10.1002/ejoc.201900092
European Journal of Organic Chemistry
FULL PAPER
7.3 Hz, 2H), 7.72 (t, J = 7.4 Hz, 1H), 7.60 - 7.48 (m, 3H), 7.04 (d, J = 8.6
Hz, 1H), 2.38 (s, 3H); 13C NMR (75 MHz, CDCl3) δ (ppm): 168.33, 148.33,
138.34, 137.61, 134.49, 134.07, 130.67, 128.86, 128.10, 122.29, 121.67,
119.40, 119.30, 114.59, 24.58; HRMS (ESI): [M+H]+ calcd. for
C17H15N2O4S 343.0747; found 343.0747.
J = 8.6 Hz, 1H), 2.35 (s, 3H); 13C NMR (75 MHz, CDCl3) δ (ppm): 168.22,
148.26, 138.88, 137.81, 135.02, 134.12, 133.37, 131.51, 131.31, 130.83,
130.76, 130.16, 129.32, 129.24, 128.97, 127.53, 122.31, 121.62, 119.32,
114.68, 24.51; HRMS (ESI): [M+H]+ calcd. for C21H17N2O4S 393.0904;
found 393.0911.
8-acetamidoquinolin-5-yl-4-chlorobenzenesulfonate (2d): white solid;
m.p. 151 - 154 oC; 1H NMR (300 MHz, CDCl3) δ (ppm): 9.77 (s, 1H), 8.87
(d, J = 4.2 Hz, 1H), 8.68 (d, J = 8.6 Hz, 1H), 8.38 (d, J = 8.5 Hz, 1H), 7.85
(d, J = 8.6 Hz, 2H), 7.54 (dd, J = 8.5, 4.2 Hz, 3H), 7.07 (d, J = 8.6 Hz, 1H),
2.38 (s, 3H); 13C NMR (75 MHz, CDCl3) δ (ppm): 168.35, 148.39, 140.95,
138.64, 137.80, 133.55, 133.06, 130.65, 129.50, 129.24, 122.22, 121.78,
119.37, 114.67, 24.57; HRMS (ESI): [M+H]+ calcd. for C17H14ClN2O4S
377.0357; found 377.0363.
8-acetamidoquinolin-5-yl-thiophene-2-sulfonate (2k): white solid; m.p.
184 - 187 oC; 1H NMR (300 MHz, CDCl3) δ (ppm): 9.72 (s, 1H), 8.80 (d, J
= 3.2 Hz, 1H), 8.66 (d, J = 8.6 Hz, 1H), 8.34 (d, J = 8.0 Hz, 1H), 7.72 (d, J
= 4.9 Hz, 1H), 7.61 (d, J = 3.2 Hz, 1H), 7.47 (dd, J = 8.4, 4.1 Hz, 1H),
7.17 - 7.04 (m, 2H), 2.35 (s, 3H); 13C NMR (75 MHz, CDCl3) δ (ppm):
168.86, 148.87, 139.27, 138.27, 135.90, 135.12, 134.14, 134.09, 130.96,
127.81, 122.72, 122.27, 119.91, 115.08, 25.14; HRMS (ESI): [M+H]+
calcd. for C15H13N2O4S2 349.0311; found 349.0317.
8-acetamidoquinolin-5-yl-4-fluorobenzenesulfonate (2e): white solid;
m.p. 120 - 122 oC; 1H NMR (300 MHz, CDCl3) δ (ppm): 9.76 (s, 1H), 8.85
(d, J = 3.5 Hz, 1H), 8.68 (d, J = 8.6 Hz, 1H), 8.36 (d, J = 8.4 Hz, 1H), 7.93
(dd, J = 8.4, 5.0 Hz, 2H), 7.52 (dd, J = 8.4, 4.2 Hz, 1H), 7.24 (t, J = 8.4
Hz, 2H), 7.08 (d, J = 8.6 Hz, 1H), 2.38 (s, 3H); 13C NMR (75 MHz, CDCl3)
δ (ppm): 168.26, 148.37, 138.69, 133.55, 132.83, 131.06, 130.93, 130.57,
122.21, 121.70, 119.37, 116.41, 116.11, 114.62, 24.51; HRMS (ESI):
[M+H]+ calcd. for C17H14FN2O4S 361.0653; found 361.0656.
8-butyramidoquinolin-5-yl-4-methylbenzenesulfonate (3a): off-white
solid; m.p. 120 - 122 oC; 1H NMR (300 MHz, CDCl3) δ (ppm): 9.77 (s, 1H),
8.85 (d, J = 2.7 Hz, 1H), 8.67 (d, J = 8.6 Hz, 1H), 8.48 - 8.32 (m, 1H),
7.79 (d, J = 8.2 Hz, 2H), 7.51 (dd, J = 8.5, 4.2 Hz, 1H), 7.35 (d, J = 8.0
Hz, 2H), 7.00 (d, J = 8.5 Hz, 1H), 2.57 (t, J = 7.4 Hz, 2H), 2.49 (s, 3H),
1.94 - 1.82 (m, 2H), 1.09 (t, J = 7.3 Hz, 3H); 13C NMR (75 MHz, CDCl3) δ
(ppm): 171.40, 148.29, 145.31, 138.83, 137.93, 133.33, 131.56, 130.78,
129.45, 128.14, 127.34, 121.61, 119.36, 114.58, 39.59, 21.23, 18.57,
13.28; HRMS (ESI): [M+H]+ calcd. for C20H21N2O4S 385.1217; found
385.1220.
8-acetamidoquinolin-5-yl-4-nitrobenzenesulfonate (2f): pale yellow
solid; m.p. 143 - 147 oC; 1H NMR (300 MHz, CDCl3) δ (ppm): 9.76 (s, 1H),
8.87 (dd, J = 4.2, 1.6 Hz, 1H), 8.69 (d, J = 8.6 Hz, 1H), 8.45 - 8.38 (m,
2H), 8.34 (dd, J = 8.5, 1.6 Hz, 1H), 8.17 - 8.08 (m, 2H), 7.54 (dd, J = 8.5,
4.2 Hz, 1H), 7.11 (d, J = 8.6 Hz, 1H), 2.38 (s, 3H); 13C NMR (75 MHz,
CDCl3) δ (ppm): 168.35, 150.67, 148.52, 140.40, 138.32, 137.81, 133.89,
130.36, 129.48, 123.99, 122.00, 121.92, 119.30, 114.69, 24.52; HRMS
(ESI): [M+H]+ calcd. for C17H14N3O6S 388.0598; found 388.0601.
8-(4-methylpentanamido)quinolin-5-yl-4-methylbenzenesulfonate
(3b): off-white solid; m.p. 98 - 101 oC; 1H NMR (300 MHz, CDCl3) δ
(ppm): 9.78 (s, 1H), 8.85 (dd, J = 4.2, 1.5 Hz, 1H), 8.67 (d, J = 8.6 Hz,
1H), 8.43 (dd, J = 8.5, 1.5 Hz, 1H), 7.79 (d, J = 8.3 Hz, 2H), 7.52 (dd, J =
8.5, 4.2 Hz, 1H), 7.35 (d, J = 8.1 Hz, 2H), 6.99 (d, J = 8.6 Hz, 1H), 2.63 -
2.56 (m, 2H), 2.49 (s, 3H), 1.79 - 1.69 (m, 3H), 1.01 (d, J = 6.3 Hz, 6H);
13C NMR (75 MHz, CDCl3) δ (ppm): 171.62, 148.27, 145.29, 138.82,
137.91, 133.37, 131.58, 130.88, 129.45, 128.16, 122.43, 121.60, 119.38,
114.60, 35.71, 33.87, 27.30, 21.86, 21.24; HRMS (ESI): [M+H]+ calcd. for
C22H25N2O4S 413.1540; found 413.1540.
8-acetamidoquinolin-5-yl-3-nitrobenzenesulfonate (2g): white solid.
m.p. 139 - 140 oC; 1H NMR (300 MHz, CDCl3) δ (ppm): 9.72 (s, 1H), 8.88
- 8.82 (m, 1H), 8.82 - 8.77 (m, 1H), 8.67 (d, J = 8.6 Hz, 1H), 8.54 (d, J =
8.2 Hz, 1H), 8.34 (d, J = 8.5 Hz, 1H), 8.20 (d, J = 7.8 Hz, 1H), 7.78 (t, J =
8.0 Hz, 1H), 7.52 (dd, J = 8.5, 4.2 Hz, 1H), 7.09 (d, J = 8.6 Hz, 1H), 2.35
(s, 3H); 13C NMR (75 MHz, CDCl3) δ (ppm): 168.73, 148.99, 148.32,
138.69, 138.33, 137.35, 134.39, 133.83, 130.75, 128.82, 123.69, 122.37,
119.77, 114.98, 24.98; HRMS (ESI): [M+H]+ calcd. for C17H14N3O6S
388.0598; found 388.0603.
8-benzamidoquinolin-5-yl-4-methylbenzenesulfonate (3c): off-white
solid; m.p. 176 - 179 oC; 1H NMR (300 MHz, CDCl3) δ (ppm): 10.68 (s,
1H), 8.98 - 8.76 (m, 2H), 8.44 (dd, J = 8.5, 1.5 Hz, 1H), 8.09 (dd, J = 7.8,
1.5 Hz, 2H), 7.81 (d, J = 8.3 Hz, 2H), 7.67 - 7.48 (m, 4H), 7.36 (d, J = 8.1
Hz, 2H), 7.08 (d, J = 8.6 Hz, 1H), 2.49 (s, 3H); 13C NMR (75 MHz, CDCl3)
δ (ppm): 164.96, 148.45, 145.31, 139.17, 138.41, 134.34, 133.40, 131.68,
131.53, 130.94, 129.46, 128.35, 128.18, 126.77, 122.53, 121.70, 119.43,
114.82, 21.21; HRMS (ESI): [M+H]+ calcd. for C23H19N2O4S 419.1060;
found 419.1062.
8-acetamidoquinolin-5-yl-3-(trifluoromethyl)benzenesulfonate (2h):
1
white solid; m.p. 150 - 152 oC; H NMR (300 MHz, CDCl3) δ (ppm): 9.75
(s, 1H), 8.92 - 8.79 (m, 1H), 8.69 (d, J = 8.6 Hz, 1H), 8.32 (d, J = 8.5 Hz,
1H), 8.22 (s, 1H), 8.07 (d, J = 7.9 Hz, 1H), 7.97 (d, J = 7.9 Hz, 1H), 7.71
(t, J = 7.9 Hz, 1H), 7.50 (dd, J = 8.5, 4.2 Hz, 1H), 7.11 (d, J = 8.6 Hz, 1H),
2.37 (s, 3H); 13C NMR (75 MHz, CDCl3) δ (ppm): 168.29, 148.41, 138.38,
137.81, 136.00, 133.75, 131.26, 130.60, 130.55, 130.30, 129.69, 125.09,
125.04, 122.00, 121.75, 119.41, 114.57, 24.49; HRMS (ESI): [M+H]+
calcd. for C18H14F3N2O4S 411.0621; found 411.0625.
8-acetamido-4-methylquinolin-5-yl-4-methylbenzenesulfonate (3d):
off-white solid; m.p. 188 - 190 oC; 1H NMR (300 MHz, CDCl3) δ (ppm):
9.94 (s, 1H), 8.65 (d, J = 4.4 Hz, 1H), 8.57 (d, J = 8.7 Hz, 1H), 7.80 (d, J
= 8.3 Hz, 2H), 7.39 (d, J = 8.1 Hz, 2H), 7.31 (d, J = 4.8 Hz, 1H), 6.83 (d, J
= 8.6 Hz, 1H), 2.99 (s, 3H), 2.51 (s, 3H), 2.35 (s, 3H); 13C NMR (75 MHz,
CDCl3) δ (ppm): 168.31, 147.56, 145.31, 144.30, 139.93, 138.59, 133.77,
132.33, 129.52, 128.24, 124.86, 122.52, 119.54, 114.19, 24.65, 23.12,
21.26; HRMS (ESI): [M+H]+ calcd. for C19H19N2O4S 371.1060; found
371.1065.
8-acetamidoquinolin-5-yl-ethanesulfonate (2i): pale brown solid; m.p.
85 - 88 oC; 1H NMR (300 MHz, CDCl3) δ (ppm): 9.81 (s, 1H), 8.91 (d, J =
2.8 Hz, 1H), 8.82 (d, J = 8.6 Hz, 1H), 8.58 (d, J = 8.5 Hz, 1H), 7.63 (dd, J
= 8.5, 4.2 Hz, 1H), 7.52 (d, J = 8.6 Hz, 1H), 3.49 (q, J = 7.4 Hz, 2H), 2.40
(s, 3H), 1.67 (t, J = 7.4 Hz, 3H); 13C NMR (75 MHz, CDCl3) δ (ppm):
168.39, 148.44, 138.14, 137.96, 133.42, 130.85, 122.43, 121.93, 119.27,
114.94, 45.15, 24.61, 7.91; HRMS (ESI): [M+H]+ calcd. for C13H15N2O4S
295.0747; found 295.0720.
8-acetamido-6-methoxyquinolin-5-yl-4-methylbenzenesulfonate (3e):
off-white solid; m.p. 160 – 163 oC; 1H NMR (300 MHz, CDCl3) δ (ppm):
9.83 (s, 1H), 8.75 - 8.65 (m, 2H), 8.44 (d, J = 8.6 Hz, 1H), 7.86 (d, J = 8.2
Hz, 2H), 7.50 (dd, J = 8.6, 4.2 Hz, 1H), 7.37 (d, J = 8.0 Hz, 2H), 3.65 (s,
3H), 2.50 (s, 3H), 2.37 (s, 3H); 13C NMR (75 MHz, CDCl3) δ (ppm):
168.90, 149.63, 146.22, 145.05, 134.71, 133.80, 130.81, 129.94, 129.31,
128.74, 128.59, 125.80, 124.93, 124.29, 122.57, 104.20, 56.02, 25.03,
8-acetamidoquinolin-5-yl-naphthalene-2-sulfonate (2j): off-white solid;
m.p. 154 - 157 oC; 1H NMR (300 MHz, CDCl3) δ (ppm): 9.72 (s, 1H), 8.81
(d, J = 3.1 Hz, 1H), 8.60 (d, J = 8.6 Hz, 1H), 8.44 (d, J = 8.7 Hz, 2H), 8.05
- 7.89 (m, 4H), 7.81 - 7.64 (m, 2H), 7.46 (dd, J = 8.5, 4.2 Hz, 1H), 7.02 (d,
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