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TAMULI ET AL.
132.02, 129.78, 129.75, 128.97, 128.65, 127.98, 21.91, 21.37;
FT-IR (KBR, cm−1): 3031, 2917, 1612, 1554, 1487, 1403, 1377,
1252, 1182, 1056, 979, 819, 721; HRMS (ESI) m/z calculated
for C23H20N2 [M + H]+: 326.5023; found: 326.5017.
5.2.12 | 2,3-di-p-tolylquinoxaline-
6-carbonitrile (3fb)
1
White solid (0.287 g, 85% yield); MP: 166ꢀC; H NMR
(500 MHz, CDCl3): δ = 8.05 (d, J = 1.5 Hz, 1H), 8.20 (d,
J = 9 Hz, 1H), 7.86 to 7.88 (d, J = 8.5 Hz, 1H), 7.43 to
7.46 (m, 4H), 7.16 to 7.18 (m, 4H), 2.38 (s, 6H); 13C NMR
(125 MHz, CDCl3): δ 156.17, 155.59, 142.73, 140.35,
140.07, 139.93135.66, 135.62, 135.23, 130.83, 130.59,
129.98, 129.37, 118.53, 113.05, 21.63; FT-IR (KBR, cm−1):
3028, 2910, 1622, 1570, 1540, 1508, 1478, 1143, 1245,
1210, 1134, 1034, 979, 859, 749; HRMS (ESI) m/z calcu-
lated for C23H17N3 [M + H]+: 336.3027; found: 336.3020.
5.2.9 | 6-chloro-2,3-di-p-
tolylquinoxaline (3cb)
Gray solid (0.312 g, 90% yield); MP: 170ꢀC; 1H NMR
(500 MHz, CDCl3): δ = 8.13 to 8.14 (d, J = 10 Hz, 1H),
8.06 to 8.08 (d, J = 15 Hz, 1H), 7.66 to 7.85 (m, 4H), 7.40
to 7.42 (m, 4H), 7.14 to 7.15 (m, 4H), 2.37 (s, 6H); 13C
NMR (125 MHz, CDCl3): δ 154.37, 153.71, 141.45, 139.68,
139.23, 139.12, 136.05, 135.97, 135.38, 130.72, 130.09,
129.78, 129.73, 129.11, 128.03, 21.44; FT-IR (KBR, cm−1):
3045, 1607, 1468, 1339, 1245, 1183, 1062, 980, 815,
729, 604; HRMS (ESI) m/z calculated for C22H17ClN2 [M
+ H]+: 346.7452; found: 346.7446.
5.2.13 | 2,3-bis(4-methoxyphenyl)
quinoxaline (3ac)
White solid (0.327 g, 95% yield); MP: 150ꢀC; 1H NMR
(500 MHz, CDCl3): δ = 8.10 to 8.12 (m, 2H), 7.69 to 7.71 (m,
2H), 7.48 to 7.50 (d, J = 9 Hz, 4H), 7.85 to 7.87 (d, J = 9 Hz,
4H), 3.80 (s, 6H); 13C NMR (125 MHz, CDCl3): δ 160.04,
152.90, 140.94, 131.58, 131.15, 129.43, 128.88, 113.66, 55.19;
FT-IR (KBR, cm−1): 3061, 2934, 2835, 1609, 1511, 1460, 1397,
1294, 1177, 1029, 838, 763; HRMS (ESI) m/z calculated for
C22H18N2O2 [M + H]+: 343.5301; found: 343.5297.
5.2.10 | 6-fluoro-2,3-di-p-
tolylquinoxaline (3db)
1
Brown solid (0.290 g, 88% yield); MP: 119ꢀC; H NMR
(500 MHz, CDCl3): δ = 8.12 to 8.15 (d, J = 15 Hz, 1H),
7.85 to 7.86 (d, J = 8 Hz, 1H), 7.75 to 7.77 (m, 1H), 7.50
to 7.53 (m, 4H),7.40 to 7.42 (m, 4H), 7.14 to 7.15 (m,
4H), 7.14 to 7.30 (m, 4H), 2.37 (s, 6H); 13C NMR
(125 MHz, CDCl3): δ 163.50, 161.50, 154.03, 152.68,
152.66, 138.89, 138.68, 135.87, 135.77, 130.95, 130.87,
129.82, 129.52, 128.83, 119.91, 112.24, 21.16; 19F NMR
(470 MHz, CDCl3): δ −108.66 (1F); FT-IR (KBR, cm−1):
3031, 2915, 1617, 1561, 1538, 1511, 1480, 1139, 1247,
1204, 1154, 1054, 981, 864, 756; HRMS (ESI) m/z calcu-
lated for C22H17FN2 [M + H]+: 329.2269; found:
329.2257.
5.2.14 | 2,3-bis(4-methoxyphenyl)-
6-methylquinoxaline (3bc)
1
White solid (0.329 g, 92% yield); MP: 127ꢀC; H NMR
(500 MHz, CDCl3): δ = 7.88 to 8.01 (dd, J = 8.5 Hz, 1.5 Hz,
2H), 7.45 to 7.48 (m, 4H), 6.83 to 6.85 (m, 4H), 3.79 (s, 6H),
2.56 (s, 3H); 13C NMR (125 MHz, CDCl3): δ 160.08, 160.02,
152.86, 152.13, 141.12, 139.97, 139.52, 131.86, 131.27,
131.23, 128.52, 127.86, 113.73, 113.72, 55.28, 21.87; FT-IR
(KBR, cm−1): 3055, 2942, 2847, 1622, 1534, 1452, 1383,
1239, 1107, 1013, 844, 793; HRMS (ESI) m/z calculated for
C23H20N2O2 [M + H]+: 357.1998; found: 357.1997.
5.2.11 | 6-nitro-2,3-di-p-
tolylquinoxaline (3eb)
1
Yellow solid (0.296 g, 83% yield); MP: 170ꢀC; H NMR
5.2.15 | 6-chloro-2,3-bis
(500 MHz, CDCl3): δ = 9.03 (d, J = 2.5 Hz, 1H), 8.47 (d,
J = 2.5 Hz, 1H), 8.24 (d, J = 9.5 Hz, 1H), 7.85 (d,
J = 8.5 Hz, 1H), 7.30 to 7.48 (m, 4H), 7.16 to 7.28 (m,
4H), 2.42 (s, 6H); 13C NMR (125 MHz, CDCl3): δ 156.21,
155.58, 147.54, 145.99, 143.48, 139.92, 139.72, 135.28,
130.56, 130.49, 129.93, 129.72, 129.62, 129.07, 125.41,
122.90, 21.82; FT-IR (KBR, cm−1): 3021, 1610, 1468,
1339, 1251, 1188, 1069, 986, 820, 729, 608; HRMS (ESI)
m/z calculated for C22H17N3O2 [M + H]+: 356.2586;
found: 356.2576.
(4-methoxyphenyl)quinoxaline (3cc)
1
White solid (0.338 g, 89% yield); MP: 149ꢀC; H NMR
(500 MHz, CDCl3): δ = 8.10 (d, J = 2 Hz, 1H), 8.03 (d,
J = 9 Hz, 1H), 7.64 to 7.65 (d, J = 2 Hz, 1H), 7.47 to 7.49
(m, 4H), 6.86 to 6.87 (m, 4H), 3.82 (s, 6H); 13C NMR
(125 MHz, CDCl3): δ 160.32, 160.24, 153.74, 153.09,
141.23, 139.45, 135.06, 131.24, 131.22, 131.15, 130.40,
130.12, 127.78, 113.75, 55.24; FT-IR (KBR, cm−1): 3027,
2908, 1621, 1559, 1529, 1488, 11,397, 1247, 1204, 1154,