HUANG ET AL.
889
1
Yellow solid (total 30 mg, 51%); m.p 46.7–47.2ꢁC. H
NMR (400 MHz, CDCl3) δ 8.29–8.14 (m, 1H), 7.99–7.86
(m, 3H), 7.60 (dd, J = 7.1, 1.2 Hz, 1H), 7.57–7.46 (m, 3H),
7.23 (d, J = 3.9 Hz, 1H), 4.73 (q, J = 7.1 Hz, 2H), 1.52 (t,
J = 7.1 Hz, 3H). 13C NMR (101 MHz, CDCl3) δ 202.5,
150.6, 144.8, 133.9, 131.7, 131.5, 131.3, 129.4, 128.5, 128.1,
126.9, 126.3, 125.3, 125.2, 68.0, 13.9. IR (film) ν 3048,
2979, 2932, 1622, 1591, 1523, 1507, 1463, 1442, 1389,
1350, 1323, 1301, 1281, 1242, 1212, 1198, 1142, 1105,
1055, 955, 796, 773, 646 cm−1. HRMS (APCI) m/z calcd
for C17H15OS2 [M + H]+: 299.0559, found 299.0557.
4.12 | O-methyl 5-phenylthiophene-
2-carbothioate(2ab)
1
Yellow solid (total 39 mg, 85%); m.p 82.4–83.0ꢁC. H
NMR (400 MHz, CDCl3) δ 7.82 (d, J = 4.0 Hz, 1H),
7.70–7.61 (m, 2H), 7.39 (dt, J = 12.1, 6.9 Hz, 3H), 7.28 (d,
J = 4.0 Hz, 1H), 4.24 (s, 3H). 13C NMR (101 MHz, CDCl3)
δ 203.0, 152.7, 143.3, 133.4, 132.7, 129.1, 129.0, 126.1,
124.1, 58.6. IR (film) ν 3093, 3056, 3019, 2987, 2923, 2852,
1623, 1528, 1490, 1436, 1354, 1284, 1251, 1216, 1205,
4.10 | O-ethyl 5-(furan-2-yl)thiophene-
2-carbothioate(2la)
1154, 1069, 1050, 958, 913, 818, 764, 691, 646 cm−1
.
HRMS (APCI) m/z calcd for C12H11OS2 [M + H]+:
235.0246, found 235.0246.
4.13 | O-benzyl 5-phenylthiophene-
2-carbothioate(2ae)
Reddish brown viscous oil (total 33 mg, 71%). 1H
NMR (400 MHz, CDCl3) δ 7.75 (d, J = 4.1 Hz, 1H), 7.46
(d, J = 1.8 Hz, 1H), 7.18 (d, J = 4.1 Hz, 1H), 6.67 (d,
J = 3.4 Hz, 1H), 6.48 (dd, J = 3.4, 1.8 Hz, 1H), 4.67 (q,
J = 7.1 Hz, 2H), 1.48 (t, J = 7.1 Hz, 3H). 13C NMR
(101 MHz, CDCl3) δ 202.0, 148.7, 143.0, 143.0, 141.3,
132.1, 123.0, 112.2, 107.8, 67.9, 13.9. IR (film) ν 3116,
2979, 2922, 1626, 2851, 1709, 1666, 1518, 1483, 1431,
1385, 1363, 1341, 1300, 1277, 1238, 1208, 1145, 1105,
Yellow acicular solid (total 38 mg, 61%); m.p
83.5–83.9ꢁC. 1H NMR (400 MHz, CDCl3) δ 7.85 (d,
J = 4.0 Hz, 1H), 7.71–7.62 (m, 2H), 7.55–7.32 (m, 8H), 7.28
(d, J = 4.0 Hz, 1H), 5.69 (s, 2H). 13C NMR (101 MHz,
CDCl3) δ 201.7, 153.0, 143.5, 135.3, 133.4, 132.8, 129.1,
129.0, 128.7, 128.5, 128.3, 126.1, 124.1, 73.3. IR (film) ν 3090,
3065, 3031, 2918, 1628, 1528, 1495, 1449, 1435, 1364, 1345,
1330, 1311, 1281, 1252, 1226, 1196, 1098, 1068, 1030, 1012,
894, 819, 756, 727, 684, 644 cm−1. HRMS (APCI) m/z calcd
for C18H15OS2 [M + H]+: 311.0559, found 311.0557.
1059, 1045, 1023, 949, 881, 807, 737, 647, 590 cm−1
.
HRMS (APCI) m/z calcd for C11H11O2S2 [M + H]+:
239.0195, found 239.0195.
4.11 | O-ethyl [2,20-bithiophene]-
5-carbothioate(2ma)
4.14 | O-ethyl 3-methyl-
5-phenylthiophene-2-carbothioate(3aa)
1
Brown solid (total 38 mg, 76%); m.p 49.8–50.0ꢁC. H
NMR (400 MHz, CDCl3) δ 7.73 (d, J = 4.1 Hz, 1H),
7.36–7.28 (m, 2H), 7.12 (d, J = 4.1 Hz, 1H), 7.04 (t,
J = 4.4 Hz, 1H), 4.68 (q, J = 7.1 Hz, 2H), 1.49 (t,
J = 7.1 Hz, 3H). 13C NMR (101 MHz, CDCl3) δ 201.9,
145.6, 143.1, 136.6, 132.1, 128.2, 126.3, 125.3, 124.3, 68.0,
13.9. IR (film) ν 3111, 3064, 2983, 2948, 2932, 1630, 1499,
1440, 1384, 1367, 1356, 1321, 1272, 1243, 1210, 1192,
1
Yellow solid (total 42 mg, 81%); m.p 56.4–56.8ꢁC. H
NMR (400 MHz, CDCl3) δ 7.67–7.61 (m, 2H), 7.44–7.29
(m, 3H), 7.13 (s, 1H), 4.67 (q, J = 7.1 Hz, 2H), 2.55 (s,
3H), 1.51 (t, J = 7.1 Hz, 3H). 13C NMR (101 MHz, CDCl3)
δ 203.18, 150.25, 143.50, 138.70, 133.30, 129.03, 128.88,
128.85, 125.96, 67.83, 18.39, 13.96. IR (film) ν 3035, 2980,
2929, 1623, 1595, 1535, 1493, 1466, 1423, 1373, 1277,
1110, 1056, 1041, 843, 807, 894, 694, 649, 611 cm−1
.
HRMS (APCI) m/z calcd for C11H11OS3 [M + H]+:
254.9967, found 254.9966.