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H. Sun et al.
Letter
Synlett
Supporting Information
(6) Wang, S.-S.; Fu, H.; Shen, Y.-H.; Sun, M.; Li, Y.-M. J. Org. Chem.
2016, 81, 2920.
(7) Li, Y.-M.; Wang, S.-S.; Yu, F.; Shen, Y.; Chang, K.-J. Org. Biomol.
Chem. 2015, 13, 5376.
Supporting information for this article is available online at
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(8) (a) Ding, F.; Fang, Y.; Jiang, Y.; Lin, K.; Shi, L. Chem. Asian J. 2018,
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358, 3616.
Primary Data
(9) Yang, T.; Zhou, J.-L.; Li, J.; Shen, Y.; Gao, C.; Li, Y.-M. Synthesis
2018, 50, 3460.
1691574 and can be cited using the following DOI:
10.4125/pd0111th.
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References and Notes
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(20) 3-Ethyl-1,3-dimethylquinoline-2,4(1H,3H)-diones
2a–p;
General Procedure
FeSO4·7H2O (0.015 mol, 15 mol%) and the appropriate N-(2-cya-
noaryl)-N-methylmethacrylamide 1 (0.1 mol, 1.0 equiv) were
sequentially weighed into a tube, and DMSO (1.0 mL) and 30%
aq H2O2 (300 L) were added from a syringe. The mixture was
then irradiated by a 6 W blue LED at r.t. under air for 12 h. The
volatile solvent and reagents were removed by rotary evapora-
tion, and the residue was purified by flash chromatography
(silica gel, PE–EtOAc).
3-Ethyl-1,3-dimethylquinoline-2,4(1H,3H)-dione (2a)
Colorless oil; yield: 15.4 mg (71%). 1H NMR (600 MHz, CDCl3):
= 8.02 (dd, J = 7.7, 1.6 Hz, 1 H), 7.63 (ddd, J = 8.4, 7.3, 1.7 Hz, 1
H), 7.23–7.11 (m, 2 H), 3.49 (s, 3 H), 2.10–1.87 (m, 2 H), 1.46 (s,
3 H), 0.79 (t, J = 7.4 Hz, 3 H). 13C NMR (150 MHz, CDCl3):
= 197.59, 173.78, 143.22, 135.90, 127.95, 122.97, 120.43,
114.68, 57.87, 32.71, 29.70, 21.97, 9.47. HRMS (ESI): m/z [M +
H]+ calcd for C13H16NO2: 218.1181; found: 218.11755.
N-(2-Cyanophenyl)-2-hydroxy-2-methylbutanamide (3a)
Colorless oil; yield: 15.9 mg (73%). 1H NMR (600 MHz, CDCl3):
= 9.41 (s, 1 H), 8.56–8.41 (m, 1 H), 7.60 (td, J = 7.6, 7.1, 1.5 Hz,
3 H), 7.18 (td, J = 7.7, 0.9 Hz, 1 H), 2.02 (dq, J = 14.9, 7.5 Hz, 1 H),
1.73 (dq, J = 14.8, 7.5 Hz, 1 H), 1.54 (s, 3 H), 0.98 (t, J = 7.5 Hz, 3
H). 13C NMR (150 MHz, CDCl3): = 174.31, 140.17, 134.16,
132.26, 124.12, 120.62, 116.23, 102.28, 33.34, 26.34, 7.82.
HRMS (ESI): m/z [M + H]+ calcd for C12H15N2O2: 219.1134;
found: 219.11276.
(4) For reviews, see: (a) Chen, J.-R.; Yu, X.-Y.; Xiao, W.-J. Synthesis
2015, 47, 604. (b) Song, R.-J.; Liu, Y.; Xie, Y.-X.; Li, J.-H. Synthesis
2015, 47, 1195. (c) Li, C.-C.; Yang, S.-D. Org. Biomol. Chem. 2016,
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R.-J.; Liu, Y.; Hu, M.; Xie, P.; Li, J.-H. Angew. Chem. Int. Ed. 2013,
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© 2019. Thieme. All rights reserved. Synlett 2019, 31, A–E