-indol-3-yl)propan-1-one (4b): White solid; mp 105–106 °C; yield 72%; Rf
=
1
0.40 (EtOAc-hexane, 1:3); H NMR (400 MHz, DMSO) δ 3.01 (t, J = 7.4 Hz, 2H), 3.19 (t, J = 7.4 Hz, 2H),
6.67 (bs, 1H), 6.96 (t, J = 7.4 Hz, 1H), 7.05 (t, J = 7.1 Hz, 1H), 7.12 (bs, 1H), 7.31 (d, J = 8.0 Hz, 1H), 7.45
13
(d, J = 3.5 Hz, 1H), 7.53 (d, J = 7.7 Hz, 1H), 7.95 (bs, 1H), 10.77 (bs, 1H); C NMR (100 MHz, DMSO)
δ = 19.8, 38.9, 111.8, 112.9, 113.8, 118.7, 118.8, 121.4, 122.9, 127.4, 136.7, 148.0, 152.4, 188.7; HRMS (ESI):
+
m/z calculated for C15 H14 NO2 [M+H] : 240.1019; found: 240.1026.
30
3-(1H-Indol-3-yl)-1-(thiophen-2-yl)propan-1-one (4c): White solid; mp 104–105 °C (lit. 105 °C);
1
yield 65%; Rf = 0.20 (EtOAc-hexane, 1:3); H NMR (400 MHz, DMSO) δ 3.09 (t, J = 7.4 Hz, 2H), 3.38 (t,
J = 7.4 Hz, 2H), 7.02 (t, J = 7.4 Hz, 1H), 7.10 (t, J = 7.5 Hz, 1H), 7.19 (bs, 1H) 7.25 (t, J = 4.3 Hz, 1H),
13
7.37 (d, J = 8.0 Hz, 1H), 7.59 (d, J = 7.8 Hz, 1H), 7.99 (bs, 1H), 8.01 (bs, 1H), 10.82 (s, 1H, NH); C NMR
(100 MHz, DMSO) δ = 20.1, 40.6, 111.8, 113.9, 118.7, 118.8, 121.4, 122.9, 127.5, 129.2, 133.6, 135.0, 136.7,
+
144.4, 193.3; HRMS (ESI): m/z calculated for C15 H14 NOS [M+H] : 256.0791; found: 256.0809.
3-(1H-Indol-3-yl)-1-(1H-pyrrol-2-yl)propan-1-one (4d): White solid; mp 167.5–168.0 °C; yield
1
20%; Rf = 0.27 (EtOAc-hexane, 1:3); H NMR (400 MHz, DMSO) δ 3.05 (t, J = 7.4 Hz, 2H), 3.15 (t, J =
7.4 Hz, 2H), 6.16–6.23 (m, 1H), 6.68–7.02 (m, 2H), 7.05–7.13 (m, 2H), 7.16 (bs, 1H), 7.35 (d, J = 8.0 Hz, 1H),
13
7.57 (d, J = 7.8 Hz, 1H), 10.79 (s, 1H), 11.81 (s, 1H); C NMR (100 MHz, DMSO) δ = 20.6, 38.5, 110.1,
111.8, 114.2, 116.8, 118.7, 118.8, 121.4, 122.8, 125.6, 127.4, 132.2, 136.6, 189.7; HRMS (ESI): m/z calculated
+
for C15 H15 N2 O [M+H] : 239.1179; found: 239.1193.
1,3-Di(1H-indol-3-yl)propan-1-one (4e): Pink solid; mp 200–201 °C; yield 42%; Rf = 0.30 (EtOAc-
1
hexane, 1:3); H NMR (400 MHz, DMSO) δ 3.09 (t, J = 7.5 Hz, 2H), 3.27 (t, J = 7.5 Hz, 2H), 6.99 (t, J =
7.3 Hz, 1H), 7.08 (t, J = 7.4 Hz, 1H), 7.14–7.25 (m, 3H), 7.34 (d, J = 8.0 Hz, 1H), 7.47 (d, J = 6.9 Hz, 1H),
13
7.59 (d, J = 7.8 Hz, 1H), 8.25 (d, J = 7.4 Hz, 1H), 8.35 (bs, 1H), 10.77 (bs, 1H), 11.91 (gt, 1H); C NMR
(100 MHz, DMSO) δ = 20.6, 111.8, 112.5, 114.6, 116.9, 118.6, 118.8, 121.3, 121.9, 122.1, 122.8, 123.2, 125.9,
+
127.6, 134.3, 136.7, 137.1, 195.4; HRMS (ESI): m/z calculated for C19 H17 N2 O [M+H] : 289.1385; found:
289.13512.
31
(E)-5-(1H-Indol-3-yl)-1-phenylpent-1-en-3-one (4f): White solid; mp 126–127 °C (lit. 127 °C);
yield 90%; Rf = 0.37 (EtOAc-hexane, 1:3); H NMR (400 MHz, DMSO) δ 3.09 (t, J = 7.6 Hz, 2H), 3.17 (t,
1
J = 7.6 Hz, 2H), 7.00 (d, J = 16.3 Hz, 1H), 7.06 (t, J = 7.9 Hz, 1H), 7.15 (t, J = 7.6 Hz, 1H), 7.22 (bs, 1H),
7.42 (d, J = 8.0 Hz, 1H), 7.45–7.52 (m, 3H), 7.64 (d, J = 7.7 Hz, 1H), 7.70 (d, J = 16.3 Hz, 1H), 7.73–7.79 (m,
13
2H), 10.86 (bs, 1H); C NMR (100 MHz, DMSO) δ = 19.9, 41.2, 111.8, 114.1, 118.7, 118.8, 121.4, 122.8, 127.0,
+
127.5, 128.9, 129.4, 130.8, 135.0, 136.8, 142.5, 200.2; HRMS (ESI): m/z calculated for C19 H18 NO: [M+H] :
276.1383; found: 276.1372.
(E)-1-(4-Hydroxyphenyl)-5-(1H-indol-3-yl)pent-1-en-3-one (4g): Yellow solid; mp 198–199 °C;
1
yield 85%; Rf = 0.14 (EtOAc-hexane, 1:3); H NMR (400 MHz, DMSO) δ 2.97–3.02 (m, 4H), 6.70 (d, J =
16.2 Hz, 1H), 6.77 (d, J = 7.8 Hz, 2H), 6.96 (t, J = 7.4 Hz, 1H), 7.05 (t, J = 7.5 Hz, 1H), 7.09 (bs, 1H), 7.31
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