The Journal of Organic Chemistry
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CDCl3) δ 183.3, 158.0, 151.0, 138.3, 130.35, 125.4, 124.9, 118.7,
117.6, 111.0, 42.5. The spectral data of the compound 2g were in
agreement with the values reported in the literature.25
yield 84% (87.5 mg); mp181−183 °C; 1H NMR (400 MHz, CDCl3) δ
7.36−7.27 (m, 5H), 5.98 (d, J = 2.0 Hz, 1H), 5.89 (d, J = 2.0 Hz, 1H),
4.86 (s, 2H), 3.94 (s, 3H), 3.81 (s, 3H); 13C NMR (100 MHz, CDCl3)
δ 177.1, 170.0, 161.2, 160.2, 153.3, 135.1, 129.0, 128.0, 127.3, 100.9,
91.9, 91.5, 56.3, 56.1, 44.0. The spectral data of the compound 2p was
in agreement with the values reported in the literature.10f
1-Ethyl-4,5,6-trimethoxy-1H-indole-2,3-dione (2q). The reac-
tion was carried out according to general method D. Red solid: yield
84% (87.9 mg); mp 115−117 °C; 1H NMR (400 MHz, CDCl3) δ 6.11
(s, 1H), 4.21 (s, 3H), 4.00 (s, 3H), 3.77 (s, 3H), 3.74 (q, J = 7.2 Hz,
2H), 1.29 (t, J = 7.2 Hz, 3H); 13C NMR (100 MHz, CDCl3) δ 178.0,
162.4, 159.0, 154.3, 148.7, 136.3, 102.5, 89.4, 62.2, 61.5, 56.9, 34.8,
13.0. The spectral data of the compound 2q was in agreement with the
values reported in the literature.10f
1-Phenyl-1H-indole-2,3-dione (2h). The reaction was carried
out according to general method D. Red solid: yield 74% (78.1 mg);
mp 127−128 °C; 1H NMR (400 MHz, CDCl3) δ 7.70 (dd, J = 7.6, 0.6
Hz, 1H), 7.58−7.51 (m, 3H), 7.47−7.41 (m, 3H), 7.19−7.15 (m, 1H),
6.90 (d, J = 8.4 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ 182.9, 157.3,
151.8, 138.3, 133.0, 130.0, 128.9, 126.04, 125.6, 124.3, 117.6, 111.3.
The spectral data of the compound 2h were in agreement with the
values reported in the literature.10e
Ethyl 2-(2,3-Dioxoindolin-1-yl)acetate (2i). The reaction was
carried out according to general method D. Red solid: yield 68% (71.6
mg); mp 127−129 °C; 1H NMR (400 MHz, CDCl3) δ 7.65−7.57 (m,
2H), 7.16 (t, m = 7.6 Hz, 1H), 6.79 (d, J = 8.0 Hz, 1H), 4.49 (s, 2H),
4.25 (q, J = 7.2 Hz, 2H), 1.28 (t, J = 7.0 Hz, 3H); 13C NMR (100
MHz, CDCl3) δ 182.5, 166.8, 158.1, 150.3, 138.41, 125.6, 124.2, 117.7,
110.1, 62.2, 41.3, 14.1. The spectral data of the compound 2i were in
agreement with the values reported in the literature.21
1-Benzyl-4,5,6-trimethoxy-1H-indole-2,3-dione (2r). The re-
action was carried out according to general method D. Red solid: yield
1
85% (88.2 mg); mp 151−152 °C; H NMR (400 MHz, CDCl3) δ
7.38−7.27 (m, 5H), 5.99 (s, 1H), 4.89 (s, 2H), 4.20 (s, 3H), 3.81 (s,
3H), 3.73 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 177.6, 162.2,
159.4, 154.2, 148.7, 136.4, 135.0, 129.1, 128.2, 127.3, 102.6, 90.5, 62.3,
61.5, 56.6, 44.0. The spectral data of the compound 2r were in
1-(2-Bromoethyl)indoline-2,3-dione (2j). The reaction was
carried out according to general method D. Red solid: yield 71%
1
10f
(74.5 mg); mp 131−133 °C; H NMR (400 MHz, CDCl3) δ 7.65−
agreement with the values reported in the literature.
7.59 (m, 2H), 7.15 (t, J = 7.6 Hz, 1H), 7.0 (d, J = 7.6 Hz, 1H), 4.15 (t,
J = 6.8 Hz, 2H), 3.61 (t, J = 6.8 Hz, 2H); 13C NMR (100 MHz,
CDCl3) δ 182.7, 158.2, 150.5, 138.4, 125.8, 124.1, 117.7, 110.2, 42.0,
27.1. The spectral data of the compound 2j were in agreement with
the values reported in the literature.21
1-Methyl-1H-indole-2,3-dione (2u). The reaction was carried
out according to general method F. Red solid: yield 76% (75.0 mg).
The reaction was carried out according to general method G: yield
1
75% (79.9 mg); mp 121−122 °C; H NMR (400 MHz, CDCl3) δ
7.63−7.59 (m, 2H), 7.13 (t, J = 7.4 Hz, 1H), 6.90 (d, J = 8.4 Hz, 1H),
3.25 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 183.3, 158.3, 151.5,
138.4, 125.3, 123.9, 117.5, 109.9, 26.2. The spectral data of the
compound 2u were in agreement with the values reported in the
literature.21
5-Chloro-1-methyl-1H-indole-2,3-dione (2k). The reaction was
carried out according to general method D. Red solid: yield 74% (78.8
mg); mp 157−159 °C; 1H NMR (400 MHz, CDCl3) δ 7.59−7.57 (m,
2H), 6.87−6.85 (m, 1H), 3.26 (s, 3H); 13C NMR (100 MHz, CDCl3)
δ 182.3, 157.7, 149.7, 137.7, 129.7, 125.3, 118.3, 111.2, 26.4. The
spectral data of the compound 2k were in agreement with the values
5-Bromo-1-methyl-1H-indole-2,3-dione (2v). The reaction was
carried out according to general method F. Red solid: yield 70% (69.4
mg); mp 173−175 °C; 1H NMR (400 MHz, CDCl3) δ 7.73 (d, J = 1.6
Hz, 2H), 7.71 (s, 1H), 6.80 (d, J = 8.4 Hz, 1H), 3.25 (s, 3H); 13C
NMR (100 MHz, CDCl3) δ 182.1, 157.5, 150.2, 140.6, 128.1, 118.6,
116.7, 111.6, 26.4. The spectral data of the compound 2v was in
agreement with the values reported in the literature.26
1-Methyl-4,5,6-trimethoxy-1H-indole-2,3-dione (2w). The
reaction was carried out according to general method F. Red solid:
yield 78% (77.3 mg); mp 110−112 °C; 1H NMR (400 MHz, CDCl3)
δ 6.11 (s, 1H), 4.21 (s, 3H), 4.00 (s, 3H), 3.77 (s, 3H), 3.20 (s, 3H);
13C NMR (100 MHz, CDCl3) δ 176.7, 161.3, 158.3, 153.3, 148.5,
135.5, 101.3, 88.3, 61.3, 60.5, 55.8, 28.7, 25.2. The spectral data of the
compound 2w were in agreement with the values reported in the
literature.10f
26
reported in the literature.
5-Bromo-1-benzyl-1H-indole-2,3-dione (2l). The reaction was
carried out according to general method D. Red solid: yield 79% (82.6
mg); mp 135−137 °C; 1H NMR (400 MHz, CDCl3) δ 7.51 (d, J = 2.0
Hz, 1H), 7.37−7.35 (dd, J = 8.4, 2.0 Hz, 1H), 7.30−7.23 (m, 5H),
6.65 (d, J = 8.4 Hz, 1H), 4.86 (s, 2H); 13C NMR (100 MHz, CDCl3) δ
182.3, 157.8, 149.0, 137.7, 134.0, 129.8, 129.2, 128.4, 127.4, 125.4,
118.5, 112.3, 44.2. The spectral data of the compound 2l were in
agreement with the values reported in the literature.27
5-Bromo-1-ethyl-1H-indole-2,3-dione (2m). The reaction was
carried out according to general method D. Red solid: yield 76% (79.7
mg); mp 147−149 °C; 1H NMR (400 MHz, CDCl3) δ 7.71 (d, J = 2
Hz, 2H), 7.70 (s, 1H), 6.83 (d, J = 8.8 Hz, 1H), 3.78 (q, J = 7.2 Hz,
2H), 1.31 (t, J = 7.2 Hz, 3H); 13C NMR (100 MHz, CDCl3) δ 182.5,
157.2, 149.4, 140.5, 128.3, 118.8, 116.4, 111.7, 35.1, 12.4. The spectral
data of the compound 2m were in agreement with the values reported
in the literature.28
5-Bromo-1-benzyl-1H-indole-2,3-dione (2n). The reaction was
carried out according to general method D. Red solid: yield 80% (83.1
mg).
The reaction was also carried out according to general method G:
yield 72% (74.3 mg); mp 149−150 °C; 1H NMR (400 MHz, CDCl3)
δ 7.71 (d, J = 2.0 Hz, 1H), 7.58 (dd, J = 8.4, 2.0 Hz, 1H), 7.37−7.29
(m, 5H), 6.67 (d, J = 8.4 Hz, 1H), 4.92 (s, 2H); 13C NMR (100 MHz,
CDCl3) δ 182.1, 157.5, 149.4, 140.5, 134.0, 129.2, 128.4, 128.2, 127.4,
118.9, 116.8, 112.7, 44.2. The spectral data of the compound 2n was in
agreement with the values reported in the literature.27
1-Butyl-1H-indole-2,3-dione (2x). The reaction was carried out
1
according to general method G. Semisolid: yield 70% (74.3 mg); H
NMR (400 MHz, CDCl3) δ 7.61−7.56 (m, 2H), 7.13−7.09 (m, 1H),
6.90 (d, J = 7.6 Hz, 1H), 3.72 (t, J = 7.2 Hz, 2H), 1.72−1.62 (m, 2H),
1.46−1.37 (m, 2H), 0.97 (t, J = 7.4 Hz, 3H); 13C NMR (100 MHz,
CDCl3) δ 183.7, 158.2, 151.1, 138.3, 125.5, 123.6, 117.6, 110.2, 40.0,
29.30, 20.2, 13.7. The spectral data of the compound 2x were in
agreement with the values reported in the literature.21
5-Iodo-1-benzyl-1H-indole-2,3-dione (4a). The reaction was
carried out according to general method E. Red solid: yield 79%
(127.3 mg); mp 151−153 °C; 1H NMR (400 MHz, CDCl3) δ 7.89 (s,
1H), 7.76 (dd, J = 8.4, 1.6 Hz, 1H), 7.37−7.29 (m, 5H), 6.57 (d, J =
8.0 Hz, 1H), 4.91 (s, 2H); 13C NMR (100 MHz, CDCl3) δ 181.9,
157.3, 150.0, 146.3, 134.0, 133.9, 129.2, 128.4, 127.4, 119.2, 113.1,
86.2, 44.2. The spectral data of the compound 4a were in agreement
with the values reported in the literature.29
5-Iodo-1(4-methoxybenzyl)-1H-indole-2,3-dione (4b). The
reaction was carried out according to general method E. Red solid:
yield 81% (124.7 mg); mp 145−147 °C; 1H NMR (400 MHz, CDCl3)
δ 7.87 (s, 1H), 7.76 (dd, J = 8.4, 1.6 Hz, 1H), 7.26−7.22 (m, 2H), 6.86
(dd, J = 6.8, 2.0 Hz, 2H), 6.59 (d, J = 8.4 Hz, 1H), 4.84 (s, 2H), 3.78
(s, 3H); 13C NMR (100 MHz, CDCl3) δ 182.0, 159.6, 157.2, 150.1,
146.3, 133.8, 128.9, 126.0, 119.3, 114.5, 113.2, 86.1, 55.3, 43.7. The
1-Ethyl-4,6-dimethoxy-1H-indole-2,3-dione (2o). The reaction
was carried out according to general method D. Yellow solid: yield
82% (86.3 mg); mp143−145 °C; 1H NMR (400 MHz, CDCl3) δ 6.01
(s, 2H), 3.95 (s, 3H), 3.93 (s, 3H), 3.71 (q, J = 7.2 Hz, 2H), 1.27 (t, J
= 7.2 Hz, 3H); 13C NMR (100 MHz, CDCl3) δ 177.6, 170.1, 161.3,
159.8, 153.3, 100.7, 91.6, 90.5, 56.3, 56.2, 35.0, 13.0. The spectral data
of the compound 2o were in agreement with the values reported in the
literature.10f
1-Benzyl-4,6-dimethoxy-1H-indole-2,3-dione (2p). The reac-
tion was carried out according to general method D. Yellow solid;
4989
dx.doi.org/10.1021/jo500550d | J. Org. Chem. 2014, 79, 4984−4991