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column chromatography to obtain pure 5a (72% yield) as a light 128.6, 128.5, 128.4, 128.0, 127.6, 126.4, 126.2, 125.0, 44.0, 43.2,
brown solid; mp 132–133 ꢀC; 1H NMR (500 MHz, CDCl3): d 8.11 40.6, 32.2; HRMS (ESI) m/z calcd for C33H24O2NCl [M]+ 489.1459;
(d, J ¼ 8.5 Hz, 1H), 7.88 (d, J ¼ 7.5 Hz, 2H), 7.76–7.73 (m, 1H), found 489.1463.
7.65–7.61 (m, 2H), 7.53–7.52 (m, 4H), 7.50–7.44 (m, 2H), 7.41–
3-(3-Acetyl-6-chloro-4-phenylquinolin-2-yl)-1-phenyl-2-(p-tolyl)
7.38 (m, 2H), 7.28–7.25 (m, 3H), 7.16 (t, J ¼ 7 Hz, 2H), 4.32–4.26 propan-1-one (5f). Yield 72%; light brown solid; mp 215–217 ꢀC;
(m, 1H), 3.67 (dd, J ¼ 16.5 Hz, 17 Hz, 1H), 3.47–3.42 (m, 1H), 1H NMR (500 MHz, CDCl3): d 7.94 (d, J ¼ 8.5 Hz, 1H), 7.86 (d, J ¼
3.38–3.30 (m, 2H), 2.03 (s, 3H); 13C NMR (125 MHz, CDCl3): 7.5 Hz, 2H), 7.61 (dd, J ¼ 9 Hz, 9 Hz, 1H), 7.57–7.50 (m, 5H), 7.41–
d 205.8, 198.7, 155.1, 147.4, 144.6, 137.2, 135.3, 135.2, 135.1, 7.37 (m, 3H), 7.30–7.28 (m, 1H), 7.21 (d, J ¼ 8 Hz, 2H), 7.08 (d, J ¼
134.8, 130.0, 128.9, 128.7, 128.4, 128.3, 128.0, 127.6, 126.6, 8 Hz, 2H), 4.24–4.22 (m, 1H), 3.64 (dd, J ¼ 17 Hz, 17 Hz, 1H),
126.5, 126.1, 126.0, 125.1, 125.0, 44.1, 43.6, 40.6, 32.2; HRMS 3.42–3.37 (m, 1H), 3.32–3.29 (m, 2H), 2.28 (s, 3H), 1.88 (s, 3H);
(ESI) m/z calcd for C33H28O2N [M + H]+ 470.2115; found 13C NMR (125 MHz, CDCl3): d 205.4, 198.6, 155.7, 145.6, 143.4,
470.2118.
141.4, 137.0, 136.0, 135.8, 134.6, 132.7, 131.0, 130.7, 130.1, 129.9,
4-(3-Acetyl-4-phenylquinolin-2-yl)-1-phenyl-3-(p-tolyl)butan- 129.2, 129.0, 128.8, 128.4, 128.0, 127.4, 125.8, 124.8, 44.1, 43.2,
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1-one (5b). Yield 70%; brown solid; mp 198–200 ꢀC; H NMR 40.0, 32.1, 21.0; HRMS (ESI) m/z calcd for C33H27O2NCl [M]+
(500 MHz, CDCl3): d 8.09 (d, J ¼ 8 Hz, 1H), 8.02 (d, J ¼ 8.5 Hz, 504.1735; found 504.1738.
1H), 7.87 (d, J ¼ 7.5 Hz, 2H), 7.53–7.49 (m, 4H), 7.40–7.37 (m,
4-(3-Acetyl-6-chloro-4-phenylquinolin-2-yl)-3-(4-methoxyphenyl)-
4H), 7.31–7.29 (m, 2H), 7.21 (d, J ¼ 8 Hz, 2H), 7.07 (d, J ¼ 8 Hz, 1-phenylbutan-1-one (5g). Yield 70%; brown solid; mp 205–207 ꢀC;
2H), 4.24–4.21 (m, 1H), 3.64 (dd, J ¼ 16.5 Hz, 16.5 Hz, 1H), 3.43– 1H NMR (500 MHz, CDCl3): d 7.99 (d, J ¼ 9 Hz, 1H), 7.87 (d, J ¼
3.34 (m, 2H), 2.27 (s, 3H), 1.87 (s, 3H); 13C NMR (125 MHz, 7.5 Hz, 2H), 7.63 (dd, J ¼ 9 Hz, 9 Hz, 1H), 7.58–7.51 (m, 6H), 7.42–
CDCl3): d 205.9, 198.8, 155.2, 147.4, 144.1, 141.5, 137.1, 135.9, 7.39 (m, 3H), 7.24 (d, J ¼ 8.5 Hz, 2H), 6.81 (d, J ¼ 8.5 Hz, 2H), 4.24–
135.3, 135.1, 132.7, 130.3, 130.2, 130.1, 129.2, 129.1, 128.9, 4.18 (m, 1H), 3.76 (s, 3H), 3.64 (dd, J ¼ 17 Hz, 17 Hz, 1H), 3.42–3.31
128.8, 128.7, 128.5, 128.3, 128.1, 127.4, 126.6, 126.5, 126.2, (m, 3H), 1.89 (s, 3H); 13C NMR (125 MHz, CDCl3): d 205.4, 155.4,
126.1, 125.0, 44.1, 43.4, 40.2, 32.2, 23.9, 21.0; HRMS (ESI) m/z 145.3, 143.5, 141.2, 137.1, 136.2, 135.2, 134.8, 133.1, 132.6, 131.0,
calcd for C34H29O2N [M + H] 483.2198; found 483.2203.
130.4, 130.1, 130.0, 129.3, 129.0, 128.6, 128.1, 127.9, 127.1, 125.6,
4-(3-Acetyl-4-phenylquinolin-2-yl)-3-(4-nitrophenyl)-1-phenyl 124.3, 55.5, 44.2, 43.5, 40.1, 32.4; HRMS (ESI) m/z calcd for
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butan-1-one (5c). Yield 75%; brown solid; mp 205–206 C; H C33H28O2N [M + H] 534.1830; found 534.1833.
NMR (500 MHz, CDCl3): d 8.13 (d, J ¼ 8.5 Hz, 2H), 8.03 (d, J ¼
4-(3-Acetyl-6-chloro-4-phenylquinolin-2-yl)-3-(4-nitrophenyl)-
8.5 Hz, 1H), 7.89 (d, J ¼ 7 Hz, 2H), 7.74–7.71 (m, 1H), 7.64 (d, J ¼ 1-phenylbutan-1-one (5h). Yield 72%; brown solid; mp 212–
8 Hz, 1H), 7.56–7.53 (m, 6H), 7.49–7.47 (m, 1H), 7.42 (t, J ¼ 8 Hz, 214 ꢀC; 1H NMR (500 MHz, CDCl3): d 7.87 (d, J ¼ 9 Hz, 1H), 7.78–
2H), 7.37–7.33 (m, 2H), 4.50–4.45 (m, 1H), 3.69 (dd, J ¼ 17.5 Hz, 7.76 (m, 2H), 7.54 (dd, J ¼ 9 Hz, 9 Hz, 1H), 7.49–7.44 (m, 5H),
17 Hz, 1H), 3.53–3.48 (m, 1H), 3.34–3.32 (m, 2H), 1.93 (s, 3H); 7.33–7.29 (m, 3H), 7.20–7.18 (m, 3H), 7.15–7.13 (m, 2H), 4.20–
13C NMR (125 MHz, CDCl3): d 205.8, 197.2, 153.9, 152.6, 147.4, 4.14 (m, 1H), 3.54 (dd, J ¼ 17 Hz, J ¼ 17 Hz, 1H), 3.33–3.28 (m,
146.5, 144.6, 136.7, 135.1, 134.7, 133.1, 130.1, 129.2, 129.1, 1H), 3.21 (d, J ¼ 7 Hz, 2H), 1.81 (s, 3H); 13C NMR (125 MHz,
128.9, 128.8, 128.7, 128.5, 128.0, 126.9, 126.2, 125.0, 123.7, 43.7, CDCl3): d 205.2, 198.2, 155.1, 142.9, 136.8, 135.6, 134.4, 133.0,
42.4, 40.0, 32.3; HRMS (ESI) m/z calcd for C33H26O4N2 [M + H] 132.1, 131.2, 130.4, 130.3, 130.0, 129.9, 129.4, 129.2, 129.1,
514.1892; found 514.1896.
129.0, 128.9, 128.6, 128.5, 128.1, 128.0, 126.1, 125.9, 124.9, 44.0,
3-(3-Acetyl-4-phenylquinolin-2-yl)-2-(4-chlorophenyl)-1-phenyl 42.7, 39.7, 32.1; HRMS (ESI) m/z calcd for C33H25ClO4N2 [M + H]
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propan-1-one (5d). Yield 71%; brown solid; mp 214–216 C; H 548.1502; found 548.1506.
NMR (500 MHz, CDCl3): d 8.03 (d, J ¼ 8 Hz, 1H), 7.88 (d, J ¼
3-(3-Acetyl-6-chloro-4-phenylquinolin-2-yl)-2-(4-chlorophenyl)-1-
7.5 Hz, 2H), 7.71 (t, J ¼ 8.5 Hz, 1H), 7.63 (d, J ¼ 8 Hz, 1H), 7.53– phenylpropan-1-one (5i). Yield 67%; brown solid; mp 220–222 ꢀC;
7.46 (m, 5H), 7.42–7.39 (m, 1H), 7.32–7.27 (m, 5H), 7.23 (d, J ¼ 1H NMR (500 MHz, CDCl3): d 7.98 (d, J ¼ 9 Hz, 1H), 7.86 (d, J ¼
8.5 Hz, 2H), 4.30–4.27 (m, 1H), 3.62 (dd, J ¼ 16.5 Hz, 18.5 Hz, 1H), 7.5 Hz, 1H), 7.65–7.63 (m, 1H), 7.63–7.51 (m, 5H), 7.42–7.37 (m,
3.43–3.39 (m, 1H), 3.34–3.32 (d, J ¼ 6.5 Hz, 2H), 1.89 (s, 3H); 13
C
3H), 7.37–7.27 (m, 4H), 7.23 (d, J ¼ 8.5 Hz, 2H), 4.27–4.23 (m, 1H),
NMR (125 MHz, CDCl3): d 205.8, 198.4, 154.6, 143.1, 136.9, 135.2, 3.64 (dd, J ¼ 17 Hz, 17 Hz, 1H), 3.42–3.37 (m, 1H), 3.31–3.30 (m,
134.9, 132.9, 132.0, 130.1, 130.0, 129.2, 129.1, 129.0, 128.9, 128.8, 2H), 1.90 (s, 3H); 13C NMR (125 MHz, CDCl3): d 205.6, 198.3, 155.1,
128.7, 128.6, 128.4, 128.0, 126.8, 126.1, 125.0, 44.0, 43.0, 39.8, 142.8, 136.7, 135.6, 133.0, 132.2, 130.0, 129.9, 129.8, 129.5, 129.1,
32.3; HRMS (ESI) m/z calcd for C33H24O2NCl [M]+ 489.1459; found 129.0, 128.9, 128.6, 128.5, 128.0, 125.9, 124.9, 43.9, 42.6, 39.7, 32.1;
489.1463.
HRMS (ESI) m/z calcd for C32H23Cl2NO2 [M + H] 524.4359; found
3-(3-Acetyl-6-chloro-4-phenylquinolin-2-yl)-1,2-diphenylpropan- 524.4360.
1-one (5e). Yield 72%; brown solid; mp 220–222 ꢀC; 1H NMR (500
4-(3-Acetyl-6-nitro-4-phenylquinolin-2-yl)-1,3-diphenylbutan-
MHz, CDCl3): d 8.10 (d, J ¼ 8 Hz, 1H), 8.04 (d, J ¼ 8.5 Hz, 1H), 1-one (5j). Yield 72%; light brown solid; mp 128–130 ꢀC; 1H
7.88 (d, J ¼ 7.5 Hz, 2H), 7.75 (t, J ¼ 7 Hz, 1H), 7.71 (t, J ¼ 7 Hz, NMR (500 MHz, CDCl3): d 8.14 (d, J ¼ 9 Hz, 2H), 8.03 (d, J ¼ 8 Hz,
1H), 7.66–7.62 (m, 2H), 7.54–7.52 (m, 4H), 7.32–7.25 (m, 5H), 1H), 7.90–7.88 (m, 2H), 7.74–7.71 (m, 1H), 7.65–7.63 (m, 1H),
7.18–7.15 (m, 1H), 4.31–4.25 (m, 1H), 3.67 (dd, J ¼ 17 Hz, 17 Hz, 7.56–7.53 (m, 6H), 7.49–7.46 (m, 1H), 7.42 (t, J ¼ 8 Hz, 2H), 7.38–
1H), 3.48–3.43 (m, 1H), 3.39–3.29 (m, 2H), 2.03 (s, 3H); 13C NMR 7.33 (m, 2H), 4.05–4.44 (m, 1H), 3.69 (dd, J ¼ 17.5 Hz, 17.5 Hz,
(125 MHz, CDCl3): d 205.9, 198.7, 155.1, 153.5, 147.4, 144.5, 1H), 3.54–3.48 (m, 1H), 3.34–3.31 (m, 2H), 1.92 (s, 3H); 13C NMR
137.1, 132.7, 130.2, 130.1, 130.0, 129.1, 128.9, 128.8, 128.7, (125 MHz, CDCl3): d 205.8, 197.4, 153.9, 152.6, 147.4, 146.5,
18878 | RSC Adv., 2017, 7, 18874–18882
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