GAVRISHOVA et al.
1144
the formed precipitate was filtered off, washed with
cold aqueous ethanol, the residue was dried and
recrystallized from heptane. In the synthesis of
methoxycarbonyl derivative VI the reaction mixture
was washed with hot aqueous ethanol, then the residue
was dissolved in a mixture of toluene with ethyl ether,
hydrochloric acid was added, the separated precipitate
was filtered off, dried, neutralized with aqueous
NaHCO3, the obtained precipitate was washed with
water, dried, and recrystallized from acetonitrile.
PhCH=СН, J 16.2 Hz), 7.64 d.t (1НHt, J 1.2, 7.5 Hz),
7.67–7.72 m (3Н, H3,5, C6H4CO, Ht), 7.75–7.82 m
(2Н, PhCH=СН, Ht), 7.93 d.d (1НHt, J 1.0, 7.9 Hz),
7.97–8.02 m (2Н, Ht), 8.06 d (2Н, H2,6, C6H4CO, J
8.3 Hz), 8.60 d (1НHt, J 8.1 Hz), 8.93 d (1НHt, J
8.6 Hz). Found, %: С 81.15; H 4.88; N 3.95.
C23H17NO2. Calculated, %: С 81.40; H 5.05; N 4.13.
The study was performed under a financial support
of the Russian Foundation for Basic Research (grants
nos. 13-03-00636 and 14-03-31326 mol_а).
3-(E)-(4-Methoxystyryl)benzo[f]quinoline (IV).
Yield 57%, light yellow crystals, mp 194–195°С
(heptane). IR spectrum, ν, cm–1: 3057, 3034, 3001,
2961, 2934, 2836, 1639 (ν, C=C), 1602, 1582, 1510,
1455, 1301, 1364, 1257 (ν, COC), 1173, 1030, 981 [δ
REFERENCES
1. Musiol, R., Jampilek, J., Buchta, V., Silva, L., Niedbala, H.,
Podeszwa, B., Palka, A., Majerz-Maniecka, K.,
Oleksynd, B., and Polanski, J., Bioorg. Med. Chem.,
2006, vol. 14, p. 3592.
2. Podeszwa, B., Niedbala, H., Polanski, J., Musiol, R.,
Tabak, D., Finster, J., Serafin, K., Milczarek, M.,
Wietrzyk, J., Boryczka, S., Mol, W., Jampilek, J.,
Dohnal, J., Kalinowski, D.S., and Richardson, D.R.,
Bioorg. Med. Chem. Lett., 2007, vol. 17, p. 6138.
3. Huang, F.-C., Galemmo, R.A. Jr., and Campbell, H.F.,
US Patent no. 4918081, 1990; Chem. Abstr., 1990, vol. 113,
p. 97461.
4. Mekouar, K., Mouscadet, J.-F., Desmaele, D., Subra, F.,
Leh, H., Auclair, L., and d’Angelo, J., J. Med. Chem.,
1998, vol. 41, p. 2846.
(CH=CH)], 836, 757. UV-Vis spectrum (ethanol), λmax
,
1
nm: 241, 297, 331, 343, 361, 378. H NMR spectrum
(CDCl3), δ, ppm: 3.85 s (3Н, OCH3), 6.94 d (2Н, H2,6,
C6H4O, J 8.7 Hz), 7.29 d (1Н, PhCH=CH, J 16.2 Hz),
7.57–7.64 m (3Н, H3,5, C6H4O, Ht), 7.66–7.74 m (2Н,
Ht, PhCH=CH), 7.75 d (1НHt, J 8.6 Hz), 7.92 d.d
(1НHt, J 1.1, 7.7 Hz), 7.96–8.01 m (2Н, Ht), 8.59 d
(1НHt, J 8.2 Hz), 8.89 d (1НHt, J 8.7 Hz). Found, %: С
84.98; H 5.61; N 4.37. C22H17NO. Calculated, %: С
84.86; H 5.50; N 4.50.
3-(E)-(3-Methoxystyryl)benzo[f]quinoline (V).
Yield 63%, light yellow crystals, mp 137–138°С
(heptane). IR spectrum, ν, cm–1: 3057, 3034, 2996,
2961, 2933, 2835 (ν, C–H), 1639 (ν, C=C), 1594,
1580, 1493, 1485, 1457, 1363, 1260 (ν, COC), 1247,
1161, 1041, 981 [δ(CH=CH)], 871, 852, 840, 829, 757,
691. UV-Vis spectrum (ethanol), λmax, nm: 235, 274,
5. Wang, M., Gao, M., Mille, K.D., Sledge, G.W.,
Hutchins, G.D., and Zheng, Q.-H., Eur. J. Med. Chem.,
2009, vol. 44, p. 2300.
6. Gavrishova, T.N., Lee, V.M., Gor’kov, K.V., and
Budyka, M.F., Russ. J. Appl. Chem., 2011, vol. 84, p. 507.
7. Li, V.M., Gavrishova, T.N., and Budyka, M.F., Russ. J.
Org. Chem., 2012, vol. 48, p. 823.
8. Budyka, M.F., Potashova, N.I., Gavrishova, T.N., and
Li, V.M., High Energy Chem., 2008, vol. 42, p. 446.
9. Budyka, M.F., Potashova, N.I., Gavrishova, T.N., and
Li, V.M., J. Mater. Chem., 2009, vol. 19, p. 7721.
10. Budyka, M.F., Potashova, N.I., Gavrishova, T.N., and
Li, V.M., Nanotechnol. Russ., 2012, vol. 7, p. 280.
11. Budyka, M.F., Sadykova, K.F., and Gavrishova, T.N.,
Mendeleev Commun., 2011, vol. 21, p. 151.
12. Budyka, M.F., Sadykova, K.F., and Gavrishova, T.N., J.
Photochem. Photobiol. A: Chem., 2012, vol. 241, p. 38.
13. Budyka, M.F., Li, V.M., and Potashova, N.I., High
Energy Chem., 2013, vol. 47, p. 107.
14. Mahajan, R.K., and Singh, M., Indian J. Chem., 1977,
1
295, 324, 336, 357, 375. H NMR spectrum (CDCl3),
δ, ppm: 3.87 s (3Н, OCH3), 6.88 d.d (1Н, H6, C6H4O, J
1.5, 8.1 Hz), 7.18–7.24 m (2Н, H2,4, C6H4O), 7.32 t
(1Н, H5, C6H4O, J 7.8 Hz), 7.42 d (1Н, PhCH=CH, J
16.2 Hz), 7.63 t (1НHt, J 7.4 Hz), 7.66–7.76 m (2Н,
PhСH=CH, Ht), 7.79 d (1НHt, J 8.6 Hz), 7.93 d (1НHt,
J 7.7 Hz), 7.96–8.01 m (2Н, Ht), 8.60 d (1НHt, J
8.1 Hz), 8.92 d (1НHt, J 8.6 Hz). Found, %: С 84.67; H
5.68; N 4.32. C22H17NO. Calculated, %: С 84.86; H
5.50; N 4.50.
3-(E)-(4-Methoxycarbonylstyryl)benzo[f]quino-
line (VI). Yield 74%, white crystals, mp 186–187оС
(acetonitrile). IR spectrum, ν, cm–1: 3075, 3053, 3035,
2984, 2952, 2890, 2843, 2348, 2321, 1718 (ν, C=O),
1604, 1436, 1281, 1178, 1110, 965 [(δ(CH=CH)], 965,
vol. 15B, p. 491.
842, 762, 733, 696. UV-Vis spectrum (ethanol), λmax
nm: 236, 297, 327, 339, 361, 378. H NMR spectrum
(CDCl3), δ, ppm: 3.93 s (3Н, OCH3), 7.50 d (1Н,
,
15. Prostakov, N.S., Pleshakov, V.G., Kholdarova, T.,
Zvolinskii, V.P., and Plaksii, L.N., Chem.
Heterocycl. Comp., 1972, vol. 8, p. 1264
1
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 50 No. 8 2014