Molecules 2017, 22, 503
15 of 20
(CDCl3):
1H), 7.49–7.45 (m, 3H), 7.34–7.32 (m, 2H), 7.20 (td, J = 7.7, 0.9 Hz, 1H), 6.79 (d, J = 7.8 Hz, 1H),
6.70 (td, J = 7.7, 0.7 Hz, 1H), 6.49 (d, J = 7.7 Hz, 1H), 3.20 (s, 3H) ppm; 13C-NMR (CDCl3):
= 166.6,
δ = 8.23–8.21 (m, 1H), 8.17–8.16 (m, 1H), 7.69 (d, J = 7.7 Hz, 1H), 7.53 (t, J = 8.0 Hz,
δ
150.6, 148.2, 143.8, 141.7, 140.1, 136.1, 129.84, 129.80, 129.5, 129.3, 128.9, 126.0, 125.0, 123.7, 123.6, 122.5,
121.9, 108.1, 26.1 ppm; HRMS (EI): calcd. for C22H16N2O3 [M+]: 356.1161, found 356.1159.
(E)-3-((2-Methoxyphenyl)(phenyl)methylene)-1-methylindolin-2-one ((E)-3l): Yellow solid; m.p. = 188.5 ◦C;
1
Rf = 0.33 (silica gel, hexanes
(CDCl3):
7.05 (t, J = 7.5 Hz, 1H), 7.00 (d, J = 8.3 Hz, 1H), 6.75 (d, J = 7.8 Hz, 1H), 6.69 (t, J = 7.7 Hz, 1H),
6.23 (d, J = 7.8 Hz, 1H), 3.63 (s, 3H), 3.19 (s, 3H) ppm; 13C-NMR (CDCl3):
= 166.7, 156.4, 151.4, 143.4,
−
EtOAc 4:1); IR (film) 2918, 2849, 1701, 1604, 1094 cm−1; H-NMR
= 7.44–7.40 (m, 3H), 7.36–7.32 (m, 3H), 7.21 (dd, J = 7.5, 1.5 Hz, 1H), 7.16 (t, J = 7.7 Hz, 1H),
δ
δ
139.7, 130.5, 130.3, 129.6, 129.2, 128.7, 128.5, 127.6, 125.0, 123.5, 123.0, 121.7, 121.5, 112.2, 107.6, 55.9,
25.9 ppm; HRMS (EI): calcd. for C23H19NO2 [M+]: 341.1416, found 341.1419.
(Z)-3-((2-Methoxyphenyl)(phenyl)methylene)-1-methylindolin-2-one ((Z)-3l): Yellow solid; m.p. = 139.3 ◦C;
Rf = 0.24 (silica gel, hexanes
1H-NMR (CDCl3):
= 7.40 (s, 5H), 7.34–7.31 (m, 1H), 7.19–7.14 (m, 2H), 6.97 (td, J = 7.5, 0.8 Hz, 1H),
6.93 (d, J = 8.3 Hz, 1H), 6.76 (d, J = 7.7 Hz, 1H), 6.68 (td, J = 7.7, 0.9 Hz, 1H), 6.52 (d, J = 7.7 Hz, 1H),
3.70 (s, 3H), 3.17 (s, 3H) ppm; 13C-NMR (CDCl3):
= 166.8, 156.7, 150.6, 143.6, 140.9, 130.4, 129.7, 129.6,
−
EtOAc 4:1); IR (film) 3053, 2925, 2854, 1704, 1606, 1469, 1095 cm−1
;
δ
δ
128.9, 128.8, 128.7, 128.6, 125.5, 123.3, 122.8, 121.4, 120.7, 111.4, 107.7, 55.8, 25.9 ppm; HRMS (EI): calcd.
for C23H19NO2 [M+]: 341.1416, found 341.1419.
(E)-3-((2-Chlorophenyl)(phenyl)methylene)-1-methylindolin-2-one ((E)-3m): Yellow solid; m.p. = 164.6 ◦C;
Rf = 0.33 (silica gel, hexanes
= 7.53–7.51 (m, 1H), 7.49–7.47 (m, 2H), 7.41–7.36 (m, 5H), 7.34–7.32 (m, 1H), 7.18 (td, J = 7.7, 1.1 Hz,
1H), 6.77 (d, J = 7.7 Hz, 1H), 6.69 (td, J = 7.7, 1.0 Hz, 1H), 6.04 (d, J = 7.7 Hz, 1H), 3.21 (s, 3H) ppm;
−
EtOAc 4:1); IR (film) 3053, 2918, 1703, 1605, 1095 cm−1; 1H-NMR (CDCl3):
δ
13C-NMR (CDCl3):
δ = 166.4, 150.1, 143.6, 140.0, 137.9, 132.5, 130.7, 130.0, 129.9, 129.7, 129.3, 129.1,
127.8, 125.7, 123.1, 123.0, 122.0, 107.9, 26.0 ppm; HRMS (EI): calcd. for C22H16ClNO [M+]: 345.0920,
found 345.0921.
(Z)-3-((2-Chlorophenyl)(phenyl)methylene)-1-methylindolin-2-one ((Z)-3m): Yellow solid; m.p. = 199.5 ◦C;
Rf = 0.34 (silica gel, hexanes
(CDCl3): = 7.49–7.43 (m, 6H), 7.32–7.29 (m, 2H), 7.25–7.21 (m, 2H), 6.79 (d, J = 7.8 Hz, 1H),
6.75 (t, J = 7.6 Hz, 1H), 6.70 (d, J = 7.7 Hz, 1H), 3.19 (s, 3H) ppm; 13C-NMR (CDCl3):
= 166.6, 149.3,
−
EtOAc 4:1); IR (film) 3054, 3017, 2931, 1706, 1606, 1099 cm−1; 1H-NMR
δ
δ
144.0, 140.1, 139.4, 132.3, 129.8, 129.6, 129.4, 129.3, 129.2, 129.0, 128.9, 127.1, 126.4, 123.5, 122.1, 121.6,
108.0, 26.0 ppm; HRMS (EI): calcd. for C22H16ClNO [M+]: 345.0920, found 345.0920.
◦
(Z)-1-Methyl-3-((2-nitrophenyl)(phenyl)methylene)indolin-2-one ((Z)-3n): Yellow solid; m.p. = 206.6 C;
Rf = 0.27 (silica gel, hexanes
EtOAc 2:1); IR (film) 3063, 3021, 2930, 1700, 1522 cm−1; 1H-NMR (CDCl3):
−
δ
= 8.15 (dd, J = 8.2, 1.0 Hz, 1H), 7.66 (td, J = 7.6, 1.1 Hz, 1H), 7.54–7.51 (m, 2H), 7.43–7.40 (m, 5H),
7.24–7.21 (m, 1H), 6.78 (d, J = 7.7 Hz, 1H), 6.75–6.74 (m, 2H), 3.15 (s, 3H) ppm; 13C-NMR (CDCl3):
δ = 166.8, 148.4, 147.7, 143.9, 138.1, 136.9, 133.7, 130.7, 129.7, 129.6, 129.0, 128.9, 125.2, 125.0, 123.4, 122.0,
121.8, 108.1, 26.0 ppm; HRMS (EI): calcd. for C22H16N2O3 [M+]: 356.1161, found 356.1163.
◦
(E)-1-Methyl-3-(phenyl(pyridin-3-yl)methylene)indolin-2-one ((E)-3p): Yellow solid; m.p. = 159.0 C;
Rf = 0.24 (silica gel, hexanes
1H-NMR (CDCl3):
= 8.73 (brs, 2H), 7.62 (d, J = 7.8 Hz, 1H), 7.42–7.36 (m, 4H), 7.33–7.30 (m, 2H),
7.19 (td, J = 7.7, 1.1 Hz, 1H), 6.79 (d, J = 7.7 Hz, 1H), 6.70 (td, J = 7.7, 1.0 Hz, 1H), 6.42 (d, J = 7.5 Hz, 1H),
−
EtOAc 2:1); IR (film) 3732, 3052, 2926, 1700, 1470, 1095, 749, 698 cm−1
;
δ
3.21 (s, 3H) ppm; 13C-NMR (CDCl3):
δ = 166.5, 150.3, 150.0, 143.7, 139.4, 137.2, 130.1, 129.5, 129.5,
128.2, 125.7, 123.0, 122.8, 121.8, 108.1, 26.0 ppm; HRMS (EI): calcd. for C21H16N2O [M+]: 312.1263,
found 312.1262.
(Z)-1-Methyl-3-(phenyl(pyridin-3-yl)methylene)indolin-2-one ((Z)-3p): Yellow oil; Rf = 0.12 (silica gel,
hexanes δ = 8.58 (d, J = 17.9 Hz, 2H), 7.65 (d, J = 7.8 Hz, 1H), 7.48–7.44
EtOAc 2:1); 1H-NMR (CDCl3):
−