CONDENSATION OF N-MONOSUBSTITUTED 2-NAPHTHYLAMINES
1331
1716 (C=O), 1684 (C=O), 1260 (C–O–C), 1227 (C–
O–C). H NMR spectrum, δ, ppm: 0.97, 1.09 s (3H,
The study was carried out under a financial support
of the Belorussian and Russian Foundation for basic
Research (grant X08P-015).
1
C4'CH3), 2.50, 2.70 d (2H, C3'H + C5'H, J 16 Hz), 3.50 s
(2H, C1H2), 3.56 s (2H, C3H2), 3.84, 3.90 s (3H, OCH3),
4.56 s (2H, NCH2Ar), 6.80–8.00 m (9Harom). Found, %:
C 76.12; H 6.82; N 3.07. C29H31NO4. Calculated, %:
C 76.12; H 6.83; N 3.06.
REFERENCES
1. Kozlov, N.S., 5,6-Benzokhinoliny (5,6-Benzoquinoline),
Minsk: Nauka i Tekhnika, 1979, p. 99.
4-(1,3-Benzodioxol-5-ylmethyl)-4',4'-dimeth-
yl-1,4-dihydro-3H-spiro[benzo[f]quinoline-2,1'-
cyclohexane]-2',6'-dione (VIIh). Yield 89%, mp
219°C IR spectrum, ν, cm–1: 3100–3000 (C–Harom),
3000–2800 (C–Haliphat), 1727 (C=O), 1698 (C=O), 1256
2. Albert, A., Rubbo, S., and Burlrill, M., J. Brit. Exp. Path.,
1949, vol. 30, p. 159.
3. Monge,A.,Alvarez, E., San, Martin, C., Nadal, E., Ruiz, I.,
Font, M., Martinez-Irujo, J. J., Santiago, E., Prieto, I., La-
sarte, J. J., Sarobe, P., and Borras, F., Drug. Des. Discov.,
1997, vol. 14, no. 4, p. 291.
1
(C–O–C), 1240 (C–O–C). H NMR spectrum, δ, ppm:
0.98, 1.11 s (3H, C4'CH3), 2.52, 2.72 d (2H, C3'H +
C5'H, J 16 Hz), 3.50 s (2H, C1H2), 3.57 s (2H, C3H2),
4.54 s (2H, NCH2Ar), 5.96 s (2H, OCH2O), 6.77–8.00 m
(9Harom). Found, %: C 76.20; H 6.17; N 3.12. C28H27NO4.
Calculated, %: C 76.17; H 6.16; N 3.17.
4. Smith, E.C., McQuaid, L.A., Goode, R.L., McNulty,A.M.,
Neubauer, B.L., Rocco, V.P., andAudia, J.E., Bioorg. Med.
Chem. Lett., 1998, vol. 8, no. 4, p. 395.
5. Cymerman, C.J., Torkelson, S.M., Findell, P.R., and
Weiner, R.I., J. Med. Chem., 1989, vol. 32, p. 961.
4-[(1,1'-Biphenyl)-4-ylmethyl]-4',4'-dimeth-
yl-1,4-dihydro-3H-spiro[benzo[f]quinoline-2,1'-
cyclohexane]-2',6'-dione (VIIi). Yield 83%, mp 209°C.
IR spectrum, ν, cm–1: 3100–3000 (C–Harom), 3000–2800
6. Xiang-Shan, Wang, Qing, Li, Chang-Sheng, Yao, and Shu-
Jiang, Tu, Eur. J. Org. Chem., 2008, p. 3513.
7. Berde, B. and Schild, H.O., Ergot Alkaloids and Related
Compounds, Berlin-Heidelberg: Springer–Verlag, 1978,
p. 156.
1
(C–Haliphat), 1725 (C=O), 1700 (C=O). H NMR spec-
trum, δ, ppm: 0.97, 1.08 s (3H, C4'CH3), 2.52, 2.73 d (2H,
C3'H + C5'H, J 16 Hz), 3.52 s (2H, C1H2), 3.63 s (2H,
C3H2), 4.68 s (2H, NCH2Ar), 6.90–8.00 m (15Harom).
Found, %: C 83.71; H 6.63; N 2.99. C33H31NO2. Calcu-
lated, %: C 83.69; H 6.60; N 2.96.
8. Kozlov, N.G. and Kadutskii,A.P., Tetrahedron Lett., 2008,
vol. 49, p. 4560.
9. Nakanishi, K., Infrared Absorption Spectroscopy. Practical,
Tokyo: Nankodo, 1962.
4-(4-Isopropylbenzyl)-4',4'-dimethyl-1,4-dihydro-
3H-spiro[benzo[f]quinoline-2,1'-cyclohexane]-2',6'-di-
one (VII j). Yield 82%, mp 192°C. IR spectrum, ν, cm–1:
3100–3000 (C–Harom), 2956, 2924, 2871 (CandльHыe,
C–Haliphat), 1728 (C=O), 1697 (C=O). 1H NMR spec-
trum, δ, ppm: 0.94, 1.08 s (3H, C4'CH3), 1.24, 1.30 s
[3H, CH(CH3)2], 2.45, 2.65 d (2H, C3'H + C5'H, J 16 Hz),
2.90 m [1H, CH(CH3)2], 3.50 s (2H, C1H2), 3.56 s (2H,
C3H2), 4.58 s (2H, NCH2Ar), 6.90–8.00 m (10Harom).
Found, %: C 81.99; H 7.57; N 3.12. C30H33NO2. Calcu-
lated, %: C 81.97; H 7.57; N 3.19.
10. Novgorodova, N.Yu., Maek, S.K., and Yunusov, S.Yu.,
Khim. Polim. Soedin., 1973, vol. 9, p. 191.
11. Osmanov, Z., Ibragimov, A.A. and Yunusov, S.Yu., Khim.
Polim. Soedin., 1977, 13, 607.
12. Osmanov, Z., Ibragimov, A.A., and Yunusov, S.Yu., Khim.
Polim. Soedin., 1982, 18, 121.
13. Takahiro, Yamane and Kunio, Ogasawara, Synlett., 1996,
vol. 9, p. 925.
14. Basalaeva, L.I., Kozlov, N.G., Firgang, S.I., and Shash-
kov, A.S., Zh. Org. Khim., 2004, 40, 549.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 46 No. 9 2010