10.1002/ejoc.201701241
European Journal of Organic Chemistry
FULL PAPER
1-(5-(Dibenzo[b,d]furan-4-yl)thiophen-2-yl)ethan-1-one (3ig) (entry 1
of table 3 and entry 4 of table 5): Obtained as a yellow solid; Yield: 72%
(0.104 g); mp: 132 – 134 °C; Rf = 0.26 (ethyl acetate/hexane 1:19); 1H
NMR (400 MHz, CDCl3): δ 8.00 – 7.89 (m, 3H), 7.79 – 7.74 (m, 2H), 7.67
(d, J = 8.2 Hz, 1H), 7.51 (t, J = 7.7 Hz, 1H), 7.39 (m, 2H), 2.62 (s, 3H) ppm;
13C NMR (100 MHz, CDCl3): δ 190.9, 156.3, 152.5, 147.0, 143.4, 133.4,
127.9, 127.1, 125.5, 125.4, 123.9, 123.4, 123.4, 121.2, 121.0, 118.5, 112.1,
26.8 ppm; IR (KBr): 3062, 1645, 1583, 1438, 1350, 1273, 1182, 1095, 835,
790, 747 cm-1; HRMS (ESI): m/z calcd for C18H13O2S [M + H]+ 293.0636,
found 293.0632.
2-(Dibenzo[b,d]furan-4-yl)pyrazine (3fg) (entry 2 of table 4): Obtained
as a white solid; Yield: 75% (0.092 g); mp: 133 – 135 °C; Rf = 0.23 (ethyl
acetate/hexane 1:19); 1H NMR (400 MHz, CDCl3): δ 9.74 (s, 1H), 8.73 (s,
1H), 8.58 (d, J = 2.1 Hz, 1H), 8.29 (d, J = 7.7 Hz, 1H), 8.02 (dd, J = 21.1,
7.5 Hz, 2H), 7.65 (d, J = 8.2 Hz, 1H), 7.50 (t, J = 7.7 Hz, 2H), 7.39 (t, J =
7.4 Hz, 1H) ppm; 13C NMR (100 MHz, CDCl3): δ 156.2, 153.6, 149.9, 145.6,
144.5, 143.2, 127.7, 127.2, 125.5, 123.8, 123.6, 123.3, 122.4, 121.1, 120.9,
112.0 ppm; IR (KBr): 3031, 2963, 1462, 1454, 1417, 1189, 1069, 1014,
877, 793, 741 cm-1; HRMS (ESI): m/z calcd for C16H11N2O [M + H]+
247.0871, found 247.0867.
1-(5-(Dibenzo[b,d]thiophen-4-yl)thiophen-2-yl)ethan-1-one (3ii) (entry
2 of table 3): Obtained as a white solid; Yield: 71% (0.108 g); mp: 100 –
102 °C; Rf = 0.29 (ethyl acetate/hexane 1:19); 1H NMR (400 MHz, CDCl3):
δ 8.21 – 8.17 (m, 2H), 7.91 – 7.87 (m, 1H), 7.77 (d, J = 4.0 Hz, 1H), 7.72
(dd, J = 7.5, 1.0 Hz, 1H), 7.65 (d, J = 3.9 Hz, 1H), 7.57 – 7.48 (m, 3H), 2.62
(s, 3H) ppm; 13C NMR (100 MHz, CDCl3): δ 190.8, 150.9, 143.8, 139.4,
137.9, 137.0, 135.4, 133.2, 128.9, 127.4, 126.9, 126.5, 125.2, 124.9, 122.8,
122.1, 122.0, 26.9 ppm; IR (KBr): 3051, 1651, 1482, 1434, 1390, 1276,
1018, 791, 755 cm-1; HRMS (ESI): m/z calcd for C18H13OS2 [M + H]+
309.0407, found 309.0431.
1-(Dibenzo[b,d]furan-4-yl)isoquinoline (3hg) (entry 3 of table 4):
Obtained as a yellow solid; Yield: 55% (0.081 g); mp: 135 – 137 °C; Rf =
0.13 (ethyl acetate/hexane 1:19); 1H NMR (400 MHz, CDCl3): δ 8.73 (d, J
= 5.7 Hz, 1H), 8.11 (dd, J = 7.7, 1.1 Hz, 1H), 8.03 (d, J = 7.6 Hz, 1H), 7.95
(d, J = 8.3 Hz, 1H), 7.84 (d, J = 8.5 Hz, 1H), 7.78 (d, J = 5.7 Hz, 1H), 7.74
– 7.67 (m, 2H), 7.52 (dt, J = 15.5, 7.4 Hz, 2H), 7.43 – 7.35 (m, 3H) ppm;
13C NMR (100 MHz, CDCl3): δ 156.8, 156.4, 154.0, 142.6, 136.8, 130.4,
129.1, 127.8, 127.6, 127.4, 127.1, 125.0, 124.3, 124.2, 123.1, 123.0, 121.3,
120.9, 112.1 ppm; IR (KBr): 3050, 1657, 1582, 1495, 1447, 1405, 1184,
833, 804, 752 cm-1; HRMS (ESI): m/z calcd for C21H14NO [M + H]+
296.1075, found 296.1071.
2-(5-Acetylthiophen-2-yl)benzothiophene (3il) (entry 3 of table 3)[40]
:
Yield: 51% (0.065 g); Rf = 0.36 (ethyl acetate/hexane 1:19); 1H NMR (400
MHz, CDCl3): δ 7.82 – 7.76 (m, 2H), 7.63 (d, 1H), 7.56 (s, 1H), 7.40 – 7.33
(m, 2H), 7.29 (d, 1H), 2.57 (s, 3H) ppm.
2-(Thianthren-1-yl)pyrazine (3fj) (entry 4 of table 4): Obtained as a pale
yellow solid; Yield: 60% (0.088 g); mp: 93 – 95 °C; Rf = 0.15 (ethyl
acetate/hexane 1:19); 1H NMR (400 MHz, CDCl3): δ 8.89 (s, 1H), 8.76 (s,
1H), 8.63 (s, 1H), 7.62 (dd, J = 7.7, 1.3 Hz, 1H), 7.48 (dd, J = 7.6, 1.3 Hz,
2H), 7.39 – 7.35 (m, 2H), 7.28 – 7.17 (m, 2H) ppm; 13C NMR (100 MHz,
CDCl3): δ 153.7, 145.1, 143.7, 143.2, 137.7, 136.7, 136.6, 136.3, 135.7,
130.3, 129.1, 129.0, 128.7, 128.1, 127.8, 127.4 ppm; IR (KBr): 3048, 1553,
1472, 1445, 1405, 1376, 1143, 1012, 789, 747, 722 cm-1; HRMS (ESI):
m/z calcd for C16H11N2S2 [M + H]+ 295.0363, found 295.0383.
2-(5-Acetyl-2-thienyl)benzo[b]furan (3ik) (entry 4 of table 3)[41]: Yield:
48% (0.058 g); Rf = 0.38 (ethyl acetate/hexane 1:19); 1H NMR (400 MHz,
CDCl3): δ 7.65 (d, 1H), 7.58 (d, 1H), 7.51 (d, 1H), 7.46 (d, 1H), 7.35 – 7.31
(m, 1H), 7.27 – 7.25 (m, 1H), 7.04 (s, 1H), 2.58 (s, 3H) ppm.
1-(5-(1H-indol-5-yl)thiophen-2-yl)ethan-1-one (3ih) (entry 5 of table 3):
Obtained as a yellow solid; Yield: 64% (0.077 g); mp: 159 – 161 °C; Rf =
0.32 (ethyl acetate/hexane 1:4); 1H NMR (400 MHz, CDCl3): δ 8.36 (s, 1H),
7.96 (s, 1H), 7.67 (d, J = 4.0 Hz, 1H), 7.51 (dd, J = 8.5, 1.6 Hz, 1H), 7.42
(d, J = 8.5 Hz, 1H), 7.30 (d, J = 4.0 Hz, 1H), 7.26 (d, J = 3.7 Hz, 1H), 6.63
– 6.58 (m, 1H), 2.57 (s, 3H) ppm; 13C NMR (100 MHz, CDCl3): δ 190.8,
155.4, 141.9, 136.4, 133.9, 128.5, 125.7, 122.9, 121.1, 119.0, 111.8, 103.4,
26.6 ppm; IR (KBr): 3448, 3261, 2919, 1613, 1437, 1356, 1296, 1036, 792,
764 cm-1; HRMS (ESI): m/z calcd for C14H12NOS [M + H]+ 242.0639, found
242.0625.
2-(Thianthren-1-yl)quinolone (3gj) (entry 5 of table 4): Obtained as a
pale yellow solid; Yield: 62% (0.106 g); mp: 139 – 141 °C; Rf = 0.38 (ethyl
acetate/hexane 1:19); 1H NMR (400 MHz, CDCl3): δ 8.89 (s, 1H), 8.57 (d,
J = 5.9 Hz, 1H), 8.03 (d, J = 7.9 Hz, 1H), 7.98 – 7.84 (m, 2H), 7.76 (t, J =
7.5 Hz, 2H), 7.69 (d, J = 7.6 Hz, 1H), 7.51 (dd, J = 7.7, 1.0 Hz, 1H), 7.45
(t, J = 7.5 Hz, 1H), 7.32 (d, J = 7.4 Hz, 1H), 7.25 (d, J = 7.0 Hz, 2H), 7.19
(t, J = 7.1 Hz, 1H) ppm; 13C NMR (100 MHz, CDCl3): δ 157.9, 147.6, 141.4,
136.7, 136.6, 136.5, 136.5, 135.9, 130.0, 129.8, 129.6, 129.1, 128.9, 128.6,
127.8, 127.7, 127.6, 127.2, 127.1, 127.0, 121.8 ppm; IR (KBr): 3044, 1591,
1499, 1444, 1423, 1395, 1142, 835, 781, 753, 723 cm-1; HRMS (ESI): m/z
calcd for C21H14NS2 [M + H]+ 344.0567, found 344.0531.
1-(5-(Thianthren-1-yl)thiophen-2-yl)ethan-1-one (3ij) (entry 6 of table
3): Obtained as a yellow solid; Yield: 62% (0.105 g); mp: 163 – 165 °C; Rf
= 0.23 (ethyl acetate/hexane 1:19); 1H NMR (400 MHz, CDCl3): δ 7.73 (d,
J = 3.9 Hz, 1H), 7.54 (dd, J = 7.7, 1.3 Hz, 1H), 7.51 – 7.48 (m, 1H), 7.45 –
7.42 (m, 1H), 7.39 (dd, J = 7.7, 1.4 Hz, 1H), 7.30 – 7.21 (m, 4H), 2.61 (s,
3H) ppm; 13C NMR (100 MHz, CDCl3): δ 191.0, 149.4, 144.8, 136.7, 136.2,
135.8, 135.4, 134.0, 132.5, 129.8, 129.7, 129.4, 129.1, 128.7, 128.2, 127.9,
127.4, 26.9 ppm; IR (KBr): 3075, 3049, 1650, 1466, 1426, 1387, 1276,
1030, 921, 794, 750 cm-1; HRMS (ESI): m/z calcd for C18H13OS3 [M + H]+
341.0128, found 341.0153.
5-Nitro-2-(thianthren-1-yl)pyridine (3ej) (entry 6 of table 4): Obtained as
a yellow solid; Yield: 65% (0.109 g); mp: 109 – 111 °C; Rf = 0.30 (ethyl
acetate/hexane 1:19); 1H NMR (400 MHz, CDCl3): δ 9.62 (s, 1H), 8.64 (d,
J = 7.0 Hz, 1H), 7.82 (d, J = 7.9 Hz, 1H), 7.66 (d, J = 7.6 Hz, 1H), 7.50 (d,
J = 7.7 Hz, 2H), 7.41 – 7.31 (m, 2H), 7.30 – 7.17 (m, 3H) ppm; 13C NMR
(100 MHz, CDCl3): δ 163.2, 144.6, 143.1, 139.1, 136.7, 136.5, 135.5,
131.6, 130.7, 130.0, 129.1, 128.9, 128.8, 128.2, 127.8, 127.3, 124.3 ppm;
IR (KBr): 3055, 1593, 1571, 1512, 1442, 1346, 1249, 856, 762, 745 cm-1;
HRMS (ESI): m/z calcd for C17H11N2O2S2 [M + H]+ 339.0262, found
339.0252.
2-(Dibenzo[b,d]furan-4-yl)-5-methylpyridine (3dg) (entry 1 of table 4):
Obtained as a white solid; Yield: 65% (0.084 g); mp: 93 – 95 °C; Rf = 0.41
(ethyl acetate/hexane 1:19); 1H NMR (400 MHz, CDCl3): δ 8.62 (s, 1H),
8.30 (d, J = 8.1 Hz, 1H), 8.24 (dd, J = 7.7, 0.9 Hz, 1H), 7.99 (d, J = 7.6 Hz,
2H), 7.71 – 7.62 (m, 2H), 7.48 (t, J = 7.7 Hz, 2H), 7.38 (t, J = 7.5 Hz, 1H),
2.43 (s, 3H) ppm; 13C NMR (100 MHz, CDCl3): δ 156.2, 153.7, 151.2, 150.4,
137.3, 132.2, 127.3, 127.8, 125.2, 124.5, 124.2, 123.9, 123.4, 123.0, 121.0,
120.8, 111.9, 18.5 ppm; IR (KBr): 2992, 2919, 1586, 1563, 1484, 1447,
1410, 1186, 837, 751 cm-1; HRMS (ESI): m/z calcd for C18H14NO [M + H]+
260.1075, found 260.1063.
2-(Dibenzo[b,d]thiophen-4-yl)quinolone (3gi) (entry 7 of table 4):
Obtained as a white solid; Yield: 75% (0.116 g); mp: 129 – 131 °C; Rf =
0.58 (ethyl acetate/hexane 1:19); 1H NMR (400 MHz, CDCl3): δ 8.43 (d, J
= 7.7 Hz, 1H), 8.33 – 8.27 (m, 2H), 8.25 – 8.22 (m, 1H), 8.19 (dd, J = 7.6,
0.9 Hz, 1H), 8.12 (d, J = 8.7 Hz, 1H), 8.00 – 7.97 (m, 1H), 7.89 – 7.85 (m,
1H), 7.81 (m, 1H), 7.65 (t, J = 7.7 Hz, 1H), 7.59 (m, 1H), 7.50 (m, 2H) ppm;
13C NMR (100 MHz, CDCl3): δ 155.8, 147.6, 142.8, 138.5, 137.6, 136.9,
134.8, 133.3, 130.0, 129.3, 127.6, 127.1, 126.9, 126.8, 125.7, 124.7, 124.2,
122.7, 122.6, 121.5, 118.7 ppm; IR (KBr): 3046, 1592, 1499, 1444, 1395,
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