R. GOPALAKRISHNAN ET AL.
(CDCI3): δ 8.31–7.38 (m, 9H), 4.65 (s, 2H), 2.06 (s, 3H); 13C NMR
(CDCl3): δ 130.60, 128.94, 128.34, 128.17, 126.19, 125.07, 123.99,
123.23, 37.54, 17.23; MS: m/z 238 (M+), 191; Anal. Calcd for
C16H14S: C, 80.63; H, 5.92; S, 13.45; Found: C, 80.58; H, 5.85; S, 13.39.
Compound 23a: White crystalline solid; mp: 132 °C; IR νmax (KBr):
3056, 2968, 2947, 2912, 1717, 1623, 1430, 1332, 1261, 754 cmÀ1
;
1H NMR (CDCI3): δ 7.37–6.98 (m, 8H), 5.59 (s, 1H), 4.71 (s, 2H), 3.76
(s, 3H), 3.75 (s, 3H), 3.59 (s, 3H); 13C NMR (CDCl3): δ 167.57, 164.07,
152.01, 145.65, 143.57, 142.79, 125.27, 125.19, 123.62, 122.16,
68.75, 59.35, 56.36, 52.33, 52.08, 50.61; MS: m/z 364 (M+); Anal.
Calcd for C22H20O5: C, 72.51; H, 5.53; Found: C, 72.35; H, 5.44.
Compound 8: Yellow puffy solid; mp: 166 °C; IR νmax (KBr): 3016,
2955, 2925, 2853, 1732, 1713, 1665, 1437, 1273, 768 cmÀ1; 1H NMR
(CDCI3): δ 8.87–7.52 (m, 8H), 4.05 (s, 3H), 3.98 (s, 3H); 13C NMR (CDCl3):
δ 182.08, 167.71, 164.69, 134.77, 133.87, 132.79, 132.16, 130.91,
130.06, 128.37, 128.22, 127.61, 127.53, 127.25, 127.22, 126.20,
124.70, 122.60, 122.08, 52.15, 52.04; MS: m/z 347 (M+ 1)+; Anal. Calcd
for C21H14O5: C, 72.83; H, 4.07; Found: C, 72.75; H, 3.98.
Compound 25a: White crystalline solid; mp: 163 °C; IR νmax (KBr
cm-1): 1715 (C=O stretch), 1231 (C-O stretch); 1H NMR (CDCl3): δ
7.41-7.03 (m, 8H), 5.62 (s, 1H), 5.44 (s, 2H), 3.76 (s, 3H), 3.75 (s,
3H), 2.13 (s, 3H); 13C NMR (CDCl3): δ 170.62, 166.89, 163.91,
150.95, 145.42, 143.82, 142.84, 125.60, 125.30, 123.91, 121.73,
60.92, 54.84, 52.46, 52.22, 50.71, 20.62; MS: m/z 392 (M+); Anal.
Calcd for C23H20O6: C, 70.40; H, 5.13. Found: C, 70.12; H, 4.95.
Compound 10a: White crystalline solid; mp: 172 °C; IR νmax (KBr):
3066, 2968, 2947, 2912, 1728, 1715, 1628, 1433, 1328, 1264,
1
754 cmÀ1; H NMR (CDCI3): δ 7.52–6.99 (m, 8H), 5.56 (s, 1H), 3.95
(s, 2H), 3.76 (s, 3H), 3.75 (s, 3H), 2.35 (s, 3H); 13C NMR (CDCl3): δ
167.36, 164.17, 152.06, 145.76, 143.83, 143.05, 125.19, 125.13,
123.54, 122.37, 72.71, 64.21, 56.05, 52.30, 51.46, 50.73, 21.93; MS:
m/z 380 (M+); Anal. Calcd for C22H20O4S: C, 69.45; H, 5.30; S, 8.43;
Found: C, 69.36; H, 5.25; S, 8.38.
Compound 26: Yellow solid, Yield: 59%; mp: 62-64 °C; IR νmax
(KBr): 3053, 2957, 2858, 1620, 1597, 1384, 722 cm-1; 1H NMR
(CDCl3): δ 8.31-7.37 (m, 9H), 4.68 (s, 2H), 3.19- 3.09 (m, 1H),
1.38-1.36 (d, 6H, J= 6.8 Hz); 13C NMR (CDCl3): δ 130.6, 128.9,
128.3, 128.2, 126.2, 125.1, 124.0, 123.2, 35.7, 26.9, 22.6; MS: m/z
266 (M+), 191; Anal. Calcd for C18H18S: C, 81.15; H, 6.81; S,
12.04; Found: C, 81.07; H, 6.76; S, 11.99.
Compound 10b: Off-white crystalline solid; mp: 178 °C; IR νmax (KBr):
3061, 3029, 2983, 2911, 2853, 1660, 1645, 1598, 1448, 1385, 1276,
1069, 690 cmÀ1; 1H NMR (CDCI3): δ 7.55–7.02 (m, 18H), 5.47 (s, 1H),
4.02 (s, 2H), 1.95 (s, 3H); 13C NMR (CDCl3): δ 194.50, 193.69, 151.88,
145.86, 138.28, 137.23, 132.89, 132.35, 128.95, 128.12, 127.81,
125.44, 125.21, 123.61, 53.44, 33.22, 18.09; MS: m/z 473 (M+ 1)+,
105; Anal. Calcd for C32H24O2S: C, 81.33; H, 5.12; S, 6.78; Found: C,
81.23; H, 5.06; S, 6.71.
Compound 27: Yellow solid, Yield: 74%; mp: 66-68 °C; IR νmax
(KBr): 3084, 2952, 2857, 1619, 1598, 1399, 723 cm-1; 1H NMR
(CDCl3): δ 8.30-7.36 (m, 9H), 4.68 (s, 2H), 3.29-3.22 (m, 1H), 2.05-
1.98 (m, 2H), 1.73-1.69 (m, 2H), 1.63-1.51 (m, 4H); 13C NMR
(CDCl3): δ 130.6, 128.9, 128.6, 128.1, 126.1, 125.0, 123.9, 123.2,
44.1, 33.2, 33.0, 28.1, 24.0, 23.8; MS: m/z 292 (M+), 191; Anal.
Calcd for C20H20S: C, 82.14; H, 6.89; S, 10.96; Found: C, 82.08; H,
6.81; S, 10.89.
Compound 11[66]: White crystalline solid; mp: 284 °C; IR νmax (KBr):
1
3057, 2922, 1667, 1595, 1449, 1229, 729 cmÀ1; H NMR (CDCI3): δ
7.44–7.16 (m, 30H); 13C NMR (CDCl3): δ 195.06, 141.26, 136.51,
133.80, 129.83, 128.16; MS: m/z 702 (M+); Anal. Calcd for C48H30O6:
C, 82.04; H, 4.30; Found: C, 81.91; H, 4.19.
Compound 28: Yellow solid, Yield: 61%; mp: 74-76 °C; IR νmax
1
(KBr): 3061, 2911, 1599, 1384, 735, 697 cm-1; H NMR (CDCl3): δ
8.36-7.32 (m, 14H), 4.60 (s, 2H), 3.89 (s, 2H); 13C NMR (CDCl3): δ
136.4, 130.5, 129.1, 128.5, 128.1, 127.5, 127.1, 126.8, 126.5,
125.1, 124.1, 123.4, 42.8, 35.9; MS: m/z 314 (M+), 191, 91; Anal.
Calcd for C22H18S: C, 84.03; H, 5.77; S, 10.20; Found: C, 83.92; H,
5.73; S, 10.12.
Compound 12: Yellow solid; mp: 232°C; IR νmax (KBr): 3056, 2926,
1682, 1663, 1599, 1447, 1245, 694 cmÀ1; 1H NMR (CDCI3): δ 7.83 (s,
2H), 7.77–7.39 (m, 20H); 13C NMR (CDCl3): δ 195.05, 141.51, 136.28,
133.72, 130.20, 129.93, 128.64; MS: m/z 494 (M+); Anal. Calcd for
C34H22O4: C, 82.58; H, 4.48; Found: C, 82.45; H, 4.39.
Compound 29: Yellow solid, Yield: 52%; mp: 94-96 °C; IR νmax
(KBr): 3080, 3046, 2931, 2860, 1598, 1380, 779, 716 cm-1; 1H
NMR: (CDCl3): δ 8.35-7.32 (m, 16H), 4.65 (s, 2H), 4.33 (s, 2H); 13C
NMR (CDCl3): δ 134.2, 133.5, 131.6, 131.5, 130.1, 129.1, 128.8,
128.3, 127.4, 127.3, 126.1, 126.0, 125.9, 125.1, 125.0, 124.1, 35.3,
29.0; MS: m/z 364 (M+), 191, 141; Anal. Calcd for C26H20S: C,
85.67; H, 5.53; S, 8.80; Found: C, 85.58; H, 5.46; S, 8.76.
Compound 13: Off-white crystalline solid; mp: 116 °C; IR νmax (KBr):
2956, 1753, 1727, 1253 cmÀ1; 1H NMR (CDCI3): δ 8.65 (s, 2H), 3.96 &
3.94 (two singlets, 30H), 3.89 (s, 6H); MS: m/z 854 (M+); Anal. Calcd
for C36H38O24: C, 50.59; H, 4.48; Found: C, 50.38; H, 4.36.
Compound 21a: Yellow waxy material; IR νmax (KBr): 3005, 2952,
2926, 2854, 1737, 1715, 1591, 1437, 1259, 1202, 1167 cmÀ1
;
1H
C
Compound 30a: White crystalline solid; mp: 130°C; IR νmax (KBr):
3024, 2998, 2957, 2915, 2858, 1712, 1697, 1592, 1380, 1328,
1297, 618 cm-1; 1H NMR (CDCI3): δ 7.54-6.98 (m, 8H), 5.55 (s,
1H), 3.96 (s, 2H), 3.75 (s, 3H), 3.74 (s, 3H), 3.15-3.05 (m, 1H),
1.43-1.41 (d, 6H, J=6.4 Hz); 13C NMR (CDCl3): δ 167.43, 164.32,
145.67, 144.60, 143.99, 125.38, 125.05, 123.61, 122.49, 56.89,
52.34, 51.97, 51.05, 38.39, 29.99, 23.46; MS: m/z 408 (M+); Anal.
Calcd for C24H24O4S: C, 70.56; H, 5.92; S, 7.85; Found: C, 70.43;
H, 5.47; S, 7.74.
NMR (CDCI3): δ 6.28 (s, 1H), 3.86 (s, 3H), 3.76 (s, 3H), 2.34 (s, 3H); 13
NMR (CDCl3): δ 164.93, 163.05, 150.39, 110.83, 52.12, 50.80, 13.62;
MS: m/z 190 (M+); Anal. Calcd for C7H10O4S: C, 44.20; H, 5.30; S,
16.86; Found: C, 44.13; H, 5.22; S, 16.78.
Compound 21b: Off-white crystalline solid; mp: 60°C; IR νmax (KBr):
3066, 2998, 2941, 2915, 1671, 1634, 1598, 1540, 1359, 1219, 1038,
1
783, 695 cmÀ1; H NMR (CDCI3): δ 8.01–7.41 (m, 10H), 7.04 (s, 1H),
2.45 (s, 3H); 13C NMR (CDCl3): δ 193.72, 185.14, 160.79, 137.26,
134.88, 133.60, 132.98, 128.74, 128.63, 128.47, 115.88, 14.93; MS: m/z
282 (M+); Anal. Calcd for C17H14O2S: C, 72.31; H, 5.00; S, 11.36;
Found: C, 72.25; H, 4.91; S, 11.27.
Compound 30b: Off-White crystalline solid; mp: 150°C; IR νmax
(KBr): 3061, 3035, 2952, 2911, 2863, 1660, 1600, 1592, 1453,
1
1396, 1318, 1256, 1240, 705, 612 cm-1; H NMR (CDCI3): δ 7.48-
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Copyright © 2015 John Wiley & Sons, Ltd.
J. Phys. Org. Chem. 2015, 28 472–479