Molecules 2015, 20
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3-(Diphenylmethylene)-1-methylindolin-2-one (12): Yellow solid, mp = 165.9 °C (lit. [13],
153.2–154.9 °C); Rf = 0.33 (silica gel, hexanes:EtOAc 4:1); IR (film) 3054, 2923, 1700, 1606, 1469 cm−1;
1H-NMR (500 MHz, CDCl3): δ = 7.45–7.41 (m, 3H), 7.37–7.32 (m, 7H), 7.17 (td, J = 7.5, 1.0 Hz, 1H),
6.76 (d, J = 8.0 Hz, 1H), 6.68 (td, J = 7.5, 1.0 Hz, 1H), 6.42 (dd, J = 7.5, 1.0 Hz, 1H), 3.21 (s, 3H) ppm;
13C-NMR (125 MHz, CDCl3): δ = 167.0, 154.7, 143.5, 141.5, 140.1, 130.1, 129.5, 129.3, 129.2, 129.1,
128.9, 128.0, 124.4, 123.4, 123.3, 121.5, 107.8, 26.0 ppm; HRMS (ESI-TOF): calcd for C22H17 NO [M
+ H]+: 312.1388, found 312.1394.
(Z)-2-Benzylidene-4-methyl-2H-benzo[b][1,4]oxazin-3(4H)-one (13): White solid; mp = 155.1 °C
(lit. [25], 155–156 °C); Rf = 0.60 (silicagel, CH2Cl2); IR (film) 3727, 2923, 2853, 1668, 1630, 1504,
1422, 1381, 1288, 1167, 1127, 1039, 743, 686 cm−1; 1H-NMR (500 MHz, CDCl3): δ = 7.85 (d, J = 7.5 Hz,
2H), 7.41 (t, J = 7.5 Hz, 2H), 7.31 (t, J = 7.3 Hz, 1H), 7.20–7.18 (m, 1H), 7.10–7.07 (m, 2H), 7.02–7.00 (m,
1H), 6.96 (s, 1H), 3.48 (s, 3H) ppm; 13C-NMR (125 MHz, CDCl3): δ = 157.4, 142.0, 141.2, 133.9, 130.1,
128.7, 128.3, 127.6, 123.9, 123.4, 116.1, 114.5, 113.0, 28.8 ppm; HRMS (EI): calcd for C16H13NO2 [M]+:
251.0946, found 251.0947.
3-(bis(4-Methoxyphenyl)methylene)-1-methylindolin-2-one (14a): Brown solid; mp = 192.2 °C; Rf = 0.2
(silica gel, hexanes:EtOAc 4:1); IR (film) 3017, 1691, 1603, 1251 cm−1; 1H-NMR (500 MHz, CDCl3):
δ = 7.29–7.24 (m, 4H), 7.14 (td, J = 8.0, 1.5 Hz, 1H), 6.93 (d, J = 9.0 Hz, 2H), 6.88 (d, J = 9.0 Hz, 2H),
6.77 (d, J = 8.0 Hz, 1H), 6.70 (td, J = 8.0, 1.5 Hz, 1H), 6.57 (dd, J = 7.5, 0.5 Hz, 1H), 3.88
(s, 3H), 3.84 (s, 3H), 3.22 (s, 3H) ppm; 13C-NMR (125 MHz, CDCl3): δ = 167.3, 161.0, 160.8, 155.1,
142.8, 133.9, 132.9, 132.4, 132.1, 128.0, 124.3, 122.7, 122.5, 121.3, 114.2, 113.2, 107.7, 55.5, 55.4, 26.0
ppm; HRMS (ESI-TOF): calcd for C24H21 NO3 [M + H]+: 372.1600, found 372.1611.
3-(bis(4-Chlorophenyl)methylene)-1-methylindolin-2-one (14b): Yellow solid; mp = 134.4 °C; Rf = 0.33
1
(silica gel, hexanes:EtOAc 4:1); IR (film) 3054, 2927, 1699, 1606, 1486, 1089 cm–1; H-NMR
(500 MHz, CDCl3): δ = 7.41 (dd, J = 7.0, 2.0 Hz, 2H), 7.33 (dd, J = 7.0, 2.0 Hz, 2H), 7.26–7.20 (m, 5H),
6.78 (d, J = 8.0 Hz, 1H), 6.73 (td, J = 7.5, 1.0 Hz, 1H), 6.52 (d, J = 7.5 Hz, 1H), 3.20 (s, 3H) ppm;
13C-NMR (125 MHz, CDCl3): δ = 166.7, 151.4, 143.5, 139.3, 138.0, 135.7, 135.6, 131.7, 131.1, 129.5,
129.4, 128.3, 125.1, 123.2, 122.8, 121.7, 108.1, 26.0 ppm; HRMS (ESI-TOF): calcd for C22H15Cl2 NO
[M + H]+: 380.0609, found 380.0612.
3-(bis(4-Nitrophenyl)methylene)-1-methylindolin-2-one (14c): Brown solid; mp = 244.5 °C; Rf = 0.21
1
(silica gel, hexanes:EtOAc 3:1); IR (film) 3073, 1703, 1601, 1517, 1486, 1344, 1098 cm−1; H-NMR
(500 MHz, CDCl3): δ = 8.34 (dd, J = 7.0, 2.0 Hz, 2H), 8.24 (dd, J = 7.0, 2.0 Hz, 2H), 7.56 (dd, J = 7.0,
2.0 Hz, 2H), 7.48 (dd, J = 7.0, 2.0 Hz, 2H), 7.29 (dd, J = 7.5, 1.0 Hz, 1H), 6.83 (d, J = 8.0 Hz, 1H), 6.76
(td, J = 8.0, 1.0 Hz, 1H), 6.45 (d, J = 7.5, 1H), 3.20 (s, 3H) ppm; 13C-NMR (125 MHz, CDCl3):
δ = 166.0, 148.4, 148.1, 147.1, 146.3, 145.6, 144.3, 130.9, 130.6, 130.4, 127.5, 124.8, 123.63,
123.61, 122.2, 121.4, 108.7, 26.1 ppm; HRMS (ESI-TOF): calcd for C22H15N3O5 [M + H]+: 402.1092, found
402.1097.
(Z)-3-((4-Methoxyphenyl)(phenyl)methylene)-1-methylindolin-2-one (Z-14d): Yellow solid; mp = 153.0 °C
(lit. [26], 163.8-164.3 °C); Rf = 0.24 (silica gel, hexanes:EtOAc 4:1); IR (film) 2931, 1696, 1604,