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RSC Advances
DOI: 10.1039/C6RA04013F
132.04, 131.46, 130.95, 128.84, 127.97, 126.68, 126.41, 123.25,
122.44, 113.33.
7.56 (dd, J = 8.7, 4.2 Hz, 1H), 7.26 (d, J = 8.2 Hz, 2H), 7.03 (d, J
60 = 8.8 Hz, 2H), 3.88 (s, 3H), 2.35 (s, 3H). 13C NMR (126 MHz,
CDCl3) δ 165.64, 159.17, 148.52, 144.92, 143.13, 140.22, 138.14,
134.87, 134.07, 133.06, 131.53, 131.00, 130.12, 129.63, 127.43,
124.46, 123.29, 113.59, 52.88, 21.60.
N-(5-((4-bromophenyl)sulfonyl)quinolin-8-yl)-4-methyl-benza
mide (3i)
5
Obtained as a white solid in 73% yield; M.p. 172ꢀ173 °C. 1H
NMR (500 MHz, CDCl3) δ 10.94 (s, 1H), 9.03 (t, J = 8.6 Hz, 2H), 65 4-bromo-N-(5-tosylquinolin-8-yl)benzamide (3n)[24a]
8.88 (d, J = 2.7 Hz, 1H), 8.54 (d, J = 8.4 Hz, 1H), 7.95 (d, J = 8.2
Hz, 2H), 7.80 (d, J = 8.7 Hz, 2H), 7.60 (d, J = 8.7 Hz, 3H), 7.35
Obtained as a white solid in 68% yield; M.p. 214ꢀ215 °C. 1H
NMR (500 MHz, CDCl3) δ 10.93 (s, 1H), 9.08 (dd, J = 8.7, 1.6
Hz, 1H), 9.03 (d, J = 8.5 Hz, 1H), 8.86 (dd, J = 4.3, 1.6 Hz, 1H),
8.54 (d, J = 8.4 Hz, 1H), 7.98 – 7.93 (m, 2H), 7.85 – 7.81 (m, 2H),
10 (d, J = 8.0 Hz, 2H), 2.45 (s, 3H). 13C NMR (126 MHz, CDCl3) δ
165.65, 148.85, 143.22, 141.15, 140.52, 138.46, 133.22, 132.59,
131.44, 129.65, 129.36, 128.71, 128.32, 128.12, 127.45, 124.27, 70 7.57 (dd, J = 8.7, 4.2 Hz, 1H), 7.35 (d, J = 7.9 Hz, 2H), 7.26 (d, J
123.52, 114.16, 77.32, 77.06, 76.81, 21.59. HRMS (ESI+):
Calculated for C23H17BrN2O3S, [M+H]+ 481.0216, Found
15 481.0226.
= 5.7 Hz, 2H), 2.36 (s, 3H). 13C NMR (126 MHz, CDCl3) δ
165.67, 148.69, 144.12, 143.12, 140.09, 139.16, 138.53, 133.57,
132.12, 131.61, 129.90, 129.64, 129.24, 127.46, 127.31, 124.34,
123.28, 114.20, 21.59.
Methyl-3-((8-(4-methylbenzamido)quinolin-5-yl)sulfonyl)
thiophene-2-carboxylate (3j)
75
4-cyano-N-(5-tosylquinolin-8-yl)benzamide (3o)
Obtained as a white solid in 71% yield; M.p. 170ꢀ171 3 . H
NMR (500 MHz, CDCl3) δ 10.99 (s, 1H), 9.09 (d, J = 8.9 Hz,
1H), 8.99 (d, J = 8.7 Hz, 1H), 8.89 (d, J = 6.8 Hz, 1H), 8.55 (d, J
1
Obtained as a white solid in 48% yield; M.p. 184ꢀ185 °C. 1H
20 NMR (500 MHz, CDCl3) δ 10.99 (s, 1H), 9.09 (d, J = 8.5 Hz,
1H), 8.90 (d, J = 7.3 Hz, 2H), 8.69 (d, J = 8.5 Hz, 1H), 7.98 (d, J
= 8.0 Hz, 2H), 7.87 (d, J = 5.2 Hz, 1H), 7.60 (d, J = 5.2 Hz, 1H), 80 = 8.6 Hz, 1H), 8.17 (d, J = 8.6 Hz, 2H), 7.85 (dd, J = 13.5, 7.9 Hz,
7.57 (d, J = 4.1 Hz, 1H), 7.37 (d, J = 7.9 Hz, 2H), 3.79 (s, 3H),
2.47 (s, 3H). 13C NMR (126 MHz, CDCl3) δ 165.66, 159.19,
25 148.54, 144.94, 143.15, 140.23, 138.15, 134.88, 134.08, 133.08,
131.54, 131.02, 130.13, 129.65, 127.91, 127.45, 124.48, 123.31,
5H), 7.30 (d, J = 9.7 Hz, 3H), 2.37 (s, 3H). 13C NMR (126 MHz,
CDCl3) δ 163.73, 148.94, 144.32, 139.13, 138.76, 138.35, 138.10,
133.67, 132.79, 131.78, 130.28, 129.95, 128.07, 127.33, 124.22,
123.52, 117.86, 115.91, 114.57, 77.30, 77.05, 76.79, 21.55.
113.60, 52.90, 21.62. HRMS (ESI+): Calculated for 85 HRMS (ESI+): Calculated for C24H17N3O3S, [M+H]+ 428.1064,
C23H18N2O5S2, [M+H]+ 467.0730, Found 467.0735.
Found 428.1074.
N-(5-tosylquinolin-8-yl)furan-2-carboxamide (3p)
Obtained as a white solid in 59% yield; M.p. 193ꢀ195 °C. 1H
NMR (500 MHz, CDCl3) δ 10.99 (s, 1H), 9.08 (dd, J = 8.7, 1.4
30 N-(5-((3,5-dimethylisoxazol-4-yl)sulfonyl)quinolin-8-yl)-2-met
hylbenzamide (3k)
Obtained as a white solid in 43% yield; M.p. 153ꢀ154 °C. 1H 90 Hz, 1H), 8.98 (d, J = 8.4 Hz, 1H), 8.90 (dd, J = 4.1, 1.4 Hz, 1H),
NMR (500 MHz, CDCl3) δ 10.51 (s, 1H), 9.06 (d, J = 8.4 Hz,
1H), 8.92 (d, J = 8.7 Hz, 1H), 8.87 (d, J = 4.2 Hz, 1H), 8.47 (d, J
35 = 8.4 Hz, 1H), 7.69 (d, J = 7.7 Hz, 1H), 7.62 (dd, J = 8.7, 4.2 Hz,
1H), 7.44 (t, J = 6.9 Hz, 1H), 7.35 (t, J = 7.8 Hz, 2H), 2.79 (s,
8.53 (d, J = 8.4 Hz, 1H), 7.85 (d, J = 8.3 Hz, 2H), 7.65 (s, 1H),
7.58 (dd, J = 8.7, 4.1 Hz, 1H), 7.35 (dd, J = 3.8, 2.6 Hz, 1H), 7.31
– 7.25 (m, 2H), 6.62 (dd, J = 3.4, 1.7 Hz, 1H), 2.37 (s, 3H). 13
C
NMR (126 MHz, CDCl3) δ 156.45, 148.83, 147.76, 145.05,
3H), 2.61 (s, 3H), 2.25 (s, 3H). 13C NMR (126 MHz, CDCl3) δ 95 144.16, 139.59, 139.03, 138.36, 133.43, 131.89, 129.90, 127.31,
173.40, 168.38, 157.51, 149.04, 140.62, 138.25, 137.16, 135.52,
132.49, 132.14, 131.70, 131.03, 128.79, 127.28, 126.20, 124.19,
40 123.55, 117.81, 113.74, 20.28, 12.99, 10.82. HRMS (ESI+):
Calculated for C22H19N3O4S, [M+H]+ 422.1169, Found 422.1178.
124.29, 123.33, 116.17, 114.28, 112.72, 21.51.
N-(5-tosylquinolin-8-yl)cyclopropanecarboxamide (3q)
Obtained as a white solid in 71% yield; M.p. 211ꢀ213 °C. 1H
100 NMR (500 MHz, CDCl3) δ 10.25 (s, 1H), 9.03 (dd, J = 8.7, 1.6
Hz, 1H), 8.85 – 8.80 (m, 2H), 8.48 (d, J = 8.4 Hz, 1H), 7.83 –
7.79 (m, 2H), 7.54 (dd, J = 8.7, 4.2 Hz, 1H), 7.25 (d, J = 8.0 Hz,
2H), 2.35 (s, 3H), 1.85 – 1.79 (m, 1H), 1.17 (dd, J = 4.5, 3.0 Hz,
2H), 0.96 (dd, J = 7.8, 3.1 Hz, 2H).13C NMR (126 MHz, CDCl3)
4-methyl-N-(5-tosylquinolin-8-yl)benzamide (3l)
Obtained as a white solid in 80% yield; M.p. 187ꢀ189 °C. 1H
45 NMR (500 MHz, CDCl3) δ 10.92 (s, 1H), 9.08 (d, J = 7.4 Hz,
1H), 9.02 (d, J = 8.4 Hz, 1H), 8.86 (d, J = 2.8 Hz, 1H), 8.54 (d, J
= 8.4 Hz, 1H), 7.96 (d, J = 8.1 Hz, 2H), 7.83 (d, J = 8.3 Hz, 2H), 105 δ 172.85, 148.54, 144.10, 139.94, 139.02, 137.88, 133.36, 132.05,
7.57 (dd, J = 8.7, 4.2 Hz, 1H), 7.35 (d, J = 8.0 Hz, 2H), 7.26 (d, J
= 5.7 Hz, 2H), 2.45 (s, 3H), 2.36 (s, 3H). 13C NMR (126 MHz,
50 CDCl3) δ 165.66, 148.69, 144.11, 143.11, 140.09, 139.15, 138.53,
133.56, 132.11, 131.60, 129.89, 129.63, 129.23, 127.45, 127.30,
124.33, 123.27, 114.19, 21.58, 21.51.
130.02, 129.87, 128.73, 128.22, 127.22, 124.21, 123.24, 113.98,
21.53, 16.45, 8.84. HRMS (ESI+): Calculated for C20H18N2O3S,
[M+H]+ 367.1111, Found 367.1118.
110 N-(2-methyl-5-tosylquinolin-8-yl)benzamide (3s) [22b]
1
Obtained as a yellow solid in 53% yield; M.p. 200ꢀ201 °C. H
4-methoxy-N-(5-tosylquinolin-8-yl)benzamide (3m)[24a]
55 Obtained as a white solid in 85% yield; M.p. 178ꢀ179 °C. 1H
NMR (500 MHz, CDCl3) δ 10.88 (s, 1H), 9.06 (d, J = 7.3 Hz,
NMR (500 MHz, CDCl3) δ 11.03 (s, 1H), 9.01 (d, J = 8.0 Hz,
1H), 8.94 (d, J = 10.0 Hz, 1H), 8.48 (d, J = 8.0 Hz, 1H), 8.06 (d, J
= 10.0 Hz, 2H), 7.83 (d, J = 8.0 Hz, 2H), 7.57 (m, 3H), 7.44 (d, J
1H), 9.00 (d, J = 8.4 Hz, 1H), 8.85 (d, J = 2.8 Hz, 1H), 8.53 (d, J 115 = 8.0 Hz, 1H), 7.26 (t, J = 4.0 Hz, 2H), 2.76 (s, 3H), 2.36 (s, 3H).
= 8.4 Hz, 1H), 8.02 (d, J = 8.8 Hz, 2H), 7.83 (d, J = 8.3 Hz, 2H),
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