The Journal of Organic Chemistry
Page 8 of 11
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ꢀButylquinoline (3e): Light yellow oil, 78% yield (72 mg). H NMR (400 MHz, CDCl ) δ 0.93 (t, J
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7.6 Hz, 3H), 1.34-1.40 (m, 2H), 1.62-1.68 (m, 2H), 2.74 (t, J = 7.6 Hz, 2H), 7.47 (t, J = 7.2 Hz, 1H),
7.61 (t, J = 7.2 Hz, 1H), 7.71 (d, J = 8.0 Hz, 1H), 7.85 (s, 1H), 8.06 (d, J = 8.6 Hz, 1H), 8.76 (d, J = 1.6
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Hz, 1H); C NMR (100 MHz, CDCl ) δ 13.7, 22.0, 32.7, 33.0, 126.4, 127.2, 128.1, 128.4, 129.1, 134.0,
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35.3, 146.7, 152.1.
,3ꢀDipropylquinoline (3f): Light yellow oil, 72% yield (76 mg). H NMR (400 MHz, CDCl ) δ 0.98-
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.09 (m, 6H), 1.66-1.76 (m, 2H), 1.79-1.89 (m, 2H), 2.75 (t, J = 8.0 Hz, 2H), 2.95 (t, J = 8.0 Hz, 2H),
7.42 (t, J = 7.2 Hz, 1H), 7.59 (t, J = 7.8 Hz, 1H), 7.69 (d, J = 8.0 Hz, 1H), 7.81(s, 1H), 8.02 (d, J = 8.4
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Hz, 1H); C NMR (100 MHz, CDCl ) δ 13.9, 14.2, 22.8, 23.4, 34.3, 37.7, 125.5, 126.9, 127.2, 128.3,
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28.5, 133.9, 134.8, 146.5, 162.1. HRMS (EI) for C H N [M ] calcd 213.1517, found 213.1521.
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Thieno[2,3ꢀb]quinoline (3g): Light yellow oil, 57% yield (52 mg). H NMR (400 MHz, CDCl ) δ
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.34 (d, J = 6.0 Hz, 1H), 7.52-7.58 (m, 2H), 7.72-7.77 (m, 1H), 7.95 (d, J = 8.0 Hz, 1H), 8.15-8.18 (m,
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H), 8.52 (s, 1H); C NMR (100 MHz, CDCl ) δ 121.2, 125.5, 125.6, 128.3, 128.4, 128.5, 129.3, 130.1,
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131.5, 146.7, 163.4.
ꢀMethoxyꢀ3ꢀphenylquinoline (3h): Light yellow solid, 78% yield (92 mg). H NMR (400 MHz,
CDCl ) δ 3.96 (s, 3H), 7.14 (d, J = 2.4 Hz, 1H), 7.38 (dd, J = 2.4, 9.2 Hz, 1H), 7.44 (t, J = 7.6 Hz, 1H),
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.53 (t, J = 7.6 Hz, 2H), 7.71 (d, J = 7.6 Hz, 2H), 8.03 (d, J = 9.2 Hz, 1H), 8.21 (s, 1 H), 9.03 (d, J = 1.6
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Hz, 1H); C NMR (100 MHz, CDCl ) δ 55.5, 105.3, 122.3, 127.5, 128.1, 129.2, 129.2, 130.7, 132.2,
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134.2, 138.1, 143.6, 147.5, 158.2.
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ꢀBromoꢀ3ꢀphenylquinoline (3i): Light yellow solid, 84% yield (119 mg), mp 114-115 C. H NMR
(400 MHz, CDCl ) δ 7.45 (t, J = 7.6 Hz, 1H), 7.53 (t, J = 8.0 Hz, 2H), 7.68-7.70 (m, 2H), 7.70 (dd, J =
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2.0, 8.8 Hz, 1H), 7.98-8.02 (m, 2H), 8.18 (d, J = 2.4 Hz, 1H), 9.17 (d, J = 2.0 Hz, 1H); C NMR (100
MHz, CDCl ) δ 120.9, 127.5, 128.5, 129.2, 129.3, 130.0, 131.0, 132.1, 132.8, 134.7, 137.4, 145.9, 150.4.
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ꢀMethylꢀ3ꢀphenylquinoline (3j): Light yellow solid, 83% yield (90 mg), mp 58-61 C. H NMR (400
MHz, CDCl ) δ 2.50 (s, 3H), 7.25-7.38 (m, 5H), 7.46 (t, J = 7.6 Hz, 1H), 7.58 (t, J = 7.6 Hz, 1H), 7.93
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