HETEROCYCLES, Vol. 83, No. 4, 2011
861
1-Methyl-9H-xanthen-9-one (2d)
o
o
White solid. mp 110.3-111 C (Lit.,24 mp 109.5-110.5 C) IR (KBr): 2963, 2922, 1655, 1600, 1473,
1344, 763 cm-1. 1H NMR (400 MHz, CDCl3) δ: 8.25 (dd, J = 8.0, 1.6 Hz, 1H), 7.66-7.62 (m, 1H), 7.50 (t,
J = 8.0 Hz, 1H), 7.40 (d, J = 8.4 Hz, 1H), 7.33-7.27 (m, 2H), 7.08 (d, J = 7.6 Hz, 1H), 2.92 (s, 3H).13C
NMR (100 MHz, CDCl3) δ: 178.5, 157.2, 154.9, 141.7, 134.0, 133.4, 126.4, 123.4, 122.5, 119.8, 117.2,
115.8, 23.3. MS (ESI): m/z = 211 (M++1).
3-Methyl-9H-xanthen-9-one (2d’)
o
o
White solid. mp 93-95 C (Lit.,24 mp 98 C). IR (KBr): 3064, 2923, 1657, 1605, 1464, 1325, 758 cm-1.
1H NMR (400 MHz, CDCl3) δ: 8.31 (d, J = 7.6 Hz, 1H), 8.19 (d, J = 8.4 Hz, 1H), 7.68 (t, J = 8.0 Hz, 1H),
7.44 (d, J = 8.4 Hz, 1H), 7.34 (t, J = 8.0 Hz, 1H), 7.25 (s, 1H), 7.16 (d, J = 8.0 Hz, 1H), 2.49 (s, 3H). 13C
NMR (100 MHz, CDCl3) δ: 176.6, 155.9, 146.0, 134.3, 126.4, 126.2, 125.2, 123.5, 121.6, 119.3, 117.7,
117.5, 22.0. MS (ESI): m/z = 211 (M++1).
2-Methoxy-9H-xanthen-9-one (2e)
White solid. mp 131.8-132.6 oC (Lit.,25 mp 132-139 oC). IR (KBr): 3033, 2958, 2834, 1649, 1615, 1466,
1317, 758 cm-1. 1H NMR (400 MHz, CDCl3) δ: 8.33 (dd, J = 8.0, 1.2 Hz, 1H), 7.72-7.67 (m, 2H), 7.47 (d,
J = 8.4 Hz, 1H), 7.42 (d, J = 9.2 Hz, 1H), 7.35 (t, J = 8.0 Hz, 1H), 7.31 (dd, J = 3.2, 9.2 Hz, 1H), 3.91 (s,
13
3H). C NMR (100 MHz, CDCl3) δ: 177.0, 156.1, 156.0, 151.0, 134.6 (2C), 126.7, 125.0, 123.8, 122.2,
121.3, 119.5, 118.1, 56.2. MS (ESI): m/z = 227 (M++1).
2-Chloro-9H-xanthen-9-one (2f)
o
o
White solid. mp 170.3-171.7 C (Lit.,25 mp 173-173 C). IR (KBr): 3079, 1663, 1617, 1460, 1316, 757
1
cm-1. H NMR (400 MHz, CDCl3) δ: 8.31 (dd, J = 8.0, 1.6 Hz, 1H), 8.28 (d, J = 2.8 Hz, 1H), 7.76-7.70
(m, 1H), 7.65 (dd, J = 8.8, 2.8 Hz, 1H), 7.49-7.43 (m, 2H), 7.39 (t, J = 7.2 Hz, 1H). 13C NMR (100 MHz,
CDCl3) δ: 175.7, 155.7, 154.1, 134.9, 134.3, 129.4, 126.5, 125.7, 124.0, 122.3, 121.2, 119.5, 117.8. MS
(EI): m/z (%) = 232 ([M++2], 32), 230 (M+, 100), 202 (21), 139 (22).
1,2,3-Trifluoro-9H-xanthen-9-one (2g)
White solid. mp 179- 180 oC. IR (KBr): 3081, 1660, 1646, 1615, 1511, 1469, 1312, 1130, 1066, 761 cm-1.
1H NMR (400 MHz, CDCl3) δ: 8.26 (dd, J = 8.0, 1.6 Hz, 1H), 7.75-7.70 (m, 1H), 7.44-7.37 (m, 2H),
13
1
2
7.14-7.09 (m, 1H). C NMR (100 MHz, CDCl3) δ: 174.1, 155.3, 153.7 (ddd, JC-F = 425 Hz, JC-F = 12
Hz, 3JC-F = 5 Hz, 1C), 150.2 (ddd, 1JC-F = 266 Hz, 2JC-F = 11 Hz, 3JC-F = 6 Hz, 1C), 137.4 (dt, 1JC-F = 349
Hz, 2JC-F = 16 Hz, 1C), 135.4, 126.6, 124.9, 121.5, 117.7, 113.3 (d, J = 9 Hz, 1C), 110.0 (d, J = 7 Hz, 1C).