Reaction of 2'-hydroxy-1,1': 3'1"-terphenyl-5'-carbaldehyde with naphthalen-1-amine, quinolin-8-amine, and 1,3-diketones

Article abstract of DOI:10.1134/S1070428009100133

Condensation of 2'-hydroxy-1,1': 3',1"-terphenyl-5'-carbaldehyde with naphthalen-1-amine and cyclohexane-1,3-dione, methyl 2,2-dimethyl-4,6- dioxocyclohexane-1-carboxylate, or dimedone gave the corresponding 7-(2'-hydroxy-1,1': 3',1"-terphenyl-5'-yl)-7,8,

Full text of DOI:10.1134/S1070428009100133

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2009, Vol. 45, No. 10, pp. 1503–1508. © Pleiades Publishing, Ltd., 2009.
Original Russian Text © A.L. Kurlovich, V.A. Tarasevich, N.G. Kozlov, 2009, published in Zhurnal Organicheskoi Khimii, 2009, Vol. 45, No. 10,
pp. 1519–1524.
Reaction of 2′-Hydroxy-1,1′:3′,1″-terphenyl-5′-carbaldehyde
with Naphthalen-1-amine, Quinolin-8-amine, and 1,3-Diketones
A. L. Kurlovicha, V. A. Tarasevicha, and N. G. Kozlovb
a Institute of New Materials Chemistry, National Academy of Sciences of Belarus,
ul. F. Skariny 36, Minsk, 220141 Belarus
e-mail: kurlovich_andrey@mail.ru
b Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus,
ul. Surganova 13, Minsk, 220072 Belarus
Received October 28, 2008
Abstract—Condensation of 2′-hydroxy-1,1′:3′,1″-terphenyl-5′-carbaldehyde with naphthalen-1-amine and
cyclohexane-1,3-dione, methyl 2,2-dimethyl-4,6-dioxocyclohexane-1-carboxylate, or dimedone gave the corre-
sponding 7-(2′-hydroxy-1,1′:3′,1″-terphenyl-5′-yl)-7,8,9,10,11,12-hexahydro-12H-benzo[c]acridin-8-ones. The
reaction of 2′-hydroxy-1,1′:3′,1″-terphenyl-5′-carbaldehyde with naphthalen-1-amine and indan-1,3-dione
produced 7-(2′-hydroxy-1,1′:3′,1″-terphenyl-5′-yl)-8H-benzo[h]indeno[1,2-b]quinolin-8-one. 7-(2′-Hydroxy-
1,1′:3′,1″-terphenyl-5′-yl)-7,8,9,10,11,12-hexahydrobenzo[b][1,10]phenanthrolin-8-ones were obtained by
three-component condensation of 2′-hydroxy-1,1′:3′,1″-terphenyl-5′-carbaldehyde with quinolin-8-amine and
cyclohexane-1,3-dione, methyl 2,2-dimethyl-4,6-dioxocyclohexane-1-carboxylate, or dimedone.
DOI: 10.1134/S1070428009100133
We previously studied three-component condensa-
tions of naphthalen-1-amine with 1,3-diketones and
mono- and disubstituted benzaldehydes [1–3]. In the
present work we selected as aldehyde component a tri-
substituted benzaldehyde, 2′-hydroxy-1,1′:3′,1″-ter-
phenyl-5′-carbaldehyde (I). Derivatives of aldehyde I
are used as dyes, medical agents, insecticides, and
stabilizers for polymeric materials [4–6]. Compound I
was synthesized in quantitative yield according to the
procedure described in [7]. We examined reactions of
aldehyde I with naphthalen-1-amine (IIa) and quino-
lin-8-amine (IIb) and a series of 1,3-diketones: cyclo-
hexane-1,3-dione (IIIa), 5,5-dimethylcyclohexan-1,3-
dione (IIIb, dimedone), methyl 2,2-dimethyl-4,6-di-
oxocyclohexane-1-carboxylate (IIIc), and indan-1,3-
dione (IV). The reactions were carried out by heating
equimolar amounts of the reactants in boiling ethanol.
VIc. In this case, the condensation involves interme-
diate formation of amino ketone A which undergoes
rearrangement to intermediate B according to the
scheme proposed in [9]; dehydration of B yields com-
pounds VIa–VIc (Scheme 1). Likewise, the reaction of
quinolin-8-amine (IIb) with aldehyde I and subsequent
addition of diketone IIIa–IIIc selectively afforded
7,8,9,10,11,12-hexahydrobenzo[b][1,10]phenanthrolin-
8-ones VId–VIf. Analogous compounds were obtained
by condensation of Schiff base V (isolated from the
reaction mixture) with diketones IIIa–IIIc on heating
in a polar solvent under reflux.
The three-component condensation with an unsym-
metrical β-diketone, methyl 2,2-dimethyl-4,6-dioxo-
cyclohexane-1-carboxylate gave rise to mixtures of
stereoisomeric products VIc and VIf. The reaction un-
der relatively mild conditions (e.g., in boiling ethanol)
was completely regioselective and highly stereoselec-
tive: the only products were the corresponding 9-me-
thoxycarbonyl derivatives, and sterically and thermo-
dynamically more favorable 7,9-trans isomer prevailed
(the trans–cis isomer ratio was ~2:1).
As we showed in [8], the direction of this reaction
is determined by the order of mixing of the reactants.
If an amine is mixed initially with diketone, the only
product is the corresponding enamine which (after
isolation as individual substance) does not react with
aldehyde I. Mixing of amine IIa with aldehyde I,
followed by addition of diketone IIIa–IIIc, leads to
selective formation of benzo[c]acridin-8-ones VIa–
The reaction of aldehyde I with amine IIa and
indan-1,3-dione (IV) was carried out by heating equi-
molar amounts of the reactants in boiling butan-1-ol.
1503

KURLOVICH et al.
Scheme 1.
NH2
1504
Ph
Ph
N
HO
Ph
X
X
OH
+
Ph
CHO
I
IIa, IIb
Va, Vb
R1
R1
R1
R1
R1
R1
R2
R2
R2
O
H2N
O
O
O
O
O
IIIa–IIIc
Ph
Ph
HN
X
X
OH
Ph
OH
Ph
A
B
R1
R1
R2
Me
Me
Me
Me
10
7
11
9
COOMe
O
COOMe
O
12
HN
8
O
1X
Ph
HN
HN
2
X
X
R
R
3
6
OH
4
5
Ph
VIc, VIf
VIa–VIf
II, V, X = CH (a), N (b); III, R1 = R2 = H (a), R1 = Me, R2 = H (b), R1 = Me, R2 = MeOCO (c); VI, X = CH (a–c), N (d–f),
R1 = R2 = H (a, d), R1 = Me, R2 = H (b, e), R1 = Me, R2 = MeOCO (c, f); VIc, VIf, R = 3,5-Ph2-4-HOC6H2.
Taking into account our previous data [10], the
from indandione IV and aldehyde I gave the same
product VIII. However, we failed to obtain the corre-
sponding condensation product from aldehyde I, in-
dan-1,3-dione (IV), and quinolin-8-amine (IIb) under
the same conditions as with amine IIa.
reaction involves intermediate formation of amino
ketone C which undergoes intramolecular cyclization
to compound VII through elimination of water, and
oxidation of VII with atmospheric oxygen yields final
7-(2′-hydroxy-1,1′:3′,1″-terphenyl-5′-yl)-8H-benzo[h]-
indeno[1,2-b]quinolin-8-one (VIII) (Scheme 2). The
use of butan-1-ol as solvent allowed us to avoid isola-
tion and dehydrogenation of compound VII, as was
reported previously for the condensation of amine IIa
with substituted benzaldehydes and indan-1,3-dione
(IV) in ethanol [11].
The structure of compounds Va, Vb, VIa–VIf, and
VII–IX was confirmed by their elemental analyses and
1H NMR and IR spectra. Compounds VIa–VIf charac-
teristically showed in the IR spectra absorption bands
due to stretching vibrations of the NH group (3266–
3258 cm–1, δNH 1609–1610 cm–1) and conjugated
ketone carbonyl group (1650–1630 cm–1). The IR
spectra of Schiff bases Va and Vb contained an ab-
sorption band at 1676 cm–1 due to stretching vibrations
of the azomethine N=C bond. Stretching vibrations of
aliphatic and aromatic C–H bonds in compounds VIa–
VIf gave rise to absorption in the regions 2959–
2933 and 3229–3024 cm–1, respectively. Compound IX
displayed in the IR spectrum a strong absorption band
By special experiment we showed that the conden-
sation of amine IIa with aldehyde I and diketone IV
involves intermediate formation of 2-(2′-hydroxy-
1,1′:3′,1″-terphenyl-5′-ylmethylidene)indan-1,3-dione
(IX). Therefore, compound VIII can be formed by re-
action of IX with amine IIa. In fact, the condensation
of amine IIa with dione IX preliminarily synthesized
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 45 No. 10 2009

REACTION OF 2′-HYDROXY-1,1′:3′,1″-TERPHENYL-5′-CARBALDEHYDE
1505
Scheme 2.
Ph
Ph
O
O
HO
Ph
HO
Ph
+
CHO
O
O
I
IV
IX
OH
Ph
O
Ph
O
HN
IIa
NH2
Ph
OH
O
Ph
C
VII
O
N
Ph
OH
Ph
VIII
at 1567 cm–1, which was assigned to stretching vibra-
tions of carbonyl groups conjugated with the aromatic
ring. The corresponding absorption band in the spec-
trum of VIII had a medium intensity and was located
at 1561 cm–1. A medium-intensity band was present in
the region 3537–3311 cm–1 in the IR spectra of Va,
Vb, VIa–VIf, and VII–IX; this band belongs to
stretching vibrations of the hydroxy group in the ter-
phenyl substituent.
spectra of VIa–VIc is determined by shielding effect
exerted by the bulky aryl substituent. The signal from
the CH proton (12-H) in the dihydropyridine fragment
of compounds VIa–VIf also appears in a weaker field
(δ 5.80–5.85 ppm) relative to the corresponding signals
of cyclic compounds due to magnetically anisotropic
effect of the neighboring aromatic ring having three
substituents. The NH signal appeared in the spectra of
heterocycles VIa–VIf as a singlet at δ 9.35–9.30 ppm,
i.e., in the region typical of NH proton in acridinone
derivatives [1].
1
The H NMR spectra of compounds VIa–VIf
and VII–IX were very consistent with the assumed
structures.
The major stereoisomers of compounds VIc and
VIf were assigned 7,9-trans configuration, taking into
account downfield position of the 9-H signal in their
1H NMR spectra (δ 3.50 ppm). This indicates that the
9-H proton is located in the area of deshielding by the
aromatic ring. The corresponding signal of the minor
7,9-cis isomer is observed in a considerably stronger
field (δ 3.04 ppm), for the 9-H proton appears above or
below the aromatic ring plane (shielding area).
Compounds VIa–VIc were assigned the structure
of benzoacridinone derivatives rather than benzophen-
anthridinones, whose formation from Schiff bases of
the naphthalene series and 1,3-diketones was presumed
in [12], on the basis of chemical shifts of protons on
the C1, C12, and N atoms. The chemical shift of 1-H in
acridinones VIa–VIc is equal to 8.05–8.10 ppm; the
corresponding proton in compounds of the phenanthri-
dine series resonates in a weaker field, at δ 8.80 ppm
1
In the H NMR spectrum of indandione IX, proton
at the C=CH bond conjugated with two carbonyl
1
[13]. The position of the 1-H signal in the H NMR
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 45 No. 10 2009

KURLOVICH et al.
1506
groups is characterized by the largest chemical shift
(apart from the OH proton); it resonates as a singlet at
δ 8.50 ppm, which is typical of structurally related
compounds [14].
15 min under reflux, 1.12 g (0.01 mol) of cyclohexane-
1,3-dione (IIIa) was added, and the mixture was
heated for 5 h under reflux. After cooling, the precip-
itate was filtered off, washed with ethanol, and recrys-
tallized from benzene. Yield 4.26 g (86%), yellow
crystals, mp 317°C. IR spectrum, ν, cm–1: 3550, 3264,
3093, 2954, 1650, 1609, 1552, 1518, 1481, 1420,
1395, 1341, 1277, 1234, 1185, 1157, 1106, 1049, 968,
EXPERIMENTAL
The IR spectra were recorded in KBr on a Specord
1
1
75IR spectrometer. The H NMR spectra were
818, 774, 762, 701, 637, 598. H NMR spectrum
(DMSO-d6), δ, ppm: 1.85–2.05 m (2H, CH2), 2.20–
2.35 m (2H, CH2), 2.60–2.70 m (2H, CH2), 5.25 s (1H,
measured on Tesla BS-567A (100 MHz) and Bruker
Avance-500 (500 MHz) instruments; the chemical
shifts were determined relative to tetramethylsilane as
internal reference.
CH), 7.02 s (2H, Harom), 7.20–7.45 m (14H, Harom
,
OH), 7.65 d (1H, Harom), 7.74 d (1H, Harom), 8.05 d
(1H, Harom), 9.35 s (1H, NH). Found, %: C 85.21;
H 5.48; N 2.82. C35H27NO2. Calculated, %: C 85.17;
H 5.51; N 2.86
2′-Hydroxy-1,1′:3′,1″-terphenyl-5′-carbaldehyde
(I) was synthesized according to the procedure
described in [7]. A mixture of 12.5 g (0.051 mol) of
1,1′:3′,1″-terphenyl-2′-ol, 14.2 g (0.101 mol) of uro-
tropin, and 50 ml of trifluoroacetic acid was stirred for
12 h at 85–95°C. The solvent was distilled off, 150 ml
of 3 N hydrochloric acid was added to the residue, and
the mixture was stirred for 3 h at 80°C. The precipitate
was filtered off, washed with water, recrystallized from
ethanol, and dried. Yield 13.2 g (95%), colorless crys-
tals, mp 168–169°C. IR spectrum, ν, cm–1: 3530, 3350,
3070, 2850, 1680, 1600, 1500, 1483, 1460, 1399,
1330, 1240, 1175, 1142, 1050, 905, 800, 760, 710, 630,
Compounds VIb and VIc were synthesized in
a similar way.
7-(2′-Hydroxy-1,1′:3′,1″-terphenyl-5′-yl)-10,10-
dimethyl-7,8,9,10,11,12-hexahydrobenzo[c]acridin-
8-one (VIb) was synthesized from aldehyde I, amine
IIa, and 5,5-dimethylcyclohexane-1,3-dione (IIIb).
Yield 4.00 g (76%), colorless crystals, mp 312°C. IR
spectrum, ν, cm–1: 3540, 3450, 3270, 2952, 1651,
1610, 1502, 1494, 1467, 1422, 1390, 1349, 1318,
1270, 1226, 1150, 1125, 1060, 1030, 960, 890, 800,
1
590. H NMR spectrum (CDCl3), δ, ppm: 7.46 d (4H,
1
770, 748, 703, 698, 632, 597, 586. H NMR spectrum
Harom), 7.50–7.55 t (6H, Harom), 7.60 d (4H, Harom), 7.84 s
(DMSO-d6), δ, ppm: 1.08 s and 1.10 s (3H each, CH3),
2.10–2.13 m (2H, CH2), 2.15–2.20 m (2H, CH2), 5.45 s
(2H, Harom), 9.94 s (1H, CHO). Found, %: C 83.17;
H 5.17. C19H14O2. Calculated, %: C 83.19; H 5.14.
(1H, CH), 7.10 s (2H, Harom), 7.20–7.49 m (14H, Harom
,
5′-(Naphthalen-2-yliminomethyl)-1,1′:3′,1″-ter-
phenyl-2′-ol (Va). A solution of 2.74 g (0.01 mol) of
aldehyde I in 10 ml of butan-1-ol was added to a solu-
tion of 1.43 g (0.01 mol) of naphthalen-1-amine (IIa)
in 20 ml of ethanol, and the mixture was heated for
15 min under reflux. The mixture was cooled, and the
precipitate was filtered off and recrystallized from
ethanol. Yield 2.95 g (85%), yellow crystals, mp 138–
139°C. IR spectrum, ν, cm–1: 3311, 3056, 2916, 2847,
1676, 1583, 1462, 1427, 1321, 1228, 1163, 1116, 1026,
OH), 7.70 d (1H, Harom), 7.78 d (1H, Harom), 8.10 d
(1H, Harom), 9.30 s (1H, NH). Found, %: C 85.18;
H 5.96; N 2.71. C37H31NO2. Calculated, %: C 85.19;
H 5.99; N 2.69.
Methyl 7-(2′-hydroxy-1,1′:3′,1″-terphenyl-5′-
yl)-10,10-dimethyl-8-oxo-7,8,9,10,11,12-hexahydro-
benzo[c]acridine-9-carboxylate (VIc) was synthe-
sized from aldehyde I, amine IIa, and methyl 2,2-di-
methyl-4,6-dioxocyclohexane-1-carboxylate (IIIc).
Yield 4.6 g (80%), grey crystals, mp 320°C. IR spec-
trum, ν, cm–1: 3550, 3450, 3320, 3060, 2960, 1740,
1610, 1520, 1500, 1470, 1440, 1400, 1340, 1260,
1230, 1170, 1150, 1040, 900, 810, 780, 750, 710, 620.
1H NMR spectrum (DMSO-d6), δ, ppm: 1.08 d (6H,
CH3), 1.10 d (6H, CH3), 1.27 s (6H, CH3), 2.10–
2.13 m (4H, CH2), 2.15–2.20 m (4H, CH2), 5.45 s (1H,
CH), 5.50 s (1H, CH), 7.13 s (4H, Harom), 7.20–7.49 m
(28H, Harom, OH), 7.72 m (4H, Harom), 8.10 m (2H,
Harom), 9.30 s (2H, NH). Found, %: C 80.9; H 5.86;
1
892, 784, 748, 699, 578, 504. H NMR spectrum, δ,
ppm: 7.20–7.50 m (10H, Harom), 7.59–7.90 m (10H,
Harom, OH), 8.50 s (1H, CH). Found, %: C 87.20;
H 5.23; N 3.52. C29H21NO. Calculated, %: C 87.22;
H 5.26; N 3.51.
7-(2′-Hydroxy-1,1′:3′,1″-terphenyl-5′-yl)-
7,8,9,10,11,12-hexahydrobenzo[c]acridin-8-one
(VIa). Aldehyde I, 2.74 g (0.01 mol), was added to
a solution of 1.43 g (0.01 mol) of naphthalen-1-amine
(IIa) in 50 ml of ethanol, the mixture was heated for
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 45 No. 10 2009

REACTION OF 2′-HYDROXY-1,1′:3′,1″-TERPHENYL-5′-CARBALDEHYDE
1507
N 2.51. C39H33NO4. Calculated, %: C 80.81; H 5.74;
N 2.42.
1340, 1265, 1230, 1170, 1150, 1040, 905, 810, 780,
750, 715, 620. 1H NMR spectrum (DMSO-d6), δ, ppm:
1.08 d (6H, CH3), 1.10 d (6H, CH3), 1.27 s (6H, CH3),
2.10–2.13 m (4H, CH2), 2.15–2.20 m (4H, CH2), 5.45 s
(1H, CH), 5.50 s (1H, CH), 7.13 s (4H, Harom), 7.20–
7.49 m (26H, Harom, OH), 7.72 m (4H, Harom), 8.10 m
(2H, Harom), 9.30 s (2H, NH). Found, %: C 78.9;
H 5.56; N 4.81. C38H32N2O4. Calculated, %: C 78.60;
H 5.55; N 4.82.
7-(2′-Hydroxy-1,1′:3′,1″-terphenyl-5″-yl)-
7,8,9,10,11,12-hexahydrobenzo[b][1,10]phenan-
throlin-8-one (VId). Aldehyde I, 2.74 g (0.01 mol),
was added to a solution of 1.43 g (0.01 mol) of quino-
lin-8-amine (IIb) in 50 ml of ethanol, the mixture was
heated for 15 min under reflux, 1.12 g (0.01 mol) of
cyclohexane-1,3-dione (IIIa) was added, and the mix-
ture was heated for 5 h under reflux. After cooling, the
precipitate was filtered off, washed with ethanol, and
recrystallized from benzene. Yield 4.1 g (81%), light
brown crystals, mp 304°C. IR spectrum, ν, cm–1: 3552,
3260, 3090, 2964, 1650, 1609, 1562, 1520, 1491,
1420, 1395, 1341, 1278, 1234, 1186, 1157, 1106, 1059,
7-(2′-Hydroxy-1,1′:3′,1″-terphenyl-5′-yl)-7,13-
dihydro-8H-benzo[h]indeno[1,2-b]quinolin-8-one
(VII). Aldehyde I, 2.74 g (0.01 mol), was added to
a solution of 1.43 g (0.01 mol) of naphthalen-1-amine
(IIa) in 50 ml of ethanol, the mixture was heated for
15 min under reflux, 1.46 g (0.01 mol) of cyclohexane-
1,3-dione (IIIa) was added, and the mixture was
heated for 1 h under reflux. Yield 4.68 g (89%), green–
yellow crystals, mp 287°C. IR spectrum, ν, cm–1: 3385,
3070, 2920, 1675, 1561, 1468, 1414, 1320, 1220, 1190,
1184, 1151, 1091, 991, 735, 699. 1H NMR spectrum, δ,
ppm: 7.40–7.70 m (16H, Harom, OH), 7.75–7.95 m (4H,
1
978, 818, 775, 762, 701, 637, 598. H NMR spectrum
(DMSO-d6), δ, ppm: 1.85–2.05 m (2H, CH2), 2.20–
2.40 m (2H, CH2), 2.65–2.70 m (2H, CH2), 5.25 s (1H,
CH), 7.02 s (2H, Harom), 7.20–7.45 m (13H, Harom
,
OH), 7.65 d (1H, Harom), 7.70 d (1H, Harom), 8.00 d
(1H, Harom), 9.50 s (1H, NH). Found, %: C 82.50;
H 5.42; N 5.59. C34H26N2O2. Calculated, %: C 82.57;
H 5.30; N 5.66.
H
arom), 8.20 d (1H, Harom), 8.50 s (2H, Harom), 9.30 s
(1H, NH). Found, %: C 86.52; H 4.76; N 2.63.
C38H23NO2. Calculated, %: C 86.50; H 4.78; N 2.65.
Compounds VIe and VIf were synthesized in
7-(2′-Hydroxy-1,1′:3′,1″-terphenyl-5′-yl)-8H-
benzo[h]indeno[1,2-b]quinolin-8-one (VIII). Solu-
tions of 1.43 g (0.01 mol) of amine IIa in 10 ml of
butan-1-ol and of 1.46 g (0.01 mol) of indan-1,3-dione
(IV) in 10 ml of butan-1-ol were added to a solution of
2.74 g (0.01 mol) of terphenylcarbaldehyde I in 20 ml
of butan-1-ol, and the mixture was heated for 4 h under
reflux. The mixture was cooled, and the precipitate
was filtered off and washed with three portions of hot
acetone. Yield 4.5 g (85%), yellow crystals, mp 300°C.
IR spectrum, ν, cm–1: 3383, 3076, 2917, 1679, 1561,
1468, 1417, 1320, 1221, 1195, 1184, 1151, 1091, 991,
a similar way.
7-(2′-Hydroxy-1,1′:3′,1″-terphenyl-5′-yl)-10,10-
dimethyl-7,8,9,10,11,12-hexahydrobenzo[b][1,10]-
phenanthrolin-8-one (VIe) was synthesized from al-
dehyde I, quinolin-8-amine (IIb), and 5,5-dimethyl-
cyclohexane-1,3-dione (IIIb). Yield 4.50 g (70%),
colorless crystals, mp 310°C. IR spectrum, ν, cm–1:
3539, 3451, 3265, 2951, 1652, 169, 1513, 1491, 1477,
1432, 1391, 1349, 1318, 1270, 1227, 1150, 1125, 1050,
1029, 959, 891, 798, 770, 749, 703, 699, 632, 597,
1
586. H NMR spectrum (DMSO-d6), δ, ppm: 1.08 s
1
(3H, CH3), 1.10 s (3H, CH3), 2.10–2.13 m (2H, CH2),
2.15–2.20 m (2H, CH2), 5.5 s (1H, CH), 7.12 s (2H,
Harom), 7.20–7.50 m (13H, Harom, OH), 7.75 d (1H,
Harom), 7.80 d (1H, Harom), 8.10 d (1H, Harom), 9.30 s
(1H, NH). Found, %: C 82.68; H 5.76; N 5.41.
C36H30N2O2. Calculated, %: C 82.73; H 5.79; N 5.36.
735, 699. H NMR spectrum, δ, ppm: 7.40–7.70 m
(15H, Harom), 7.75–7.95 m (4H, Harom), 8.20 d (1H,
Harom), 8.50 s (2H, Harom), 9.48 br.s (1H, OH). Found,
%: C 86.84; H 4.40; N 2.63. C38H23NO2. Calculated,
%: C 86.86; H 4.38; N 2.66.
2-(2′-Hydroxy-1,1′:3′,1″-terphenyl-5′-ylmethyli-
dene)indan-1,3-dione (IX). A solution of 2.74 g
(0.01 mol) of aldehyde I and 1.46 g (0.01 mol) of in-
dandione IV in 30 ml of butan-1-ol was heated for
30 min under reflux. The precipitate was filtered off,
washed with diethyl ether, and recrystallized from ace-
tone. Yield 2.80 g (70%), yellow crystals, mp 246°C.
IR spectrum, ν, cm–1: 3460, 2923, 1681, 1567, 1468,
1418, 1326, 1282, 1219, 1193, 1153, 1086, 995, 960,
Methyl 7-(2′-hydroxy-1,1′:3′,1″-terphenyl-5′-
yl)-10,10-dimethyl-8-oxo-7,8,9,10,11,12-hexahydro-
benzo[b][1,10]phenanthroline-9-carboxylate (VIf)
was synthesized from aldehyde I, amine IIb, and
methyl 2,2-dimethyl-4,6-dioxocyclohexane-1-car-
boxylate (IIIc). Yield 4.23 g (73%), grey crystals,
mp 315°C. IR spectrum, ν, cm–1: 3550, 3450, 3320,
3060, 2960, 1745, 1613, 1525, 1499, 1470, 1450, 1400,
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 45 No. 10 2009

KURLOVICH et al.
1508
926, 880, 779, 733, 704, 691, 601, 526. 1H NMR spec-
trum, δ, ppm: 7.35–7.45 m (3H, Harom), 7.47–7.50 m
(6H, Harom) 7.60–7.68 m (2H, Harom), 7.80–7.96 m (5H,
7. Shiraishi, T., Kameyama, K., Imai, N., Domoto, T.,
Katsumi, I., and Watanabe, K., Chem. Pharm. Bull.,
1988, vol. 36, p. 974.
8. Kozlov, N.G., Tarasevich, V.A., Vasilevskii, D.A., and
Basalaeva, L.I., Russ. J. Org. Chem., 2006, vol. 42,
p. 107.
H
arom), 8.50 s (1H, CH), 9.25 br.s (1H, OH). Found,
%: C 83.60; H 4.49. C28H18O3. Calculated, %: C 83.58;
H 4.48.
9. Cortes, E., Martinez, R., Avila, J.G., and Toscano, R.A.,
J. Heterocycl. Chem., 1988, vol. 25, p. 895.
10. Kozlov, N.G. and Gusak, K.N., Russ. J. Org. Chem.,
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