10.1002/ejoc.201601443
European Journal of Organic Chemistry
FULL PAPER
(100 MHz, CDCl3): δ = 163.8, 158.5, 147.3, 138.6, 131.2, 130.8, 130.4,
130.3, 128.9, 128.6, 127.6, 117.4, 114.3, 55.5 ppm. HRMS (ESI): calcd
for C16H13NO3SNa [M+Na]+ 322.0514; found 322.0526.
2-(thiophen-2-ylsulfonyl)quinoline (3m)[11] : Yellow solid (69 mg, 25%
yield); 1H NMR (400 MHz, CDCl3): δ = 8.37 (d, J = 8.4 Hz, 1H), 8.18 (d, J
= 8.4 Hz, 2H), 7.89–7.86 (m, 2H), 7.80–7.76 (m, 1H), 7.70 (dd, J = 4.8, 1.2
Hz, 1H), 7.67–7.63 (m, 1H), 7.12–7.09 (m, 1H) ppm. 13C NMR (100 MHz,
CDCl3): δ = 157.9, 147.3, 139.7, 138.8, 135.3, 135.2, 131.1, 130.3, 129.2,
128.9, 127.8, 127.7, 117.3 ppm. HRMS (ESI): calcd for C13H10NO2S2
[M+H]+ 276.0147; found 276.0152.
2-((4-nitrophenyl)sulfonyl)quinoline (3g): Light yellow solid (195 mg,
62% yield). m.p. 143.0 – 145.0 °C. 1H NMR (400 MHz, CDCl3): δ = 8.41 (d,
J = 8.8 Hz, 1H), 8.36–8.30 (m, 4H), 8.22 (d, J = 8.8 Hz, 1H), 8.09 (d, J =
8.8 Hz, 1H), 7.89 (d, J = 8.4 Hz, 1H), 7.79 (d, J = 7.6 Hz, 1H), 7.76 (d, J =
7.6 Hz, 1H) ppm. 13C NMR (100 MHz, CDCl3): δ = 156.8, 150.7, 147.3,
144.6, 139.1, 131.3, 130.5, 130.1, 129.6, 128.9, 127.7, 124.0, 117.4 ppm.
IR: ν˜ = 3015, 1521, 1380, 1345, 1212, 1178, 966, 768, 549 cm-1. HRMS
(ESI): calcd for C15H10N2O4SNa [M+Na]+ 337.0259, found 337.0253.
2-(methylsulfonyl)quinoline (3n) [12]: Yellow solid (163 mg, 79% yield),
1H NMR (400 MHz, CDCl3): δ = 8.39 (d, J = 8.4 Hz, 1H), 8.15 (d, J = 8.4
Hz, 1H), 8.07 (d, J = 8.4 Hz, 1H), 7.90–7.87 (m, 1H), 7.82–7.78 (m, 1H),
7.68–7.64 (m, 1H), 3.34 (s, 3H) ppm. 13C NMR (100 MHz, CDCl3): δ =
157.4, 146.8, 138.8, 131.1, 129.9, 129.1, 129.0, 127.8, 116.0, 39.7 ppm.
HRMS (ESI): calcd for C10H9NO2SNa [M+Na]+ 230.0252; found 230.0263.
4-(quinolin-2-ylsulfonyl)benzonitrile (3h): White solid (199 mg, 68%
yield). m.p. 192.6 – 194.8 °C. 1H NMR (400 MHz, CDCl3): δ = 8.40 (d, J =
8.4 Hz, 1H), 8.25–8.21 (m, 3H), 8.09 (d, J = 8.8 Hz, 1H), 7.87 (d, J = 8.0
Hz, 1H), 7.82–7.76 (m, 3H), 7.68–7.64 (m, 1H) ppm. 13C NMR (100 MHz,
CDCl3): δ = 156.9, 147.3, 143.1, 139.0, 132.6, 131.3, 130.1, 129.7, 129.6,
128.9, 127.7, 117.4, 117.3, 117.1 ppm. IR: ν˜ = 3091, 2922, 2235, 1558,
1497, 1319, 1168, 1130, 1074, 833, 683, 651, 558 cm-1; HRMS (ESI):
calcd for C16H10N2O2SNa [M+Na]+ 317.0374; found 317.0361.
3-methyl-2-tosylquinoline (4a1)[14]: Yellow solid (262 mg, 88% yield). 1H
NMR (400 MHz, CDCl3): δ = 8.01 (s, 1H), 7.92–7.87 (m, 3H), 7.71 (d, J =
8.0 Hz, 1H), 7.60 (dt, J = 8.4, 1.2 Hz, 1H), 7.56–7.52 (m, 1H), 7.32 (d, J =
8.0 Hz, 2H), 2.82 (s, 3H), 2.42 (s, 3H) ppm.13C NMR (100 MHz, CDCl3): δ
= 156.9, 144.6, 144.4, 139.7, 135.7, 129.8, 129.6, 129.3, 129.2, 129.0,
128.8, 128.4, 126.5, 21.5, 18.7 ppm. HRMS (ESI): calcd for
C17H15NO2SNa [M+Na]+ 320.0721; found 320.0729.
2-(o-tolylsulfonyl)quinoline (3i): Off-white solid (209 mg, 74% yield).
m.p. 192.6 – 194.8 °C. 1H NMR (400 MHz, CDCl3): δ = 8.36 (d, J = 8.8 Hz,
1H), 8.29 (dd, J = 8.0, 1.2 Hz, 1H), 8.15 (d, J = 8.8 Hz, 1H), 8.08 (d, J =
8.4 Hz, 1H), 7.86 (d, J = 8.0 Hz, 1H), 7.77–7.72 (m, 1H), 7.65–7.61 (m,
1H),7.49–7.45 (m, 1H), 7.41–7.38 (m, 1H), 7.24–7.21 (m, 1H), 2.53 (s, 3H)
ppm. 13C NMR (100 MHz, CDCl3): δ = 158.1, 147.1, 139.1, 138.6, 137.1,
133.9, 132.4, 130.9, 130.6, 130.3, 129.1, 128.8, 127.7, 126.4, 117.7, 20.7
ppm. IR ν˜ = 3057, 2965, 1577, 1472, 1309, 1163, 1094, 751, 708, 639
cm-1. HRMS (ESI): calcd for C16H13NO2SNa [M+Na]+ 306.0565; found
306.0568.
3-methyl-2-(methylsulfonyl)quinoline (4a2): White solid (172 mg, 78%
yield). m.p. 118.2 – 120.1 °C. 1H NMR (400 MHz, CDCl3): δ 8.06–8.01 (m,
2H), 7.79–7.76 (m, 1H), 7.73–7.69 (m, 1H), 7.63–7.59 (m, 1H), 3.52 (s,
3H), 2.82 (d, J = 0.8 Hz, 3H) ppm. 13C NMR (100 MHz, CDCl3): δ = 158.8,
144.2, 139.7, 129.9, 129.5, 129.2, 128.9, 127.6, 126.9, 39.9, 17.7 ppm. IR
ν˜ = 3013, 2931, 1561, 1292, 1128, 960, 788, 766, 599, 508 cm-1. HRMS
(ESI): calcd for C11H12NO2S [M+H]+ 222.0583; found 222.0591.
8-methyl-2-tosylquinoline (4b1) [14]: White solid (247 mg, 83% yield); 1H
NMR (400 MHz, CDCl3): δ = 8.30 (d, J = 8.4 Hz, 1H), 8.17 (d, J = 8.4 Hz,
1H), 8.03 (dd, J = 6.8, 1.2 Hz, 2H), 7.65 (d, J = 8.0 Hz, 1H), 7.56 (d, J =
6.8 Hz, 1H), 7.48 (t, J = 8.0 Hz, 1H), 7.31 (d, J = 8.0 Hz, 2H), 2.66 (s, 3H),
2.39 (s, 3H) ppm. 13C NMR (100 MHz, CDCl3): δ = 157.3, 146.3, 144.6,
138.7, 138.3, 135.9, 130.8, 129.4, 129.3, 128.8, 128.7, 125.5, 116.7, 21.6,
17.5 ppm. HRMS (ESI): calcd for C17H15NO2SNa [M+Na]+ 320.0721;
found 320.0734.
2-((2-bromophenyl)sulfonyl)quinoline (3j): Yellow solid (232 mg, 67%
yield). m.p. 162.3 – 164.7 °C. 1H NMR (400 MHz, CDCl3): δ = 8.51 (d, J =
8.0 Hz, 1H), 8.40 (d, J = 8.8 Hz, 1H), 8.31 (dd, J = 8.8, 2.0 Hz, 1H), 7.99
(d, J = 8.4 Hz, 1H); 7.88 (d, J = 8.4 Hz, 1H), 7.74–7.69 (m, 1H), 7.65–7.56
(m, 3H), 7.44 (dt, J = 8.0, 1.6 Hz, 1H) ppm. 13C NMR (100 MHz, CDCl3): δ
= 157.1, 147.1, 138.3, 135.0, 134.8, 132.5, 130.9, 130.2, 129.2, 128.9,
127.8, 127.7, 121.3, 118.6 ppm. IR ν˜ = 3054, 1572, 1425, 1317, 1171,
1140, 1023, 827, 735, 569 cm-1. HRMS (ESI): calcd for C15H10BrNO2SNa
[M+Na]+ 369.9508; found 369.9517.
8-methyl-2-(methylsulfonyl)quinoline (4b2): Colorless oil (159 mg, 72%
yield). 1H NMR (400 MHz, CDCl3): δ = 8.38 (d, J = 8.4 Hz, 1H), 8.07 (d, J
= 8.4 Hz, 1H), 7.73 (d, J = 8.0 Hz, 1H), 7.66 (d, J = 8.0 Hz, 1H), 7.59–7.55
(m, 1H), 3.40 (s, 3H), 2.79 (s, 3H) ppm. 13C NMR (100 MHz, CDCl3): δ =
156.5, 148.4, 145.9, 139.1, 138.1, 131.2, 129.0, 125.7, 115.5, 39.4, 17.6
ppm. IR ν˜ = 3016, 2929, 1573, 1494, 1304, 1162, 1114, 960, 762 cm-1.
HRMS (ESI): calcd for C11H12NO2S [M+H]+ 222.0583; found 222.0592.
2-(mesitylsulfonyl)quinoline (3k)[14]: Off-white solid (130 mg, 42% yield).
1H NMR (400 MHz, CDCl3): δ = 8.35 (d, J = 8.4 Hz, 1H), 8.12 (d, J = 8.4
Hz, 1H), 8.06 (d, J = 8.4 Hz, 1H), 7.86 (d, J = 8.4 Hz, 1H), 7.76–7.71 (m,
1H), 7.64–7.60 (m, 1H), 6.93 (s, 2H), 2.66 (s, 6H), 2.27 (s, 3H) ppm.13
C
NMR (100 MHz, CDCl3): δ = 159.5, 147.1, 143.5, 141.1, 138.3, 132.8,
132.4, 131.9, 130.7, 130.4, 128.8, 127.6, 116.8, 23.0, 21.0 ppm. IR ν˜ =
2925, 1602, 1498, 1305, 1162, 1129, 755, 685, 659 cm-1. HRMS (ESI):
calcd for C18H17NO2SNa [M+Na]+ 334.0878; found 334.0898.
8-isopropyl-2-tosylquinoline (4c1): Yellow oil (246 mg, 76% yield). 1H
NMR (400 MHz, CDCl3): δ = 8.31 (d, J = 8.8 Hz, 1H), 8.17 (d, J = 8.8 Hz,
1H), 8.02 (d, J = 8.0 Hz, 2H), 7.66 (dd, J = 8.0, 2.0 Hz, 1H), 7.61–7.53 (m,
2H), 7.31 (d, J = 8.0 Hz, 2H), 4.03 (sep, J = 6.8 Hz, 1H), 2.38 (s, 3H), 1.22
(d, J = 6.8 Hz, 6H) ppm. 13C NMR (100 MHz, CDCl3): δ = 157.2, 148.1,
145.1, 144.5, 138.8, 135.8, 129.4, 129.3, 129.0, 128.8, 126.6, 125.3, 116.4,
27.9, 23.0, 21.5 ppm. IR ν˜ = 3064, 2962, 2869, 1596, 1491, 1373, 1320,
1166, 1077, 813, 704 cm-1. HRMS (ESI): calcd for C19H19NO2SNa [M+Na]+
348.1034; found 348.1047.
2-(pyridin-3-ylsulfonyl)quinoline (3l): White solid (134 mg, 50% yield).
m.p. 118.2 – 120.1 °C. 1H NMR (400 MHz, CDCl3): δ = 9.31–9.30 (m, 1H),
8.80 (dd, J = 4.8, 1.2 Hz, 1H), 8.43 – 8.39 (m, 2H), 8.21 (d, J = 8.4 Hz, 1H),
8.10 (d, J = 8.4 Hz, 1H), 7.87 (d, J = 8.4 Hz, 1H), 7.80–7.75 (m, 1H), 7.67–
7.63 (m, 1H), 7.49–7.45 (m, 1H) ppm. 13C NMR (100 MHz, CDCl3): δ 157.4,
154.0, 149.9, 147.4, 139.0, 136.8, 135.5, 131.2, 130.2, 129.5, 128.9, 127.7,
123.6, 117.2 ppm. IR ν˜ = 3098, 3076, 1575, 1418, 1318, 1169, 1087, 764,
650, 573 cm-1. HRMS (ESI): calcd for C14H10N2O2SNa [M+Na]+ 293.0355;
found 293.0362.
8-isopropyl-2-(methylsulfonyl)quinoline (4c2): Yellow oil (99 mg, 40%
yield).1H NMR (400 MHz, CDCl3): δ = 8.39 (d, J = 8.4 Hz, 1H), 8.05 (d, J =
8.4 Hz, 1H), 7.74–7.69 (m, 2H), 7.63 (t, J = 7.6 Hz, 1H), 4.22 (sep, J = 6.8
Hz, 1H), 3.39 (s, 3H), 1.37 (d, J = 6.8 Hz, 6H) ppm.13C NMR (100 MHz,
CDCl3): δ = 156.3, 147.9, 144.6, 139.3, 129.3, 129.2, 127.0, 125.6, 115.2,
This article is protected by copyright. All rights reserved.