TRASHAKHOVA et al.
760
(63%), mp 191–193°С. 1Н NMR spectrum, δ, ppm: 6.12 d
(1Н, СН=, 3J 15.5 Hz), 7.13 m (2Н, H2',6'), 7.21 m (3Н,
H3',4',5'), 7.45 m (1Н, Н8), 7.51 m (2Н, Н3'',4''), 7.61 m
(2Н, Н6'',7''), 7.73 m (1Н, Н6), 7.80 m (1Н, Н2''), 7.87 m
N 6.90. C27H20N2O2. Calculated, %: C 80.18; H 4.98;
N 6.93. M 404.47.
ACNOWLEDGMENTS
3
(1Н, Н7), 7.94 d (1Н, СН=, J 15.6 Hz), 8.10 m (1Н,
Н5), 8.16 m (2Н, Н5'',8''). Mass spectrum, m/z (Irel, %):
375 [M + H]+ (100). Found, %: C 83.39; H 4.80; N 7.52.
C26H18N2O. Calculated, %: C 83.42; H 4.85; N 7.48.
M 374.45.
The study was carried out under the financial sup-
port of the Ministry of Education and Science (State
contract GK-02.740.11.0260), of the Council on grants
of the President of the Russian Federation (Program of
support of scientific schools, grant NSh-65261.2010.3),
and of the Russian Foundation for Basic Research (grant
no. 11-03-00718а).
Compounds VIIIc, VIIId were similarly prepared.
trans-3-(1-Naphthyl)-2-[2-(4-nitrophenyl)vinyl]-
3Н-quinazolin-4-one (VIIIc). Yield 68%, mp 236–
1
238°С. Н NMR spectrum, δ, ppm: 6.30 d (1Н, СН=,
REFERENCES
3J 15.5 Hz), 7.41 d (2Н, H2',6', 3J 8.8 Hz), 7.45 m (1Н, Н8),
7.49–7.63 m (4Н, Н3'',4'',7'',6''), 7.73 m (1Н, Н6), 7.83 m
(1Н, Н2''), 7.90 m (1Н, Н7), 8.01 d (1Н, СН=, 3J 15.6 Hz),
8.08 d (2Н, H3',5', 3J 8.8 Hz), 8.10 m (1Н, Н5), 8.17 m
(2Н, Н5'',8''). Mass spectrum, m/z (Irel, %): 420 [M + H]+
(100). Found, %: C 74.48; H 4.12; N 9.98. C26H17N3O3.
Calculated, %: C 74.45; H 4.09; N 10.02. M 419.44.
1. De Silva, A.P., Gurarantane, H.Q.N., Gunnlaugsson, T.,
Huxley, A.J.M., McCoy, C.P., Rademacher, J.T., and
Rice, T.E., Chem. Rev., 1997, vol. 97, p. 1515; Yang, J.S.,
Liau, K.L., Wang, C.M., and Hwang, C.Y., J. Am. Chem.
Soc., 2004, vol. 126, p. 12325; Yang, J.S., Hwang, C.Y.,
Hsieh, C.C., and Chiou, S.Y., J. Org. Chem., 2004, vol. 69,
p. 719; Saito, H., Mori, T., Wada, T., and Inoue, Y., J. Am.
Chem. Soc., 2004, vol. 126, p. 1900.
2. Haroutounian, S.A. and Katzenellenbogen, J.A.,
Tetrahedron, 1995, vol. 51, p. 1585.
3. Kim, B.R., Cho, S.D., Lee, H.G., Yim, H.S., Kim, M.J.,
Hwang, J., Park, S.E., Kim, J.J., Jung, K.J., and Yoon, Y.J.,
J. Heterocycl. Chem., 2009, vol. 46, p. 691.
4. Wang, T.T., Zeng, G.C., Zeng, H.P., Liu, P.Y., Wang, R.X.,
Zhang, Z.J., and Xiong, Y.L., Tetrahedron, 2009, vol. 65,
p. 6325; Barberis, V.P. and Mikroyannidis, J.A., Synthetic
Metals, 2006, vol. 156, p. 865.
5. Welch, W.M., Ewing, F.E., Huang, J., Menniti, F.S.,
Pagnozzi, M.J., Kelly, K., Seymour, P.A., Guanowsky, V.,
Guhan, S., Guinn, M.R., Critchett, D., Lazzaro, J.,
Ganong, A.H., DeVries, K.M., Staigers, T.L., and
Chenard, B.L., Bioorg. Med. Chem. Lett., 2001, vol. 11,
p. 177.
6. Derbala, H.A., Monatsh. Chem., 1996, vol. 127, p. 103.
7. Kelarev, V.I., Silin, M.A., Koshelev, V.N., and
Borisova, O.A., Kh. Geterotsikl. Soedin., 2004, p. 616.
8. Kovalenko, S., Belenichev, I., Nikitin, V., and Karpenko,A.,
Acta Polon. Pharm., 2003, vol. 60, p. 275.
9. Bakalova, S.M., Santos, A.G., Timcheva, I., Kaneti, J.,
Filipova, I.L., Dobrikov, G.M., and Dimitrov, V.D., J. Mol.
Struct. THEOCHEM., 2004, vol. 710, p. 229.
trans-2-[2-(4-Dimethylaminophenyl)vinyl]-3-(1-
naphthyl)-3Н-quinazolin-4-one (VIIId). Yield 57%,
mp 230–232°С. 1Н NMR spectrum, δ, ppm: 3.92 s (3Н,
СН3), 5.82 d (1Н, СН=, 3J 15.3 Hz), 6.51 d (2Н, H3',5'
,
3J 7.8 Hz), 7.07 d (2Н, H2',6', 3J 7.8 Hz), 7.44–7.51 m (2Н,
Н8,3'',4''), 7.60 m (2Н, Н7'',6''), 7.73 m (2Н, Н6,2''), 7.83 m
(1Н, Н7), 7.86 m (1Н, Н5), 8.12 d (1Н, СН=, 3J 15.4 Hz),
8.14 m (2Н, Н5'',8''). Mass spectrum, m/z (Irel, %): 418
[M + H]+ (100). Found, %: C 80.51; H 5.50; N 10.10.
C28H23N3O. Calculated, %: C 80.55; H 5.55; N 10.06.
M 417.52.
trans-2-[2-(4-Methoxyphenyl)vinyl]-3-(1-
naphthyl)-3Н-quinazolin-4-one (VIIIb). To a mixture
of 0.8 g (3.06 mmol) of azomethine IX and 15 ml of
glacial acetic acid was added 0.4 g (2.48 mmol) of ben-
zoxazinone Ib and 0.21 g (1.2 mmol) of molten sodium
acetate; the mixture was boiled for 6 h. On cooling the
reaction mixture was poured into 50 ml of cold water, the
separated precipitate was filtered off and recrystallized
from ethanol. Yield 0.6 g (60%), mp 188–190°С. 1Н NMR
spectrum, δ, ppm: 3.72 s (3Н, СН3), 5.94 d (1Н, СН=,
3
3J 15.4 Hz), 6.75 d (2Н, H3',5', J 8.6 Hz), 7.07 d (2Н,
H2',6', 3J 8.6 Hz), 7.46 m (1Н, Н8), 7.52 m (2Н, Н3'',4''),
7.58 m (2Н, Н7'',6''), 7.72 m (1Н, Н6), 7.78 m (1Н, Н2''),
7.85 m (1Н, Н7), 7.91 d (1Н, СН=, 3J 15.4 Hz), 8.09 m
(1Н, Н5), 8.15 m (2Н, Н5'',8''). Mass spectrum, m/z (Irel,
%): 405 [M + H]+ (100). Found, %: C 80.22; H 5.03;
10. Laeva, A.A., Nosova, E.V., Lipunova, G.N.,
Golovchenko, A.V., Adonin, N.Yu., Parmon, V.N., and
Charushin, V.N. Zh. Org. Khim., 2009, vol. 45, p. 925.
11. Chong, J.A., Fanger, C., Larsen, G.R., Lumma, W.C.,
Moran, M.M., Ripka, A., Underwood, D.J., Weigele, M.,
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 47 No. 5 2011