6
KABOUDIN ET AL.
3.10 | 6,8-Dibromo-4-phenyl-
1,2,3,4-tetrahydro-quinoline (3 h)
13C NMR (100 MHz, CDCl3) δ: 28.9, 33.5, 41.6, 46.2,
55.2, 118.6, 122.30, 122.31, 126.3, 128.4, 128.6, 128.7,
129.1, 146.5, 150.1.
Yellow oil (63%, 230 mg).
1H NMR (400 MHz, CDCl3) δ: 2.03–2.26 (m, 2H),
3.29–3.44 (m, 2H), 4.15 (t, 1H, J = 4 Hz), 4.62 (br, 1H),
6.87 (s, 1H), 7.05–7.40 (m, 5H), 7.46 (s, 1H).
13C NMR (100 MHz, CDCl3) δ: 29.9, 38.9, 43.0,
106.9, 108.7, 125.6, 125.5, 127.9, 131.6, 132.6,
141.1, 145.2.
ACKNOWLEDGMENT
The authors gratefully acknowledge support by the Insti-
tute for Advanced Studies in Basic Sciences (IASBS)
Research Council.
DATA AVAILABILITY STATEMENT
Anal. Calcd for C15H13NBr2. C, 49.32; H, 3.59; N, 3.83.
Found: C, 49.56; H, 3.70; N, 3.64.
The data that supports the findings of this study are
available in the supplementary material of this article.
ORCID
3.11 | 6-Methyl-8-nitro-4-phenyl-
1,2,3,4-tetrahydro-quinoline (3i)
REFERENCES
Yellow oil (63%, 170 mg).
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1H NMR (400 MHz, CDCl3) δ: 2.09–2.25(m, 2H), 2.18
(s, 3H), 3.37–3.57 (m, 2H), 4.20 (t, 1H, J = 4 Hz), 6.89 (s,
1H), 7.12 (d, 2H, J = 8 Hz), 7.18–7.38 (m, 3H), 7.91
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13C NMR (100 MHz, CDCl3) δ: 20.1, 28.4, 29.6, 38.0,
42.4, 123.7, 124.6, 126.7, 127.8, 128.3, 128.7, 130.7, 138.2,
141.8, 144.7.
Anal. Calcd for C16H16N2O2. C, 71.61; H, 6.01; N,
10.44. Found: C, 71.65; H, 6.11; N, 10.30.
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3.12 | 6-Methoxy-8-nitro-4-phenyl-
1,2,3,4-tetrahydro-quinoline (3j)
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1H NMR (400 MHz, CDCl3) δ: 2.10–2.26 (m, 2H),
3.40–3.58 (m, 2H), 3.73 (s, 3H), 4.16 (t, 1H, J = 4 Hz),
6.73 (d, 1H, J = 4 Hz), 7.13 (d, 2H, J = 8 Hz), 7.18–7.48
(m, 3H), 7.51 (s, 1H), 8.55 (br, 1H).
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13C NMR (100 MHz, CDCl3) δ: 28.6, 38.7, 43.24, 55.7,
93.8, 104.7, 125.6, 126.8, 127.7, 128.2, 129.0, 129.9, 139.9,
143.9, 148.7.
Anal. Calcd for C16H16N2O3. C, 67.57; H, 5.67; N,
5.59. Found: C, 67.81; H, 5.80; N, 5.43.
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3.13 | 6-Phenyl-1,2,5,6-tetrahydro-4H-
pyrrolo[3,2,1-ij]quinoline (4)
Yellow oil (33%, 77 mg) [18].
1H NMR (400 MHz, CDCl3) δ: 2.19–2.44 (m, 2H),
2.99–3.45 (m, 6H), 4.14 (t, 1H, J = 8 Hz), 6.61 (d,
2H, J = 4 Hz), 7.01 (t, 1H, J = 8 Hz), 7.20–
7.36 (m, 5H).