EASY AND GREEN SYNTHESIS
2885
chromatography on silica gel using methylene chloride–
ethanol (95/5) as eluent.
6-[2-(Furan-2-yl)ethenyl]-4-hydroxy-3-(phenyl-
sulfanyl)-2H-pyran-2-one (6d). Yield 65%, brown
solid, mp 210°C (from MeOH). IR spectrum, ν, cm–1:
3650–3200 (OH), 1620 (C=O), 1581, 1534, 1475,
1411, 1353, 1275, 1219, 1016, 964, 736, 689. 1Н NMR
spectrum (DMSO-d6), δ, ppm: 6.49 s (1H, 5-H), 6.67
d.d (1H, furyl), 6.82 d (1H, α-H), 6.93 d (1H, 3′-H),
7.14–7.19 m (3H, Harom), 7.28 d (1H, β-H), 7.27–7.38
m (2H, Harom), 7.85 (1H, furyl), 12.44 s (1H, OH). 13C
NMR spectrum (DMSO-d6), δC, ppm: 92.4 (C3),
101.24 (C5), 112.99 (C3′), 114.65 (C4′), 116.74 (Cα),
122.74 (Cβ), 125.22 (Cp), 125.95 (Cm), 129.09 (Co),
136.93 (Ci), 145.43 (C5′), 151.36 (C2′), 159.11 (C6),
162.1 (C2), 172.55 (C4). Mass spectrum, m/z (Irel, %):
314 (8.5), 313 (12.2), 312 (100) [M]+, 203 (4.9),
202 (4.9), 163 (39.0), 140 (6.1), 122 (4.9), 121 (72.0),
107 (12.2), 69 (9.8), 49 (8.5). C17H12O3S. Calculated:
M 312.34.
4-Hydroxy-6-methyl-3-(phenylsulfanyl)-2H-pyran-
2-one (6a). Yield 78%, white solid, mp 166°C. IR
spectrum, ν, cm–1: 3000–3400 (OH), 2634, 2570, 1724,
1652 (C=O), 1556, 1482, 1444, 1406, 1388, 1348,
1
1348, 1290, 1170, 1066, 946, 832, 762, 736, 688. Н
NMR spectrum (DMSO-d6), δ, ppm: 2.26 s (3H, CH3),
6.20 s (1H, 5-H), 7.07–7.15 m (3H, o-H, p-H), 7.27 t
(2H, m-H). 13C NMR spectrum (DMSO-d6), δC, ppm:
19.75 (CH3), 90.57 (C3), 100.15 (C5), 125.13 (C4),
125.79 (C2′), 128.84 (C3), 129.06 (C3′), 137.01 (C1′),
163.36 (C6), 164.45 (C2), 173.10 (C4). Mass spectrum,
m/z (Irel, %): 236 (6), 235 (11), 234 (100) [M]+, 229
(49), 177 (8), 149 (58), 133 (7), 121 (60), 120 (77),
113 (16), 108 (48), 107 (8), 105 (6). C12H10O3S.
Calculated: M 234.27.
6-[2-(3,4-Dihydroxyphenyl)ethenyl]-4-hydroxy-
3-(phenylsulfanyl)-2H-pyran-2-one (6b). Yield 62%,
black solid, mp 259°C. IR spectrum, ν, cm–1: 3600–
3350 (OH), 1762, 1626 (C=O), 1502, 1444, 1406,
1300, 1210, 1176, 1137, 1044, 1018, 976, 738, 690. 1Н
NMR spectrum (DMSO-d6), δ, ppm: 6.41 (1H, 5-H),
6.82 d (1H, α-H), 7.19 d (2H, o-H), 7.22–7.32 m (3H,
m-H, p-H), 7.59 d (1H, 5′-H), 7.67 s (1H, 2′-H), 7.86 d
(1H, 6′-H), 8.02 d (1H, β-H), 10.42 s (OH)). Mass
spectrum, m/z (Irel, %): 354 (0.31) [M]+, 281 (0.86),
231 (0.31), 218 (9.11), 207 (8.9), 168 (8.5), 185 (9.5),
154 (9.6), 110 (62.3), 109 (24.3), 84 (17.5), 78 (74.1),
66 (28.5), 64 (44.9), 51 (27.7), 44 (100). C19H14O5S.
Calculated: M 354.38.
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4-Hydroxy-6-(2-phenylethenyl)-3-(phenylsulfanyl)-
2H-pyran-2-one (6c). Yield 68%, brown solid, mp
238°C. IR spectrum, ν, cm–1: 3600–3350 (OH), 1634
(C=O), 1604, 1548, 1416, 1364, 1208, 1174, 970, 732,
689. 1Н NMR spectrum (DMSO-d6), δ, ppm: 6.25 (1H,
5-H), 6.64 d (1H, α-H), 7.07–7.26 m (5H, Harom), 7.26–
7.45 m (2H, Harom), 7.41 d (1H, β-H), 7.46–7.60 m
(3H, Harom). 13C NMR spectrum (DMSO-d6), δC, ppm:
13C NMR spectrum (DMSO-d6), δC, ppm: 92.51 (C3),
102.39 (C5), 118.60 (Cα), 124.89 (C4"), 126.12
(C2′,C6′), 127.11 (C3′,C5′), 128.41 (C3'', C5''), 128.53
(C4′), 129.11 (C2″, C6″) 134.83 (C1″), 135.68 (Cβ),
136.50 (C1′), 158.71 (C2), 160.42 (C6), 163.63 (C4).
Mass spectrum, m/z (Irel, %): 324, 322 (100) [M]+, 213
(8.0), 174 (5.7), 173 (21.4), 150 (3.6), 131 (6.6), 121
(11.0), 109 (4.5), 103 (6.0), 69 (5.4), 51 (40.0), 43
(9.5). C19H14O3S. Calculated: M 322.38.
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RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 86 No. 12 2016