Paper
Organic & Biomolecular Chemistry
1H), 7.83–7.79 (m, 2H), 7.77–7.68 (m, 1H), 7.63–7.62 (m,
2-Cyclopropylquinoline (3az″).14a Eluent: petroleum ether/
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1H), 7.51–7.48 (m, 1H), 7.26–7.21 (m, 1H), 6.59–6.58 (m, 1H); ethyl acetate (19 : 1). Pale-yellow oil (*71% and 32%, *120 mg
13C NMR (100 MHz, CDCl3):
δ (ppm) = 153.7, 149.0, and 54 mg). H NMR (500 MHz, CDCl3): δ (ppm) = 7.97–7.90
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148.1, 144.1, 136.6, 129.8, 129.3, 127.5, 127.1, 126.2, 117.4, (m, 2H), 7.69 (d, J = 6.0 Hz, 1H), 7.64–7.57 (m, 1H), 7.41–7.35
112.2, 110.1.
(m, 1H), 7.12–7.10 (m, 1H), 2.25–2.17 (m, 1H), 1.17–1.13 (m,
3-Methyl-2-phenylquinoline (3av).12b,i,14a Eluent: petroleum 2H), 1.11–1.05 (m, 2H); 13C NMR (125 MHz, CDCl3): δ (ppm) =
ether/ethyl acetate (19 : 1). Pale-yellow oil (*68% and #50%, 163.4, 148.0, 135.8, 129.3, 128.6, 127.5, 126.7, 125.2, 119.3,
*149 mg and 110 mg). H NMR (400 MHz, CDCl3): δ (ppm) = 18.1, 10.3.
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8.03 (d, J = 8.4 Hz, 1H), 7.88 (s, 1H), 7.65 (d, J = 7.6 Hz, 1H),
8-Methyl-2-phenylquinoline (3ba).12e,14a Eluent: petroleum
7.54 (t, J = 7.2, 1H), 7.48 (d, J = 7.2 Hz, 2H), 7.41–7.32 (m, 4H), ether/ethyl acetate (19 : 1). Pale-yellow oil (*82% and #76%,
2.34 (s, 3H); 13C NMR (100 MHz, CDCl3): δ (ppm) = 160.5, *180 mg and 167 mg). H NMR (400 MHz, CDCl3): δ (ppm) =
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146.6, 140.9, 136.8, 129.3, 129.2, 128.9, 128.8, 128.3, 128.2, 8.12 (d, J = 8.0 Hz, 2H), 7.97 (d, J = 8.4 Hz, 1H), 7.71 (d, J =
127.5, 126.6, 126.8, 126.4, 20.7.
8.4 Hz, 1H), 7.48 (d, J = 8.0 Hz, 1H), 7.42–7.36 (m, 3H),
3-Ethyl-2-phenylquinoline (3aw).12i,14a Eluent: petroleum 7.33–7.29 (m, 1H), 7.25 (t, J = 7.6 Hz, 1H), 2.78 (s, 3H);
ether/ethyl acetate (19 : 1). Pale-yellow oil (*65% and #45%, 13C NMR (100 MHz, CDCl3): δ (ppm) = 155.5, 147.1, 139.8,
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*152 mg and 105 mg). H NMR (400 MHz, CDCl3): δ(ppm) = 137.6, 136.9, 129.6, 129.2, 128.7, 127.4, 127.0, 126.0, 125.3,
8.12 (d, J = 3.2 Hz, 1H), 8.05 (s, 1H), 7.82–7.79 (m, 1H), 7.66 (t, 118.1, 17.9.
J = 4.8 Hz, 1H), 7.56–7.50 (m, 3H), 7.49–7.45 (m, 2H), 7.42 (d,
6-Methyl-2-phenylquinoline (3ca).12d,14a Eluent: petroleum
J = 6.0 Hz, 1H), 2.82–2.77 (m, 2H), 1.91 (t, J = 5.6 Hz, 3H); 13C ether/ethyl acetate (19 : 1). White solid (*89% and #81%,
NMR (100 MHz, CDCl3): δ (ppm) = 160.7, 146.2, 140.8, 135.4, *195 mg and #178 mg). Mp: 62–63 °C; 1H NMR (400 MHz,
134.7, 129.4, 128.6, 128.5, 128.3, 128.2, 127.5, 127.0, 126.4, CDCl3): δ (ppm) = 8.12 (d, J = 8.0 Hz, 2H), 8.04 (t, J = 8.8 Hz,
26.2, 14.6.
2H), 7.76 (d, J = 8.8 Hz, 1H), 7.52–7.47 (m, 4H), 7.44–7.42 (m,
11H-Indeno[1,2-b]quinoline (3ax).12i Eluent: petroleum 1H), 2.49 (s, 3H); 13C NMR (100 MHz, CDCl3): δ (ppm) = 156.5,
ether/ethyl acetate (19 : 1). Yellow solid (*89% and #80%, 146.8, 139.8, 136.114, 136.083, 131.9, 129.4, 129.1, 128.8,
*193 mg and 174 mg). Mp: 169–170 °C; H NMR (300 MHz, 127.5, 127.2, 126.3, 119.0, 21.6.
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CDCl3): δ (ppm) = 8.31 (d, J = 2.8 Hz, 1H), 8.21 (d, J = 6.6 Hz,
8-Bromo-6-methyl-2-phenylquinoline (3da). Eluent: pet-
1H), 8.19 (s, 1H), 7.83 (dd, J = 6.3, 0.9 Hz, 1H), 7.73–7.68 (m, roleum ether/ethyl acetate (19 : 1). White solid (*64% and
1H), 7.62–7.60 (m, 1H), 7.53–7.49 (m, 3H), 4.04 (s, 2H). 13C #54%, *162 mg and #137 mg). Mp: 80–82 °C. 1H NMR
NMR (75 MHz, CDCl3): δ (ppm) = 161.9, 148.1, 145.2, 140.4, (400 MHz, CDCl3): δ (ppm) = 8.15 (dd, J = 8.4, 1.2 Hz, 2H), 7.86
134.7, 131.2, 130.0, 129.1, 128.9, 127.8, 127.6, 127.4, 125.7, (d, J = 8.4 Hz, 1H), 7.73–7.68 (m, 2H), 7.35–7.30 (m, 2H). 13C
125.4, 122.1, 34.0.
NMR (125 MHz, CDCl3): δ (ppm) = 156.6, 143.5, 138.9, 136.7,
5,6-Dihydrobenzo[c]acridine (3ay).14a Eluent: petroleum 136.5, 135.2, 129.5, 128.8, 128.2, 127.5, 126.2, 125.0, 119.1,
ether/ethyl acetate (19 : 1). White solid (*88% and #83%, 21.2. HRMS (ESI, positive ions): m/z calcd for C16H12BrN+
*204 mg and #192 mg). Mp: 65–66 °C; 1H NMR (300 MHz, [M + H+] 299.1851, found 299.1847.
CDCl3): δ (ppm) = 8.59 (d, J = 6.5, 1H), 8.14 (d, J = 8.2 Hz, 1H),
7.91 (s, 1H), 7.74 (d, J = 7.6 Hz, 1H), 7.67 (t, J = 6.9 Hz, 1H), ether/ethyl acetate (19 : 1). White solid (*79% and #74%,
7.50–7.35 (m, 3H), 7.28 (d, J = 7.5 Hz, 1H), 3.12 (d, J = 7.2, 2H), *189 mg and 177 mg). Mp: 107–109 °C; H NMR (400 MHz,
3.02 (d, J = 6.9 Hz, 2H); 13C NMR (125 MHz, CDCl3): δ (ppm) = CDCl3): δ (ppm) = 8.07–8.04 (m, 4H), 7.74 (t, J = 8.4 Hz, 1H),
153.3, 147.6, 139.4, 134.7, 133.7, 130.5, 129.6, 129.3, 128.6, 7.62 (t, J = 8.8 Hz, 1H), 7.45–7.32 (m, 4H). 13C NMR (100 MHz,
7-Chloro-2-phenylquinoline (3ea).12e,14a Eluent: petroleum
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127.9, 127.8, 127.3, 126.9, 126.0, 28.8, 28.4.
CDCl3): δ (ppm) = 158.2, 148.6, 139.2, 136.6, 135.5, 129.7,
1,2,3,4-Tetrahydroacridine (3az).12i,14b Eluent: petroleum 128.9, 128.7, 127.6, 127.3, 125.5, 119.1.
ether/ethyl acetate (19 : 1). Yellow solid (*83% and #75%,
6-Chloro-2-phenylquinoline (3fa).12b,14a Eluent: petroleum
*152 mg and #137 mg). Mp: 50–53 °C; 1H NMR (400 MHz, ether/ethyl acetate (19 : 1). White solid (*72% and #62%,
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CDCl3): δ (ppm) = 7.97 (d, J = 8.5 Hz, 1H), 7.78 (s, 1H), 7.68 (d, *173 mg and 149 mg); mp: 107–109 °C; H NMR (400 MHz,
J = 8.0 Hz, 1H), 7.58 (dd, J = 13.9, 6.7 Hz, 1H), 7.42 (t, J = 7.4 CDCl3): δ (ppm) = 8.14 (t, J = 9.6 Hz, 3H), 8.11 (d, J = 10.8 Hz,
Hz, 1H), 3.12 (t, J = 6.5 Hz, 2H), 3.01–2.90 (t, J = 6.5 Hz, 2H), 1H), 7.91 (d, J = 10.4 Hz, 1H), 7.81 (d, J = 4.8 Hz, 1H),
2.04–1.93 (m, 2H), 1.93–1.83 (m, 2H). 13C NMR (100 MHz, 7.67–7.65 (m, 1H), 7.52 (t, J = 5.6 Hz, 2H), 7.48 (t, J = 6.0 Hz,
CDCl3): δ (ppm) = 159.39, 146.67, 135.08, 131.05, 128.57, 1H); 13C NMR (100 MHz, CDCl3): δ (ppm) = 157.6, 146.7,
128.34, 127.28, 126.98, 125.61, 33.67, 29.35, 23.33, 23.0.
139.2, 135.8, 131.9, 131.3, 130.6, 129.6, 128.9, 127.7, 127.5,
2-tert-Butylquinoline (3az′).14a Eluent: petroleum ether/ethyl 126.1, 119.8.
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acetate (19 : 1). Pale-yellow oil (*60% and 29%, *111 mg and
7-Bromo-2-phenylquinoline (3ga).14a Eluent: petroleum
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#54 mg). H NMR (400 MHz, CDCl3): δ (ppm) = 8.06 (d, J = 7.2 ether/ethyl acetate (19 : 1). White solid (*69% and #61%,
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Hz, 2H), 7.75 (d, J = 8.4 Hz, 1H), 7.66 (t, J = 6.0 Hz, 1H), *196 mg and 173 mg). Mp: 114–115 °C; H NMR (400 MHz,
7.52–7.51 (m, 1H), 7.46 (t, J = 5.2 Hz, 1H), 1.47 (s, 9H); 13C CDCl3): δ (ppm) = 8.36 (d, J = 2.0 Hz, 1H), 8.18–8.13 (m, 3H),
NMR (100 MHz, CDCl3): δ (ppm) = 169.5, 147.6, 135.9, 129.6, 7.88 (d, J = 6.4 Hz, 1H), 7.68 (d, J = 10.4 Hz, 1H), 7.60 (dd, J =
128.9, 127.4, 126.6, 125.4, 118.3, 38.2, 30.0.
7.2 and 1.6 Hz, 1H), 7.54–7.51 (m, 2H), 7.49–7.45 (m, 1H); 13C
282 | Org. Biomol. Chem., 2018, 16, 274–284
This journal is © The Royal Society of Chemistry 2018