Organic & Biomolecular Chemistry
Paper
JH–H = 1.0 Hz, 1H), 7.86 (d, JH–H = 8.5 Hz, 2H), 7.66 (d, JH–H
=
1H), 8.21 (d, JH–H = 7.8 Hz, 1H), 8.13 (td, JH–H = 7.6 Hz, JH–H =
8.5 Hz, 2H), 7.50 (td, JH–H = 7.8 Hz, JH–H = 1.3 Hz, 1H), 7.39 (td, 1.4 Hz, 1H), 7.77–7.74 (m, 1H), 7.70 (d, JH–H = 8.0 Hz, 1H),
JH–H = 7.6 Hz, JH–H = 0.9 Hz, 1H), 7.33 (d, JH–H = 8.3 Hz, 1H), 3.80 7.57–7.51 (m, 2H), 7.39 (td, JH–H = 7.3 Hz, JH–H = 1.9 Hz, 1H),
(s, 3H); 13C NMR (100 MHz, CDCl3) δ: 163.3, 151.3, 144.1, 132.7, 3.71 (s, 3H); 13C NMR (100 MHz, DMSO-d6) δ: 160.8 (CvO),
132.2 (CH), 130.8, 129.5 (CH), 129.1 (CH), 128.6 (CH), 127.7, 151.3, 149.3 (CH), 149.0, 144.4, 139.1 (CH), 131.9, 131.7, 128.6
124.8 (CH), 113.7 (CH), 29.9 (CH3); HR MS (ESI) m/z: calcd for (CH), 128.3 (CH), 124.6 (CH), 122.9 (CH), 115.3 (CH), 30.2
C16H13BrN3O2 [M + H]+ 358.0186, found 358.0188.
(CH3); HR MS (ESI) m/z: calcd for C15H13N4O2 [M + H]+
281.1033, found 281.1031.
2-Bromo-N-(4-methyl-3-oxo-3,4-dihydroquinoxalin-2-yl)
benzamide (3ag)
N-(4-Methyl-3-oxo-3,4-dihydroquinoxalin-2-yl)thiophene-2-
Light yellow crystal, mp 162–163 °C (lit.11 168–169 °C); IR
(KBr) ν(cm−1): 3342, 1721, 1647, 1612, 1584, 1498, 1465, 1427,
1355, 1267, 1199; 1H NMR (400 MHz, CDCl3) δ: 9.71 (s, 1H),
7.64 (dd, JH–H = 7.6 Hz, JH–H = 1.6 Hz, 1H), 7.60 (dd, JH–H = 8.0
Hz, JH–H = 0.8 Hz, 1H), 7.46 (td, JH–H = 8.6 Hz, JH–H = 1.4 Hz,
1H), 7.39 (td, JH–H = 7.6 Hz, JH–H = 1.1 Hz, 1H), 7.35–7.27 (m,
3H), 3.71 (s, 3H); 13C NMR (100 MHz, CDCl3) δ: 165.0 (CvO),
151.0, 143.8 (CH), 137.2, 133.4 (CH), 131.8, 131.7 (CH), 130.9,
129.8 (CH), 129.2 (CH), 128.6 (CH), 127.6 (CH), 124.5 (CH),
119.2, 113.7 (CH), 29.8 (CH3); HR MS (ESI) m/z: calcd for
C16H13BrN3O2 [M + H]+ 358.0186, found 358.0189.
carboxamide (3ak)
Colorless solid, mp 178–180 °C (lit.11 184–185 °C); IR (KBr)
ν(cm−1): 3484, 3096, 2920, 1688, 1651, 1622, 1592, 1505, 1490,
1472, 1414, 1274, 1204; H NMR (400 MHz, DMSO-d6) δ: 10.32
(s, 1H), 8.02 (dd, JH–H = 3.7 Hz, JH–H = 0.9 Hz, 1H), 7.96 (dd,
JH–H = 5.0 Hz, JH–H = 1.0 Hz, 1H), 7.69 (d, JH–H = 7.9 Hz, 1H),
1
7.57 (d, JH–H = 3.7 Hz, 1H), 7.41–7.37 (m, 1H), 7.25 (dd, JH–H
=
4.9 Hz, JH–H = 3.8 Hz, 1H), 3.70 (s, 3H); 13C NMR (100 MHz,
DMSO-d6) δ: 159.4 (CvO), 151.3, 145.6, 139.1, 133.8, 132.2,
131.6, 131.0, 129.1, 128.9, 128.4, 124.5, 115.3, 30.1 (CH3); HR
MS (ESI) m/z: calcd for C14H12N3O2S [M + H]+ 286.0645, found
286.0647.
2-Iodo-N-(4-methyl-3-oxo-3,4-dihydroquinoxalin-2-yl)
benzamide (3ah)
N-(4-Methyl-3-oxo-3,4-dihydroquinoxalin-2-yl)acetamide (3al)
Light yellow crystal, mp 197–198 °C (lit.11 195–196 °C); IR
(KBr) ν(cm−1): 3343, 2919, 2850, 1716, 1641, 1498, 1476, 1418,
1319, 1265; 1H NMR (400 MHz, CDCl3) δ: 9.46 (s, 1H), 7.92 (dd,
JH–H = 7.9 Hz, JH–H = 0.8 Hz, 1H), 7.81 (d, JH–H = 7.8 Hz, 1H),
7.54 (dd, JH–H = 7.6 Hz, JH–H = 1.6 Hz, 1H), 7.51–7.47 (m, 1H),
7.44 (td, JH–H = 7.6 Hz, JH–H = 1.0 Hz, 1H), 7.36 (td, JH–H = 7.6
Hz, JH–H = 1.2 Hz, 1H), 7.31 (dd, JH–H = 8.3 Hz, JH–H = 0.9 Hz,
Colorless crystal, mp 192–194 °C (lit.11 209–210 °C); IR (KBr)
ν(cm−1): 3246, 2931, 1686, 1655, 1603, 1506, 1470, 1366, 1285,
1203; 1H NMR (400 MHz, DMSO-d6) δ: 9.73 (s, 1H), 7.61 (d,
JH–H = 7.9 Hz, 1H), 7.51–7.33 (m, 2H), 7.37–7.33 (m, 1H), 3.66
(s, 3H), 2.35 (s, 3H); 13C NMR (100 MHz, DMSO-d6) δ: 169.7,
151.0, 145.0, 131.7, 131.6, 128.4 (CH), 128.0 (CH), 124.4 (CH),
115.0 (CH), 30.1 (CH3), 25.4 (CH3); HR MS (ESI) m/z: calcd for
C11H12N3O2 [M + H]+ 218.0924, found 218.0924.
1H), 7.18 (td, JH–H = 7.8 Hz, JH–H = 1.7 Hz, 1H), 3.77 (s, 3H); 13
C
NMR (100 MHz, CDCl3) δ: 166.6 (CvO), 151.1, 143.8, 141.3,
140.0, 131.8, 131.7, 129.5, 128.7, 128.6, 128.3, 124.6, 113.6,
92.1, 29.9 (CH3); HR MS (ESI) m/z: calcd for C16H13IN3O2 [M +
H]+ 406.0047, found 406.0049.
N-(4-Methyl-3-oxo-3,4-dihydroquinoxalin-2-yl)propionamide
(3am)
Colorless solid, mp 161–162 °C (lit.11 161–162 °C); IR (KBr)
ν(cm−1): 3256, 2922, 1682, 1659, 1608, 1507, 1472, 1370, 1216;
N-(4-Methyl-3-oxo-3,4-dihydroquinoxalin-2-yl)-4-
(trifluoromethyl)benzamide (3ai)
1H NMR (400 MHz, DMSO-d6) δ: 9.71 (s, 1H), 7.61 (d, JH–H
8.0 Hz, 1H), 7.53–7.47 (m, 2H), 7.35 (td, JH–H = 7.0 Hz, JH–H
=
=
Colorless crystal, mp 152–153 °C; IR (KBr) ν(cm−1): 3365, 1700,
1
2.1 Hz, 1H), 3.66 (s, 3H), 2.71 (q, JH–H = 7.4 Hz, 2H), 1.07 (t,
JH–H = 7.4 Hz, 3H); 13C NMR (100 MHz, DMSO-d6) δ: 173.1,
151.0, 145.0, 131.7, 131.6, 128.3 (CH), 128.0 (CH), 124.4 (CH),
115.1 (CH), 30.4 (CH3), 30.1 (CH2), 9.39 (CH3); HR MS (ESI) m/z:
calcd for C12H14N3O2 [M + H]+ 232.1081, found 232.1083.
1647, 1612, 1515, 1504, 1489, 1473, 1324, 1276, 1111; H NMR
(400 MHz, CDCl3) δ: 9.90 (s, 1H), 8.08 (d, JH–H = 8.1 Hz, 2H),
7.87 (dd, JH–H = 8.0 Hz, JH–H = 1.3 Hz, 1H), 7.76 (d, JH–H = 8.2
Hz, 2H), 7.48–7.43 (m, 1H), 7.35 (td, JH–H = 7.6 Hz, JH–H = 1.2
Hz, 1H), 7.29 (d, JH–H = 0.9 Hz, 1H), 3.74 (s, 3H); 13C NMR
(100 MHz, CDCl3) δ: 162.9 (CvO), 151.1, 144.0 (CH), 137.0,
134.0 (q, JH–H = 32.7 Hz), 131.8, 130.8, 129.3 (CH), 128.6 (CH),
N-(4-Methyl-3-oxo-3,4-dihydroquinoxalin-2-yl)isobutyramide (3an)
128.0 (CH), 125.9 (q, JH–H = 3.6 Hz, CH), 124.7 (CH), 123.5 (q, Colorless solid, mp 126–128 °C (lit.11 116–117 °C); IR (KBr)
JH–H = 271.1 Hz), 113.7 (CH), 29.9 (CH3); 19F NMR (376 MHz, ν(cm−1): 3254, 2966, 2931, 2873, 1675, 1652, 1606, 1500, 1484,
1
CDCl3) δ: −63.0; HR MS (ESI) m/z: calcd for C17H13F3N3O2 1468, 1382, 1358, 1223, 1158; H NMR (400 MHz, DMSO-d6) δ:
[M + H]+ 348.0954, found 348.0954.
9.77 (s, 1H), 7.59 (d, JH–H = 7.9 Hz, 1H), 7.48 (d, JH–H = 3.8 Hz,
2H), 7.35–7.31 (m, 1H), 3.64 (s, 3H), 3.17–3.10 (m, 1H), 1.11 (d,
JH–H = 6.8 Hz, 6H); 13C NMR (100 MHz, DMSO-d6) δ: 175.8,
N-(4-Methyl-3-oxo-3,4-dihydroquinoxalin-2-yl)picolinamide (3aj)
Colorless solid, mp 232–233 °C; IR (KBr) ν(cm−1): 3302, 2921, 151.0, 145.0, 131.7, 131.6, 128.3 (CH), 128.0 (CH), 124.3 (CH),
1715, 1647, 1588, 1502, 1491, 1466, 1434, 1353; 1H NMR 115.0 (CH), 35.0 (CH3), 30.0 (CH2), 19.6 (CH3); HR MS (ESI) m/
(400 MHz, DMSO-d6) δ: 11.60 (s, 1H), 8.78 (d, JH–H = 4.6 Hz, z: calcd for C13H16N3O2 [M + H]+ 246.1237, found 246.1235.
This journal is © The Royal Society of Chemistry 2019
Org. Biomol. Chem., 2019, 17, 10178–10187 | 10183