KURLOVICH et al.
1326
227°C. IR spectrum, ν, cm–1: 3445 (O–H), 1725 (C=O),
1695 (C=O). H NMR spectrum (CD3COCD3), δ, ppm:
1.85–1.95 m (2H, CH2), 2.40 m (2H, CH2), 2.75 m (2H,
CH2), 3.40 C (2H, CH2), 3.82 d (2H, NCH2, J 13 Hz),
δ, ppm: 3.40 s (2H, CH2), 3.82 d (2H, NCH2, J 13 Hz),
4.64 d (2H, NCH2Ar, J 11 Hz), 5.20 m (2H, CH2),
7.20–7.25 m (4Harom; 1H, OH), 7.35 t (3Harom, J 7.5 Hz),
7.40–7.45 t (5Harom, J 7.6 Hz), 7.60 d (4Harom, J 7.5 Hz),
7.65 d (1Harom, J 7.5 Hz), 7.90 d (1Harom, J 7.6 Hz). Found,
%: C 79.96; H 5.14; N 2.62. C35H27NO4. Calculated, %:
C 79.98; H 5.18; N 2.66.
1
4.64 d (2H, NCH2Ar, J 11 Hz), 7.20–7.25 m (4Harom
;
1H, OH), 7.35 t (3Harom, J 7.5 Hz), 7.40–7.45 t (5Harom
J 7.6 Hz), 7.60 d (4Harom, J 7.5 Hz), 7.65 d (1Harom
,
,
J 7.5 Hz), 7.90 d (1Harom, J 7.6 Hz). Found, %: C 82.59;
H 5.84; N 2.62. C37H31NO3. Calculated, %: C 82.66;
H 5.81; N 2.61.
Spiro[{1-(2'-hydroxy[1,1':3',1'']terphenyl-5'-
ylmethyl)-1,2,3,4-tetrahydro-1-azaphenanthrene}-
3,2'-(H-indan-1',3'-dione)] (VII). To a solution of 1.37 g
(0.005 mol) of paraformaldehyde in 20 ml of 1-butanol
was added a solution of 2.68 g (0.005 mol) of amine III
in 10 ml of 1-butanol and a solution of 0.73 g (0.005 mol)
of indandione VI in 10 ml of 1-butanol. The reaction
mixture was boiled for 4 h. On cooling the reaction
mixture the separated crystalline precipitate was filtered
off and three times washed with hot acetone. Yield 5.2 g
(91%), colorless crystals, mp 227°C. IR spectrum, ν,
cm–1: 3450 (O–H), 1724 (C=O), 1695 (C=O). 1H NMR
spectrum (DMSO-d6), δ, ppm: 3.40 s (2H, CH2), 3.80 d
(2H, NCH2, J 13 Hz), 4.60 d (2H, NCH2CHAr, J 11 Hz),
7.20–7.25 m (6Harom; 1H, OH), 7.35 t (3Harom, J 7.5 Hz),
7.40–7.45 t (5Harom, J 7.6 Hz), 7.60 d (4Harom, J 7.5 Hz),
7.65 d (1Harom, J 7.5 Hz), 7.90 d (1Harom, J 7.6 Hz). Found,
%: C 84.06; H 5.18; N 2.42. C40H29NO3. Calculated, %:
C 84.04; H 5.11; N 2.45.
Compounds Vb–Vd were similarly prepared.
Spiro[{1-(2'-hydroxy[1,1':3',1"]terphenyl-5'-
ylmethyl)-1,2,3,4-tetrahydro-1-azaphenanthrene}-
3,1'-(4',4'-dimethyl-2',6'-dioxocyclohexane)] (Vb) was
obtained from amine III and dimedone (IVb). Yield 5.2 g
(92%), colorless crystals, mp 229°C. IR spectrum, ν,
cm–1: 3445 (O–H), 1724 (C=O), 1695 (C=O). 1H NMR
spectrum (CD3COCD3), δ, ppm: 1.05 s (3H, CH3), 1.20 s
(3H, CH3), 2.50 m (2H, CH2), 3.25 m (2H, CH2), 3.40 s
(2H, CH2), 3.80 d (2H, NCH2, J 13 Hz), 4.60 d (2H,
NCH2Ar, J 11 Hz), 7.20–7.25 m (4Harom, 1H, OH), 7.35 t
(3Harom, J 7.5 Hz), 7.40–7.45 t (5Harom, J 7.6 Hz), 7.60
d (4Harom, J 7.5 Hz), 7.65 d (1Harom, J 7.5 Hz), 7.90 d
(1Harom, J 7.6 Hz). Found, %: C 82.75; H 6.26; N 2.46.
C39H35NO3. Calculated, %: C 82.80; H 6.24; N 2.48.
Spiro[{1-(2'-hydroxy[1,1':3',1'']terphenyl-5'-
ylmethyl)-1,2,3,4-tetrahydro-1-azaphenanthrene}-
3,1'-(4',4'-dimethyl-3'-methoxycarbonyl-2',6'-dioxo-
cyclohexane)] (Vc) was obtained from amine III and
methyl 2,2-dimethyl-4,6-dioxocyclohexanecarboxylate
(IVc). Yield 5.3 g (85%), Grey crystals, mp 219°C.
IR spectrum, ν, cm–1: 3450 (O–H), 1724 (C=O), 1705
(C=O), 1695 (C=O), 1233 (C–O–C). 1H NMR spectrum
(CDCl3), δ, ppm: 0.90 s (3H, CH3), 0.98 s (3H, CH3),
1.05 s (3H, CH3), 1.20 s (3H, CH3), 2.40 s (1H, CH2),
2.45 s (1H, CH2), 3.20 m (4H, CH2), 3/30 s (3H, CH3),
3,35 s (3H, CH3), 3.45 m (4H, CH2), 3.85 m (4H, NCH2),
4.64 m (4H, NCH2Ar), 7.20–7.25 m (8Harom; 1H, OH),
7.35 m (6Harom), 7.40–7.45 m (10Harom), 7.60 m (8Harom),
7.65 m (2Harom), 7.90 m (2Harom). Found, %: C 78.91;
H 5.94; N 2.22. C41H37NO5. Calculated, %: C 78.95;
H 5.98; N 2.25.
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3,3'-{2',4'(1'H,5'H)-dioxofuran}] (Vd) was obtained
from amine III and furan-2,4(3H,5H)-dione (IVd). Yield
4.9 g (93%), colorless crystals, mp 230°C. IR spectrum, ν,
cm–1: 3450 (O–H), 1780 (C=O), 1720 (C=O), 1265 (C–
O–C). 1H NMR spectrum (CD3COCD3 and DMSO-d6),
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RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 46 No. 9 2010