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Organic & Biomolecular Chemistry
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(d, J = 2.5 Hz, 1H), 6.85 (dd, J = 16.6Hz, J = 2.5 Hz, 1H). 13C NMR (100 131.7, 130.9, 128.6, 128.2, 127.4, 126.6, 125.7, 122.8, 117.5, 117.2,
MHz, CDCl3): δ = 161.6, 159.7, 156.2, 154.9, 154.4, 134.6, 131.7, 113.8, 97.8, 84.2, 55.5, 21.7. HRMS (ESI) calDcdO.I:f1o0r.1C02359H/1D9O0O3 B[M00+4H79]+K:
130.2, 129.4, 129.1, 129.0, 128.7, 128.5, 128.2, 125.3, 122.6, 120.5, 367.1329, found: 367.1330.
114.7, 114.6, 108.7, 105.0, 98.0, 83.9. HRMS (ESI) calcd. for C29H19O3
[M+H]+: 415.1329, found: 415.1326.
4-(4-fluorophenyl)-7-methyl-3-(phenylethynyl)-2H-chromen-2-
o
one (4k). Yellow solid (52.6 mg, 74%). mp. 187.7-188.8 C. IR (KBr)
1
4-phenyl-3-(phenylethynyl)-2H-chromen-2-one (4e).10e Light 3066, 1717, 1611, 1535, 1488, 1224, 1065, 751, 684 cm-1. H NMR
yellow solid (45.9 mg, 71%). mp. 169.3-170.4 oC. IR (KBr) 3054, 2922, (400 MHz, CDCl3): δ = 7.52-7.48 (m, 2H), 7.29-7.25 (m, 7H), 7.68-7.55
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1719, 1601, 1538, 1484, 1445, 1059, 748, 696 cm-1. H NMR (400 (m, 5H), 7.21 (s, 1H), 7.14 (d, J = 8.2 Hz, 1H), 7.04 (d, J = 8.2 Hz, 1H),
MHz, CDCl3): δ = 7.60-7.55 (m, 3H), 7.51-7.47 (m, 3H), 7.40 (d, J = 8.1 2.46 (s, 3H). 13C NMR (100 MHz, CDCl3): δ = 163.2 (d, J = 250.2 Hz),
Hz, 1H), 7.30-7.19 (m, 7H). 13C NMR (100 MHz, CDCl3): δ = 159.5, 159.7, 155.1, 152.9, 143.8, 131.7, 131.2 (d, J = 8.1 Hz), 130.5, 128.9,
156.3, 152.9, 134.4, 132.1, 131.8, 129.4, 129.1, 128.8, 128.5, 128.2, 128.3, 127.1, 125.9, 122.4, 117.3, 115.7, 115.5, 110.2, 98.4, 83.7,
127.6, 124.5, 122.5, 119.7, 117.0, 111.2, 98.7, 83.8. HRMS (ESI) calcd. 21.7. 19F NMR (376.5 MHz, CDCl3): δ = -111.1. HRMS (ESI) calcd. for
for C23H15O2 [M+H]+: 323.1067, found: 323.1068.
C24H16FO2 [M+H]+: 355.1129, found: 355.1130.
7-fluoro-4-phenyl-3-(phenylethynyl)-2H-chromen-2-one
(4f).
4-(4-chlorophenyl)-7-methyl-3-(phenylethynyl)-2H-chromen-2-
Light yellow solid (50.9 mg, 75%). mp. 204.1-205.2 oC. IR (KBr) 3059, one (4l). Light yellow solid (58.4 mg, 79%). mp. 185.2-186.7 C. IR
1737, 1603, 1546, 1495, 1431, 1050, 853, 748, 695 cm-1. 1H NMR (400 (KBr) 2362, 2333, 1717, 1617, 1534, 1483, 1065, 752, 728, 686 cm-1.
MHz, CDCl3): δ = 7.60-7.54 (m, 3H), 7.49-7.48 (m, 2H), 7.29-7.20 (m, 1H NMR (400 MHz, CDCl3): δ = 7.56-7.54 (m, 2H), 7.46-7.44 (m, 2H),
6H), 7.11 (dd, J = 8.8 Hz, J = 2.3 Hz, 1H), 6.95 (td, J = 8.3 Hz, J = 2.3 Hz, 7.29-7.26 (m, 5H), 7.21 (s, 1H), 7.12 (d, J = 8.2 Hz, 1H), 7.03 (dd, J =
1H). 13C NMR (100 MHz, CDCl3): δ = 164.5 (d, J = 256.0 Hz), 159.2, 33.4 Hz, J = 1.0 Hz, 1H), 2.46 (s, 3H), 2.43 (s, 3H). 13C NMR (100 MHz,
155.7, 153.9 (d, J = 13.2 Hz), 134.2, 131.7, 130.0, 129.4 (d, J = 9.5 Hz), CDCl3): δ = 159.6, 154.8, 152.9, 143.8, 135.5, 133.0, 131.7, 130.6,
129.0, 128.9, 128.6, 128.2, 122.4, 116.5, 112.6 (d, J = 22.7 Hz), 110.1, 128.9, 128.8, 128.3, 127.0, 125.9, 122.4, 117.3, 117.0, 110.2, 98.7,
104.5 (d, J = 25.7 Hz), 98.7, 83.5. 19F NMR (376.5 MHz, CDCl3): δ = - 83.6, 21.7. HRMS (ESI) calcd. for C24H16ClO2 [M+H]+: 371.0833, found:
104.5. HRMS (ESI) calcd. for C23H14FO2 [M+H]+: 341.0972, found: 371.0834.
o
341.0971.
7-methyl-4-phenyl-3-(p-tolylethynyl)-2H-chromen-2-one (4m).
7-chloro-4-phenyl-3-(phenylethynyl)-2H-chromen-2-one
(4g). Light yellow solid (52.1 mg, 74%). mp. 191.5-192.8 oC. IR (KBr) 2363,
Light yellow solid (50.4 mg, 71%). mp. 177.8-178.4 oC. IR (KBr) 3058, 2333, 1717, 1617, 1535, 1509, 1368, 1063, 811, 763, 712 cm-1. H
1
2923, 1735, 1596, 1518, 1484, 1413, 1054, 755, 693 cm-1. H NMR NMR (400 MHz, CDCl3): δ = 7.58-7.53 (m, 3H), 7.51-7.47 (m, 2H), 7.20
1
(400 MHz, CDCl3): δ = 7.58-7.57 (m, 3H), 7.49-7.47 (m, 2H), 7.41 (d, J (s, 1H), 7.16-7.10 (m, 3H), 7.05-7.00 (m, 3H), 2.45 (s, 3H), 2.30 (s, 3H).
= 1.2 Hz, 1H), 7.30-7.16 (m, 7H). 13C NMR (100 MHz, CDCl3): δ = 158.9, 13C NMR (100 MHz, CDCl3): δ = 159.9, 156.0, 152.9, 143.4, 139.0,
155.4, 153.0, 138.0, 134.0, 131.8, 129.6, 129.0, 128.9, 128.6, 128.5, 134.6, 131.6, 129.3, 129.2, 129.0, 128.4, 127.3, 125.7, 119.6, 117.4,
128.3, 125.1, 122.3, 118.4, 117.3, 111.1, 99.2, 83.6. HRMS (ESI) calcd. 117.2, 110.2, 98.6, 83.4, 21.7, 21.6. HRMS (ESI) calcd. for C25H19O2
for C23H14ClO2 [M+H]+: 357.0677, found: 357.0676.
[M+H]+: 351.1380, found: 351.1384.
4-phenyl-3-(phenylethynyl)-7-(trifluoromethyl)-2H-chromen-2-
3-((4-methoxyphenyl)ethynyl)-7-methyl-4-phenyl-2H-chromen-
o
one (4h). Yellow solid (50.6 mg, 65%). mp. 169.3-170.8 C. IR (KBr) 2-one (4n). Light yellow solid (58.0 mg, 79%). mp. 180.9-182.4 oC. IR
1
3056, 2924, 1739, 1613, 1546, 1497, 1425, 1058, 748, 682 cm-1. H (KBr) 3056, 3018, 2970, 2926, 1732, 1612, 1503, 1449, 1058, 1023,
NMR (400 MHz, CDCl3): δ = 7.65 (s, 1H), 7.62-7.58 (m, 3H), 7.51-7.49 821, 756, 694 cm-1. 1H NMR (400 MHz, CDCl3): δ = 7.53-7.53 (m, 3H),
(m, 2H), 7.46-7.40 (m, 2H), 7.32-7.22 (m, 5H). 13C NMR (100 MHz, 7.49-7.47 (m, 2H), 7.19 (s, 1H), 7.16-7.13 (m, 3H), 7.01 (d, J = 8.1 Hz,
CDCl3): δ = 158.5, 153.5 (d, J = 230.4 Hz), 133.8, 133.3 (d, J = 33.0 Hz), 1H), 6.76 (d, J = 8.8 Hz, 2H) 3.77 (s, 3H), 2.44 (s, 3H). 13C NMR (100
131.9, 129.8, 129.2, 129.0, 128.7, 128.3, 128.2, 124.5, 122.4, 122.1, MHz, CDCl3): δ = 160.0 159.9, 155.5, 152.8, 143.3, 134.7, 133.2, 129.2,
121.8, 120.9 (q, J = 7.3 Hz, J = 3.7 Hz), 114.4 (q, J = 8.1 Hz, J = 3.7 Hz), 129.1, 128.4, 127.2, 125.7, 117.4, 117.1, 114.7, 113.9, 110.3, 98.5,
113.3, 100.3, 83.4. 19F NMR (376.5 MHz, CDCl3): δ = -62.9. HRMS (ESI) 82.9, 55.3, 21.7. HRMS (ESI) calcd. for C25H19O3 [M+H]+: 367.1329,
calcd. for C24H14F3O2 [M+H]+: 391.0940, found: 391.0936.
found: 367.1328.
6,8-dimethyl-4-phenyl-3-(phenylethynyl)-2H-chromen-2-one (4i).
3-((4-fluorophenyl)ethynyl)-7-methyl-4-phenyl-2H-chromen-2-
o
Yellow solid (54.9 mg, 78%). mp. 189.4-190.7 oC. IR (KBr) 3054, 3017, one (4o). Yellow solid (52.9 mg, 75%). mp. 208.7-210.2 C. IR (KBr)
1
2916, 1721, 1600, 1541, 1480, 1077, 1051, 752, 690 cm-1. H NMR 3064, 3030, 2922, 2332, 1721, 1611, 1499, 1366, 1323, 1221, 1057,
(400 MHz, CDCl3): δ = 7.57-7.55 (m, 3H), 7.48-7.46 (m, 2H), 7.25-7.21 761, 700, 643 cm-1. 1H NMR (400 MHz, CDCl3): δ = 7.57-7.55 (m, 3H),
(m, 6H), 6.85 (s, 1H), 2.47 (s, 3H), 2.26 (s, 3H). 13C NMR (100 MHz, 7.49-7.47 (m, 2H), 7.21-7.14 (m, 4H), 7.02 (d, J = 8.1 Hz, 1H), 6.93 (t,
CDCl3): δ = 159.8, 156.8, 149.5, 135.0, 134.7, 133.6, 131.7, 129.2, J = 8.7 Hz, 2H), 2.46 (s, 3H). 13C NMR (100 MHz, CDCl3): δ = 162.7 (d,
129.1, 128.7, 128.4, 128.2, 126.1, 125.0, 122.6, 119.2, 110.8, 98.4, J = 250.9 Hz), 159.8, 156.4, 153.0, 143.7, 134.6, 133.6 (d, J = 8.8 Hz),
84.2, 20.9, 15.6. HRMS (ESI) calcd. for C25H19O2 [M+H]+: 351.1380, 129.4, 129.1, 128.4, 127.3, 125.8, 118.7 (d, J = 3.7 Hz), 117.3, 117.2,
found: 351.1382.
115.5 (d, J = 22.0 Hz), 109.8, 97.1, 83.7, 21.7. 19F NMR (376.5 MHz,
CDCl3): δ = -109.9. HRMS (ESI) calcd. for C24H16FO2 [M+H]+: 355.1129,
4-(4-methoxyphenyl)-7-methyl-3-(phenylethynyl)-2H-chromen-
2-one (4j). Yellow solid (31.7 mg, 43%). mp. 169.1-170.2 oC. IR (KBr) found: 355.1126.
3020, 1724, 1608, 1539, 1490, 1441, 1060, 1027, 757, 690 cm-1. H
3-((4-chlorophenyl)ethynyl)-7-methyl-4-phenyl-2H-chromen-2-
1
o
NMR (400 MHz, CDCl3): δ = 7.47 (d, J = 8.7 Hz, 2H), 7.32-7.20 (m, 7H), one (4p). Yellow solid (51.7 mg, 70%). mp. 234.3-236.4 C. IR (KBr)
7.08 (d, J = 8.7 Hz, 2H), 7.03 (d, J = 21.4 Hz, 1H), 3.92 (s, 3H), 2.46 (s, 3055, 3042, 2909, 1716, 1614, 1582, 1531, 729, 692, 630 cm-1. H
1
3H). 13C NMR (100 MHz, CDCl3): δ = 160.5, 160.0, 156.0, 153.0, 143.5, NMR (400 MHz, CDCl3): δ = 7.59-7.54 (m, 3H), 7.49-7.47 (m, 2H),
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