Synthesis and antidepressant evaluation of dihydroisobenzofurans
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1612, 1456, 1273, 1064, 817, 750, 685 cm−1. 1H NMR 1464, 1365, 1307, 1049, 809, 761, 693, 517 cm−1. H
(500 MHz, CDCl3): δH 5.24 (s, 2H); 6.49 (s, 1H); 7.08– NMR (500 MHz, CDCl3): δH 0.91 (t, 3H, J = 7.3 Hz);
7.12 (m, 2H); 7.19 (t, 1H, J = 7.6 Hz); 7.27 (t, 1H, 1.29–1.58 (m, 4H); 1.66–1.81 (m, 4H), 1.90–2.01 (m,
J = 6.9 Hz); 7.34–7.37 (m, 1H); 7.39–7.42 (m, 2H); 1H); 5.60 (dd, 1H, J = 7.8, 3.8 Hz); 5.88 (s, 1H);
7.75–7.77 (m, 2H). 13C NMR (125 MHz, CDCl3): δC 7.10–7.18 (m, 1H); 7.19–7.23 (m, 1H); 7.24–7.37
69.1, 101.3, 123.5, 123.9, 125.1, 126.5, 128.1, 128.3, (m, 1H); 7.46–7.52 (m, 1H); 7.72–7.80 (m, 2H). 13C
128.4, 128.9, 132.0, 134.3. 154.1. MS (ESI): m/z = NMR (125 MHz, CDCl3): δC 14.0, 22.6, 27.1, 35.7,
209 [M+H]+. Anal. Calcd. for C15H12O: C, 86.51; H, 86.1, 95.7, 119.9, 121.2, 125.1, 127.7, 128.1, 128.3,
5.81%. Found: C, 86.75; H, 5.75%.
128.6, 135.0, 136.7, 142.8, 155.8. MS (ESI): m/z =
265 [M+H]+. Anal. Calcd. for C19H20O: C, 86.32; H,
7.63%. Found: C, 86.15; H, 7.70%.
2.2d (Z)-1-(4-Methoxy-benzylidene)-1,3-dihydro-
isobenzofuran (2b): Colourless solid; Mp 122–124◦C;
IR (KBr): 3033, 2843, 2331, 1678, 1616, 1550, 1446, 2.2h (Z)-1,1-Diethyl-3-pentylidcene-1,3-dihydroisoben-
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1384, 1271, 1062, 906, 811, 755, 679 cm−1. H NMR zofuran (2f): Yellow oil; IR (neat): 2964, 2930, 2874,
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(500 MHz, CDCl3): δH 3.83 (s, 3H); 5.20 (s, 2H); 6.35 2853, 1679, 1463, 1354, 1296, 1050, 752 cm−1. H
(s, 1H); 6.90 (d, 2H, J = 9.1 Hz); 7.05 (t, 2H, J = NMR (500 MHz, Benzene-d6): δH 0.75 (t, J = 7.3 Hz);
7.6 Hz); 7.14 (t, 1H, J = 7.6 Hz); 7.24 (t, 1H, J = 0.95 (t, 3H, J = 7.3 Hz); 1.36–1.76 (m, 6H); 1.80–1.95
7.6 Hz); 7.67 (d, 2H, J = 8.4 Hz). 13C NMR (125 MHz, (m, 2H); 2.54 (q, 3H. J = 7.2 Hz) 4.94 (t, 1H, J =
CDCl3): δC 55.4, 69.1, 99.6, 113.8, 123.2, 123.8, 126.1, 7.2 Hz); 6.71–6.77 (m, 1H); 7.01–7.06 (m, 2H); 7.22–
126.7, 126.9, 127.8, 128.2, 132.3, 154.1, 160.3. MS 7.28 (m, 1H). MS (ESI): m/z = 245 [M+H]+. Anal.
(ESI): m/z = 239 [M+H]+. Anal. Calcd. for C16H14O2: Calcd. for C17H24O: C, 83.55; H, 9.90%. Found: C,
C, 80.65; H, 5.92%. Found: C, 80.88; H, 5.85%.
83.35; H, 9.95%.
2.2e (Z)-1-(3-Methyl-benzylidene)-1,3-dihydro- 2.2i (Z)-3-Benzylidene-1,1-diethyl-1,3-dihydroisoben-
isobenzofuran (2c): Pink solid; Mp 112–114◦C; IR zofuran (2g): Colourless solid; Mp 62–64◦C; IR
(KBr): 3042, 2840, 1946, 1698, 1602, 1448, 1383, (KBr): 2960, 1649, 1462, 1358, 1096, 1051, 939, 820,
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1283, 1175, 1069, 881, 782, 691 cm−1. 1H NMR 761 cm−1. H NMR (500 MHz, Benzene-d6): δH 0.68
(500 MHz, CDCl3): δH 2.42 (s, 3H); 5.24 (s, 2H); 6.48 (t, 6H, J = 7.3 Hz); 1.53-1.66 (m, 2H); 1.80-1.94 (m,
(s, 1H); 7.08–7.12 (m, 2H); 7.17–7.19 (m, 2H); 7.27– 2H); 5.95 (s, 1H); 6.66–6.74 (m, 1H); 7.00–7.14 (m,
7.32 (m, 2H); 7.56–7.59 (m, 2H). 13C NMR (125 MHz, 3H); 7.20–7.26 (m, 1H); 7.30–7.40 (m, 2H); 8.00-8.05
CDCl3): δC 21.6, 69.1, 101.2, 122.3, 123.5, 123.8, (m, 2H). 13C NMR (125 MHz, Benzene-d6): δC 7.9,
125.8, 126.5, 128.1, 128.3 (2C), 129.7, 132.1, 134.3, 33.0, 94.7, 96.0, 120.1, 121.1, 125.4, 128.0, 128.4,
138.0, 154.3. MS (ESI): m/z = 223 [M+H]+. Anal. 128.6, 136.5, 137.6, 144.5, 156.0. MS (ESI): m/z =
Calcd. for C16H14O: C, 86.45; H, 6.35%. Found: C, 265 [M+H]+. Anal. Calcd. for C19H20O: C, 86.32; H,
86.60; H, 6.30%.
7.63%. Found: C, 86.50; H, 7.55%.
2.2f (Z)-1-(4-Methyl-benzylidene)-1,3-dihydro- 2.2j (Z)-1-(3H-Isobenzofuran-1-ylidene)-propan-2-one
isobenzofuran (2d): Colourless solid; Mp 96–98◦C; (2h): Yellow oil; IR (neat): 1671, 1624, 1590,
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IR (KBr): 2846, 1910, 1605, 1448, 1270, 1193, 1061, 706 cm−1. H NMR (500 MHz, CDCl3): δH 2.46 (s,
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931, 802 cm−1. H NMR (500 MHz, CDCl3): δH 2.39 3H); 5.58 (s, 2H); 5.83 (s, 1H); 7.35–7.71 (m, 4H). 13C
(s, 3H); 5.22 (s, 2H); 6.43 (s, 1H); 7.08 (t, 2H, J = NMR (125 MHz, CDCl3): δC 31.4, 77.0, 98.2, 121.8,
8.4 Hz); 7.17 (t, 1H, J = 7.6 Hz); 7.20 (d, 2H, 129.2, 132.0, 135.6, 141.8, 167.4, 197.6. MS (ESI):
J = 7.6 Hz); 7.24 (t, 1H, J = 8.4 Hz) 7.64 (d, 2H, m/z = 175 [M+H]+. Anal. Calcd. for C11H10O2: C,
J = 8.4 Hz). 13C NMR (125 MHz, CDCl3): δC 21.4, 75.84; H, 5.79%. Found: C, 76.05; H, 5.71%.
69.0, 100.5, 123.4, 123.8, 125.1, 126.3, 128.0, 128.2,
129.1, 131.5, 132.2, 139.0. 154.3. MS (ESI): m/z =
223 [M+H]+. Anal. Calcd. for C16H14O: C, 86.45; H,
6.35%. Found: C, 86.25; H, 6.40%.
2.2k (Z)-5-Benzylidene-5,7-dihydro-furo[3ꢁ,4ꢁ:4,5]benzo
[1,2-d][1,3]dioxole (2i): Pale yellow solid; Mp 132–
134◦C; IR (KBr): 2898, 1733, 1632, 1481, 1367,
1291, 1152, 1035, 860, 757 cm−1. 1H NMR (500 MHz,
2.2g (Z)-1-Benzylidene-3-butyl-1,3-dihydroisobenzofuran CDCl3): δH 5.11 (s, 2H); 5.93 (s, 2H); 6.36 (s, 1H); 6.60
(2e): Yellow oil; IR (neat) 2955, 2929, 2869, 1655, (d, 2H, J = 10.7 Hz); 7.32–7.38 (m, 3H); 7.69 (d, 2H,