764 JOURNAL OF CHEMICAL RESEARCH 2009
2-(4-Methylphenyl)quinoxaline (3e): Solid, m.p. 93–94°C (lit.33
90–91°C); 1H NMR (300 MHz, CDCl3): d 2.44 (s, 3H), 7.36 (d,
J = 8.0 Hz, 2H), 7.71–7.77 (m, 2H), 8.09–8.16 (m, 4H), 9.30 (s,
1H); 13C NMR (75 MHz, CDCl3) d 21.3, 127.3, 129.0, 129.2, 129.4,
129.8, 130.1,133.8, 140.4, 141.3, 142.2, 143.2, 151.7.
6,7-Dichloro-2-phenylquinoxaline (3r): Solid, m.p. 153–156°C
(not reported);40 1H NMR (300 MHz, CDCl3): d 7.58–7.61 (m, 3H),
8.19–8.22 (m, 2H), 8.26 (s, 1H), 8.30 (s, 1H), 9.34 (s, 1H); 13C NMR
(75 MHz, CDCl3): d 127.6, 129.3, 129.8, 130.2, 130.8, 134.1, 136.1,
140.3, 141.1, 144.3, 152. 7.
2-(4-Nitrophenyl)quinoxaline (3f): Solid, m.p. 188–191°C (not
reported);34 1H NMR (300 MHz, DMSO-d6): d 7.90–7.93 (m, 2H),
8.13–8.16 (m, 2H), 8.39–8.42 (m, 2H), 8.56–8.59 (m, 2H), 9.67 (s,
1H); 13C NMR (75 MHz, DMSO-d6) d 124.6, 129.2, 129.36, 129.9,
131.4, 131.5, 141.8, 142.0, 142.4, 144.4, 148. 9, 149.4.
6,7-Dichloro-2-(4-methoxyphenyl) quinoxaline (3s): Solid, m.p.
199–201°C; IR (KBr) nmax/cm-1: 2920, 2417, 1460, 1260, 1180, 1114,
837; 1H NMR (300 MHz, CDCl3): d 3.92 (s, 3H), 7.1 (d, J = 8.8 Hz,
2H), 8.16 (d, J = 8.8 Hz, 2H), 8.19 (s, 1H), 8.22 (s, 1H), 9.27 (s,
1H); 13C NMR (75 MHz, CDCl3): d 55.5, 114.7, 128.4, 129.1, 129.7,
129.9, 133.3, 134.7, 139.9, 141.1, 144.0, 152.2. 161.9; MS (EI,
70 eV) m/z (%): 308 (M+ + 4, 11), 306 (M+ + 2, 63), 304 (M+, 100),
289 (21), 133 (19). Anal. Calcd for C15H10Cl2N2O: C, 59.04; H, 3.30;
N, 9.18. Found: C, 59.16; H, 3.43; N, 9.27%.
2-(2-Chlorophenyl)quinoxaline (3g): Solid, m.p. 86–88°C (not
reported);35 1H NMR (300 MHz, CDCl3): d 7.45–7.48 (m, 2H), 7.55–
7.74 (m, 2H),7.81–7.84 (m, 2H), 8.16–8.19 (m, 2H), 9.22 (s, 1H);
13C NMR (75 MHz, CDCl3): d 127.4, 129.1, 129.5, 130.1, 130.2,
130.2,1 30.7, 131.8, 132.5, 136.4, 141.2, 142.2, 146.1, 152.3.
2-Methyl-3-phenyl-quinoxaline (3h): Solid, m.p. 54–56°C (lit.11
6,7-Dichloro-2-(4-nitrophenyl) quinoxaline (3t): Solid, m.p.
223–225°C; IR (KBr) nmax/cm-1: 2921, 2398, 1733, 1458, 1348,
1
56°C); H NMR (300 MHz, CDCl3): d 2.77 (s, 3H), 7.48–7.52 (m,
1
1110, 859; H NMR (300 MHz, acetone-d6): d 8.39 (d, J = 8.7 Hz,
3H), 7.63–7.66 (m, 4H), 7.69–7.73 (m, 2H); 13C NMR (75 MHz,
CDCl3): 24.3, 128.2, 128.5, 128.8, 128.9, 129.1, 129.2, 129.7, 138.9,
140.9, 141.1, 152.4, 154.8.
2H), 8.43 (s, 2H), 8.53 (d, J = 8.7 Hz, 2H), 9.68 (s, 1H); 13C NMR
(75 MHz, acetone-d6): d 124.10, 128.86 (× 2), 130.02, 130.41,
134.08, 134.39, 140.92, 141.77, 145.04, 205.22, 205.48; MS (EI,
70 eV) m/z (%): 323 (M+ + 4, 11), 321 (M+ + 2, 62), 319 (M+, 100),
289 (26), 144 (22), 77 (32). Anal. Calcd for C14H7Cl2N3O2: C, 52.53;
H, 2.20; N, 13.13. Found: C, 52.41; H, 2.29; N, 13.22%.
2-(2-Furanyl)quinoxaline(3i):Solid,m.p.98–99°C(lit.3397–98°C);
1H NMR (300 MHz, CDCl3): d 6.61–6.62 (m, 1H), 7.30–7.31 (m,
1H), 7.67–7.75 (m, 3H), 8.04–8.10 (m, 2H), 9.23 (s, 1H); 13C NMR
(75 MHz, CDCl3): d 111.8, 112.5, 129.2, 129.2, 129.3, 130.5, 141.2,
142.0, 142.1, 143.8, 145.1, 151.5.
6,7-Dichloro-2-(2-chlorophenyl)quinoxaline (3u): Solid, m.p.
113–115°C; IR (KBr) nmax/cm-1: 3048, 2918, 1453, 1316, 1112, 939,
2-(4-Fluorophenyl)quinoxaline (3j): Solid, m.p. 120–122°C
(lit.33 120–121°C); 1H NMR (300 MHz, CDCl3): d 7.21–7.27 (m,
2H), 7.75–7.78 (m, 2H), 8.09–8.21 (m, 4H), 9.27 (s, 1H); 13C NMR
1
752; H NMR (300 MHz, CDCl3): d 7.46–7.57 (m, 3H), 7.70–7.72
(m, 1H), 8.28 (s, 1H), 8.29 (s, 1H), 9.22 (s, 1H); 13C NMR (75 MHz,
CDCl3): d 127.6, 129.9, 130.2, 130.4, 131.2, 131.9, 132.5, 134.7,
134.9, 135.8, 140.0, 141.0, 147.1, 153.3; MS (EI, 70 eV) m/z (%):
314 (M+ + 6, 3), (312 (M+ + 4, 24), 310 (M+ + 2, 68), 308 (M+, 77),
275 (52), 273 (100), 109 (35). Anal. Calcd for C14H7Cl3N2: C, 54.32;
H, 2.28; N, 9.05. Found: C, 54.49; H, 2.17; N, 8.96%.
2
(75 MHz, CDCl3): d 116.16 (d, JCF = 21.3 Hz), 129.07, 129.43 (d,
3JCF = 8.25 Hz), 129.46, 129.54, 130.36, 132.84 (d, 3JCF = 3.45 Hz),
141.4, 142.1, 142.9, 150.7, 164.2 (d, 1JCF = 248.93 Hz).
6,7-Dimethyl-2-phenylquinoxaline (3k): Solid, m.p. 127–129°C
(lit.33 128–129°C); 1H NMR (300 MHz, CDCl3): d 2.49 (s, 6H),
7.49–7.55 (m, 3H), 7.84 (s, 1H), 7.89 (s, 1H), 8.14–8.18 (m, 2H),
9.21 (s, 1H); 13C NMR (75 MHz, CDCl3): d 20.3, 20.3, 127.3, 128.1,
128.6, 129.0, 129.8, 137.0, 140.1, 140.5, 140.7, 141.1, 142.3, 150.9.
6,7-Dimethyl-2-(4-chlorophenyl)quinoxalin (3l): Solid, m.p. 160–
163°C (not reported);36,37 1H NMR (300 MHz, CDCl3): d 2.49 (s,
6H), 7.49 (d, J = 8.57 Hz, 2H), 7.82 (s, 1H), 7.85 (s, 1H), 8.09 (d,
J = 8.57 Hz, 2H), 9.15 (s, 1H); 13C NMR (75 MHz, CDCl3): d 20.3,
20.4, 128.1, 128.5, 128.5, 129.2, 135.4, 136.1, 140.4, 140.5, 141.0,
141.0, 141.8, 149.6.
2-Methyl-6,7-dichloro-3-phenylquinoxaline (3v): Solid, m.p. 151–
153°C (not reported);39 1H NMR (300 MHz, CDCl3): d 2.78 (s, 3H),
7.54–7.56 (m, 3H), 7.64–7.65 (m, 2H), 8.17 (s, 1H), 8.23 (s, 1H); 13
C
NMR (75 MHz, CDCl3): d 24.5, 128.6, 128.96, 129.1, 129.4, 129.8,
133.6, 134.1, 138.2, 139.7, 139.9, 154.0, 155.9.
We are grateful to the Natural Science Foundation of Zhejiang
Province (Y4080107) for financial support.
6,7-Dimethyl-2-(4-bromophenyl)quinoxalin (3m): Solid, m.p. 140–
142°C (lit.38 141–142°C); 1H NMR (300 MHz, CDCl3): d 2.50
(s, 6H), 7.66 (d, J = 8.7 Hz, 2H); 7.83 (s, 1H), 7.86 (s, 1H), 8.03 (d,
J = 8.7 Hz, 2H), 9.16 (s, 1H); 13C NMR (75 MHz, CDCl3): d 20.3,
20.4, 124.5, 128.1, 128.5, 128.8, 132.2, 135.9, 140.4, 140.6, 141.0,
141.1, 141.8, 149.7.
Received 14 September 2009; accepted 20 November 2009
Paper 09/0785 doi:10.3184/030823409X12591655855261
Published online: 8 December 2009
References
6,7-Dimethyl-2-(4-methoxyphenyl)quinoxaline (3n): Solid, m.p.
126–129°C; 1H NMR (300 MHz, CDCl3): d 2.48 (s, 6H), 3.89 (s,
3H), 7.06 (d, J = 8.57 Hz, 2H), 7.82 (s, 1H), 7.85 (s, 1H), 8.13 (d,
J = 8.57 Hz,2H), 9.17 (s, 1 H); 13C NMR (75 MHz, CDCl3): d 20.2,
20.3, 55.3, 114.4, 128.0, 128.4, 128.7, 129.5, 139.5, 140.0, 140.58,
141.1, 142.0, 150.5, 161.1. MS (EI, 70 eV) m/z (%): 266 (M+ + 2, 2),
265 (M+ + 1, 19), 264 (M+, 100), 249 (32). Anal. Calcd for C17H16N2O:
C, 77.25; H, 6.10; N, 10.60. Found: C, 77.29; H, 6.07; N, 10.65%.
6,7-Dimethyl-2-(4-nitrophenyl)quinoxaline (3o): Solid, m.p. 197–
1
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200°C; H NMR (300 MHz, CDCl3): d 2.54 (s, 6H), 7.88 (s, 1H),
7.91 (s, 1H), 8.33 (d, J = 9.11 Hz,2H), 8.38 (d, J = 9.11 Hz, 2H),
9.26 (s, 1H); 13C NMR (75 MHz, CDCl3): d 20.4, 20.4, 124.2, 128.0,
128.2, 128.7, 141.1, 141.1, 141.5, 141.6, 141.8, 142.9, 148.2, 148.5.
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100), 103 (42). Anal. Calcd for C16H13N3O2: C, 68.81; H, 4.69; N,
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6,7-Dimethyl-2-(2-Chlorophenyl)quinoxaline (3p): Solid, m.p. 96–
98°C; IR (KBr) nmax/cm-1: 3044, 2917, 1736, 1482, 1439, 1035, 755;
1H NMR (300 MHz, CDCl3): 2.50–2.51 (m, 6H), 7.40–7.44 (m, 2H),
7.51–7.52 (m, 1H), 7.69–7.72 (m, 1H), 7.89–7.91 (m, 2H), 9.10 (s,
1H); 13C NMR (75 MHz, CDCl3): d 20.3, 20.4, 127.1, 127.3, 128.1,
128.5, 130.1, 130.5, 131.8, 132.5, 136.7, 140.2, 140.8, 141.1, 145.1,
151.3; MS (EI, 70 eV) m/z (%): 270 (M+ + 2, 26), 268 (M+, 72), 233
(100), 134 (15), 103 (28). Anal. Calcd for C16H13ClN2: C, 71.51; H,
4.88; N, 10.42. Found: C, 71.64; H, 4.96; N, 10.27%.
2,6,7-Trimethyl-3-phenylquinoxaline (3q): Solid, m.p. 92–95°C
(not reported);39 1H NMR (300 MHz, CDCl3): d 2.48 (s, 3H), 2.49
(s, 3H), 2.75 (s, 3H), 7.48–7.52 (m, 3H), 7.63–7.66 (m, 2H), 7.80 (s,
1H), 7.86 (s, 1H); 13C NMR (75 MHz, CDCl3): d 20.3, 20.4, 24.2,
127.3, 128.2, 128.4, 128.7, 128.9, 139.3, 139.5, 139.9, 140.1, 140.1,
151.3, 153.8.
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PAPER: JC090785
JCR_12_2009 Book.indb 764
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