The Journal of Organic Chemistry
Note
6-Fluoro-3-phenyl-1H-isochromen-1-one (3ga):22a Light yel-
low solid; mp 163−165 °C, yield: 35% (67 mg); 1H NMR (500 MHz,
CDCl3) δ 8.36 (dd, J = 8.6, 5.6 Hz, 1H), 7.95−7.85 (m, 2H), 7.55−
7.45 (m, 3H), 7.24−7.15 (m, 2H), 6.93 (s, 1H); 13C NMR (500 MHz,
CDCl3): δ 168.0, 165.4, 161.3, 154.9, 140.2, 140.1, 133.0, 132.9, 131.5,
130.3, 128.9, 125.4, 117.0, 116.9, 116.5, 116.3, 111.6, 111.4, 101.2,
101.2; IR (KBr, cm−1) 3103, 3087, 3072, 3037, 2921, 2852, 1714,
1569, 1454, 1349, 1257, 1066, 883, 771, 682.
3,6-Diphenyl-1H-isochromen-1-one (3ha): Light yellow solid;
mp 170−173 °C, yield: 35% (84 mg); 1H NMR (500 MHz, CDCl3) δ
8.39 (d, J = 8.2 Hz, 1H), 7.97−7.90 (m, 2H), 7.74 (dd, J = 8.2, 1.8 Hz,
1H), 7.72−7.67 (m, 3H), 7.56−7.44 (m, 7H), 7.03 (s, 1H); 13C NMR
(500 MHz, CDCl3): δ 162.9, 154.7, 148.4, 140.1, 138.7, 132.7, 130.9,
130.7, 129.7, 129.5, 129.4, 128.1, 127.9, 126.0, 124.8, 119.9, 102.6; IR
(KBr, cm−1) 3095, 2919, 2852, 1712, 1608, 1446, 1342, 1068, 892,
756, 690; HRMS (ESI) m/z: calcd. for C21H14NaO2 [M + Na]+
321.0892, found 321.0894.
(d, J = 0.8 Hz, 1H), 7.48 (dd, J = 8.0, 1.3 Hz, 1H), 7.23 (d, J = 8.0 Hz,
1H), 6.22 (s, 1H), 2.44 (s, 3H), 2.26 (s, 3H); 13C NMR (400 MHz,
CDCl3) δ 163.1, 153.6, 137.6, 135.9, 135.1, 129.1, 124.7, 119.7, 103.3,
21.2, 19.5; IR (KBr, cm−1) 3064, 3031, 2958, 2921, 1729, 1660, 1344,
1153, 1066, 979, 844, 738, 694.
3,6-Dimethyl-1H-isochromen-1-one (3de):23c Light yellow
solid, mp 70−72 °C, yield 63% (88 mg); 1H NMR (400 MHz,
CDCl3) δ 8.10 (d, J = 8.1 Hz, 1H), 7.23 (d, J = 8.2 Hz, 1H), 7.10 (s,
1H), 6.17 (s, 1H), 2.44 (s, 3H), 2.25 (s, 3H); 13C NMR (400 MHz,
CDCl3) δ 163.0, 154.5, 145.7, 137.7, 129.3, 128.8, 124.8, 117.4, 103.4,
21.9, 19.6; IR (KBr, cm−1) 3079, 2958, 2919, 1718, 1660, 1160, 1056,
775, 686.
6-Methoxy-3-methyl-1H-isochromen-1-one (3ee):23a White
1
solid, mp 100−103 °C, yield 61% (93 mg); H NMR (400 MHz,
CDCl3) δ 8.14 (d, J = 8.8 Hz, 1H), 6.97 (dd, J = 8.8, 2.5 Hz, 1H), 6.70
(d, J = 2.5 Hz, 1H), 6.17 (s, 1H), 3.89 (s, 3H), 2.25 (d, J = 0.9 Hz,
3H); 13C NMR (400 MHz, CDCl3) δ 164.6, 162.7, 155.1, 140.0,
131.6, 115.8, 113.0, 106.9, 103.5, 55.5, 19.6; IR (KBr, cm−1) 3074,
3014, 2921, 2842, 1716, 1658, 1602, 1357, 1253, 1222, 1056, 999, 858,
777, 686.
3-Phenyl-1H-benzo[h]isochromen-1-one (3ia): Light yellow
1
solid; mp 185−188 °C, yield: 73% (159 mg); H NMR (500 MHz,
CDCl3) δ 9.75 (d, J = 8.7 Hz, 1H), 8.11 (d, J = 8.5 Hz, 1H), 8.00−7.94
(m, 2H), 7.90 (d, J = 8.0 Hz, 1H), 7.78 (ddd, J = 8.5, 6.9, 1.4 Hz, 1H),
7.63 (ddd, J = 8.0, 7.0, 1.1 Hz, 1H), 7.54−7.45 (m, 4H), 7.06 (s, 1H);
13C NMR (500 MHz, CDCl3): δ 161.4, 155.0, 140.1, 136.3, 132.9,
131.7, 131.6, 130.2, 129.4, 128.8, 128.6, 126.8, 126.6, 125.4, 123.9,
113.8, 102.6; IR (KBr, cm−1) 3097, 3054, 2962, 2925, 2852, 1708,
1639, 1598, 1047, 1031, 852, 740, 682; HRMS (ESI) m/z: calcd. for
C19H12NaO2 [M + Na]+ 295.0735, found 295.0731.
6-Chloro-3-methyl-1H-isochromen-1-one (3fe):23b White
1
solid, mp 148−150 °C, yield 62% (97 mg); H NMR (400 MHz,
CDCl3) δ 8.16 (d, J = 8.5 Hz, 1H), 7.39 (dd, J = 8.5, 2.0 Hz, 1H), 7.31
(d, J = 2.0 Hz, 1H), 6.19 (s, 1H), 2.29 (d, J = 0.9 Hz, 3H); 13C NMR
(400 MHz, CDCl3) δ 162.0, 156.0, 141.3, 138.9, 131.1, 128.0, 124.3,
118.2, 102.6, 19.7; IR (KBr, cm−1) 3089, 3064, 3041, 2966, 2927,
1747, 1654, 1598, 1558, 1336, 1159, 1054, 864, 840, 775, 680.
6-Fluoro-3-methyl-1H-isochromen-1-one (3ge):23b Light yel-
3-(4-Methoxyphenyl)-1H-isochromen-1-one (3ab):22a Light
1
1
low solid, mp 88−89 °C, yield 69% (98 mg); H NMR (400 MHz,
yellow solid; mp 118−123 °C, yield: 60% (121 mg); H NMR (500
CDCl3) δ 8.22 (dd, J = 8.8, 5.6 Hz, 1H), 7.10 (td, J = 8.6, 2.5 Hz, 1H),
6.95 (dd, J = 9.0, 2.5 Hz, 1H), 6.20 (s, 1H), 2.26 (d, J = 0.9 Hz, 3H);
13C NMR (400 MHz, CDCl3) δ 167.9, 165.3, 161.8, 156.0, 140.3,
140.2, 132.8, 132.7, 116.3, 116.3, 115.8, 115.6, 110.5, 110.3, 103.0,
103.0, 19.6; IR (KBr, cm−1) 3074, 2975, 2923, 1731, 1662, 1618, 1344,
1168, 1058, 771, 678.
3-Methyl-6-phenyl-1H-isochromen-1-one (3he): White solid;
mp 142−144 °C, yield: 54% (102 mg); 1H NMR (400 MHz, CDCl3)
δ 8.31 (d, J = 8.3 Hz, 1H), 7.70−7.63 (m, 3H), 7.54−7.48 (m, 3H),
7.44 (ddd, J = 5.8, 4.4, 2.0 Hz, 1H), 6.31 (s, 1H), 2.31 (d, J = 0.9 Hz,
3H); 13C NMR (400 MHz, CDCl3): δ 162.8, 154.9, 147.5, 139.5,
138.1, 130.0, 129.0, 128.6, 127.3, 126.6, 123.0, 118.6, 103.6, 19.6; IR
(KBr, cm−1) 3066, 3033, 2958, 2921, 2848, 1720, 1658, 1560, 1160,
1066, 889, 765, 690; HRMS (ESI) m/z: calcd. for C16H12NaO2 [M +
Na]+ 259.0735, found 259.0729.
MHz, CDCl3) δ 8.28 (d, J = 8.2 Hz, 1H), 7.84−7.78 (m, 2H), 7.68
(td, J = 7.8, 1.3 Hz, 1H), 7.45 (ddd, J = 4.7, 3.7, 1.9 Hz, 2H), 6.98−
6.95 (m, 2H), 6.81 (s, 1H), 3.86 (s, 3H); 13C NMR (500 MHz,
CDCl3): δ 162.4, 161.0, 153.7, 137.9, 134.7, 129.5, 127.6, 126.7, 125.6,
124.5, 120.1, 114.2, 100.2, 55.3; IR (KBr, cm−1) 3076, 2996, 2960,
2931, 2836, 1727, 1633, 1600, 1511, 1255, 1234, 1178, 1064, 1027,
823, 754, 686.
3-(p-Tolyl)-1H-isochromen-1-one (3ac):22a Light yellow solid;
mp 117−119 °C, yield: 49% (93 mg); 1H NMR (400 MHz, CDCl3) δ
8.28 (dd, J = 8.1, 0.7 Hz, 1H), 7.78−7.73 (m, 2H), 7.72−7.66 (m,
1H), 7.48−7.43 (m, 2H), 7.25 (dd, J = 8.5, 0.6 Hz, 2H), 6.88 (s, 1H),
2.39 (s, 3H); 13C NMR (400 MHz, CDCl3): δ 162.3, 153.7, 140.2,
137.6, 134.8, 129.5, 129.5, 129.1, 127.8, 125.8, 125.1, 120.3, 101.0,
21.3; IR (KBr, cm−1) 3066, 3031, 2952, 2919, 2854, 1731, 1629, 1064,
815, 752, 686, 526.
3-(4-Chlorophenyl)-1H-isochromen-1-one (3ad):22a Light yel-
Methyl 3-Methyl-1-oxo-1H-isochromene-6-carboxylate
1
1
low solid; mp 148−150 °C, yield: 49% (101 mg); H NMR (400
(3ie): Light yellow solid; mp 178−181 °C, yield: 22% (38 mg); H
MHz, CDCl3) δ 8.31−8.27 (m, 1H), 7.82−7.78 (m, 2H), 7.75−7.70
(m, 1H), 7.50 (ddd, J = 7.8, 5.4, 1.7 Hz, 2H), 7.45−7.40 (m, 2H), 6.92
(s, 1H); 13C NMR (400 MHz, CDCl3): δ 161.9, 152.4, 137.2, 135.9,
134.9, 130.4, 129.6, 129.0, 128.3, 126.4, 126.0, 120.5, 102.0; IR (KBr,
cm−1) 3097, 3035, 2962, 2921, 1722, 1639, 1492, 1068, 1012, 823,
750, 682, 524.
NMR (500 MHz, CDCl3) δ 8.29 (d, J = 8.2 Hz, 1H), 8.03 (d, J = 8.3
Hz, 1H), 8.00 (s, 1H), 6.31 (s, 1H), 3.97 (s, 3H), 2.30 (s, 3H); 13C
NMR (500 MHz, CDCl3): δ 165.8, 162.1, 155.4, 137.5, 135.5, 129.7,
127.7, 126.4, 122.8, 103.3, 52.6, 19.6; IR (KBr, cm−1) 3072, 3010,
2960, 2921, 2848, 1737, 1718, 1666, 1338, 1290, 1105, 964, 914, 844,
744, 680; HRMS (ESI) m/z: calcd. for C12H10NaO4 [M + Na]+
241.0477, found 241.0473.
3-Methyl-1H-isochromen-1-one (3ae):23a White solid, mp 75−
77 °C, yield 59% (76 mg); 1H NMR (500 MHz, CDCl3) δ 8.22 (d, J =
8.5 Hz, 1H), 7.65 (ddd, J = 8.6, 7.6, 1.3 Hz, 1H), 7.45−7.40 (m, 1H),
7.32 (d, J = 7.9 Hz, 1H), 6.24 (s, 1H), 2.26 (s, 3H); 13C NMR (500
MHz, CDCl3) δ 162.9, 154.5, 137.6, 134.7, 129.4, 127.5, 124.8, 119.8,
103.5, 19.5; IR (KBr, cm−1) 3076, 3029, 2950, 2919, 1720, 1660, 1162,
1068, 757, 688.
3-Methyl-1H-benzo[h]isochromen-1-one (3je):23d Light yel-
1
low solid; mp 152−154 °C, yield: 68% (114 mg); H NMR (500
MHz, CDCl3) δ 9.64 (d, J = 8.6 Hz, 1H), 7.95 (d, J = 8.5 Hz, 1H),
7.80 (d, J = 8.0 Hz, 1H), 7.69 (ddd, J = 8.5, 6.9, 1.4 Hz, 1H), 7.54
(ddd, J = 8.0, 7.0, 1.1 Hz, 1H), 7.21 (d, J = 8.5 Hz, 1H), 6.24 (s, 1H),
2.27 (d, J = 0.9 Hz, 3H); 13C NMR (500 MHz, CDCl3): δ 162.1,
156.3, 140.2, 136.1, 132.5, 131.4, 129.1, 128.5, 126.4, 126.3, 123.1,
112.8, 104.6, 19.5; IR (KBr, cm−1) 3110, 3076, 3014, 2923, 1716,
1589, 1249, 1051, 840, 790, 756, 690; HRMS (ESI) m/z: calcd. for
C14H10NaO2 [M+Na]+ 233.0578, found 233.0576.
3,8-Dimethyl-1H-isochromen-1-one (3be): Light yellow solid;
1
mp 91−93 °C, yield: 68% (95 mg); H NMR (400 MHz, CDCl3) δ
7.47 (t, J = 7.7 Hz, 1H), 7.19 (d, J = 7.5 Hz, 1H), 7.12 (d, J = 7.8 Hz,
1H), 6.16 (d, J = 0.9 Hz, 1H), 2.79 (s, 3H), 2.22 (d, J = 1.0 Hz, 3H);
13C NMR (400 MHz, CDCl3): δ 162.2, 154.0, 143.2, 139.1, 133.8,
130.3, 123.0, 118.3, 103.9, 23.1, 19.3; IR (KBr, cm−1) 3091, 3068,
3043, 2969, 2921, 2848, 1724, 1668, 1573, 1475, 1390, 1193, 1162,
1037, 987, 835, 800, 779, 688; HRMS (ESI) m/z: calcd. for
C11H10NaO2 [M + Na]+ 197.0579, found 197.0574.
3-Methyl-1H-benzo[g]isochromen-1-one (3ke):23e Light yel-
1
low solid; mp 194−197 °C, yield: 61% (103 mg); H NMR (400
MHz, CDCl3) δ 8.84 (s, 1H), 7.96 (d, J = 8.7 Hz, 1H), 7.85 (d, J = 8.1
Hz, 1H), 7.69 (s, 1H), 7.60 (ddd, J = 8.3, 6.8, 1.2 Hz, 1H), 7.50 (ddd, J
= 8.1, 6.8, 1.2 Hz, 1H), 6.31 (s, 1H), 2.28 (d, J = 0.8 Hz, 3H); 13C
NMR (400 MHz, CDCl3): δ 163.0, 152.7, 136.5, 132.3, 132.0, 131.7,
129.6, 129.2, 127.5, 126.2, 122.7, 118.5, 103.3, 19.6; IR (KBr, cm−1)
3,7-Dimethyl-1H-isochromen-1-one (3ce):23b White solid, mp
123−126 °C, yield 65% (91 mg); 1H NMR (400 MHz, CDCl3) δ 8.04
E
dx.doi.org/10.1021/jo502231y | J. Org. Chem. XXXX, XXX, XXX−XXX