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H7), 6.92 m, 7.07 m, 7.17 m, 7.34 m (9H, Harom), 7.40 d.d
(1H, H2, 3J 7.9, 4J 4.2), 7.48 d, 7.55 d (2H, H5,6, 3J 8.9),
8.82 d (1H, H3, 3J 4.2), 8.90 d (1H, H1, 3J 7.9), 9.32 s,
9.40 s (1H, NH). Found, %: C 83.47; H 5.58; N 6.54.
C29H24N2O. Calculated, %: C 83.63; H 5.81; N 6.73.
10-(p-Methoxyphenyl)-7-(p-fluorophenyl)-
7,10,11,12-tetrahydro-9H-benzo[b][1,7]phenan-
throlin-8-one (Vq). Yield 74%, mp 256–257°C. 1H NMR
spectrum, δ, ppm (J, Hz): 2.54 m (2H, H11), 2.88 m (2H,
H9), 3.34 m, 3.41 m (1H, H10), 5.22 s, 5.29 s (1H, H7),
6.95 d, 7.01 d, 7.32 d, 7.39 m (8H, Harom, 3J 8.2), 7.45 d.d
(1H, H2, 3J 8.0, 4J 4.3), 7.53 d, 7.60 d (2H, H5,6, 3J 9.0),
8.81 d (1H, H3, 3J 4.3), 8.87 d (1H, H1, 3J 8.0), 9.40 s,
9.46 s (1H, NH). Found, %: N 6.09. C29H23FN2O2.
Calculated, %: N 6.22.
7-(4-Benzyloxyphenyl)-10-phenyl-7,10,11,12-
tetrahydro-9H-benzo[b][1,7]phenanthrolin-8-one
1
(Vm). Yield 67%, mp 264–265°C. H NMR spectrum,
δ, ppm (J, Hz): 2.50 m (2H, H11), 3.02 m (2H, H9),
3.34 m, 3.44 m (1H, H10), 4.98 m (2H, OCH2Ph), 5.18 s,
5.24 s (1H, H7), 6.76 m, 7.08 m, 7.21 m, 7.33 m (14H,
7-(o-Methoxyphenyl)-10-(p-methoxyphenyl)-
7,10,11,12-tetrahydro-9H-benzo[b][1,7] phenan-
throlin -8-one (Vr). Yield 62%, mp 243–244°C. 1H NMR
spectrum, δ, ppm (J, Hz): 2.55 m (2H, H11), 3.04 m (2H,
H9), 3.38 m, 3.44 m (1H, H10), 3.71 s (3H, MeO), 3.79 s
(3H, MeO), 5.18 s, 5.25 s (1H, H7), 6.46 m, 6.88 m,
3
4
H
arom), 7.42 d.d (1H, H2, J 8.0, J 4.1), 7.51 d, 7.59 d
(2H, H5,6, 3J 8.8), 8.83 d (1H, H3, 3J 4.1), 8.91 d (1H, H1,
3J 8.0), 9.36 s, 9.43 s (1H, NH). Found, %: C 82.47;
H 5.36; N 5.38. C35H28N2O2. Calculated, %: C 82.65;
H 5.55; N 5.51.
3
7.23 d, (8H, Harom, 3J 8.0), 7.43 d.d (1H, H2, J 7.9,
10-Phenyl-4-cyclohexenyl-7,10,11,12-tetra-
hydro-9H-benzo[b][1,7]phenanthrolin-8-one (Vn).
Yield 43%, mp 161–162°C. 1H NMR spectrum, δ, ppm
(J, Hz): 0.92–2.03 m (7Hcycloaliph.), 2.49 m (2H, H11),
2.97 m (2H, H9), 3.31 m, 3.42 m (1H, H10), 4.77 d,
5.40 d (CH=CH), 5.18 s, 5.24 s (1H, H7), 7.10 m, 7.22 m,
4J 4.1), 7.50 d, 7.57 d (2H, H5,6, 3J 8.9), 8.76 d (1H, H3,
3J 4.1), 8.80 d (1H, H1, 3J 7.9), 9.37 s, 9.44 s (1H. NH).
Found, %: C 77.63; H 5.49; N 5.74. C30H26N2O3.
Calculated, %: C 77.92; H 5.63; N 6.06.
7-(o,p-Dimethoxyphenyl)-10-(p-methoxyphenyl)-
7,10,11,12-tetrahydro-9H-benzo[b][1,7]phenan-
throlin-8-one (Vs). Yield 60%, mp 261–263°C. 1H NMR
spectrum, δ, ppm (J, Hz): 2.50 m (2H, H11), 2.98 m (2H,
H9), 3.30 m, 3.41 m (1H, H10), 3.70 s (3H, MeO), 3.78 s
(3H, MeO), 3.93 s (3H, MeO), 5.19 s, 5.25 s (1H, H7),
6.44 m, 6.86 m, 7.24 d, (7H, Harom, 3J 7.7), 7.42 d.d (1H,
H2, 3J 7.9, 4J 4.2), 7.55 d, 7.61 d (2H, H5,6, 3J 9.1), 8.80 d
3
4
7.34 m (5H, Harom), 7.42 d.d (1H, H2, J 8.0, J 4.1),
7.50 d, 7.57 d (2H, H5,6, 3J 8.8), 8.82 d (1H, H3, 3J 4.1),
8.89 d (1H, H1, 3J 8.0), 9.38 s, 9.46 s (1H, NH). Found,
%: C 82.55; H 6.29; N 6.64. C28H25N2O. Calculated, %:
C 82.73; H 6.45; N 6.89.
7-(4-Methylsulfanyl)-10-phenyl-7,10,11,12-
tetrahydro-9H-benzo[b][1,7]phenanthrolin-8-one
(Vo). Yield 79%, mp 212–213°C. 1H NMR spectrum, δ,
ppm (J, Hz): 2.37 C (3H, SMe), 2.51 m (2H, H11), 3.04 m
(2H, H9), 3.40 m, 3.48 m (1H, H10), 5.21 s, 5.28 s (1H,
H7), 7.00 m, 7.08 m, 7.24 m (9H, Harom), 7.42 d.d (1H,
H2, 3J 7.8, 4J 4.1), 7.48 d, 7.56 d (2H, H5,6, 3J 8.9), 8.83 d
3
(1H, H3, 3J 4.2), 8.88 d (1H, H1, J 7.9), 9.50 s, 9.55 s
(1H, NH). Found, %: C 75.55; H 5.42; N 5.44.
C31H28N2O4. Calculated, %: C 75.61; H 5.69; N 5.69.
7-(4-Hydroxy-3-methoxyphenyl)-10-(p-
methoxyphenyl)-7,10,11,12-tetrahydro-9H-
benzo[b][1,7]-phenanthrolin-8-one (Vt). Yield 75%,
mp 281–282°C. 1H NMR spectrum, δ, ppm (J, Hz):
2.52 m (2H, H11), 3.09 m (2H, H9), 3.41 m, 3.46 m (1H,
H10), 3.65 s (3H, MeO), 3.80 s (3H, MeO), 5.13 s, 5.20 s
(1H, H7), 6.52 m, 6.90 m, 7.22 d, (7H, Harom, 3J 8.1),
7.48 d.d (1H, H2, 3J 7.8, 4J 4.0), 7.52 d, 7.60 d (2H, H5,6,
3J 8.8), 8.60 C (1H, OH), 8.83 d (1H, H3, 3J 4.0), 8.90 d
3
(1H, H3, 3J 4.1), 8.92 d (1H, H1, J 7.8), 9.34 s, 9.43 s
(1H, NH). Found, %: C 77.47; H 5.21; N 6.05; S 6.86.
C29H24N2OS. Calculated, %: C 77.65; H 5.39; N 6.24;
S 7.15.
7-[(3-Methyl-2-thienyl)-10-phenyl-7,10,11,12-
tetrahydro-9H-benzo[b][1,7]phenanthrolin-8-one
(Vp). Yield 49%, mp 166–167°C. 1H NMR spectrum, δ,
ppm (J, Hz): 2.37 C (3H, Me), 2.52 m (2H, H11), 3.07 m
(2H, H9), 3.40 m, 3.49 m (1H, H10), 5.55 C, 5.61 C (1H,
H7), 6.61 m, 6.94 m, 7.28 m (7H, Harom, heteroarom), 7.34 d.d
(1H, H2, 3J 7.8, 4J 4.1), 7.42 d, 7.51 d (2H, H5,6, 3J 8.9),
8.82 d (1H, H3, 3J 4.1), 8.91 d (1H, H1, 3J 7.8), 9.50 C,
9.59 s (1H, NH). Found, %: C 76.52; H 5.07; N 6.42;
S 7.27. C27H22N2OS. Calculated, %: C 76.75; H 5.25;
N 6.63; S 7.59.
3
(1H, H1, J 7.8), 9.45 s, 9.53 s (1H, NH). Found, %:
C 75.19; H 5.27; N 5.72. C30H26N2O4. Calculated, %:
C 75.31; H 5.44; N 5.86.
10-(n-Methoxyphenyl)-7-(3-pyridyl)-7,10,11,12-
tetrahydro-9H-benzo[b][1,7]phenanthrolin-8-one
(Vu). Yield 70%, mp 266–267°C. 1H NMR spectrum, δ,
ppm (J, Hz): 2.58 m (2H, H11), 3.05 m (2H, H9), 3.40 m,
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 45 No. 2 2009