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X.-F. Xia et al. / Tetrahedron xxx (2015) 1e5
1H), 6.98 (d, J¼8.0 Hz, 1H), 3.32 (s, 3H), 2.08e2.26 (m, 4H), 2.05 (s,
3H), 1.45 (s, 3H); 13C NMR (100 MHz, CDCl3): 206.7, 180.0, 148.7,
143.5, 134.3, 125.4, 118.5, 107.6, 47.2, 38.1, 31.4, 29.7, 26.5, 23.1.
7.22e7.24 (m, 1H), 7.08e7.12 (m, 1H), 6.88e6.90 (m, 1H), 3.76e3.84
(m, 2H), 3.24 (s, 3H), 2.68 (s, 1H, OH), 2.26 (m, 2H), 2.03e2.13 (m,
2H), 2.02 (s, 3H); 13C NMR (100 MHz, CDCl3): 207.7, 178.6, 144.0,
129.5, 128.6, 123.2, 122.9, 108.2, 66.8, 53.6, 37.9, 29.7, 26.5, 26.1;
HRMS (ESI) m/z: calcd for C14H17NNaO3: MþNa¼270.1106. Found:
270.1101. IR (cmꢁ1): 3379, 2987, 2929, 1712, 1594, 1171, 1088, 1017,
814, 737.
4.2.10. 1,3-Dimethyl-3-(3-oxobutyl)-1H-benzo[g]indol-2(3H)-one, 3j.
62% yield, oil. 1H NMR (400 MHz, CDCl3): 7.74 (d, J¼8.0 Hz, 1H),
7.53e7.56 (m, 2H), 7.41e7.47 (m, 2H), 6.97 (d, J¼8.0 Hz, 1H), 3.55 (s,
3H), 2.54e2.61 (m,1H), 2.26e2.29 (m, 2H), 2.03e2.09 (m,1H),1.94 (s,
3H),1.68 (s, 3H); 13C NMR (100 MHz, CDCl3): 207.9,172.8,137.3,136.6,
133.3, 126.2, 122.6, 119.6, 108.5, 46.7, 39.7, 36.9, 30.9, 29.8, 29.6.
4.2.18. 3-(Methoxymethyl)-1-methyl-3-(3-oxobutyl)indolin-2-one,
3r. 60% yield, oil. 1H NMR (400 MHz, CDCl3): 7.28e7.32 (m, 1H),
7.23e7.25 (m, 1H), 7.08 (t, J¼8.0 Hz, 1H), 6.86 (d, J¼4.0 Hz, 1H),
3.59e3.68 (m, 2H), 3.23 (s, 3H), 3.22 (s, 3H), 2.08e2.13 (m, 3H),
1.91e1.99 (m, 4H); 13C NMR (100 MHz, CDCl3): 207.3, 177.7, 143.9,
130.2, 128.2, 123.3, 122.6, 107.9, 76.5, 59.4, 52.7, 37.7, 29.7, 27.1, 26.1;
HRMS (ESI) m/z: calcd for C15H20NO3: MþH¼262.1443. Found:
262.1438. IR (cmꢁ1): 2987, 2929, 1712, 1594, 1171, 1088, 1017, 817,
737, 706.
4.2.11. 4-Chloro-1,3-dimethyl-3-(3-oxobutyl)indolin-2-one, 3k. 40%
yield, oil. 1H NMR (400 MHz, CDCl3): 7.22e7.24 (m, 1H), 7.01 (d,
J¼8.0 Hz, 1H), 6.79 (d, J¼8.0 Hz, 1H), 3.23 (s, 3H), 2.47e2.53 (m, 1H),
2.18e2.25 (m, 1H), 1.92e2.21 (m, 5H), 1.52 (s, 3H); 13C NMR
(100 MHz, CDCl3): 207.2, 179.3, 144.8, 130.5, 129.2, 128.9, 123.7,
106.5, 48.9, 38.8, 29.6, 28.9, 26.3, 21.0; HRMS (ESI) m/z: calcd for
C
14H17ClNO2: MþH¼266.0948. Found: 266.0940. IR (cmꢁ1): 2965,
2931, 1710, 1128, 1083, 779.
4.2.19. 1,3,5-Trimethyl-3-(2-methyl-3-oxobutyl)indolin-2-one,
3s.
35% yield, oil. 1H NMR (400 MHz, CDCl3): 7.05e7.08 (m, 1H), 6.96 (s,
1H), 6.74e6.76 (m, 1H), 3.32 (m, 1H), 3.25 (s, 3H), 3.08e3.09 (m,
3H), 2.38e2.40 (m, 2H), 2.32 (s, 3H), 1.99 (s, 3H), 1.33 (s, 3H); 13C
NMR (100 MHz, CDCl3): 204.6, 180.2, 172.2, 141.3, 131.7, 130.0, 128.1,
122.7, 107.9, 74.7, 74.2, 50.5, 45.3, 37.8, 29.9, 26.4, 24.4, 21.1; HRMS
(ESI) m/z: calcd for C16H22NO2: MþH¼260.1651. Found: 260.1645.
IR (cmꢁ1): 2987, 2929, 1712, 1594, 1171, 1088, 1017, 814, 737.
4.2.12. 1,3,7-Trimethyl-3-(3-oxobutyl)indolin-2-one, 3l. 46% yield,
oil. 1H NMR (400 MHz, CDCl3): 6.92e7.01 (m, 3H), 3.5 (s, 3H), 2.59
(s, 3H), 2.10e2.19 (m, 2H), 1.91e2.04 (m, 5H), 1.34 (s, 3H); 13C NMR
(100 MHz, CDCl3): 207.7, 180.7, 140.8, 133.8, 131.6, 122.6, 120.4,
119.6, 46.5, 38.5, 31.9, 29.4, 24.0, 18.9; HRMS (ESI) m/z: calcd for
C
15H20NO2: MþH¼246.1494. Found: 246.1491. IR (cmꢁ1): 2966,
2928, 1714, 1605, 1129, 1077, 780, 750.
4.2.20. 2-(tert-Butylperoxy)-2-methyl-5-oxo-N-phenyl-N-tosyl-
hexan-amide, 4a. 50% yield, oil. 1H NMR (400 MHz, CDCl3):
7.81e7.84 (m, 2H), 7.35e7.44 (m, 5H), 7.29e7.31 (m, 2H), 2.33e2.47
4.2.13. 1,3,6-Trimethyl-3-(3-oxobutyl)indolin-2-one, 3m. 64% yield,
oil. 1H NMR (400 MHz, CDCl3): 7.17e7.21 (m, 1H), 7.03e7.04 (m,
0.6H), 6.88e6.89 (m, 0.6H), 6.84 (d, J¼8.0 Hz, 1H), 6.69e6.72 (m,
1.5H), 3.22e3.23 (m, 4.5H), 2.40 (s,1.8H), 2.36 (s, 3H), 2.29e2.34 (m,
1H), 2.07e2.23 (m, 4H), 1.98 (s, 1.8H), 1.95 (s, 3H), 1.81e1.90 (m, 2H),
1.46 (s, 3H), 1.35 (s, 1.8H); 13C NMR (100 MHz, CDCl3): 207.7, 207.5,
180.4, 180.0, 143.4, 143.2, 138.1, 134.4, 129.7, 127.8, 125.2, 123.1,
122.3, 108.9, 105.8, 48.4, 47.1, 38.7, 38.6, 29.8, 26.2, 21.7, 18.1.
(m, 5H), 2.08 (s, 3H), 1.75e1.89 (m, 2H), 1.3 (s, 3H), 0.98 (s, 9H); 13
C
NMR (100 MHz, CDCl3): 207.1, 173.3, 144.5, 135.8, 135.2, 130.9, 129.6,
129.4, 129.1, 128.4, 86.9, 80.2, 37.9, 30.8, 29.8, 26.4, 22.3, 21.6; HRMS
(ESI) m/z: calcd for
C
24H31NNaO6S: MþNa¼484.1770. Found:
484.1767. IR (cmꢁ1): 2979, 2930, 1715, 1698, 1364, 1171, 1086, 814,
697.
4.2.14. 3-Methyl-3-(3-oxobutyl)-1-phenylindolin-2-one, 3n. 65%
yield, oil. 1H NMR (400 MHz, CDCl3): 7.53e7.57 (m, 2H), 7.43e7.45
(m, 2H), 7.32e7.34 (m, 1H), 7.21e7.26 (m, 2H), 7.11e7.14 (m, 1H),
4.2.21. N-(4-Bromophenyl)-2-(tert-butylperoxy)-2-methyl-5-oxo-N-
tosylhexanamide, 4b. 35% yield, oil. 1H NMR (400 MHz, CDCl3): 7.81
(d, J¼8.0 Hz, 2H), 7.51e7.54 (m, 2H), 7.30e7.32 (m, 2H), 7.23e7.27
(m, 2H), 2.44 (s, 3H), 2.37e2.43 (m, 2H), 2.08 (s, 3H), 1.81e1.89 (m,
1H), 1.75e1.77 (m, 1H), 1.31 (s, 3H), 0.99 (s, 9H); 13C NMR (100 MHz,
CDCl3): 208.1, 206.8, 174.8, 173.0, 144.8, 134.4, 131.8, 129.8, 129.2,
126.6, 121.3, 116.7, 87.0, 80.5, 50.5, 39.1, 37.8, 29.6, 26.4, 23.9, 22.1,
6.87e6.89 (m, 1H), 2.21e2.25 (m, 4H), 2.01 (s, 3H), 1.50 (s, 3H); 13
C
NMR (100 MHz, CDCl3): 207.4, 179.4, 142.9, 134.3, 132.9, 129.5, 128.8,
127.9,127.8,126.3,123.1,122.9,109.3, 47.3, 38.4, 29.8, 26.4, 23.9;HRMS
(ESI) m/z: calcd for C19H12NO2: MþH¼294.1494; found: 294.1491. IR
(cmꢁ1): 3060, 2970, 2927, 1727, 1714, 1657, 1163, 1023, 761, 700.
21.6, 20.9; HRMS (ESI) m/z: calcd for
C24H30BrNNaO6S:
MþNa¼562.0875. Found: 562.0869. IR (cmꢁ1): 2980, 2925, 1715,
4.2.15. 1-Benzyl-3,5-dimethyl-3-(3-oxobutyl)indolin-2-one, 3o. 50%
yield, 79e81 ꢀC. 1H NMR (400 MHz, CDCl3): 7.24e7.30 (m, 5H),
6.95e6.97 (m, 2H), 6.64e6.66 (m, 2H), 4.84e4.94 (m, 2H), 2.29 (s,
3H), 2.04e2.14 (m, 3H), 1.90e1.98 (m, 4H), 1.41 (s, 3H); 13C NMR
(100 MHz, CDCl3): 207.6, 180.1, 139.7, 136.1, 133.2, 132.2, 128.7, 128.1,
127.5, 127.3, 123.5, 108.7, 47.3, 43.6, 38.6, 31.8, 29.8, 23.9, 21.0; HRMS
1699, 1487, 1172, 1071, 1014, 816, 705.
4.2.22. 2-(tert-Butylperoxy)-N-(4-chlorophenyl)-2-methyl-5-oxo-N-
tosylhexanamide, 4c. 30% yield, oil. 1H NMR (400 MHz, CDCl3):
7.80e7.83 (m, 2H), 7.36e7.38 (m, 2H), 7.30e7.32 (m, 4H), 2.44 (s,
3H), 2.37e2.42 (m, 2H), 2.07 (s, 3H), 1.80e1.88 (m, 1H), 1.69e1.76
(m, 1H), 1.31 (s, 3H), 0.99 (s, 9H); 13C NMR (100 MHz, CDCl3): 206.8,
173.0, 144.7, 135.6, 132.1, 129.3, 128.8, 126.6, 121.0, 87.0, 80.4, 50.4,
39.1, 37.8, 29.8, 26.3, 23.9, 22.1, 21.6; HRMS (ESI) m/z: calcd for
(ESI) m/z: calcd for
C
21H23NO2Na: MþNa¼344.1626. Found:
344.1621. IR (cmꢁ1): 2965, 2925,1713,1620,1601,1174,1077, 808, 703.
4.2.16. 1-Methyl-1-(3-oxobutyl)-5,6-dihydro-1H-pyrrolo[3,2,1-ij]-
quino-lin-2(4H)-one, 3p. 35% yield, oil. 1H NMR (400 MHz, CDCl3):
7.02e7.04 (m, 1H), 6.94e7.00 (m, 2H), 3.71e3.74 (m, 2H), 2.79e2.82
(m, 2H), 2.17e2.23 (m, 2H), 1,98e2.14 (m, 7H), 1.38 (s, 3H); 13C NMR
(100 MHz, CDCl3): 207.8,178.9,138.8,131.8,126.7,122.1, 120.5,120.1,
48.7, 38.7, 31.6, 29.8, 24.5, 23.3, 21.2; HRMS (ESI) m/z: calcd for
C
24H30ClNNaO6S: MþNa¼518.1380. Found: 518.1375. IR (cmꢁ1):
2987, 2929, 1712, 1594, 1171, 1088, 1017, 814.
Acknowledgements
We thank the National Science Foundation of China NSF
21402066, the Natural Science Foundation of Jiangsu Province
(BK20140139), and the Fundamental Research Funds for the Central
Universities (JUSRP11419) for financial support. Financial support
from MOE&SAFEA for the 111 project (B13025) is also gratefully
acknowledged.
C
16H20NO2: MþH¼258.1494; found: 258.1490. IR (cmꢁ1): 2964,
2933, 1712, 1626, 1353, 1240, 1166, 753.
4.2.17. 3-(Hydroxymethyl)-1-methyl-3-(3-oxobutyl)indolin-2-one,
3q. 45% yield, oil. 1H NMR (400 MHz, CDCl3): 7.28e7.35 (m, 1H),