10.1002/ejoc.202001455
European Journal of Organic Chemistry
FULL PAPER
4H), 2.87 (t, J = 6.9 Hz, 4H). 13C{1H} NMR (CDCl3, 100 MHz): δ 167.5,
149.7, 148.5, 142.0, 137.0, 132.7, 130.3, 130.1, 129.8, 129.0, 127.7,
125.2, 124.4, 118.3, 41.0, 35.0. IR (ν=max/cm-1): 3215, 3061, 2929,
2864, 1632, 1580, 1486, 1439, 1315, 1246, 1086,1043, 811, 770, 636,
456. HRMS (DART, [M+H]+) m/z calcd for C18H16ClN2O1 [M+H]+
311.0951, found 311.094.
Pyrrolidin-1-yl(quinolin-4-yl)methanone (11t). Using the general
procedure, this compound was obtained from 1-vinylindoline-2,3-
dione (8a) (50.0 mg, 0.2887 mmol) as a brown oil (43.2 mg, 0.1909
mmol) in 66 % yield after purification by flash column chromatography.
1H NMR (CDCl3, 400 MHz): δ 8.95 (d, J = 4.3 Hz, 1H), 8.14 (d, J = 8.5
Hz, 1H), 7.91 – 7.81 (m, 1H), 7.80 – 7.69 (m, 1H), 7.66 – 7.52 (m, 1H),
7.34 (d, J = 4.3 Hz, 1H), 3.78 (t, J = 7.0 Hz, 2H), 3.11 (t, J = 6.7 Hz,
2H), 2.01 (p, J = 7.0 Hz, 2H), 1.85 (p, J = 6.8 Hz, 2H). 13C{1H} NMR
(CDCl3, 100 MHz): δ 166.9, 166.7, 150.1, 148.5, 130.0, 127.6, 124.8,
123.8, 117.8, 48.4, 45.7, 26.0, 24.5. IR (ν=max/cm-1): 3489, 3057, 2971,
2878, 1633, 1588, 1442, 1382, 1184, 855, 769, 638. HRMS (DART,
[M+H]+) m/z calcd for C14H15N2O1 [M+H]+ 227.1184, found 227.1189.
N-(2-Methoxybenzyl)quinoline-4-carboxamide (11o). Using the
general procedure, this compound was obtained from 1-vinylindoline-
2,3-dione (8a) (50.0 mg, 0.2887 mmol) as a beige solid (48.2 mg,
0.1649 mmol) in 57 % yield after purification by flash column
chromatography. m. p. 104-106°C 1H NMR (CDCl3, 400 MHz): δ 8.76
(d, J = 4.3 Hz, 1H), 8.09 (dd, J = 8.5, 1.3 Hz, 1H), 7.99 (d, J = 8.9 Hz,
1H), 7.63 (ddd, J = 8.4, 6.9, 1.4 Hz, 1H), 7.46 (ddd, J = 8.3, 6.9, 1.3
Hz, 1H), 7.31 (d, J = 1.6 Hz, 1H), 7.29 (s, 1H), 7.25 – 7.20 (m, 1H),
6.89 (td, J = 7.5, 1.0 Hz, 1H), 6.82 (d, J = 8.2 Hz, 1H), 6.67 (s, 1H),
4.63 (d, J = 5.8 Hz, 2H), 3.76 (s, 3H). 13C{1H} NMR (CDCl3, 100 MHz):
δ 178.1, 150.8, 140.8, 134.3, 132.5, 129.6, 127.8, 127.5, 127.0, 126.4,
124.8, 123.4, 109.8, 108.8, 103.3, 61.4, 60.4, 47.5, 29.8, 21.1, 14.2.
IR (ν=max/cm-1): 3273, 3073, 2926, 2838, 1645, 1546, 1460, 1242,
1024, 868, 751, 705. HRMS (DART, [M+H]+) m/z calcd for
C18H17N2O2 [M+H]+ 293.1290, found 293.1295.
N-Heptyl-6-methylquinoline-4-carboxamide (11aa). Using the general
procedure, this compound was obtained from 5-methyl-1-
vinylindoline-2,3-dione (8c) (54.0 mg, 0.2887 mmol) as a beige solid
(53.0 mg, 0.1864 mg) in 65 % yield after purification by flash column
chromatography, mp 81-83 °C. 1H NMR (CDCl3, 400 MHz): δ 8.67 (d,
J = 4.3 Hz, 1H), 7.92 (d, J = 8.6 Hz, 1H), 7.87 (s, 1H), 7.52 (dd, J =
8.6, 1.9 Hz, 1H), 7.21 (d, J = 4.3 Hz, 1H), 6.46 (s, 1H), 3.55 – 3.41 (m,
2H), 2.50 (s, 3H), 1.63 (p, J = 7.7, 7.3 Hz, 2H), 1.45 – 1.23 (m, 8H),
0.95 – 0.83 (m, 3H). 13C{1H} NMR (CDCl3, 100 MHz): δ 167.6, 148.8,
147.2, 141.7, 137.8, 132.3, 129.4, 124.5, 124.1, 118.3, 40.2, 31.9,
29.7, 29.1, 27.1, 22.7, 21.9, 14.2. IR (ν=max/cm-1): 3291, 3063, 2957,
2925, 2854, 1638, 1577, 1540, 1463, 1307, 1150, 1041, 856, 825,
N-(2,4-Dichlorobenzyl)quinoline-4-carboxamide (11p). Using the
general procedure, this compound was obtained from 1-vinylindoline-
2,3-dione (8a) (50.0 mg, 0.2887 mmol) as a white solid (29.7 mg,
0.0897 mmol) in 31 % yield after purification by flash column
chromatography, mp 175-177 °C. 1H NMR (CDCl3, 400 MHz): δ 8.76
(d, J = 4.3 Hz, 1H), 8.09 – 8.04 (m, 1H), 8.00 (d, J = 8.4 Hz, 1H), 7.66
(ddd, J = 8.4, 6.9, 1.4 Hz, 1H), 7.49 (ddd, J = 8.3, 6.9, 1.3 Hz, 1H),
7.35 (d, J = 2.2 Hz, 1H), 7.28 (d, J = 4.3 Hz, 1H), 7.19 (d, J = 1.8 Hz,
1H), 6.71 (t, J = 5.1 Hz, 1H), 4.65 (d, J = 6.0 Hz, 2H). 13C{1H} NMR
(CDCl3, 100 MHz): δ 167.4, 148.7, 141.5, 134.7, 134.5, 133.8, 131.5,
130.2, 130.0, 129.7, 127.9, 127.7, 125.2, 124.5, 118.5, 41.8. IR
(ν=max/cm-1): 3296, 3057, 1634, 1583, 1531, 1456, 1288, 1098, 1056,
899, 791, 666. 451 HRMS (DART, [M+H]+) m/z calcd for
C17H13Cl2N2O1 [M+H]+ 331.0405, found 331.0417.
711, 622, 477. HRMS (DART, [M+H]+) m/z
calcd for
C18H25N2O1 [M+H]+ 285.1967, found 285.1967.
N-(3,4-Dimethoxyphenethyl)-6-methylquinoline-4
carboxamide
(11ab). Using the general procedure, this compound was obtained
from 5-methyl-1-vinylindoline-2,3-dione (8c) (54.0 mg, 0.2887 mmol)
as a beige solid (53.5 mg, 01527 mmol) in 53 % yield after purification
by flash column chromatography, mp 123-125 °C. 1H NMR (CDCl3,
400 MHz): δ 8.64 (d, J = 3.5 Hz, 1H), 7.90 (d, J = 8.6 Hz, 1H), 7.83 (s,
1H), 7.51 (d, J = 8.6 Hz, 1H), 7.18 (d, J = 4.2 Hz, 1H), 6.77 (s, 2H),
6.74 (s, 1H), 6.48 (s, 1H), 3.82 (s, 3H), 3.79 (s, 5H), 2.93 (t, J = 6.9
Hz, 2H), 2.48 (s, 3H) 13C{1H} NMR (CDCl3, 100 MHz): δ 167.7, 149.2,
148.7, 147.9, 147.2, 141.4, 137.8, 132.3, 131.0, 129.4, 124.4, 124.0,
120.8, 118.3, 111.9, 111.5, 56.0, 55.9, 41.2, 35.2, 21.9. IR (ν=max/cm-
1): 3322, 3063, 2963, 2933, 2876, 2836, 1637, 1578, 1537, 1462,
1443, 1330, 1261, 1236, 1156, 1025, 855, 805, 655, 633. HRMS
(DART, [M+H]+) m/z calcd for C21H23N2O3 [M+H]+ 351.1709, found
351.1702.
N-(2,4-Dimethoxybenzyl)quinoline-4-carboxamide (11q). Using the
general procedure, this compound was obtained from 1-vinylindoline-
2,3-dione (8a) (50.0 mg, 0.2887 mmol) as a beige solid (32.2 mg,
0.0999 mmol) in 35 % yield after purification by flash column
chromatography, mp 119-121 °C. 1H NMR (CDCl3, 400 MHz): δ 8.84
(d, J = 4.3 Hz, 1H), 8.23 – 8.14 (m, 1H), 8.07 (d, J = 8.4 Hz, 1H), 7.71
(ddd, J = 8.4, 6.9, 1.4 Hz, 1H), 7.55 (ddd, J = 8.3, 6.9, 1.2 Hz, 1H),
7.37 (d, J = 4.3 Hz, 1H), 7.29 (d, J = 8.8 Hz, 1H), 6.63 (s, 1H), 6.46
(dq, J = 4.1, 2.4 Hz, 2H), 4.63 (d, J = 5.7 Hz, 2H), 3.81 (s, 3H), 3.80
(s, 3H). 13C{1H} NMR (CDCl3, 100 MHz): δ 166.9, 161.0, 158.8, 149.9,
148.7, 142.4, 131.0, 130.0, 129.9, 127.6, 125.4, 124.6, 118.6, 118.2,
104.2, 98.8, 55.5, 39.9. IR (ν=max/cm-1): 3295, 3074, 2924, 2837,
1641, 1616, 1584, 1539, 1461, 1428, 1295, 1262, 1209, 1126, 1034,
834, 755 634, 463. HRMS (DART, [M+H]+) m/z calcd for
C19H19N2O3 [M+H]+ 323.1396, found 323.1386.
(6-Methylquinolin-4-yl)(pyrrolidin-1-yl)methanone (11ac). Using the
general procedure, this compound was obtained from 5-methyl-1-
vinylindoline-2,3-dione (8c) (54.0 mg, 0.2887 mmol) as a brown oil
(47.9 mg, 0.1993 mmol) in 69 % yield after purification by flash column
1
chromatography. H NMR (CDCl3, 400 MHz): δ 8.86 (d, J = 4.3 Hz,
1H), 8.01 (d, J = 8.4 Hz, 1H), 7.56 (d, J = 9.1 Hz, 2H), 7.28 (d, J = 4.3
Hz, 1H), 3.79 (t, J = 7.1 Hz, 2H), 3.12 (t, J = 6.8 Hz, 2H), 2.52 (s, 3H),
2.01 (p, J = 6.9 Hz, 2H), 1.86 (p, J = 6.8 Hz, 2H). 13C{1H} NMR (CDCl3,
100 MHz): δ 167.0, 149.2, 147.3, 142.9, 137.8, 132.4, 129.8, 124.0,
1
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