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Organic & Biomolecular Chemistry
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cm-1; HRMS (ESI) Calcd. for C12 H12NO2S [M+H]+ 234.0589, found (dd, J = 7.7, 1.6 Hz, 1H), 7.26 – 7.20 (m, 1H), 7.07 (d, J = 16.0 Hz, 1H),
234.0587.
6.94 (t, J = 7.2 Hz, 1H), 6.87 (d, J = 8.3 Hz, 1H), 6.23 (dd, J = 16.0, 6.9
DOI: 10.1039/C9OB00054B
Hz, 1H), 6.10-6.04 (m, 1H), 5.42 (dd, J = 17.3, 1.6 Hz, 1H), 5.30 (dd, J
= 10.5, 1.4 Hz, 1H), 4.65 – 4.61 (m, 1H), 4.58 (d, J = 5.2 Hz, 2H), 3.24
(dd, J = 13.2, 4.3 Hz, 1H), 3.12 (dd, J = 13.2, 7.8 Hz, 1H), 2.17 (br.s,
1H); 13C NMR (100 MHz, CDCl3): δ 155.96, 133.11, 129.41, 128.43,
128.25, 127.27, 124.87, 120.91, 117.68, 112.50, 112.35, 77.00, 71.74,
69.16, 40.48; IR (neat) 3433,2873, 2156, 1686, 1593, 1493, 1239,
1008,933, 761 cm-1; HRMS (ESI) Calcd. for C14 H16NO2S
[M+H]+,262.0902. found262.0895
(E)-4-(3-Phenoxyphenyl)-1-thiocyanatobut-3-en-2-ol (5c): 8h;
yellow liquid; yield = 202mg (68%); 1H NMR (400 MHz, CDCl3): δ 7.35-
7.25 (m, 3H), 7.11 (dd, J = 10.6, 4.2 Hz, 2H), 7.01 (dd, J = 7.7, 6.6 Hz,
3H), 6.92 (dd, J = 8.1, 1.6 Hz, 1H), 6.67 (d, J = 15.9 Hz, 1H), 6.14 (dd, J
= 15.9, 6.5 Hz, 1H), 4.60 (d, J = 4.6 Hz, 1H), 3.18 (dd, J = 13.3, 4.3 Hz,
1H), 3.06 (dd, J = 13.3, 7.7 Hz, 1H), 2.60 (s, 1H); 13C NMR (125 MHz,
CDCl3): δ 157.6, 156.8, 137.5, 132.5, 130.0, 129.8, 128.4, 123.4,
121.7, 118.9, 118.7, 116.7, 112.4, 71.0, 40.3; IR (neat) 3438, 2924,
2157, 1581, 1484, 1221, 967, 761, 691 cm-1; HRMS (ESI) Calcd. for C17 (E)-2-Methyl-4-phenyl-1-thiocyanatobut-3-en-2-ol (5h): 6h; yellow
H16NO2S [M+H]+ 298.0902, found 298.0896.
liquid; yield = 206mg (94%); 1H NMR (500 MHz, CDCl3): δ 7.40 (d, J =
7.2 Hz, 2H), 7.34 (t, J = 7.5 Hz, 2H), 7.29 – 7.25 (m, 1H), 6.73 (d, J =
16.0 Hz, 1H), 6.23 (d, J = 16.0 Hz, 1H), 3.24 (dd, J = 35.0, 13.2 Hz, 2H),
2.14 (d, J = 26.9 Hz, 1H), 1.57 (s, 3H); 13C NMR (100 MHz, CDCl3): δ
135.8, 132.1, 130.3, 128.7, 128.2, 126.7, 113.2, 72.7, 46.4, 27.2; IR
(neat) 3463, 2930, 2158, 1679, 1452, 1378, 1231, 975, 756, 699 cm-
1; HRMS (ESI) Calcd. for C12 H14NOS [M+H]+ 220.0796, found
220.0788.
(E)-4-(3-Phenoxyphenyl)-1-thiocyanatobut-3-en-2-one (6c): 8h;
yellow liquid; yield = 47mg (16%); 1H NMR (400 MHz, CDCl3): δ 7.61
(d, J = 16.1 Hz, 1H), 7.42 – 7.35 (m, 4H), 7.18 (d, J = 6.4 Hz, 2H), 7.04
(d, J = 8.7 Hz, 3H), 6.76 (d, J = 16.1 Hz, 1H), 4.29 (s, 2H); 13C NMR (100
MHz, CDCl3): δ 190.0, 158.2, 156.3, 145.7, 135.2, 130.5, 130.0, 124.0,
123.6, 123.0, 121.7, 119.3, 119.0, 117.9, 43.1; IR (neat) 2924, 2159,
1678,1584, 1487, 1240, 1166, 980,778,693 cm-1; HRMS (ESI) Calcd.
for C17 H17N2O2S [M+NH4]+ 295.0667, found 313.1003.
(E)-tert-Butyl 3-(3-hydroxy-4-thiocyanatobut-1-en-1-yl)-1H-indole-
1-carboxylate (5i): 8h; yellow liquid; yield = 179mg (52%); 1H NMR
(500 MHz, CDCl3) δ 8.17 (d, J = 8.0 Hz, 1H), 7.75 (d, J = 7.8 Hz, 1H),
7.65 (s, 1H), 7.35 (t, J = 7.2 Hz, 1H), 7.29 (t, J = 7.5 Hz, 1H), 6.84 (d, J
= 16.0 Hz, 1H), 6.27 (dd, J = 16.0, 6.7 Hz, 1H), 4.65 (d, J = 4.6 Hz, 1H),
3.26 (d, J = 17.6 Hz, 1H), 3.19 – 3.10 (m, 1H), 1.67 (s, 9H); IR (neat)
3487, 3384, 2973, 2929, 1738, 1465, 1373, 1255, 1159, 765 cm-1. (ESI-
MS) Calcd. for C18 H21N2O3S [M+H]+ 345.
(E)-4-(2-Bromophenyl)-1-thiocyanatobut-3-en-2-ol (5d): 6h; yellow
liquid; yield = 212mg (75%); H NMR (400 MHz, CDCl3): δ 7.57-7.50
1
(m,2H), 7.31 – 7.26 (m, 1H), 7.16-7.06 (m, 2H), 6.15 (dd, J = 15.8, 6.4
Hz, 1H), 4.71-4.67 (m, 1H), 3.25 (dd, J = 13.3, 4.4 Hz, 1H), 3.13 (dd, J
= 13.3, 7.5 Hz, 1H), 2.75 (s, 1H); 13C NMR (100 MHz, CDCl3): δ 135.8,
133.1, 132.0, 130.8, 129.7, 127.7, 127.3, 123.9, 112.63, 8.12, 71.0,
40.4; IR (neat) 3442, 3063, 2159, 1602, 1431, 1289, 1031, 971, 758
cm-1; HRMS (ESI) Calcd. for C11 H11BrNOS [M+H]+ 283.9745, found (3E, 5E)-6-Phenyl-1-thiocyanatohexa-3,5-dien-2-ol (5k): 6h; yellow
283.9738.
liquid; yield = 162mg (70%); 1H NMR (400 MHz, CDCl3): δ 7.41 (d, J =
7.2 Hz, 2H), 7.33 (t, J = 7.4 Hz, 2H), 7.29 – 7.22 (m, 2H), 6.76 (dd, J =
15.5, 10.5 Hz, 1H), 6.63 (d, J = 15.6 Hz, 1H), 6.54 (dd, J = 15.5, 10.0
Hz, 1H), 5.79 (dd, J = 15.2, 6.7 Hz, 1H), 4.59-4.55 (m, 1H), 3.19 (dd, J
= 13.2, 4.3 Hz, 1H), 3.06 (dd, J = 13.2, 7.8 Hz, 1H); 13C NMR (125 MHz,
CDCl3): δ 136.6, 134.8, 133.6, 131.1, 128.7, 128.1, 127.1, 126.6,
112.4, 71.0, 40.3; ); IR (neat) 3433, 3030, 2340, 2158, 1665,1406,
1083,993, 771cm-1; (ESI-MS) Calcd. for C13 H14NOS [M+H]+ 232.
(E)-4-(2-Bromophenyl)-1-thiocyanatobut-3-en-2-one (6d):
6h;
yellow liquid; yield = 42mg (15%); 1H NMR (500 MHz, CDCl3): δ 8.05
(d, J = 16.2 Hz, 1H), 7.67-7.63 (m, 2H), 7.37 (t, J = 7.6 Hz, 1H), 7.30 (t,
J = 7.7 Hz, 1H), 6.76 (d, J = 16.2 Hz, 1H), 4.38 (s, 2H); 13C NMR (100
MHz, CDCl3): δ 190.0, 144.6, 133.7, 133.4, 132.4, 128.0, 127.9, 126.2,
125.3, 111.5, 42.9; IR (neat) 2928, 2161, 1689, 1612, 1470, 1322,
1172, 1084, 980, 760, 667cm-1; HRMS (ESI) Calcd. for C11 H9BrNOS
[M+H]+ 281.9588, found 281.9584.
4-Phenylthiazol-2-ol (7a): Solid; yield = 127 mg (72%); 1H NMR (400
MHz, CDCl3): δ 10.94 (s, 1H), 7.56 (d, J = 7.5 Hz, 2H), 7.44 (t, J = 7.4
Hz, 3H), 7.38 (d, J = 7.2 Hz, 1H), 6.32 (s, 1H); 13C NMR (125 MHz,
CDCl3): δ 175.6, 134.4, 129.6, 129.2, 129.0, 124.8, 98.0; IR (neat)
3157, 3034, 1651, 1447, 1281, 1168, 904, 767, 696, 642 cm-1; HRMS
(ESI) Calcd. for C9 H8NOS [M+H]+ 178.0327, found 178.0325.
(E)-4-(3-Hydroxy-4-thiocyanatobut-1-en-1-yl)benzonitrile (5e): 6h;
yellow liquid; yield = 196mg (85%); 1H NMR (400 MHz, CDCl3): δ 7.63
(d, J = 8.4 Hz, 2H), 7.49 (d, J = 8.3 Hz, 2H), 6.79 (d, J = 15.9 Hz, 1H),
6.35 (dd, J = 15.9, 6.0 Hz, 1H), 4.74-4.69 (m, 1H), 3.25 (dd, J = 13.4,
4.4 Hz, 1H), 3.12 (dd, J = 13.4, 7.4 Hz, 1H); 13C NMR (125 MHz, CDCl3):
δ 140.2, 132.5, 131.6, 131.2, 127.2, 118.7, 112.2, 111.5, 70.7, 40.2; 4-(m-Tolyl)thiazol-2-ol (7b): Solid; yield = 130 mg (68%); H NMR
IR (neat) 3442, 230, 2158, 1685, 1452, 1179, 1093, 975,822, 727cm- (400 MHz, CDCl3): δ 10.57 (d, J = 45.0 Hz, 1H), 7.33 (d, J = 5.1 Hz, 3H),
1; HRMS (ESI) Calcd. for C12 H11N2OS [M+H]+ 231.0592, found 7.19 (t, J = 4.3 Hz, 1H), 6.28 (d, J = 1.7 Hz, 1H), 2.40 (s, 3H); 13C NMR
1
231.0584.
(125 MHz, CDCl3): δ 175.7, 138.9, 134.6, 129.8, 129.6, 129.1, 125.5,
122.0, 97.7; IR (neat) 3146, 3031, 1656, 1456, 1214, 1173, 784 cm-1;
HRMS (ESI) Calcd. for C10 H10NOS [M+H]+ 192.0483, found 192.0482.
(E)-4-(4-Nitrophenyl)-1-thiocyanatobut-3-en-2-ol (5f): 8h; yellow
liquid; yield = 220mg (88%); 1H NMR (500 MHz, CDCl3): δ 8.19 (d, J =
8.6 Hz, 2H), 7.53 (d, J = 8.5 Hz, 2H), 6.85 (d, J = 15.9 Hz, 1H), 6.40 (dd, 4-(p-Tolyl)thiazol-2-ol (7c): Solid; yield = 134 mg (70%); 1H NMR (500
J = 15.9, 5.9 Hz, 1H), 4.75-4.72 (m, , 1H), 3.27 (dd, J = 13.4, 4.3 Hz, MHz, CDCl3): δ 10.36 (s, 1H), 7.41 (d, J = 8.2 Hz, 2H), 7.24 (d, J = 7.9
1H), 3.14 (dd, J = 13.4, 7.4 Hz, 1H), 2.94 (s, 1H); 13C NMR (125 MHz, Hz, 2H), 6.24 (d, J = 1.8 Hz, 1H), 2.38 (s, 3H); 13C NMR (100MHz,
CDCl3): δ 147.3, 142.1, 132.4, 130.8, 127.3, 124.1, 112.2, 70.7, 40.2; CDCl3): δ 175.7, 139.1, 134.5, 129.9, 129.1, 126.9, 124.7, 97.0, 21.3;
IR (neat) 3399, 2927, 2157, 1673, 1517, 1344, 1106, 973, 868, 758, IR (neat) 3156, 2923, 1660,1452, 1286, 1183, 908, 826, 767 cm-1;
694 cm-1; HRMS (ESI) Calcd. for C11 H11N2O3S [M+H]+ 251.0490, found HRMS (ESI) Calcd. for C10 H10NOS [M+H]+ 192.0483, found 192.0481.
251.0483.
4-(4-(tert-Butyl)phenyl)thiazol-2-ol (7d): Solid; yield = 163 mg (70%);
(E)-4-(2-(Allyloxy)phenyl)-1-thiocyanatobut-3-en-2-ol (5g): 6h; 1H NMR (500 MHz, CDCl3): δ 11.15 (s, 1H), 7.50 (d, J = 8.0 Hz, 2H),
yellow liquid; yield = 209mg (80%); 1H NMR (500 MHz, CDCl3): δ 7.43 7.46 (d, J = 8.7 Hz, 2H), 6.26 (d, J = 1.8 Hz, 1H), 1.33 (s, 9H); 13C NMR
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