GORBUNOVA, MAMEDOV
1530
NH). Found, %: C 49.61; H 2.27; Br 21.18; N 11.14.
C15H10BrN3O3. Calculated, %: C 50.02; H 2.80;
Br 22.19; N 11.07.
3-(3-Nitrobenzoyl)quinoxalin-2(1H)-one (IId).
Yield quantitative, mp 285–287°C (from AcOH). IR
spectrum, ν, cm–1: 418, 571, 695, 755, 875, 897, 936,
1095, 1219, 1251, 1305, 1320, 1352, 1497, 1529,
3-(α-Bromo-4-nitrobenzyl)quinoxalin-2(1H)-one
(Ie). Yield 65%, mp 270–273°C. IR spectrum, ν, cm–1:
413, 579, 757, 766, 851, 869, 911, 1111, 1294, 1320,
1351, 1437, 1491, 1514, 1603, 1668, 2720, 3476.
1H NMR spectrum, δ, ppm: 6.86 s (1H), 7.35 d.d (1H,
6-H, J = 8.24, 8.92 Hz), 7.36 d (1H, 8-H, J = 7.44 Hz),
7.57 d.d (1H, 7-H, J = 7.44, 8.24 Hz), 7.76 d (2H, 2'-H,
6'-H, J = 8.24 Hz), 7.97 d (2H, 3'-H, 5'-H, J =
8.24 Hz), 7.98 d (1H, 5-H, J = 8.92 Hz), 12.46 s (1H,
NH). Found, %: C 49.61; H 2.47; Br 22.10; N 11.14.
C15H10BrN3O3. Calculated, %: C 50.02; H 2.80;
Br 22.19; N 11.07.
1
1611, 1654, 1708, 3088. H NMR spectrum, δ, ppm:
7.42 d.d (1H, 6-H, J = 7.52, 6.88 Hz), 7.47 d (1H, 8-H,
J = 7.56 Hz), 7.71 d.d (1H, 7-H, J = 7.56, 7.52 Hz),
7.87 d (1H, 5'-H, J = 8.20 Hz), 7.91 d.d (1H, 6'-H, J =
7.56, 8.24 Hz), 8.44 d (1H, 4'-H, J = 7.56 Hz), 8.56 d
(1H, 5-H, J = 6.84 Hz), 8.74 s (1H, 2'-H), 12.81 s (1H,
NH). Found, %: C 62.55; H 4.09; N 13.61. C15H9N3O4.
Calculated, %: C 61.02; H 3.07; N 14.23.
3-(4-Nitrobenzoyl)quinoxalin-2(1H)-one (IIe).
Yield quantitative, mp 302–304°C (from AcOH). IR
spectrum, ν, cm–1: 569, 698, 754, 851, 866, 919, 1026,
1150, 1253, 1294, 1351, 1515, 1606, 1655, 1703,
3-Aroylquinoxalin-2(1H)-ones IIa–IIe (general
procedure). A solution of 2 mmol of 3-(α-bromo-
benzyl)quinoxalin-2(1H)-one Ia–Ie in 10 ml of DMSO
was kept for 10–15 min and poured into 25 ml of
water, and the precipitate was filtered off and washed
with water (2×15 ml).
1
2954, 3433. H NMR spectrum, δ, ppm: 7.38 d.d (1H,
6-H, J = 8.24, 6.88 Hz), 7.45 d (1H, 8-H, J = 7.60 Hz),
7.67 d.d (1H, 7-H, J = 6.88, 7.60 Hz), 7.82 d (1H, 5-H,
J = 8.24 Hz), 8.22 d (2H, 2'-H, 6'-H, J = 8.88 Hz),
8.34 d (1H, 3'-H, 5'-H, J = 8.88 Hz), 12.81 s (1H, NH).
Found, %: C 60.73; H 3.01; N 14.32. C15H9N3O4. Cal-
culated, %: C 61.02; H 3.07; N 14.23.
3-Benzoylquinoxalin-2(1H)-one (IIa). Yield 96%.
Its properties and spectral parameters were in agree-
ment with those reported in [18].
REFERENCES
3-(4-Bromobenzoyl)quinoxalin-2(1H)-one (IIb).
Yield quantitative, mp 280–282°C (from AcOH). IR
spectrum, ν, cm–1: 566, 757, 842, 897, 917, 1068,
1151, 1253, 1293, 1304, 1395, 1495, 1569, 1590,
1. Zimmer, H., Amer, A., Ho, D., and Palmer-Sungail, R.,
J. Heterocycl. Chem., 1991, vol. 28, p. 1501.
2. Markees, D.G., J. Heterocycl. Chem., 1989, vol. 26,
1
p. 29.
1606, 1652, 1700, 3096, 3568. H NMR spectrum, δ,
ppm: 7.40 d.d (1H, 7-H, J = 7.52, 7.52 Hz), 7.48 d
(1H, 8-H, J = 7.52 Hz), 7.68 d.d (1H, 6-H, J = 7.52,
8.24 Hz), 7.80 d (2H, 3'-H, 5'-H, J = 8.24 Hz), 7.85 d
(1H, 5-H, J = 8.24 Hz), 7.93 d (2H, 2'-H, 6'-H, J =
8.24 Hz), 8.32 br.s (1H, NH). Found, %: C 57.50;
H 2.60; Br 24.54; N 8.88. C15H9BrN2O2. Calculated,
%: C 54.74; H 2.76; Br 24.28; N 8.51.
3. Matoba, K., Iton, K., Kondo, K., Yamazaki, T., and
Nagata, M., Chem. Pharm. Bull., 1981, vol. 29, p. 2442.
4. Matoba, K., Iton, K., Nagata, M., and Yamazaki, T.,
Heterocycles, 1980, vol. 14, p. 465.
5. Matoba, K., Terada, T., Suguira, M., and Yamazaki, T.,
Heterocycles, 1987, vol. 26, p. 55.
6. Matoba, K., Miyata, Y., and Yamazaki, T., Chem.
Pharm. Bull., 1983, vol. 31, p. 476.
3-(2,4-Dichlorobenzoyl)quinoxalin-2(1H)-one
(IIc). Yield quantitative, mp 240–242°C (from AcOH).
IR spectrum, ν, cm–1: 425, 600, 774, 806, 830, 855,
923, 958, 1057, 1102, 1162, 1260, 1297, 1422, 1495,
1553, 1582, 1611, 1663, 1688, 3069, 3215, 3567.
1H NMR spectrum (DMSO-d6), δ, ppm: 7.36 d.d (1H,
6-H, J = 7.52, 6.84 Hz), 7.40 d (1H, 8-H, J = 8.24 Hz),
7.61 d.d (1H, 3'-H, J = 8.24, J 2.04 Hz), 7.66 d.d (1H,
7-H, J = 6.84, 8.24 Hz), 7.75 d (1H, 5'-H, J = 2.04 Hz),
7.79 d (1H, 5-H, J = 7.52 Hz), 7.88 d (1H, 6'-H, J =
8.24 Hz), 8.26 s (1H, NH). Found, %: C 57.35; H 2.37;
Cl 20.44; N 8.79. C15H8Cl2N2O2. Calculated, %:
C 56.45; H 2.53; Cl 22.22; N 8.78.
7. Atfah, A., Abu-Shuheil, M.Y., and Hill, J., Tetrahedron
Lett., 1990, vol. 46, p. 6483.
8. Eiden, F. and Bachmann, G., Arch. Pharm., 1973,
vol. 306, p. 876.
9. Glushkov, R.G., Dronova, L.N., Elina, A.S., Musato-
va, I.S., Porokhovaya, M.V., Solov’eva, N.P., Chistya-
kov, V.V., and Sheinker, Yu.N., Khim.-Farm. Zh., 1988,
no. 3, p. 336.
10. Kurasawa, Y., Ichikawa, M., and Takada, A., Hetero-
cycles, 1988, vol. 20, p. 269.
11. Mamedov, V.A., Kalinin, A.A., Rizvanov, I.Kh., Azan-
cheev, N.M., Efremov, Yu.Ya., and Levin, Ya.A., Khim.
Geterotsikl. Soedin., 2002, no. 9, p. 1279.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 42 No. 10 2006