KOZLOV, BASALAEVA
590
5-(4-Bromophenyl)-1-methyl-1,2,3,4-tetrahydro-
5-(1,3-Benzodioxol-5-yl)-1-methyl-1,2,3,4-tetra-
hydrobenzo[a]phenanthridine (Vf). Yield 11%,
colorless crystals, mp 175°C. IR spectrum, ν, cm–1:
3061, 3050, 2920, 2878, 2710, 1810, 1754, 1531,
benzo[a]phenanthridine (Vc). Yield 20%, colorless
crystals, mp 190–192°C. IR spectrum, ν, cm–1: 3062,
3058, 2860, 1724, 1517, 1409, 1392, 1237, 822, 570.
1H NMR spectrum, δ, ppm: 1.52 d (3H, CH3), 1.68–
2.00 m (4H, 2-H, 3-H), 2.90–3.00 m (2H, 4-H), 4.41–
4.89 m (1H, 1-H); 7.42 m and 7.60 m (6H, Harom);
7.84 m, 7.89 m, and 7.93 m (3H, Harom); 8.80 d (1H,
1
1406, 1372, 1203, 865. H NMR spectrum, δ, ppm:
1.51 d (3H, CH3), 1.70–2.08 m (4H, 2-H, 3-H), 2.91–
3.02 m (2H, 4-H), 3.62 s (2H, OCH2O), 4.63 m (1H,
1-H); 7.48 m and 7.60 m (6H, Harom); 7.80 m, 7.89 m,
and 7.96 m (3H, Harom); 8.82 d (1H, Harom). Mass spec-
trum, m/z (Irel, %): 367 (100), 366 (64), 352 (32), 246
(43), 231 (12). Found, %: C 81.76; H 5.71; N 3.84.
C25H21NO2. Calculated, %: C 81.74; H 5.72; N 3.81.
H
arom). Mass spectrum, m/z (Irel, %): 402 (100), 401
(63), 387 (42), 322 (24), 246 (29), 231 (22), 166
(27). Found, %: C 71.64; H 5.00; Br 19.93; N 3.49.
C24H20BrN. Calculated, %: C 71.64; H 4.98; Br 19.90;
N 3.48.
This study was performed under financial support
by the Byelorussian Republican Foundation for Basic
Research (project no. Kh07-007).
1-Methyl-5-(4-nitrophenyl)-1,2,3,4-tetrahydro-
benzo[a]phenanthridine (Vd). Yield 25%, colorless
crystals, mp 187–188°C. IR spectrum, ν, cm–1: 2933,
2861, 1750, 1600, 1518, 1439, 1350, 1313, 1105, 858,
833, 735, 701. 1H NMR spectrum, δ, ppm: 1.52 d (3H,
CH3), 1.70–2.09 m (4H, 2-H, 3-H), 2.90–3.08 m (2H,
4-H), 4.42–4.45 m (1H, 1-H), 7.60–7.73 m (2H, Harom),
7.80–8.00 m (5H, Harom), 8.39 d (2H, Harom), 8.84 d
(1H, Harom). Mass spectrum, m/z (Irel, %): 368 (100),
367(60), 353 (62), 322 (31), 246 (33), 231 (25). Found,
%: C 78.25; H 5.40; N 7.64. C24H20N2O2. Calculated,
%: C 78.26; N 5.43; N 7.61.
REFERENCES
1. Kozlov, N.G. and Basalaeva, L.I., Russ. J. Gen. Chem.,
2001, vol. 71, p. 250.
2. Kozlov, N.G., Basalaeva, L.I., Firgang, S.I., and Shash-
kov, A.S., Russ. J. Org. Chem., 2004, vol. 40, p. 518.
3. Belousov, A.K., Blokhin, N.N., Borisov, V.I., Gauze, G.F.,
Giller, S.A., Gorbacheva, L.B., Dudnik, Yu.V., Li-
dak, M.Yu., Lorie, Yu.I., Lukevits, E.Ya., Perevodchi-
kova, N.I., Sof’ina, Z.P., and Syrkin, A.B., Khimiotera-
piya zlokachestvennykh opukholei (Chemotherapy of
Malignant Tumors), Moscow: Meditsina, 1977.
5-(4-Ethoxyphenyl)-1-methyl-1,2,3,4-tetrahydro-
benzo[a]phenanthridine (Ve). Yield 37%, colorless
crystals, mp 178°C. IR spectrum, ν, cm–1: 3050, 2910,
2880, 2840, 1730, 1613, 1549, 1436, 1452, 1325,
4. Dyson, G.M. and May, P., The Chemistry of Synthetic
Drugs, London: Longmans, 1959, 5th ed.
1
1371, 1239, 847. H NMR spectrum, δ, ppm: 1.47 t
5. Watts, V.J., Lawler, C.P., Knoerzer, T., Mayleben, M.A.,
Neve, K.A., Nichols, D.E., and Mailman, R.B., Eur. J.
Pharmacol., 1993, vol. 239, p. 271.
(3H, CH2CH3), 1.50 d (3H, CH3), 1.70–2.08 m (4H,
2-H, 3-H), 2.90–3.00 m (2H, 4-H), 4.10 q (2H, OCH2),
4.40–4.48 m (1H, 1-H), 7.52–7.63 m (2H, Harom),
7.75–8.02 m (5H, Harom), 8.37 d (2H, Harom), 8.79 d
(1H, Harom). Mass spectrum, m/z (Irel, %): 367 (100),
366 (50), 352 (47), 322 (24), 307 (11), 246 (49), 231
(34). Found, %: C 85.00; H 6.80; N 3.84. C26H25NO.
Calculated, %: C 85.01; H 6.82; N 3.82.
6. Smidrekal, J., Collect. Czech. Chem. Commun., 1988,
vol. 53, p. 3186.
7. Desenko, S.M. and Orlov, V.D., Azageterotsikly na
osnove aromaticheskikh nepredel’nykh ketonov (Aza
Heterocycles on the Basis of Aromatic Unsaturated
Ketones), Khar’kov: Folio, 1998, p. 110.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 45 No. 4 2009