2-(2,5,9-Trimethyl-3-phenyl-7-oxo-7H-furo[3,2-g]chromen-6-yl)acetic Αcid (32). Yield 85%, C H O , mp234-
22 18
5
-1
235°C. IR spectrum (KBr, cm ): 3312, 1723, 1708, 1596, 1399, 1361, 1332, 1306, 1176, 1130, 754. UV spectrum (EtOH,
, nm, log ε): 202 (4.61), 217 (4.56), 256 (4.59), 302 (4.32). PMR spectrum (300 MHz, DMSO-d , δ, ppm): 2.44 (3H, s,
λ
max
6
Me-9′), 2.55 (3H, s, Me-2′), 2.57 (3H, s, Me-5′), 3.60 (2H, s, CH -2), 7.41 (1H, m, H-4″), 7.55 (4H, m, H-2″, H-3″, H-5″, H-6″),
2
7.66 (1H, s, H-4′), 12.24 (1H, br.s, COOH).
2-(5-Methyl-3-phenyl-7-oxo-7H-furo[3,2-g]chromen-6-yl)acetic Acid(33). Yield 92%, C H O , mp209-211°C.
20 14
5
-1
IR spectrum (KBr, cm ): 2923, 1710, 1696, 1631, 1580, 1396, 1335, 1226, 1161, 1114, 1091, 882, 844, 764. UV spectrum
(CH CN, λ , nm, log ε): 226 (4.44), 251 (4.47), 298 (4.25), 335 (3.89). PMR spectrum (400 MHz, DMSO-d , δ, ppm): 2.55
3
max
6
(3H, s, Me-5′), 3.66 (2H, s, CH -2), 7.44 (1H, m, H-4″), 7.56 (2H, t, J = 8.0, H-2″, H-6″), 8.21 (1H, s, H-4′), 8.50 (1H, s, H-2′),
2
12.32 (1H, br.s, COOH).
2-(5,9-Dimethyl-3-phenyl-7-oxo-7H-furo[3,2-g]chromen-6-yl)acetic Acid (34). Yield 93%, C H O , mp 270-
21 16
5
-1
271°C. IR spectrum (KBr, cm ): 1737, 1706, 1677, 1591, 1390, 1358, 1304, 1178, 1164, 1134, 865, 796. UV spectrum
(dioxane, λ , nm, log ε): 216 (4.33), 253 (4.39), 300 (4.19), 336 (3.76). PMR spectrum (300 MHz, DMSO-d , δ, ppm): 2.48
max
6
(3H, s, Me-5′), 2.56 (3H, s, Me-9′), 3.62 (2H, s, CH -2), 7.40 (1H, m, H-4″), 7.52 (2H, m, H-3″, H-5″), 7.76 (2H, m, H-2″,
2
H-6″), 7.99 (1H, s, H-4′), 8.36 (1H, s, H-2′), 12.36 (1H, br.s, COOH).
2-[3-(4-Fluorophenyl)-5-methyl-7-oxo-7H-furo[3,2-g]chromen-6-yl)acetic Acid (35). Yield 89%, C H O ,
20 13
5
-1
mp 245-247°C. IR spectrum (KBr, cm ): 3106, 1744, 1704, 1668, 1628, 1575, 1508, 1398, 1348, 1327, 1229, 1165, 1122,
1092, 856, 827. UV spectrum (dioxane, λ , nm, log ε): 215 (4.47), 252 (4.50), 293 (4.25), 301 (4.23), 329 (4.00). PMR
max
spectrum (400 MHz, DMSO-d , δ, ppm): 2.54 (3H, s, Me-5′), 3.66 (2H, s, CH -2), 7.39 (2H, t, J = 8.8, H-3″, H-5″), 7.81 (1H,
6
2
s, H-9′), 7.87 (2H, m, H-2″, H-6″), 8.18 (1H, s, H-4′), 8.48 (1H, s, H-2′), 12.51 (1H, br.s, COOH).
2-[3-(4-Fluorophenyl)-5,9-dimethyl-7-oxo-7H-furo[3,2-g]chromen-6-yl)acetic Acid(36). Yield90%, C H FO ,
21 15
5
-1
mp 305-306°C. IR spectrum (KBr, cm ): 3105, 1715, 1675, 1571, 1508, 1398, 1348, 1327, 1291, 1165, 1130, 1095, 838, 812.
UV spectrum (EtOH, λ , nm, log ε): 207 (4.37), 229 (4.25), 252 (4.29), 305 (4.08). PMR spectrum (300 MHz, DMSO-d ,
max
6
δ, ppm): 2.49 (3H, s, Me-5′), 2.56 (3H, s, Me-9′), 3.61 (2H, s, CH -2), 7.28 (2H, m, H-3″, H-5″), 7.78 (2H, m, H-2″, H-6″), 7.93
2
(1H, s, H-4′), 8.30 (1H, s, H-2′), 12.32 (1H, br.s, COOH).
2-[3-(4-Chlorophenyl)-5-methyl-7-oxo-7H-furo[3,2-g]chromen-6-yl)acetic Acid (37). Yield 85%, C H ClO ,
20 13
5
-1
mp 235-237°C. IR spectrum (KBr, cm ): 3140, 1756, 1706, 1665, 1627, 1578, 1493, 1396, 1367, 1347, 1296, 1189, 1166,
1124, 1097, 1075, 864, 805. UV spectrum (EtOH, λ , nm, log ε): 203 (4.79), 251 (4.73), 299 (4.51), 335 (4.15). PMR
max
spectrum (400 MHz, DMSO-d , δ, ppm, J/Hz): 2.51 (3H, s, Me-5′), 3.66 (2H, s, CH -2), 7.60 (2H, d, J = 8.0, H-3″, H-5″), 7.83
6
2
(1H, s, H-9′), 7.87 (2H, d, J = 8.0, H-2″, H-6″), 8.20 (1H, s, H-4′), 8.54 (1H, s, H-2′), 12.48 (1H, br.s, COOH).
2-[3-(4-Chlorophenyl)-5,9-dimethyl-7-oxo-7H-furo[3,2-g]chromen-6-yl)aceticAcid(38). Yield83%, C H ClO ,
21 15
5
-1
mp 292-293°C. IR spectrum (KBr, cm ): 1718, 1673, 1589, 1494, 1389, 1357, 1291, 1165, 1132, 1099, 864, 838, 812.
UV spectrum (dioxane, λ , nm, log ε): 212 (4.56), 251 (4.60), 296 (4.37), 308 (4.30), 338 (3.91). PMR spectrum (300 MHz,
max
DMSO-d , δ, ppm, J/Hz): 2.49 (3H, s, Me-5′), 2.56 (3H, s, Me-9′), 3.61 (2H, s, CH -2), 7.53 (2H, d, J = 8.4, H-3″, H-5″), 7.78
6
2
(2H, d, J = 8.4, H-2″, H-6″), 7.93 (1H, s, H-4′), 8.32 (1H, s, H-2′), 12.32 (1H, br.s, COOH).
2-[3-(4-Bromophenyl)-5-methyl-7-oxo-7H-furo[3,2-g]chromen-6-yl)acetic Acid (39). Yield 92%, C H BrO ,
20 13
5
-1
mp 240-242°C. IR spectrum (KBr, cm ): 3298, 1743, 1710, 1682, 1629, 1581, 1392, 1348, 1157, 1116, 1090, 1071, 1006,
814. UV spectrum (CH CN, λ , nm, log ε): 212 (4.55), 248 (4.56), 295 (4.31), 333 (3.92). PMR spectrum (400 MHz,
3
max
DMSO-d , δ, ppm, J/Hz): 2.54 (3H, s, Me-5′), 3.66 (2H, s, CH -2), 7.73 (2H, d, J = 8.0, H-3′″, H-5′″), 7.80 (2H, d, J = 8.0, H-2″,
6
2
H-6″), 7.82 (1H, s, H-9′), 8.19 (1H, s, H-4′), 8.54 (1H, s, H-2′), 12.51 (1H, br.s, COOH).
2-[3-(4-Bromophenyl)-5,9-dimethyl-7-oxo-7H-furo[3,2-g]chromen-6-yl)acetic Acid(40). Yield95%, C H BrO ,
21 15
5
-1
mp 298-299°C. IR spectrum (KBr, cm ): 3290, 1741, 1708, 1676, 1614, 1586, 1391, 1358, 1160, 1190, 1095, 1006, 836.
UV spectrum (EtOH, λ , nm, log ε): 206 (4.65), 219 (4.52), 252 (4.55), 303 (4.32), 315 (4.21). PMR spectrum (300 MHz,
max
DMSO-d , δ, ppm, J/Hz): 2.56 (3H, s, Me-5′), 2.62 (3H, s, Me-9′), 3.62 (2H, s, CH -2), 7.63 (2H, d, J = 8.1, H-3″, H-5″), 7.70
6
2
(2H, d, J = 8.1, H-2″, H-6″), 7.96 (1H, s, H-4′), 8.37 (1H, s, H-2′), 12.38 (1H, br.s, COOH).
2-[3-(4-Methoxyphenyl)-5-methyl-7-oxo-7H-furo[3,2-g]chromen-6-yl)acetic Acid (41). Yield 80%, C H O ,
21 16
6
-1
mp 224-226°C. IR spectrum (KBr, cm ): 2932, 1702, 1630, 1585, 1567, 1509, 1395, 1346, 1324, 1247, 1230, 1158, 1114,
1076, 1020, 833. UV spectrum (CH CN, λ , nm, log ε): 231 (4.55), 251 (4.58), 304 (4.35). PMR spectrum (400 MHz,
3
max
DMSO-d , δ, ppm, J/Hz): 2.54 (3H, s, Me-5′), 3.66 (2H, s, CH -2), 3.83 (3H, s, OMe-4″), 7.11 (2H, d, J = 8.0, H-3″, H-5″), 7.75
6
2
(2H, d, J = 8.0, H-2″, H-6″), 7.80 (1H, s, H-9′), 8.17 (1H, s, H-4′), 8.40 (1H, s, H-2′), 12.50 (1H, br.s, COOH).
259