10.1002/adsc.201900960
Advanced Synthesis & Catalysis
+
J = 21.9 Hz), 52.7 .HRMS (EI) for C28H20FN2O3
Hz, 2H), 7.26 – 7.15 (m, 5H), 6.93 (d, J = 6.9 Hz, 2H),
6.89 (s, 4H), 5.22 (s, 2H), 2.43 – 2.37 (m, 2H), 1.49 –
1.40 (m, 2H), 0.73 (t, J = 7.3 Hz, 3H); 13C NMR (126
MHz, CDCl3) δ 175.64 , 153.12 , 145.86 , 144.24 ,
143.59 , 140.64 , 136.16 , 132.68 , 132.30 , 130.92 ,
128.96 , 128.91 , 128.51 , 127.63 , 127.22 , 126.76 ,
125.42 , 124.17 , 122.53 , 122.47 , 117.35 , 52.67 ,
(M+H)+ : calculated 451.1452, found 451.1447.
1-benzyl-2-(4-chlorophenyl)-3-(4-
nitrophenyl)quinolin-4(1H)-one (3db) (35.5 mg,
76%). White solid. ethyl acetate : hexane = 1 : 4. H
1
NMR (500 MHz, CDCl3) δ 8.55 (d, J = 7.7 Hz, 1H),
7.99 (d, J = 7.9 Hz, 2H), 7.61 (t, J = 7.6 Hz, 1H), 7.46
– 7.39 (m, 2H), 7.35 – 7.27 (m, 3H), 7.24 (d, J = 8.0
Hz, 2H), 7.15 (d, J = 7.4 Hz, 2H), 7.04 – 6.97 (m, 4H),
+
37.43 , 23.93 , 13.37; HRMS (EI) for C31H27N2O3
(M+H)+ : calculated 475.2016, found 475.2011.
5.25 (s, 2H); 13C NMR (126 MHz, CDCl3) δ 175.7 , 1-benzyl-2-(3-fluorophenyl)-3-(4-
151.5 , 146.2 , 142.9 , 140.7 , 135.8 , 135.7 , 133.0 , nitrophenyl)quinolin-4(1H)-one (3dg) (41.4 mg,
132.3 , 132.0 , 130.3 , 129.1 , 128.9 , 127.9 , 127.3 , 91%). White solid. ethyl acetate : hexane = 1 : 4. 1H
126.6 , 125.3 , 124.5 , 122.9 , 122.6 , 117.3 , 52.7; NMR (500 MHz, CDCl3) δ 8.52 – 8.48 (m, 1H), 7.93
+
HRMS (EI) for C28H20ClN2O3 (M+H)+ : calculated (d, J = 8.8 Hz, 2H), 7.57 – 7.52 (m, 1H), 7.40 – 7.33
467.1157, found 467.1155.
(m, 2H), 7.29 – 7.17 (m, 5H), 7.09 (q, J = 7.8 Hz, 1H),
6.95 – 6.86 (m, 3H), 6.82 (d, J = 7.6 Hz, 1H), 6.73 (d,
J = 8.5 Hz, 1H), 5.19 (s, 2H); 13C NMR (126 MHz,
CDCl3) δ 175.7, 162.1 (d, J = 249.8 Hz), 151.1, 146.2,
142.9, 140.7, 135.7, 135.5 (d, J = 7.8 Hz), 133.0,
132.2, 130.4 (d, J = 8.3 Hz), 129.1, 127.9, 127.3,
126.7, 125.3, 125.0 (d, J = 3.3 Hz), 124.5, 122.8,
122.5, 117.3, 116.7 (d, J = 20.7 Hz), 116.4 (d, J =
1-benzyl-2-(4-bromophenyl)-3-(4-
nitrophenyl)quinolin-4(1H)-one (3dc) (35.5 mg,
76%). White solid. ethyl acetate : hexane = 1 : 4. 1H
NMR (500 MHz, CDCl3) δ 8.57 – 8.54 (m, 1H), 8.00
(d, J = 8.9 Hz, 2H), 7.63 – 7.57 (m, 1H), 7.45 – 7.39
(m, 2H), 7.34 – 7.28 (m, 5H), 7.25 (d, J = 8.8 Hz, 2H),
7.02 – 6.94 (m, 4H), 5.24 (s, 2H). 13C NMR (126
MHz, CDCl3) δ 175.6 , 151.4 , 146.2 , 143.0 , 140.7 ,
135.7 , 132.9 , 132.5 , 132.3 , 131.8 , 130.6 , 129.1 ,
+
22.7 Hz); HRMS (EI) for C28H20FN2O3 (M+H)+ :
calculated 451.1452, found 451.1447.
127.8 , 127.2 , 126.7 , 125.3 , 124.4 , 124.0 , 122.8 , 1-benzyl-3-(4-nitrophenyl)-2-(thiophen-3-
+
122.5 , 117.3 , 52.7; HRMS (EI) for C28H20BrN2O3
yl)quinolin-4(1H)-one (3dh) (35.1 mg, 80%). White
solid. ethyl acetate : hexane = 1 : 4. 1H NMR (500
MHz, CDCl3) δ 8.52 – 8.43 (m, 1H), 7.93 (d, J = 8.5
Hz, 2H), 7.55 – 7.46 (m, 1H), 7.38 – 7.29 (m, 2H),
7.27 (t, J = 7.2 Hz, 2H), 7.26 – 7.17 (m, 3H), 7.13 –
7.07 (m, 1H), 6.98 (d, J = 7.3 Hz, 2H), 6.95 – 6.89 (m,
1H), 6.71 (d, J = 4.8 Hz, 1H), 5.24 (d, J = 9.1 Hz, 2H);
13C NMR (126 MHz, CDCl3) δ 175.4 , 148.3 , 146.0 ,
143.5 , 140.7 , 136.2 , 133.5 , 132.8 , 131.9 , 129.1 ,
128.0 , 127.8 , 127.2 , 127.0 , 126.8 , 126.7 , 125.3 ,
124.3 , 123.0 , 122.7 , 117.3 , 52.8; HRMS (EI) for
C26H19N2O3S+ (M+H)+ : calculated 439.1111, found
439.1107.
(M+H)+ : calculated 511.0652, found 511.0646.
1-benzyl-2-(4-methoxyphenyl)-3-(4-
nitrophenyl)quinolin-4(1H)-one (3dd) (34.3 mg,
74%). White solid. ethyl acetate : hexane = 1 : 4. 1H
NMR (500 MHz, CDCl3) δ 8.50 – 8.47 (m, 1H), 7.91
(d, J = 8.6 Hz, 2H), 7.53 – 7.47 (m, 1H), 7.36 – 7.30
(m, 2H), 7.26 – 7.17 (m, 5H), 6.96 – 6.89 (m, 4H),
6.59 (d, J = 8.1 Hz, 2H), 5.22 (s, 2H), 3.64 (s, 3H).
13C NMR (126 MHz, CDCl3) δ 175.67 , 160.03 ,
152.84 , 145.88 , 143.68 , 140.69 , 136.14 , 132.70 ,
132.31 , 130.42 , 128.98 , 127.63 , 127.20 , 126.73 ,
125.80 , 125.39 , 124.17 , 122.70 , 122.66 , 117.38 ,
+
113.85 , 55.15 , 52.62; HRMS (EI) for C29H23N2O4
1-benzyl-2-butyl-3-(4-nitrophenyl)quinolin-4(1H)-
one (3di) (24.9 mg, 60%). White solid. ethyl acetate :
hexane = 1 : 4. 1H NMR (500 MHz, CDCl3) δ 8.49 –
8.45 (m, 1H), 8.31 (d, J = 8.8 Hz, 2H), 7.58 – 7.53 (m,
1H), 7.50 (d, J = 8.4 Hz, 2H), 7.41 – 7.36 (m, 4H),
7.34 (d, J = 8.5 Hz, 1H), 7.10 (d, J = 7.6 Hz, 2H),
5.51 (s, 2H), 2.61 – 2.45 (m, 2H), 1.59 – 1.43 (m, 2H),
1.15 (q, J = 7.3 Hz, 2H), 0.69 (t, J = 7.3 Hz, 3H); 13C
NMR (126 MHz, CDCl3) δ 175.9 , 152.5 , 147.0 ,
144.4 , 141.1 , 135.5 , 132.5 , 132.1 , 129.3 , 128.0 ,
127.1 , 126.3 , 125.2 , 123.9 , 123.6 , 122.3 , 116.4 ,
50.5 , 31.2 (d, J = 19.9 Hz), 22.5 , 13.3; HRMS (EI)
(M+H)+ : calculated 463.1652, found 463.1646.
1-benzyl-3-(4-nitrophenyl)-2-(p-tolyl)quinolin-
4(1H)-one (3de) (38.2 mg, 86%). White solid. ethyl
acetate : hexane = 1 : 4. 1H NMR (500 MHz, CDCl3)
δ 8.51 – 8.45 (m, 1H), 7.89 (d, J = 8.6 Hz, 2H), 7.52 –
7.47 (m, 1H), 7.36 – 7.30 (m, 2H), 7.26 – 7.16 (m,
5H), 6.93 (d, J = 7.1 Hz, 2H), 6.89 (s, 4H), 5.20 (s,
2H), 2.17 (s, 3H); 13C NMR (126 MHz, CDCl3) δ
175.7 , 153.1 , 145.9 , 143.6 , 140.6 , 139.6 , 136.1 ,
132.7 , 132.3 , 130.7 , 129.2 , 129.0 , 128.8 , 127.6 ,
127.2 , 126.7 , 125.4 , 124.2 , 122.6 , 122.5 , 117.4 ,
+
for C26H25N2O3 (M+H)+ : calculated 413.1860, found
52.6 , 21.2; HRMS (EI) for C29H23N2O3 (M+H)+ :
calculated 447.1703, found 447.1701.
+
413.1863.
1-benzyl-2-cyclopropyl-3-(4-nitrophenyl)quinolin-
4(1H)-one (3dj) (27.4 mg, 69%). White solid. ethyl
acetate : hexane = 1 : 4. 1H NMR (500 MHz, CDCl3)
δ 8.49 – 8.46 (m, 1H), 8.23 (d, J = 8.7 Hz, 2H), 7.59
(d, J = 8.4 Hz, 2H), 7.56 – 7.52 (m, 1H), 7.40 (d, J =
8.7 Hz, 1H), 7.34 (q, J = 6.8 Hz, 3H), 7.29 (t, J = 7.3
1-benzyl-3-(4-nitrophenyl)-2-(4-
propylphenyl)quinolin-4(1H)-one (3df) (42.7 mg,
1
90%). White solid. ethyl acetate : hexane = 1 : 4. H
NMR (500 MHz, CDCl3) δ 8.51 – 8.47 (m, 1H), 7.90
– 7.86 (m, 2H), 7.53 – 7.48 (m, 1H), 7.34 (t, J = 7.6
10
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