FULL PAPERS
(E)-3-Benzyl-5-benzylidene-3-methyl-1-(quinolin-8-yl)pyr-
rolidin-2-one (3e). 29.91 mg. Yield, 74%. The ratio of two
isomers was 2:1 as determined by H NMR. Rf1 =0.50, Rf2 =
1.48 (s, 3H). 13C NMR (CDCl3, 100 MHz) d 181.8, 181.0,
149.9, 149.9, 143.7, 143.3, 138.8, 138.4, 135.7, 135.7, 135.0,
134.7, 134.4, 134.1, 134.0, 134.0, 133.9, 133.6, 133.2, 129.3,
129.3, 129.2, 129.0, 128.8, 128.8, 128.6, 128.2, 128.1, 128.1,
128.0, 127.8, 127.8, 127.6, 127.6, 127.4, 126.1, 126.0, 125.8,
125.6, 125.6, 125.5, 124.9, 124.9, 124.7, 124.6, 121.2, 121.0,
104.0, 103.4, 46.3, 46.1, 40.3, 40.3, 39.5, 37.9, 25.4, 23.6.
HRMS (EI-TOF) calcd for C32H26N2O (M+): 454.2045,
found: 454.2043.
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0.52 (hexane/EtOAc=2:1). Yellow oil. 1H NMR (CDCl3,
400 MHz, a mixture of two isomer) d 8.79–8.80 (m, 2H),
8.09–8.14 (m, 2H), 7.80–7.87 (m, 2H), 7.49–7.61 (m, 3H),
7.31–7.34 (m, 3H), 7.00–7.26 (m, 14H), 6.92–7.11 (m, 6H),
5.22 (s, 1H), 4.97 (s, 1H), 3.15–3.27 (m, 4H), 2.74–3.02 (m,
4H), 1.53 (s, 3H), 1.32 (s, 3H). 13C NMR (CDCl3, 100 MHz)
d 179.2, 178.6, 150.1, 150.0, 143.2, 143.2, 141.7, 141.7, 136.5,
136.4, 135.9, 135.8, 135.1, 132.2, 132.0, 129.7, 129.3, 129.3,
128.6, 128.4, 128.3, 128.2, 127.5, 127.3, 127.2, 127.1, 126.8,
126.5, 125.7, 125.5, 125.3, 124.2, 124.1, 120.9, 120.8, 103.8,
103.0, 44.9, 44.5, 43.2, 42.1, 36.6, 36.2, 24.5, 23.7. HRMS (EI-
TOF) calcd for C28H24N2O (M+): 404.1889, found: 404.1893.
(E)-5-Benzylidene-3-methyl-3-(4-methylbenzyl)-1-(quino-
lin-8-yl)pyrrolidin-2-one (3 f). 28.44 mg. Yield, 68%. The
ratio of two isomers was 2:1 as determined by 1H NMR.
Rf1 =0.50, Rf2 =0.52 (hexane/EtOAc=2:1). Yellow oil.
1H NMR (CDCl3, 400 MHz, a mixture of two isomer) d
8.85–8.88 (m, 2H), 8.17–8.22 (m, 2H), 7.89–7.94 (m, 2H),
7.58–7.70 (m, 3H), 7.34–7.44 (m, 3H), 7.00–7.25 (m, 18H),
5.30 (s, 1H,), 5.07 (s, 1H), 3.20–3.46 (m, 4H), 2.78–3.01 (m,
4H), 2.36 (s, 6H), 1.59 (s, 3H), 1.39 (s, 3H). 13C NMR
(CDCl3, 100 MHz) d 180.4, 179.8, 151.2, 151.1, 144.3, 144.3,
142.9, 137.0, 136.9, 136.3, 136.1, 136.0, 134.4, 133.3, 133.2,
130.7, 130.4, 130.3, 130.2, 129.6, 129.5, 129.3, 129.2, 129.0,
128.9, 128.3, 128.2, 127.6, 127.5, 126.4, 125.2, 125.1, 121.9,
121.8, 104.8, 104.1, 45.9, 45.5, 43.7, 42.8, 37.7, 37.2, 25.6, 23.9,
21.2. HRMS (EI-TOF) calcd for C29H26N2O (M+): 418.2045,
found: 418.2044.
(E)-5-Benzylidene-3-methyl-3-phenethyl-1-(quinolin-8-yl)-
pyrrolidin-2-one (3i). 29.28 mg. Yield, 70%. The ratio of
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two isomers was 1:1.2 as determined by H NMR. Rf1 =0.51,
Rf2 =0.53 (hexane/EtOAc =2:1). Yellow oil. 1H NMR
(CDCl3, 400 MHz, a mixture of two isomer) d 8.88 (dd, J1 =
1.6 Hz; J2 =4.0 Hz, 1H), 8.84 (dd, J1 =1.6 Hz; J2 =4.0 Hz,
1H,), 8.22 (s, 1H), 8.20 (s, 1H), 7.94 (d, J=2.0 Hz, 1H), 7.92
(d, J=1.2 Hz, 1H), 7.63–7.73 (m, 4H), 7.38–7.43 (m, 2H),
7.18–7.29 (m, 14H), 7.11 (d, J=8.0 Hz, 6H), 5.30 (s, 1H, Z-
isomer), 5.28 (s, 1H, E-isomer), 3.03–3.41 (m, 4H), 2.72–
2.97 (m, 4H), 2.09–2.20 (m, 4H), 1.59 (s, 3H), 1.49 (s, 3H).
13C NMR (CDCl3, 100 MHz) d 180.2, 180.2, 151.2, 151.1,
144.3, 143.0, 142.7, 141.9, 137.0, 136.2, 133.5, 133.3, 130.4,
130.4, 129.6, 129.3, 129.3, 129.1, 129.0, 128.9, 128.7, 128.6,
128.5, 128.4, 128.3, 128.2, 128.1, 128.0, 127.6, 127.6, 126.4,
126.4, 126.0, 125.8, 125.3, 121.9, 104.4, 104.3, 44.4, 44.3, 41.1,
40.8, 39.0, 38.6, 31.1, 31.0, 24.9, 24.5. HRMS (EI-TOF) calcd
for C29H26N2O (M+): 418.2045, found: 418.2044.
(E)-5-Benzylidene-3-(3-(2,5-dimethylphenoxy)p-ropyl)-3-
methyl-1-(quinolin-8-yl)pyrrolidin-2-one (3j). 45.24 mg.
Yield, 95%. The ratio of two isomers was 1:1.1 as deter-
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mined by H NMR. Rf1 =0.50, Rf2 =0.52 (hexane/EtOAc=
1
(E)-5-Benzylidene-3-(4-fluorobenzyl)-3-methyl-1-(quino-
lin-8-yl)pyrrolidin-2-one (3g). 23.64 mg. Yield, 56%. The
ratio of two isomers was 2:1 as determined by 1H NMR.
Rf1 =0.51, Rf2 =0.52 (hexane/EtOAc=2:1). Yellow oil.
1H NMR (CDCl3, 400 MHz, a mixture of two isomer) d 8.82
(dd, J1 =1.6 Hz; J2 =4.0 Hz, 1H), 8.80 (dd, J1 =1.6 Hz; J2 =
4.0 Hz, 1H), 7.90 (dd, J1 =1.6 Hz; J2 =8.0 Hz, 1H), 7.85 (dd,
J1 =1.6 Hz; J2 =8.4 Hz, 1H), 7.17–7.47 (m, 17H), 6.33–6.56
(m, 7H), 6.09 (d, J=7.6 Hz, 2H), 5.69 (s, 1H), 5.51 (s, 1H),
2.87–3.30 (m, 8H), 1.57 (s, 3H), 1.39 (s, 3H). 13C NMR
(CDCl3, 100 MHz) d 181.4, 180.9, 150.0, 150.0, 143.7, 143.5,
138.6, 138.4, 137.7, 137.6, 135.7, 135.7, 134.9, 134.8, 134.3,
134.2, 130.8, 130.5, 129.3, 129.2, 128.8, 128.7, 128.3, 128.3,
128.2, 128.0, 127.9, 126.9, 126.6, 126.1, 125.9, 125.6, 125.5,
125.0, 124.8, 121.2, 121.1, 104.0, 103.2, 45.4, 44.4, 43.0, 40.6,
39.8, 29.8, 25.0, 23.0. HRMS (EI-TOF) calcd for
C28H23FN2O (M+): 422.1794, found: 422.1796.
2:1). Yellow oil. H NMR (CDCl3, 400 MHz, a mixture of
two isomer) d 8.87 (dd, J1 =1.6 Hz; J2 =4.0 Hz, 1H), 8.79
(dd, J1 =1.6 Hz; J2 =4.0 Hz, 1H), 8.16–8.20 (m, 2H), 7.90–
7.92 (m, 2H), 7.61–7.70 (m, 4H), 7.36–7.42 (m, 2H), 7.21–
7.22 (m, 4H), 7.07–7.11 (m, 6H), 7.00 (d, J=7.2 Hz, 2H),
6.63–6.67 (m, 4H), 5.29 (s, 1H, Z-isomer), 5.28 (s, 1H),
3.98–4.08 (m, 4H), 3.05–3.40 (m, 4H), 2.29 (d, J=8.0 Hz,
6H), 2.19 (d, J=4.0 Hz, 6H), 1.91–2.04 (m, 8H), 1.57 (s,
3H), 1.46 (s, 3H). 13C NMR (CDCl3, 100 MHz) d 181.5,
180.4, 157.1, 156.9, 151.2, 151.1, 144.3, 144.2, 143.0, 143.0,
137.0, 136.6, 136.5, 136.2, 136.1, 133.4, 133.2, 130.5, 130.4,
130.3, 129.6, 129.6, 129.4, 129.3, 128.4, 128.0, 128.0, 127.6,
127.6, 126.4, 126.4, 126.1, 126.1, 125.3, 123.7, 121.9, 120.9,
120.7, 112.1, 104.4, 104.4, 68.2, 67.9, 44.1, 38.8, 38.6, 35.4,
35.3, 24.9, 24.8, 24.8, 24.5, 21.5, 20.4, 16.0, 16.0, 13.8. HRMS
(EI-TOF) calcd for C32H32N2O2 (M+): 476.2464, found:
476.2466.
(E)-5-Benzylidene-3-methyl-3-(naphthalen-2-yl-methyl)-1-
(quinolin-8-yl)pyrrolidin-2-one (3h). 33.16 mg. Yield, 73%.
The ratio of two isomers was 1.7:1 as determined by
1H NMR. Rf1 =0.48, Rf2 =0.50 (hexane/EtOAc=2:1).
Yellow oil. 1H NMR (CDCl3, 400 MHz, a mixture of two
isomer) d 8.81 (dd, J1 =1.6 Hz; J2 =4.0 Hz, 1H), 8.79 (dd,
J1 =1.6 Hz; J2 =4.0 Hz, 1H), 8.43 (d, J=7.6 Hz, 1H), 8.30
(d, J=7.6 Hz, 1H), 7.88–7.92 (m, 3H), 7.79–7.84 (m, 3H),
7.43–7.60 (m, 8H), 7.37–7.39 (m, 2H), 7.21–7.30 (m, 3H),
7.06 (t, J=8.0 Hz, 1H), 6.76 (dd, J1 =1.2 Hz; J2 =7.6 Hz,
1H), 6.43–6.59 (m, 3H), 6.30–6.37 (m, 3H), 5.93 (d, J=
7.6 Hz, 2H) 5.61 (s, 1H), 5.33 (s, 1H), 3.92 (d, J=14.4 Hz,
1H), 3.73 (d, J=14.0 Hz, 1H), 3.55 (d, J=14.0 Hz, 1H),
3.44 (d, J=14.0 Hz, 1H), 2.90–3.11 (m, 4H), 1.67 (s, 3H),
(E)-5-Benzylidene-3-methyl-3-phenyl-1-(quino-lin-8-yl)-
pyrrolidin-2-one (3k). 24.19 mg. Yield, 62%. The ratio of
two isomers was 1.1:1 as determined by H NMR. Rf1 =0.59,
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Rf2 =0.57 (hexane/EtOAc =2:1). Yellow oil. 1H NMR
(CDCl3, 400 MHz, a mixture of two isomer) d 8.91 (d, J=
1.2 Hz, 1H), 8.90 (d, J=0.8 Hz, 1H), 8.23 (d, J=1.6 Hz,
1H), 8.21 (d, J=1.6 Hz, 1H), 7.96 (dd, J1 =1.6 Hz; J2 =
2.8 Hz, 1H), 7.94 (dd, J1 =1.6 Hz; J2 =2.8 Hz, 1H), 7.75–7.83
(m, 3H), 7.67–7.71 (m, 3H), 7.58–7.61 (m, 2H), 7.36–7.46
(m, 7H), 7.28 (d, J=7.6 Hz, 2H), 7.19–7.23 (m,4H), 7.05–
7.12 (m, 5H), 5.36 (s, 1H), 5.31 (s, 1H), 3.65–3.74 (m, 2H),
3.67 (dd, J1 =2.0 Hz; J2 =16.0 Hz, 1H), 3.44 (dd, J1 =2.0 Hz;
J2 =16.4 Hz, 1H), 1.95 (s, 3H), 1.86 (s, 3H). 13C NMR
(CDCl3, 100 MHz) d 179.1, 178.8, 151.2, 151.1, 144.3, 144.1,
Adv. Synth. Catal. 2016, 358, 1778 – 1793
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