USTALAR et al./Turk J Chem
MHz, CDCl3): δH 7.68 (dd, 1H, J = 8.0, 1.6 Hz), 7.56 (td, 1H, J = 8.0, 1.6 Hz), 7.43 (d, 2H, J = 7.2 Hz),
7.35 (t, 2H, J = 8.0 Hz), 7.31–7.26 (m, 3H), 6.77 (d, 1H, J = 15.6 Hz, Holefin), 6.36 (dd, 1H, J = 16.0, 8.0
Hz, Holefin), 5.71 (ddd, 1H, J = 10.0, 8.0, 7.6 Hz, H-2), 3.44 (dd, 1H, J = 15.2, 10.0 Hz, Ha-3), 3.06 (dd, 1H,
J = 15.2, 7.6 Hz, Hb-3); 13 C NMR (100 MHz, CDCl3): δC 166.6 (C=O), 160.8, 155.1, 135.7, 134.3, 132.6,
128.9, 128.8, 127.1, 126.3, 124.2, 123.0, 117.1, 112.7, 102.1, 87.9, 33.3; LC-MS: m/z % 291 [M+H]+ , 100%.
Anal. Calcd. for C19 H14 O3 C, 78.61; H, 4.86. Found C, 78.53; H, 4.94.
2-(2,2-Diphenylvinyl)-2,3-dihydro-4H -furo[3,2-c]chromen-4-one (3b): Yellow solid, yield 83%, mp 125–
128 ◦ C. IR (ATR): 3507, 2918, 1718, 1647, 1606, 1496, 1413, 1271, 1157, 1026, 894, 748, 702, 690. 1 H NMR
(400 MHz, CDCl3) δH 7.68 (dd, 1H, J = 7.6, 1.6 Hz), 7.55 (td, 1H, J = 7.6, 1.6 Hz), 7.47–7.25 (m, 13H), 6.25
(d, 1H, J = 9.2 Hz, Holefin), 5.60 (ddd, 1H, J = 10.0, 9.2, 7.6 Hz, H-2), 3.39 (dd, 1H, J = 15.2, 10.0 Hz,
Ha-3), 3.10 (dd, 1H, J = 15.2, 8.0 Hz, Hb-3); 13 C NMR (100 MHz, CDCl3): δC 166.6 (C=O), 160.8, 155.1,
147.4, 141.0, 138.5, 130.1, 128.7, 128.6, 128.5, 128.4, 128.0, 125.4, 124.1, 123.0, 117.1, 112.8, 102.2, 85.2, 34.1.
LC-MS: m/z % 367 [M+H]+ , 100%. Anal. Calcd. for C25 H18 O3 C, 81.95; H, 4.95. Found C, 81.73; H, 5.06.
2-Methyl-2-[(E)-2-phenylvinyl]-2,3-dihydro-4H -furo[3,2-c]chromen-4-one (3c) White oil, yield 78%. IR
(ATR): 3024, 1714, 1641, 1604, 1496, 1408, 1026, 962, 893, 746, 731, 692. 1 H NMR (400 MHz, CDCl3) δH
7.71 (dd, 1H, J = 7.6, 1.6 Hz), 7.58 (td, 1H, J = 7.6, 1.6 Hz), 7.42–7.22 (m, 7H), 6.70 (d, 1H, J = 16.0 Hz,
Holefin), 6.42 (d, 1H, J = 16.0 Hz, Holefin), 3.30 (d, 1H,J = 15.2 Hz, Ha-3), 3.11 (d, 1H, J = 14.8 Hz, Hb-3),
1.80 (s, 3H, –CH3); 13 C NMR (100 MHz, CDCl3): δC 165.6 (C=O), 161.0, 155.2, 136.0, 132.5, 131.2, 129.5,
128.9, 128.5, 126.9, 124.1, 123.0, 117.2, 113.0, 101.6, 93.6, 39.5, 27.0. LC-MS: m/z % 305 [M+H]+ , 100%. Anal.
Calcd. for C20 H16 O3 C, 78.93; H, 5.30. Found C, 78.68; H, 5.52.
2-Phenyl-2-[(E)-2-phenylethenyl]-2,3-dihydro-4H -furo[3,2-c]chromen-4-one (3d): Yellow oil, yield 70%.
IR (ATR): 3026, 2974, 2924, 1759, 1701, 1654, 1494, 1446, 1384, 1325, 1176, 966, 746, 692. 1 H NMR (400 MHz,
CDCl3) δH 7.7 (dd, 1H, J = 8.0, 1.6 Hz), 7.5 (t, 1H, J = 8.0 Hz), 7.45–7.1 (m, 14H), 3.6 (d, 1H, J = 15.2 Hz,
Ha-3), 3.5 (d, 1H, J = 15.2 Hz, Hb-3); 13 C NMR (100 MHz, CDCl3): δC 164.1 (C=O), 159.3, 154.0, 141.3,
134.5, 131.4, 129.6, 129.5, 127.7, 127.6, 127.3, 127.2, 125.8, 125.1, 124.3, 123.0, 121.7, 111.5, 100.5, 95.0, 39.0.
LC-MS: m/z % 367 [M+H]+ , 100%. Anal. Calcd. for C25 H18 O3 C, 81.95; H, 4.95. Found C, 82.10; H, 4.73.
2-[(E)-2-(2-Thienyl)vinyl]-2,3-dihydro-4H -furo[3,2-c]chromen-4-one (3e): Yellow solid, yield 46%, mp
97–100 ◦ C. IR (ATR): 3093, 3076, 1710, 1639, 1568, 1498, 1409, 1263, 1203, 1028, 893, 727, 655. 1 H NMR (400
MHz, CDCl3) δH 7.68 (dd, 1H, J = 8.0, 1.6 Hz), 7.58 (td, 1H, J = 7.6, 1.6 Hz), 7.38 (d, 1H, J = 8.0 Hz),
7.30–7.20 (m, 2H), 7.08 (d, 1H, J = 3.6 Hz), 7.0 (dd, 1H, J = 5.2, 3.6 Hz), 6.90 (d, 1H, J = 15.6 Hz, Holefin),
6.20 (dd, 1H, J = 15.6, 8.0 Hz, Holefin), 5.68 (ddd, 1H, J = 10.0, 8.0, 1.2 Hz, H-2), 3.48 (dd, 1H, J = 15.2,
10.0 Hz, Ha-3), 3.08 (dd, 1H, J = 15.2, 8.0 Hz, Hb-3); 13 C NMR (100 MHz, CDCl3): δC 166.5 (C=O), 160.7,
155.1, 140.6, 132.6, 127.8, 127.7, 127.4, 125.9, 125.5, 124.2, 123.0, 117.1, 112.7, 102.1, 87.6. LC-MS: m/z % 297
[M+H]+ , 100%. Anal. Calcd. for C17 H12 O3 S C, 68.90; H, 4.08. Found C, 68.78; H, 4.30.
2-Methyl-2-[(E)-2-(2-thienyl)vinyl]-2,3-dihydro-4H -furo[3,2-c]chromen-4-one (3f): Yellow oil, yield 36%,
IR (ATR): 3068, 2976, 2927, 1712, 1641, 1498, 1408, 1278, 1028, 954, 750, 727, 698. 1 H NMR (400 MHz,
CDCl3) δH 7.70 (dd, 1H, J = 8.0, 1.6 Hz), 7.58 (td, 1H, J = 7.6, 1.6 Hz), 7.38 (d, 1H, J = 8.0 Hz), 7.32 (td,
1H, J = 7.6, 1.2 Hz), 7.20 (d, 1H, J = 5.2 Hz), 7.02 (d, 1H, J = 3.6 Hz), 6.97 (dd, 1H, J = 5.2, 3.6 Hz), 6.82
(d, 1H, J = 16.0 Hz, Holefin), 6.28 (d, 1H, J = 16.0 Hz, Holefin), 3.28 (d, 1H, J = 15.2 Hz, Ha-3), 3.10 (d,
1H, J = 14.8 Hz, Hb-3), 1.78 (s, 3H, –CH3); 13 C NMR (100 MHz, CDCl3): δC 165.5 (C=O), 160.9, 155.2,
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