1
052
KOTOVSKAYA et al.
ethanol. The mixture was heated for 0.5 1 h on
a water bath and cooled, and the precipitate was fil-
tered off, dried, and recrystallized from acetonitrile.
3. Cheesman, G.W.H. and Cookson, R.F., The Chem-
istry of Heterocyclic Compounds, Weissberger, A.
and Taylor, E.C., Eds., New York: Wiley Intersci.,
1
979, vol. 35.
6
-Fluoro-2,3-dimethyl-7-(1-pyrrolidinyl)quino-
xaline (XIIIa). Pyrrolidine, 0.17 ml (2 mmol), and
DBU, 0.15 ml (1 mmol), were added dropwise to
a solution of 0.19 g (1 mmol) of quinoxaline V in
4. Barlin, G.B. The Chemistry of Heterocyclic Com-
pounds, Weissberger, A. and Taylor, E.C., Eds.,
New York: Wiley Intersci., 1982, vol. 41.
4
1
ml of DMF. The mixture was heated for 5 h at
20 C on a glycerol bath, cooled, and poured into
5
6
7
8
9
.
.
.
.
.
Francis, I., Landquist, I.K., Levi, A.A., Silk, I.A.,
and Thor, I.M., Biochem. J., 1956, no. 63, p. 455.
cold water (25 ml). The precipitate was filtered off,
dried, and recrystallized from ethanol water (1:1).
Yield 0.2 g.
Valenta, I.R., Hoover, I.R.E., and Pagano, I.F., Anti-
microb. Agents Chemother., 1966, p. 453.
Haley, T.I., Flesher, A.V., and Komescu, A.V.,
Nature, 1959, no. 184, p. 198.
7
-Azido-3-cyano-6-fluoro-2-phenylquinoxaline
XIV). A solution of 0.07 g (1 mmol) of sodium azide
in 1 ml of water was added to a suspension of 0.27 g
1 mmol) of quinoxaline IV in 5 ml of acetonitrile.
(
US Patent no. 3635971, 1971; Chem. Abstr., 1972,
vol. 76, no. 99708r.
(
Boido, A., Vazzana, L., and Saratore, F., Farmaco,
The mixture was heated for 2 h under reflux, cooled,
and poured into cold water (30 ml). The precipitate
was filtered off, washed with water on a filter, and
recrystallized from acetonitrile. Yield 0.3 g.
1
994, vol. 49, p. 97.
10. Monge, A., Palop, I.A., De Cerain, A.L., Sena-
edor, V., Martinez-Crespo, F.I., Sainz, I., Narro, S.,
Garica, E., De Miquel, C., Gonzalez, M., Hamil-
ton, E., Barker, A.I., Clarke, E.D., and Green-
how, D.T., J. Med. Chem., 1995, vol. 38, p. 1786.
3
-Cyano-6-fluoro-7-methoxy-2-phenylquinoxa-
line (XVa). Quinoxaline IV, 0.27 g (1 mmol), was
added to a solution of 0.05 g (2 mmol) of metallic
sodium in 6 ml of methanol. The mixture was stirred
for 2 h at 20 25 C and cooled, and the precipitate
was washed with water on a filter, dried, and recrys-
11. Bouzard, D., Antibiotics and Antiviral Compounds.
Chemical Synthesis and Modification, Krohn, R.,
Kirst, H.A., and Maag, H., Eds., Weinheim: VCH,
1993, pp. 187 203.
1
tallized from acetonitrile. Yield 0.3 g. H NMR
spectrum (DMSO-d ), , ppm: 4.12 s (3H, OCH ),
12. Granik, V.G., Lekarstva (Medicines), Moscow:
6
3
4
7
5
.24 d [1H, 8-H, J(8-H,6-F) = 8.5 Hz], 7.73 d [1H,
-H, J(5-H,6-F) = 12.2 Hz], 7.80 m (5H, Ph).
Vuzovskaya Kniga, 2001, pp. 135 254.
3
1
1
3. Evans, T.A. and Seddon, K.R., J. Chem. Soc., Chem.
Commun., 1997, vol. 21, p. 2023.
3
-Cyano-6,7-dimethoxy-2-phenylquinoxaline
(
XVb). Quinoxaline IV, 0.27 g (1 mmol), was added
4. Kotovskaya, S.K., Charushin, V.N., Chupakhin, O.N.,
and Kozhevnikova, E.O., Russ. J. Org. Chem., 1998,
vol. 34, no. 3, pp. 369 374.
to a solution of 0.05 g (2 mmol) of metallic sodium
in 6 ml of methanol. The mixture was heated for 2.5 h
on a water bath and cooled, and the precipitate was
filtered off, washed with water on a filter, dried, and
1
1
1
1
5. Kotovskaya, S.K., Perova, N.M., Charushin, V.N.,
and Chupakhin, O.N., Mendeleev Commun., 1999,
no. 2, pp. 76 77.
1
recrystallized from acetonitrile. Yield 0.2 g. H NMR
spectrum (DMSO-d ), , ppm: 4.05 s (6H, 2MeO),
6
6. Chupakhin, O.N., Kotovskaya, S.K., Perova, N.M.,
Baskakova, Z.M., and Charushin, V.N., Khim.
Geterotsikl. Soedin., 1999, no. 4, pp. 520 531.
8
.28 m (5H, Ph), 7.27 s (2H, 5-H, 8-H).
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RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 38 No. 7 2002