spectrum (KBr, cm-1): 1721, 1650, 1607, 1576, 1503, 1418, 1303, 1274, 1162, 1119, 1101, 769. UV spectrum (CH CN, λmax
,
3
nm, log ε): 232 (4.57), 248 (4.64), 255 (4.63), 287 (4.06), 328 (4.00). PMR spectrum (400 MHz, DMSO-d , δ, ppm, J/Hz):
6
2.51 (3H, m, Me-7), 2.55 (3H, s, Me-9), 7.46 (1H, m, H-4′), 7.58 (2H, t, J = 8.0, H-3′, H-5′), 7.62 (3H, m, H-3, H-2′, H-6′), 7.88
(1H, t, J = 8.0, H-2), 8.19 (1H, s, H-11), 8.22 (1H, d, J = 8.0, H-1), 8.43 (1H, d, J = 8.0, H-4).
10-Phenyl-5H-benzo[c]furo[3,2-g]chromen-5-one (45). Yield 90%, mp 177-178°C, C21H12O3. IR spectrum (KBr,
cm-1): 1737, 1607, 1444, 1293, 1262, 1164, 1155, 1108, 1088, 1033, 763. UV spectrum (CH CN, λmax, nm, log ε): 231 (4.68),
3
244 (4.68), 286 (4.08), 326 (4.10). PMR spectrum (400 MHz, DMSO-d , δ, ppm, J/Hz): 7.47 (1H, t, J = 8.0, H-4′), 7.56 (2H,
6
t, J = 8.0, H-3′, H-5′), 7.68 (1H, t, J = 8.0, H-3), 7.81 (1H, s, H-7), 7.88 (2H, d, J = 7.2, H-2′, H-6′), 7.96 (1H, t, J = 8.0, H-2),
8.26 (1H, d, J = 8.0, H-1), 8.49 (1H, s, H-11), 8.67 (1H, d, J = 8.0, H-4), 8.76 (1H, s, H-9).
7-Methyl-10-phenyl-5H-benzo[c]furo[3,2-g]chromen-5-one (46). Yield 91%, mp 241-242°C, C22H14O3. IR
spectrum (KBr, cm-1): 1723, 1607, 1577, 1450, 1316, 1294, 1277, 1252, 1119, 1082, 767. UV spectrum (CH CN, λmax, nm,
3
log ε): 231 (4.66), 246 (4.71), 252 (4.67), 279 (4.21), 287 (4.16), 324 (4.10), 338 (4.00). PMR spectrum (400 MHz, DMSO-d ,
6
δ, ppm, J/Hz): 2.48 (3H, s, Me-7), 7.44 (1H, t, J = 8.0, H-4′), 7.55 (2H, t, J = 8.0, H-3′, H-5′), 7.61 (1H, t, J = 8.0, H-3), 7.83
(2H, d, J = 7.2, H-2′, H-6′), 7.88 (1H, t, J = 8.0, H-2), 8.18 (1H, d, J = 8.0, H-1), 8.43 (1H, s, H-11), 8.46 (1H, s, H-9), 8.51 (1H,
d, J = 8.0, H-4).
10-(4-Methylphenyl)-5H-benzo[c]furo[3,2-g]chromen-5-one (47). Yield 81%, mp 209-210°C, C22H14O3. IR
spectrum (KBr, cm-1): 1736, 1631, 1608, 1444, 1293, 1262, 1153, 1109, 1077, 1033, 865, 808, 764. UV spectrum (CH CN,
3
λ
max, nm, log ε): 231 (4.66), 244 (4.62), 324 (4.01). PMR spectrum (400 MHz, DMSO-d , δ, ppm, J/Hz): 2.40 (3H, s, Me-4′),
6
7.36 (2H, d, J = 8.0, H-3′, H-5′), 7.66 (1H, t, J = 8.0, H-3), 7.75 (2H, d, J = 8.0, H-2′, H-6′), 7.78 (1H, s, H-7), 7.95 (1H, t,
J = 8.0, H-2), 8.25 (1H, d, J = 8.0, H-1), 8.42 (1H, s, H-11), 8.63 (1H, d, J = 8.0, H-4), 8.71 (1H, s, H-9).
7-Methyl-10-(4-methylphenyl)-5H-benzo[c]furo[3,2-g]chromen-5-one (48). Yield84%, mp236-237°C, C23H16O3.
IR spectrum (KBr, cm-1): 1724, 1606, 1576, 1313, 1294, 1275, 1251, 1117, 1080, 1041, 770. UV spectrum (CH CN, λmax, nm,
3
log ε): 232 (4.68), 247 (4.70), 290 (4.12), 324 (4.06). PMR spectrum (400 MHz, DMSO-d , δ, ppm, J/Hz): 2.40 (3H, s, Me-4′),
6
2.50 (3H, s, Me-7), 7.35 (2H, d, J = 8.0, H-3′, H-5′), 7.61 (1H, t, J = 8.0, H-3), 7.71 (2H, d, J = 8.0, H-2′, H-6′), 7.89 (1H, t,
J = 8.0, H-2), 8.19 (1H, d, J = 8.0, H-1), 8.38 (1H, s, H-11), 8.46 (1H, s, H-9), 8.52 (1H, d, J = 8.0, H-4).
10-(4-Fluorophenyl)-5H-benzo[c]furo[3,2-g]chromen-5-one (49). Yield 92%, mp 248-249°C, C21H11FO3. IR
spectrum (KBr, cm-1): 1734, 1608, 1573, 1509, 1446, 1305, 1292, 1264, 1227, 1159, 1117, 1090, 764. UV spectrum (CH CN,
3
λ
max, nm, log ε): 232 (4.73), 244 (4.74), 277 (4.22), 326 (4.19), 340 (4.09). PMR spectrum (400 MHz, DMSO-d , δ, ppm,
6
J/Hz): 7.37 (2H, m, H-3′, H-5′), 7.65 (1H, t, J = 8.0, H-3), 7.75 (1H, s, H-7), 7.89 (2H, m, H-2′, H-6′), 7.94 (1H, t, J = 8.0, H-2),
8.23 (1H, d, J = 8.0, H-1), 8.44 (1H, s, H-11), 8.61 (1H, d, J = 8.0, H-4), 8.68 (1H, s, H-9).
7-Methyl-10-(4-fluorophenyl)-5H-benzo[c]furo[3,2-g]chromen-5-one (50). Yield87%, mp237-238°C, C22H13FO3.
IR spectrum (KBr, cm-1): 1735, 1608, 1574, 1508, 1305, 1292, 1276, 1253, 1219, 1124, 1112, 1041, 764. UV spectrum
(CH CN, λmax, nm, log ε): 232 (4.56), 246 (4.61), 278 (4.06), 326 (3.93). PMR spectrum (400 MHz, DMSO-d , δ, ppm, J/Hz):
3
6
2.45 (3H, s, Me-7), 7.35 (2H, m, H-3′, H-5′), 7.58 (1H, t, J = 8.0, H-3), 7.71 (2H, d, J = 8.0, H-2′, H-6′), 7.89 (3H, m, H-2, H-2′,
H-6′), 8.14 (1H, d, J = 8.0, H-1), 8.38 (1H, s, H-11), 8.39 (1H, s, H-9), 8.47 (1H, d, J = 8.0, H-4).
10-(4-Chlorophenyl)-5H-benzo[c]furo[3,2-g]chromen-5-one (51). Yield 86%, mp 303-304°C, C21H11ClO3). IR
spectrum (KBr, cm-1): 1735, 1632, 1608, 1445, 1303, 1291, 1267, 1156, 1109, 1094, 867, 815, 764. UV spectrum (dioxane,
λ
max, nm, log ε): 215 (4.42), 233 (4.58), 245 (4.63), 251 (4.60), 289 (4.08), 326 (4.04). PMR spectrum (400 MHz, DMSO-d ,
6
δ, ppm, J/Hz): 7.59 (2H, d, J = 8.4, H-3′, H-5′), 7.67 (1H, t, J = 8.0, H-3), 7.78 (1H, s, H-7), 7.90 (2H, d, J = 8.4, H-2′, H-6′),
7.96 (1H, t, J = 8.0, H-2), 8.25 (1H, d, J = 8.0, H-1), 8.49 (1H, s, H-11), 8.64 (1H, d, J = 8.0, H-4), 8.72 (1H, s, H-9).
7-Methyl-10-(4-chlorophenyl)-5H-benzo[c]furo[3,2-g]chromen-5-one (52). Yield89%, mp249-250°C, C22H13ClO3.
IR spectrum (KBr, cm-1): 1725, 1606, 1577, 1488, 1306, 1288, 1273, 1252, 1115, 1094, 1080, 1039, 811, 771. UV spectrum
(CH CN, λmax, nm, log ε): 210 (4.32), 231 (4.34), 247 (4.36), 278 (4.04), 321 (3.94). PMR spectrum (400 MHz, DMSO-d ,
3
6
δ, ppm, J/Hz): 2.42 (3H, s, Me-7), 7.54 (2H, d, J = 8.4, H-3′, H-5′), 7.56 (1H, t, J = 8.0, H-3), 7.79 (2H, d, J = 8.4, H-2′, H-6′),
7.83 (1H, t, J = 8.0, H-2), 8.12 (1H, d, J = 8.0, H-1), 8.35 (1H, s, H-11), 8.42 (1H, s, H-9), 8.44 (1H, d, J = 8.0, H-4).
10-(4-Bromophenyl)-5H-benzo[c]furo[3,2-g]chromen-5-one (53). Yield 87%, mp 299-300°C, C21H11BrO3. IR
spectrum (KBr, cm-1): 1735, 1631, 1607, 1575, 1444, 1303, 1290, 1266, 1155, 1110, 1088, 1033, 867, 812, 764. UV spectrum
(dioxane, λmax, nm, log ε): 215 (4.48), 231 (4.61), 245 (4.66), 252 (4.63), 288 (4.17), 326 (4.09). PMR spectrum (400 MHz,
DMSO-d , δ, ppm, J/Hz): 7.67 (1H, t, J = 8.0, H-3), 7.73 (2H, d, J = 8.8, H-3′, H-5′), 7.79 (1H, s, H-7), 7.83 (2H, d, J = 8.8,
6
H-2′, H-6′), 7.96 (1H, t, J = 8.0, H-2), 8.25 (1H, d, J = 8.0, H-1), 8.52 (1H, s, H-11), 8.65 (1H, d, J = 8.0, H-4), 8.72 (1H, s, H-9).
431