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J. Zhang et al. / Tetrahedron 67 (2011) 9347e9351
4.2.1. 3-Hydroxy-1-methyl-3-m-tolylindolin-2-one (3ac) (Table 2,
entry 3). Solid; mp 75.1e76.3 ꢀC; 1H NMR (DMSO-d6, 500 MHz):
127.6, 128.2, 128.5, 129.9, 131.5, 133.0, 133.1, 137.4, 143.5, 177.5; IR
(KBr): 3324, 3057, 2352, 1699, 1611, 1470, 1354, 1222, 1098, 752,
694 cmꢁ1; MS (EI, 70 eV): m/z (%)¼289 (Mþ, 36), 273 (100), 260
(50), 244 (84),127 (25), 77 (20). Anal. Calcd for C19H15NO2: C, 78.87;
H, 5.23. Found: C, 78.94; H, 5.28.
d
2.25 (3H, s), 3.15 (3H, s), 6.66 (1H, s), 7.00e7.19 (7H, m), 7.33e7.36
(1H, m). 13C NMR (DMSO-d6, 125 MHz):
d
21.2, 26.2, 77.1, 108.9,
122.6, 122.8, 124.4, 126.0, 128.1, 128.3, 129.4, 133.2, 137.3, 141.3,
143.4,176.8. IR (KBr): 3402, 2982, 2783,1704,1614,1358,1221,1086,
747 cmꢁ1. MS (EI, 70 eV): m/z (%)¼253 (Mþ, 100), 237 (45), 224 (82),
208 (99), 134 (32), 91 (51), 77 (30). Anal. Calcd for C16H15NO2: C,
75.87; H, 5.97. Found: C, 75.93; H, 6.02.
4.2.8. 3-(Biphenyl-4-yl)-3-hydroxy-1-methylindolin-2-one (3am) (Table
2, entry 13). Solid; mp 174.0e174.2 ꢀC; 1H NMR (CDCl3, 500 MHz):
d
3.18 (3H, s), 3.65 (1H, s), 6.85 (1H, d, J¼5 Hz), 7.04 (1H, t, J¼10 Hz),
7.25e7.38 (7H, m), 7.45e7.46 (4H, m); 13C NMR (CDCl3, 125 MHz):
d 26.5, 77.9, 108.7, 123.6, 125.0, 125.8, 127.1, 127.3, 127.4, 128.7, 129.9,
4.2.2. 3-Hydroxy-1-methyl-3-o-tolylindolin-2-one (3ad) (Table 2,
entry 4). Solid; mp 231.6e233.4 ꢀC; 1H NMR (DMSO-d6, 500 MHz):
131.5, 139.1, 140.5, 141.2, 143.5, 177.5; IR (KBr): 3059, 2319, 1700, 1612,
1471, 1366, 1223, 1089, 750, 695 cmꢁ1; MS (EI, 70 eV): m/z (%)¼315
(Mþ, 80), 286 (100), 270 (68), 210 (28), 152 (32). Anal. Calcd for
C21H17NO2: C, 79.98; H, 5.43. Found: C, 79.94; H, 5.49.
d
1.66 (3H, s), 3.19 (3H, s), 6.70 (1H, s), 6.87 (1H, d, J¼10 Hz),
6.97e7.09 (3H, m), 7.18e7.21 (1H, m), 7.28 (1H, t, J¼5 Hz), 7.33e7.36
(1H, m), 7.88e7.89 (1H, m); 13C NMR (DMSO-d6, 125 MHz):
18.6,
d
26.0, 76.2, 108.6, 122.7, 123.9, 125.5, 126.4, 127.6, 129.5, 131.0, 131.5,
134.0, 139.0, 143.9, 176.0; IR (KBr): 3320, 2987, 2622, 1699, 1615,
1460, 1120, 1090, 1029, 918, 770, 753 cmꢁ1; MS (EI, 70 eV): m/z (%)¼
253 (Mþ, 100), 237 (24), 224 (47), 210 (75), 91 (51), 77 (26). Anal.
Calcd for C16H15NO2: C, 75.87; H, 5.97. Found: C, 75.94; H, 5.92.
4.2.9. 3-Hydroxy-1-methyl-3-(thiophen-3-yl)indolin-2-one (3an) (Table
2, entry 14). Solid; mp 155e158 ꢀC; 1H NMR (CDCl3, 500 MHz):
d 3.22
(3H, s), 3.62 (1H, s), 6.89 (1H, d, J¼10 Hz), 7.11e7.43 (6H, m); 13C NMR
(CDCl3, 125 MHz):
d 26.5, 75.8, 108.7, 123.0, 123.4, 124.8, 125.7, 126.7,
130.0, 130.7, 140.8, 176.9; IR (KBr): 2981, 1704, 1357, 1220, 1094,
758 cmꢁ1; MS (EI, 70 eV): m/z (%)¼245 (Mþ, 78), 229 (28), 200 (60),
184 (100), 111 (25), 77 (33). Anal. Calcd for C13H11NO2S: C, 63.65; H,
4.52. Found: C, 63.72; H, 4.47.
4.2.3. 3-Hydroxy-3-(3-methoxyphenyl)-1-methylindolin-2-one (3af)
(Table 2, entry 5). Solid; mp 141.0e141.1 ꢀC; 1H NMR (DMSO-d6,
500 MHz):
d
3.14 (3H, s), 3.72 (3H, s), 6.67 (1H, d, J¼5 Hz), 6.72 (1H,
s), 6.82e7.37 (7H, m); 13C NMR (DMSO-d6, 125 MHz):
d
26.2, 55.1,
77.0, 108.9, 111.7, 112.6, 117.7, 122.8, 124.4, 129.3, 129.5, 133.0, 142.9,
143.4, 159.2, 176.6; IR (KBr): 3212, 2785, 1699, 1610, 1488, 1470,
1371,1349, 1256, 1033, 753, 691 cmꢁ1; MS (EI, 70 eV): m/z (%)¼269
(Mþ, 83), 253 (30), 240 (100), 224 (50), 210 (48), 134 (25), 77 (38).
Anal. Calcd for C16H15NO3: C, 71.36; H, 5.61. Found: C, 71.42; H, 5.68.
4.2.10. 1-Hexyl-3-hydroxy-3-phenylindolin-2-one (3ca) (Table 2, entry
16). Solid; mp 82.2e82.5 ꢀC; 1H NMR (CDCl3, 500 MHz):
d 0.80 (3H, t,
J¼10 Hz), 1.21e1.29 (6H, m), 1.61e1.64 (2H, m), 3.52e3.73 (2H, m), 3.82
(1H, s), 6.83 (1H, d, J¼5 Hz), 6.97 (1H, t, J¼10 Hz), 7.17e7.29 (7H, m);
13C NMR (CDCl3, 125 MHz):
d 13.9, 22.5, 26.5, 27.3, 31.4, 40.3, 77.9,
108.9, 123.3, 125.0, 125.2, 128.1, 128.5,129.7, 131.9, 140.3, 142.9, 177.5; IR
(KBr): 2987, 2818, 1699, 1466, 1354, 1166, 1098, 748, 695 cmꢁ1; MS (EI,
70 eV): m/z (%)¼309 (Mþ, 38), 210 (100), 194 (24), 146 (25), 132 (33),
105 (25), 91 (23), 77 (31). Anal. Calcd for C20H23NO2: C, 77.64; H, 7.49.
Found: C, 77.71; H, 7.53.
4.2.4. 3-(4-Bromophenyl)-3-hydroxy-1-methylindolin-2-one (3ah)
(Table 2, entry 8). Solid; mp 166.3e166.6 ꢀC; 1H NMR (CDCl3,
500 MHz):
d
3.15 (3H, s), 3.93 (1H, s), 6.83 (1H, d, J¼10 Hz), 7.02 (1H,
t, J¼10 Hz), 7.14e7.17 (3H, m), 7.27e7.35 (3H, m); 13C NMR (CDCl3,
125 MHz):
d 26.6, 77.7, 108.8, 122.4, 123.8, 124.8, 127.2, 130.1, 131.2,
131.6, 139.1, 143.3, 177.2; IR (KBr): 3286, 2991, 1698, 1612, 1470,
1350, 1090, 815, 754 cmꢁ1; MS (EI, 70 eV): m/z (%)¼319 ([Mþ2]þ,
78), 317 (Mþ, 76), 301 (55), 289 (100), 272 (75), 222 (45), 193 (63),
165 (43), 134 (53), 77 (73). Anal. Calcd for C15H12BrNO2: C, 56.62; H,
3.80. Found: C, 56.69.42; H, 3.74.
4.2.11. 3-Hydroxy-3-phenyl-1-(3-phenylpropyl)indolin-2-one (3ea)
(Table 2, entry 18). Solid; mp 96.6e98.0 ꢀC; 1H NMR (CDCl3,
500 MHz):
m), 6.71 (1H, d, J¼10 Hz), 6.95e7.11 (4H, m), 7.16e7.23 (7H, m),
7.27e7.29 (2H, m); 13C NMR (CDCl3, 125 MHz):
28.8, 33.1, 39.8,
d 1.88e2.02 (2H, m), 2.59e2.62 (2H, m), 3.69e3.75 (2H,
d
77.9, 108.8, 123.4, 125.1, 125.2, 126.1, 128.2, 128.3, 128.4, 128.5, 129.7,
131.9, 140.2, 140.9, 142.7, 177.5; IR (KBr): 2987, 1704, 1358, 1221,
1090, 754, 699 cmꢁ1; MS (EI, 70 eV): m/z (%)¼343 (Mþ, 74), 327
(22), 221 (100), 183 (75), 132 (43), 105 (40), 91 (62), 77 (41). Anal.
Calcd for C23H21NO2: C, 80.44; H, 6.16. Found: C, 80.49; H, 6.22.
4.2.5. 3-Hydroxy-1-methyl-3-(3-nitrophenyl)indolin-2-one (3aj) (Table
2, entry 10). Solid; mp 164.8e165.4 ꢀC; 1H NMR (CDCl3, 500 MHz):
d
3.20 (3H, s), 4.21 (1H, s), 6.89 (1H, d, J¼5 Hz), 7.04 (1H, t, J¼10 Hz),
7.15e7.61 (5H, m), 8.05e8.16 (2H, m); 13C NMR (CDCl3, 125 MHz):
26.7, 77.5, 109.2, 120.7, 123.2, 124.0, 124.8, 129.5, 130.5, 130.7, 131.7,
d
142.4, 143.4, 148.3, 176.7; IR (KBr): 3387, 3028, 1699, 1611, 1527, 1470,
1346,1091, 754, 734 cmꢁ1; MS (EI, 70 eV): m/z (%)¼284 (Mþ, 100), 256
(81), 239 (85), 209 (44), 134 (65), 77 (46). Anal. Calcd for C15H12N2O4:
C, 63.38; H, 4.25. Found: C, 63.43; H, 4.31.
4.2.12. 3-(4-Fluorophenyl)-3-hydroxy-1-(3-phenylpropyl)indolin-2-
one (3eo) (Table 2, entry 19). Solid; mp 102e103 ꢀC; 1H NMR
(CDCl3, 500 MHz):
d 1.95e2.02 (2H, m), 2.61e2.64 (2H, m), 3.57
(1H, s), 3.60e3.66 (1H, m), 3.70e3.76 (1H, m), 6.74 (1H, d, J¼10 Hz),
6.91e7.15 (6H, m), 7.17e7.28 (6H, m); 13C NMR (CDCl3, 125 MHz):
4.2.6. 3-Hydroxy-1-methyl-3-(4-nitrophenyl)indolin-2-one (3ak) (Table
2, entry 11). Solid; mp 165.6e166.6 ꢀC; 1H NMR (CDCl3, 500 MHz):
d
28.7, 33.1, 39.9, 77.4, 109.0, 115.5 (1C, d, 2JCeF¼21 Hz), 123.5, 125.0,
3
2
126.2, 127.3 (1C, d, JCeF¼7.5 Hz), 128.4 (1C, d, JCeF¼21 Hz), 130.0,
1
d
3.19 (3H, s), 4.13 (1H, s), 6.88e7.33 (4H, m), 7.45e8.07 (4H, m); 13
C
131.5, 136.0, 140.8, 142.7, 162.6 (1C, d, JCeF¼246.3 Hz), 177.2; IR
NMR (CDCl3, 125 MHz):
d
26.7, 77.8, 109.1, 123.7, 124.0, 124.8, 126.5,
(KBr): 3185, 2987, 1699, 1611, 1506, 1488, 1359, 1224, 1159, 829, 747,
700 cmꢁ1; MS (EI, 70 eV): m/z (%)¼361 (Mþ, 74), 345 (26), 239
(100), 228 (75), 201 (65), 132 (50), 123 (36), 91 (50) 77 (23). Anal.
Calcd for C23H20FNO2: C, 76.44; H, 5.58. Found: C, 76.49; H, 5.64.
130.5, 130.8, 143.3, 147.2, 147.7, 176.6; IR (KBr): 3217, 2988, 1703, 1611,
1517, 1343, 1096, 753 cmꢁ1; MS (EI, 70 eV): m/z (%)¼284 (Mþ, 100),
256 (99), 239 (86), 209 (74), 134 (55), 77 (50). Anal. Calcd for
C15H12N2O4: C, 63.38; H, 4.25. Found: C, 63.44; H, 4.20.
4.2.13. 3-(4-Chlorophenyl)-3-hydroxy-1-(3-phenylpropyl)indolin-2-
4.2.7. 3-Hydroxy-1-methyl-3-(naphthalene-2-yl)indolin-2-one (3al)
(Table 2, entry 12). Solid; mp 166.0e166.3 ꢀC; 1H NMR (CDCl3,
one (3eg) (Table 2, entry 20). Solid; mp 100e102 ꢀC; 1H NMR
(CDCl3, 500 MHz):
d 1.92e2.02 (2H, m), 2.59e2.63 (2H, m), 3.57
500 MHz):
d
3.20 (3H, s), 3.65 (1H, s), 6.86 (1H, d, J¼5 Hz), 7.01 (1H,
(1H, s), 3.59e3.64 (1H, m), 3.68e3.74 (1H, m), 6.73 (1H, d, J¼5 Hz),
t, J¼10 Hz), 7.22e7.39 (5H, m), 7.67e7.83 (4H, m); 13C NMR (CDCl3,
6.98e7.01 (1H, m), 7.09e7.24 (11H, m); 13C NMR (CDCl3, 125 MHz):
125 MHz):
d
26.6, 78.2, 108.8, 123.1, 123.6, 124.3, 125.0, 126.2, 126.3,
d 28.7, 33.1, 39.9, 77.5, 109.0, 123.5, 125.0, 126.2, 126.8, 128.3, 128.5,