Page 9 of 12
The Journal of Organic Chemistry
CDCl3) δ 2.07-2.17 (m, 1H), 2.34-2.44 (m, 1H), 2.46-2.54 (m,
3,3-dimethylisoindolin-1-one (2j).7a Eluent: petroleum
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1H), 2.56-2.64 (m, 1H), 5.02 (t, J = 6.6 Hz, 1H), 6.62 (s, 1H),
6.93-7.02 (m, 2H), 7.24 (d, J = 4.0 Hz, 1H); 13C{1H} NMR (100
MHz, CDCl3) δ 30.2, 31.2, 54.0, 124.1, 124.8, 127.0, 146.5,
178.1
ether/ethyl acetate/methanol = 10:10:1~5:5:1; White solid (39
mg, 99 %); m.p. = 152-154 oC; 1H NMR (400 MHz, CDCl3) δ
1.58 (s, 6H), 7.41 (d, J = 7.6 Hz, 1H), 7.44 (td, J = 0.4, 7.4 Hz,
1H), 7.56 (td, J = 0.8, 7.4 Hz, 1H), 7.83 (d, J = 7.6 Hz, 1H),
8.08 (brs, 1H); 13C{1H} NMR (100 MHz, CDCl3) δ 27.7, 59.2,
120.9, 123.8, 127.9, 130.8, 132.0, 153.2, 170.1
3-methylisoindolin-1-one (2k).7a Eluent: petroleum ether/ethyl
acetate/methanol = 10:10:1~5:5:1; White solid (29 mg, 71 %);
m.p. = 102-104 oC; 1H NMR (400 MHz, CDCl3) δ 1.52 (d, J =
6.8 Hz, 3H), 4.72 (q, J = 6.8 Hz, 1H), 7.46 (q, J = 7.4 Hz, 2H),
7.57(t, J = 7.4 Hz, 1H), 7.85 (d, J = 7.4 Hz, 1H), 8.18 (brs, 1H);
13C{1H} NMR (100 MHz, CDCl3) δ 20.2, 52.8, 122.2, 123.6,
128.0, 131.7, 131.9, 149.0, 171.3
3-benzylisoindolin-1-one (2l).13 Eluent: petroleum ether/ethyl
acetate/methanol, 10:10:1~5:5:1; White solid (22 mg, 71 %);
m.p. = 128-130 oC;1H NMR (400 MHz, CDCl3) δ 2.79 (dd, J =
10.0, 12.4 Hz, 1H), 3.24 (dd, J = 4.2, 13.6 Hz, 1H), 4.80 (t, J =
7.4 Hz, 1H), 6.45 (brs, 1H), 7.20-2.25 (m, 2H), 7.30 (d, J = 6.6
Hz, 1H), 7.34 (d, J = 7.4 Hz, 3H), 7.48 (t, J = 7.4 Hz, 1H), 7.55
(t, J = 7.4 Hz, 1H), 7.84 (d, J = 7.4 Hz, 1H); 13C{1H} NMR (100
MHz, CDCl3) δ 41.4, 58.0, 122.7, 123.9, 127.2, 128.4, 128.9,
129.3, 131.8, 131.9, 137.0, 146.9, 170.4
5-phenylpyrrolidin-2-one
(2b).7a
Eluent:
petroleum
ether/ethyl acetate/methanol = 10:10:1~5:5:1; White solid (26
o
1
mg, 81%); m.p. = 98-101 C; H NMR (400 MHz, CDCl3) δ
1.91-2.00 (m, 1H), 2.35-2.49 (m, 2H), 2.50-2.59 (m, 1H), 4.75
(t, J = 7.0 Hz, 1H), 6.64 (brs, 1H), 7.23 -7.30 (m, 3H), 7.34-7.38
(m, 2H); 13C{1H} NMR (100 MHz, CDCl3) δ 31.4, 31.3, 58.1,
125.6, 127.9, 128.9, 142.5, 178.8
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5-(4-methoxyphenyl)pyrrolidin-2-one
(2c).7a
Eluent:
petroleum ether/ethyl acetate/methanol = 10:10:1~5:5:1; White
o
solid (61 mg, 76 %); m.p. = 118-120 C;1H NMR (400 MHz,
CDCl3) δ 1.87-1.95 (m, 1H), 2.32-2.46 (m, 2H), 2.47-2.58 (m,
1H), 3.79 (s, 3H), 4.69 (t, J = 7.0 Hz, 1H), 6.79 (s, 1H), 6.88 (d,
J = 8.0 Hz, 2H), 7.21 (d, J = 8.0 Hz, 2H); 13C{1H} NMR (100
MHz, CDCl3) δ 30.6, 31.4, 55.3, 57.7, 114.2, 126.9, 134.6,
159.2, 178.8
5-(p-tolyl)pyrrolidin-2-one (2d).9b Eluent: petroleum
ether/ethyl acetate/methanol = 10:10:1~5:5:1; White solid (26
o
1
mg, 51%); m.p. = 112-115 C; H NMR (400 MHz, CDCl3) δ
1.93-2.00 (m, 1H), 2.35 (s, 3H), 2.39-2.47 (m, 2H), 2.51-2.58
(m, 1H), 4.72 (t, J = 7.0 Hz, 1H), 5.90 (brs, 1H), 7.18 (s, 4H);
13C{1H} NMR (100 MHz, CDCl3) δ 21.1, 30.4, 31.4, 57.9,
125.6, 129.5, 137.6, 139.5, 178.6.
2-(((3aR,7aR)-2-oxooctahydro-3aH-indol-3a-
yl)methyl)isoindoline-1,3-dione (2m).7a Eluent: petroleum
ether/ethyl acetate/methanol, 10:10:1~5:5:1; White solid (16
o
1
mg, 92%); m.p. = 173-176 C; H NMR (400 MHz, CDCl3) δ
1.45-1.59 (m, 6H), 1.68-1.75 (m, 1H), 1.82-1.91 (m, 1H), 2.01
(d, J = 16.4 Hz, 1H), 2.49 (d, J = 16.4 Hz, 1H), 3.58 (s, 1H),
3.79 (s, 2H), 6.04 (s, 1H), 7.75 (d, J = 2.2 Hz, 2H), 7.86 (d, J =
2.2 Hz, 2H); 13C{1H} NMR (100 MHz, CDCl3) δ 19.8, 21.1,
26.3, 30.7, 42.4, 42.9, 43.2, 55.4, 123.5, 131.8, 134.3, 168.9,
176.8
5-vinylpyrrolidin-2-one (2e).9c Eluent: petroleum ether/ethyl
acetate/methanol = 10:10:1~5:5:1; Colorless oil (15 mg, 56 %);
1H NMR (400 MHz, CDCl3) δ 1.77-1.86 (m, 1H), 2.25-2.42 (m,
3H), 4.16 (q, J = 6.4 Hz, 1H), 5.13 (d, J = 10.2 Hz, 1H), 5.22
(d, J = 17.2 Hz, 1H), 5.75-5.85 (m, 1H), 6.12 (brs, 1H); 13C{1H}
NMR (100 MHz, CDCl3) δ 28.0, 29.9, 56.7, 115.7, 138.7, 178.5
hexahydrocyclopenta[b]pyrrol-2(1H)-one (2f).9c Eluent:
5-methoxyindolin-2-one (2n).7a Eluent: petroleum ether/ethyl
acetate/methanol, 10:10:1~5:5:1; White solid (36 mg, 65 %);
m.p. = 140-142 oC; 1H NMR (400 MHz, CDCl3) δ 3.52 (s, 2H),
3.78 (s, 3H), 6.77 (q, J = 8.2 Hz, 2H), 6.85 (s, 1H), 8.50 (brs,
1H); 13C{1H} NMR (100 MHz, CDCl3) δ 36.8, 55.8, 110.2,
111.7, 112.5, 126.7, 136.2, 155.7, 178.2
7-methoxyindolin-2-one (2n’).7a Eluent: petroleum ether/ethyl
acetate/methanol, 10:10:1~5:5:1; White solid (9 mg, 16 %);
m.p. = 139-141 oC; 1H NMR (400 MHz, CDCl3) δ 3.56 (s, 2H),
3.88 (s, 3H), 6.83 (dd, J = 7.4, 17.2 Hz, 2H), 6.98 (t, J = 7.8 Hz,
1H), 8.08 (brs, 1H); 13C{1H} NMR (100 MHz, CDCl3) δ 36.8,
55.7, 110.2, 117.0, 122.8, 126.0, 131.3, 143.8, 176.6
petroleum ether/ethyl acetate/methanol
= 10:10:1~5:5:1;
1
Colorless oil (27 mg, 76 %); H NMR (400 MHz, CDCl3) δ
1.49-1.55 (m, 1H), 1.60-1.73 (m, 4H), 1.74-1.82 (m, 1H), 2.05
(dd, J = 3.6, 17.6 Hz, 1H), 2.63 (dd, J = 10.2 Hz, 1H), 2.78-2.86
(m, 1H), 4.09-4.13 (m, 1H), 6.52 (brs, 1H); 13C{1H} NMR (100
MHz, CDCl3) δ 23.7, 34.3, 34.5, 37.2, 38.0, 59.3, 178.5
1-azaspiro[4.5]decan-2-one (2g).7a Eluent: petroleum ether
/ethyl acetate/methanol = 10:10:1~5:5:1; White solid (51 mg,
83 %); m.p. = 120-122 oC; 1H NMR (400 MHz, CDCl3) δ1.42
(s, 2H), 1.47-1.62 (m, 8H), 1.89 (t, J = 8.0 Hz, 2H), 2.38 (t, J =
8.0 Hz, 2H), 7.07 (brs, 1H); 13C{1H} NMR (100 MHz, CDCl3)
δ 23.0, 25.2, 30.0, 32.7, 38.3, 59.5, 177.5
5,6-dimethoxyindolin-2-one (2o).7a Eluent: petroleum
ether/ethyl acetate/methanol, 10:10:1~5:5:1; White solid (22
mg, 95 %); m.p. = 170-173 oC; 1H NMR (400 MHz, CDCl3) δ
3.50 (s, 2H), 3.85 (s, 3H), 3.86 (s, 3H), 6.55 (s, 1H), 6.84 (s,
1H), 8.77 (brs, 1H); 13C{1H} NMR (100 MHz, CDCl3) δ 36.5,
56.3, 56.8, 95.7, 109.7, 115.9, 136.1, 145.0, 149.4, 178.4
5,5-dimethylpyrrolidin-2-one (2h).7a Eluent: petroleum
ether/ethyl acetate/methanol = 10:10:1~5:5:1; Colorless oil (30
mg, 84 %); 1H NMR (400 MHz, CDCl3) δ 1.29 (s, 6H), 1.92 (t,
J = 8.0 Hz, 2H), 2.42 (t, J = 8.0 Hz, 2H), 7.10 (brs, 1H); 13C{1H}
NMR (100 MHz, CDCl3) δ 29.2, 30.7, 35.3, 56.6, 177.1
3-phenylisoindolin-1-one (2i).9d Eluent: petroleum ether/ethyl
acetate/methanol = 10:10:1~5:5:1; White solid (29 mg, 99 %);
6,7-dimethoxy-3,4-dihydroquinolin-2(1H)-one
(2p).7a
Eluent: petroleum ether/ethyl acetate/methanol, 10:10:1~5:5:1;
White solid (19 mg, 98 %); m.p. = 123-125 oC; 1H NMR (400
MHz, CDCl3) δ 2.62 (t, J = 7.4 Hz, 2H), 2.89 (t, J = 7.4 Hz, 2H),
3.85 (s, 3H), 3.87 (s, 3H), 6.53 (s, 1H), 6.84(s, 1H), 8.46 (s, 1H);
13C{1H} NMR (100 MHz, CDCl3) δ 25.0, 30.9, 56.2, 56.4,
100.6, 111.7, 114.8, 130.8, 144.7, 148.4, 172.3
o
m.p. = 209-212 C;1H NMR (400 MHz, DMSO-d6) δ 5.73 (s,
1H), 7.30 (t, J = 8.0 Hz, 4H), 7.36 (t, J = 7.2 Hz, 2H), 7.48 (t, J
= 7.2 Hz, 1H), 7.54 (t, J = 7.2 Hz, 1H), 7.72 (d, J = 7.2 Hz, 1H),
9.07 (brs, 1H); 13C{1H} NMR (100 MHz, DMSO-d6) δ 60.0,
123.3, 123.9, 127.0, 128.4, 128.6, 129.2, 131.8, 132.3, 140.1,
148.6, 170.1
6,7,8-trimethoxy-3,4-dihydroquinolin-2(1H)-one
(2q).
Eluent: petroleum ether/ethyl acetate/methanol, 10:10:1~5:5:1;
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