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B. Zhou et al.
Paper
Synthesis
1-(1-Benzyl-1H-indol-3-yl)-2-(thiophen-2-yl)ethane-1,2-dione
HRMS (TOF): m/z [M + Na]+ calcd for C17H12BrNO2: 363.9944; found:
(3ac)
363.9951.
Light yellow solid; yield: 0.197 g (57%); mp 100–102 °C.
1-(5-Methoxy-1-methyl-1H-indol-3-yl)-2-phenylethane-1,2-di-
one (3ai)
1H NMR (400 MHz, CDCl3): = 8.50 (d, J = 7.9 Hz, 1 H), 8.25 (s, 1 H),
8.10 (dd, J = 3.9, 1.1 Hz, 1 H), 7.77 (dd, J = 4.9, 1.1 Hz, 1 H), 7.37–7.27
(m, 6 H), 7.16 (dd, J = 8.4, 3.7 Hz, 3 H), 5.34 (s, 2 H).
Light yellow solid; yield: 0.208 g (71%); mp 153–155 °C.
1H NMR (400 MHz, CDCl3): = 8.10–8.06 (m, 2 H), 7.95 (d, J = 2.4 Hz, 1
H), 7.71 (s, 1 H), 7.63–7.58 (m, 1 H), 7.47 (t, J = 7.7 Hz, 2 H), 7.26–7.22
(m, 1 H), 6.98 (dd, J = 8.9, 2.5 Hz, 1 H), 3.92 (s, 3 H), 3.77 (s, 3 H).
13C NMR (100 MHz, CDCl3): = 184.71, 184.42, 139.81, 139.41,
137.08, 136.84, 136.81, 135.33, 129.18, 128.46, 128.44, 127.32,
127.10, 124.34, 123.67, 122.95, 112.66, 110.72, 51.29.
13C NMR (100 MHz, CDCl3): = 193.89, 187.58, 157.23, 139.48,
134.34, 133.61, 132.68, 130.39, 128.82, 127.40, 114.65, 112.66,
110.98, 104.03, 55.94, 34.04.
HRMS (TOF): m/z [M + Na]+ calcd for C21H15NO2S: 368.0716; found:
368.0712.
1-(1-Benzyl-1H-indol-3-yl)-2-(furan-2-yl)ethane-1,2-dione (3ad)
HRMS (TOF): m/z [M + Na]+ calcd for C18H15NO3: 316.0944; found:
316.0947.
Light yellow solid; yield: 0.211 g (64%); mp 113–115 °C.
1H NMR (400 MHz, CDCl3): = 8.48 (d, J = 7.8 Hz, 1 H), 8.23 (s, 1 H),
7.72 (d, J = 1.1 Hz, 1 H), 7.66 (dd, J = 3.6, 0.6 Hz, 1 H), 7.37–7.27 (m, 6
H), 7.15 (dd, J = 7.5, 1.8 Hz, 2 H), 6.59 (dd, J = 3.6, 1.7 Hz, 1 H), 5.33 (s,
2 H).
13C NMR (100 MHz, CDCl3): = 184.26, 179.67, 150.26, 148.74,
139.68, 137.04, 135.23, 129.14, 128.41, 127.21, 127.14, 124.31,
124.15, 123.64, 122.84, 112.88, 112.65, 110.69, 51.24.
Funding Information
This research was supported by the National Key Research and Devel-
opment Program of China (2016YFB0301501), the National Natural
Science Foundation of China (Grant Nos. 21776130 & 21878145), the
Jiangsu Synergetic Innovation Center for Advanced Bio-Manufacture
(Nos. X1821 & X1802), the Top-notch Academic Programs Project of
Jiangsu Higher Education Institutions (TAPP), and the Postgraduate
HRMS (TOF): m/z [M + Na]+ calcd for C21H15NO3: 352.0944; found:
352.0957.
Research & Practice Innovation Program of Jiangsu Province.
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1-(1,2-Dimethyl-1H-indol-3-yl)-2-phenylethane-1,2-dione (3ae)
Light yellow solid; yield: 0.147 g (53%); mp 152–155 °C.
Supporting Information
1H NMR (400 MHz, CDCl3): = 8.02 (d, J = 7.2 Hz, 2 H), 7.86 (d, J = 7.7
Hz, 1 H), 7.59 (t, J = 7.4 Hz, 1 H), 7.46 (t, J = 7.7 Hz, 2 H), 7.28–7.16 (m,
3 H), 3.65 (s, 3 H), 2.61 (s, 3 H).
Supporting information for this article is available online at
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13C NMR (100 MHz, CDCl3): = 195.54, 190.15, 147.68, 137.16,
134.51, 133.48, 130.16, 129.08, 126.24, 123.17, 123.15, 120.94,
110.71, 109.73, 29.92, 12.87.
References
HRMS (TOF): m/z [M + Na]+ calcd for C18H15NO2: 300.0993; found:
300.0995.
(1) (a) Zhang, Z.; Yang, Z.; Wong, H.; Zhu, J.; Meanwell, N. A.;
Kadow, J. F.; Wang, T. J. Org. Chem. 2002, 67, 6226. (b) Cacchi, S.;
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Nat. Prod. Rep. 2005, 22, 73. (d) Movassaghi, M.; Schmidt, M. A.
Angew. Chem. Int. Ed. 2007, 46, 3725.
1-(1-Methyl-2-phenyl-1H-indol-3-yl)-2-phenylethane-1,2-dione
(3af)
(2) (a) Sessler, J. L.; Cho, D.; Lynch, V. J. Am. Chem. Soc. 2006, 128,
16518. (b) Tang, R.-Y.; Guo, X.-K.; Xiang, J.-N.; Li, J.-H. J. Org.
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Zappalà, M.; Monforte, A.-M.; Debyser, Z.; Witvrouw, M.;
Chimirri, A. J. Med. Chem. 2005, 48, 7084. (c) Nicolaou, I.;
Demopoulos, V. J. J. Med. Chem. 2003, 46, 417. (d) Kobayashi, J.;
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Light yellow solid; yield: 0.207 g (61%); mp 108–110 °C.
1H NMR (400 MHz, CDCl3): = 8.58–8.45 (m, 1 H), 7.55 (dd, J = 8.2, 1.1
Hz, 2 H), 7.44 (t, J = 7.4 Hz, 1 H), 7.37 (dd, J = 6.8, 3.1 Hz, 3 H), 7.27–
7.21 (m, 3 H), 7.11–7.01 (m, 4 H), 3.46 (d, J = 0.9 Hz, 3 H).
13C NMR (100 MHz, CDCl3): = 193.84, 191.12, 149.86, 137.20,
133.64, 133.55, 131.05, 129.76, 129.32, 129.02, 128.26, 127.97,
126.51, 124.17, 123.68, 122.64, 112.55, 110.02, 31.01.
HRMS (TOF): m/z [M + Na]+ calcd for C23H17NO2: 362.1151; found:
362.1132.
1-(5-Bromo-1-methyl-1H-indol-3-yl)-2-phenylethane-1,2-dione
(3ag)
Light yellow solid; yield: 0.208 g (61%); mp 184–186 °C.
1H NMR (400 MHz, CDCl3): = 8.65 (d, J = 1.8 Hz, 1 H), 8.11–8.07 (m, 2
H), 7.81 (s, 1 H), 7.64 (t, J = 7.4 Hz, 1 H), 7.53–7.46 (m, 3 H), 7.26 (s, 1
H), 3.83 (s, 3 H).
13C NMR (100 MHz, CDCl3): = 193.42, 187.21, 140.13, 136.49,
134.54, 133.39, 130.47, 128.89, 128.08, 127.36, 125.47, 117.42,
112.47, 111.52, 34.06.
(4) (a) Cremlyn, R. J.; Lynch, J. M.; Swinbourne, F. J. Phosphorus,
Sulfur Silicon Relat. Elem. 1991, 57, 173. (b) Bark, T.;
Weyhermüller, T.; Heirtzler, F. Chem. Commun. 1998, 1475.
(c) Barta, T. E.; Stealey, M. A.; Collins, P. W.; Weier, R. M. Bioorg.
Med. Chem. Lett. 1998, 8, 3443. (d) Heirtzler, F.; Neuburger, M.;
© 2019. Thieme. All rights reserved. — Synthesis 2019, 51, A–I