Synthesis of photoactive polyfunctional molecules based on 1-aryloxyanthraquinone aminoderivatives

Article abstract of DOI:10.1134/S1070428006110145

By alternating stages of condensation of 1-(4-tert-butylphenoxy)-2-amino-9, 10-anthraquinone with 5-nitroisophthaloyl dichloride, cyanuric chloride, and 4-aminobenzocrown ethers with stages of catalytic reduction of nitro group photoactive polyfunctional

Full text of DOI:10.1134/S1070428006110145

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2006, Vol. 42, No. 11, pp. 1690−1695.  Pleiades Publishing, Inc. 2006.
Original Russian Text  L.S. Klimenko, S.Z. Kusov, V.M. Vlasov, 2006, published in Zhurnal Organicheskoi Khimii, 2006, Vol. 42, No. 11,
pp. 1702−1707.
Synthesis of Photoactive Polyfunctional Molecules Based
on 1-AryloxyanthraquinoneAminoderivatives
L. S. Klimenkoa,b, S. Z. Kusova, and V. M. Vlasova
aVorozhtsov Novosibirsk Institute of Organic Chemisty,
Siberian Division, Russian Academy of Sciences, Novosibirsk, 630090 Russia
e-mail: vmvlasov@nioch.nsc.ru
bYugorskii State University, Khanty-Mansiisk, Russia
Received August 8, 2005
Abstract—By alternating stages of condensation of 1-(4-tert-butylphenoxy)-2-amino-9,10-anthraquinone with
5-nitroisophthaloyl dichloride, cyanuric chloride, and 4-aminobenzocrown ethers with stages of catalytic reduction
of nitro group photoactive polyfunctional compounds were prepared containing both several photoactive groups
and complex-forming crown ether moieties.
DOI: 10.1134/S1070428006110145
Recently a considerable interest grew in the chemistry
of dendrimeric molecules resulting from a discovery of
new specific features inherent to the dendrimeric
architecture of highly efficient catalysts, pharmaceuticals,
and polymeric materials [1–5]. Every year increases the
number of various dendrimers synthesized, but only single
instances are known of preparation of photoactive
dendrimeric molecules. For instance, certain examples
exist of incorporation of photosensitive azobenzene
fragments into macrocyclic, catenane, and dendrite
structures [6–9]. A unique feature of these compounds is
first of all their capability to light-induced reversible
structural transformations, molecular photo-switching
arrangement, that can significantly extend their
applicability, e.g., in materials for molecular electronic
devices, for recording and storage of optical information.
dendrimeric molecules we chose the convergent one
involving a primary synthesis of the dendrimer branches,
dendrones, followed by their linking to the stem of the
dendrimer. The target of this study was a development
of synthetic methods for previously unknown photo-
sensitive polyfunctional molecules including two or more
fragments of the photochromic 1-arloxy-9,10-anthra-
quinone aminoderivative which could serve as dendrones
in building up photoactive dendrimers.
In the framework of this approach condensations were
carried out of 1-(4-tert-butylphenoxy)-2-amino-9,10-
anthraquinone (I) with 5-nitroisophtaloyl dichloride (II),
cyanuric chloride, and 4-aminobenzocrown ether. The
latter was brought into the condensation to endow the
molecule with complexing properties. It should be noted
that the use of compound I with a tert-butyl substituent
in the aryloxy group improves the solubility of compounds
obtained in organic solvents.
The most promising procedure in designing photoactive
dendrimers is application of photochromic substances as
building blocks. The photochromic properties of 1-aryloxy-
and 1-acyloxy-9,10-anthraquinones are fairly well
documented [10]. Different derivatives of 1-aryloxy- and
1-acyloxy-9,10-anthraquinones were shown to suffer
under irradiation with light a reversible migration of aryl
and acyl groups to the peri-oxygen giving 9-aryloxy- and
9-acyloxy-1,10-anthraquinones accompanied with
significant spectral changes. We did not find any examples
of application at these derivatives to building dendrimeric
structures. From two possible procedures of building up
In the first stage reaction of compounds I and II gave
isophthalamide III in 85% yield. Then on catalytic
reduction with hydrazine hydrate amino derivative IV was
obtained in 60% yield .
In the third stage amine IV was acylated with acyl
dichloride II into compound V in 72% yield. Thus
isophthalamide V containing four photoactive centers was
prepared in three stages. To get more complex branched
molecules containing eight and more anthraquinone
1690

SYNTHESIS OF PHOTOACTIVE POLYFUNCTIONAL MOLECULES
1691
Scheme 1.
O
O
OAr
ClOC
RHNC
O
CNHR
NH2
COCl
RHNC
O
CNHR
O
[H]
O
NH2
IV
NO2
NO2
II
I
III
O
O
CNHR
CNHR
Bu-t
II
Bu-t
O
O
O
.
HNC
O
CNH
, Ar =
R =
O
CNHR
O
CNHR
O
NO2
V
Then by the pattern described above amino derivative
VIII was prepared whose acylation with dichloride II
led to the formation of polyfunctional molecule IX in 75%
yield (Scheme 2).
moieties the reduction and acylation stages can be
repeated (Scheme 1).
In the same manner photoactive polyfunctional
molecules with a crown ether fragment were prepared.
On mixed condensation of equimolar amounts of anthra-
quinone I and 4-aminobenzo-15-crown-5 (VI) with acyl
dichloride II isophthalamide VII was isolated in 67% yield.
By condensation of 1-aryloxy-2-amino-9,10-anthraqui-
none I with 2,4,6-trichloro-1,3,5-triazine (X) in phenol at
200°C was obtained in 76% yield photoactive triazine XI
(Scheme 3).
Scheme 2.
O
O
RHNC
O
CNHR'
O
RHNC
O
CNHR'
O
H2N
O
[H]
I + II +
O
O
NO2
NH2
VI
VII
VIII
O
O
CNHR
CNHR
Bu-t
, R' =
O
II
O
O
O
O
R =
HNC
CNH
O
O
O
O
R'HNC
CNHR'
O
O
O
NO2
IX
Scheme 3.
Bu-t
RHN
N
NHR
Cl
N
Cl
O
O
O
I +
.
R =
N
N
N
N
NHR
Cl
X
XI
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 42 No. 11 2006

KLIMENKO et al.
1692
formerly [10–12] that on irradiation the 1-aryloxy-2(4)-
The study of photochemical activity of synthesized
R-9,10-anthraquinones easily react with water and amines
yielding the corresponding hydroxy and amino derivatives.
For instance, on photolysis in the presence of alkyl- and
arylamines we isolated 1-hydroxy-2-(4)-R-9,10-anthra-
quinone 9-imines[12]. The ready formation of such com-
pounds on photolysis originated from the high reactivity
of the intermediate derivatives of 1,10-anthraquinone
(ana-quinone) with respect to nucleophilic agents.
macromolecular compounds III, V, IX, and XI containing
several fragments of 1-aryloxy-9,10-anthraquinone
showed that they are endowed with photochromic
qualities. Like in case of their monomeric analog, 1-(4-
tert-butylphenoxy)-2-(4-nitrobenzoylamino)-9,10-
anthraquinone (XII) [11], on irradiation of benzene
solutions of compounds obtained (λmax < 400 nm) in their
electron absorption spectrum gradually disappeared the
longwave absorption maximum of the initial compound
concurrently with the appearance of the absorption band
of photoproduct. Therewith the solution color changed
from light yellow to red-violet, and the maximum shift of
the longwave absorption band into the visible region
attained 180 nm. The photochemical isomerization of the
newly synthesized derivatives is reversible. On irradiation
with a longwave visible light (λmax > 500 nm) the
photoinduced form completely disappeared, and the
spectrum of the initial compound is recovered. The direct
and reverse photoisomerisation can be repeated many
times; thus synthesized macromolecular compounds III,
V, IX, and XI are typical photochromic substances. They
are characterized by high photo-sensitivity, good color
contrast, low rate of reverse dark reaction at room
temperature ensuring long dark storage of the photoform.
Interestingly, the quantum yield of the reverse
photorearrangement in these compounds reduced about
twice compared to compound XII.
The photolysis of a benzene solution containing a mix-
ture of isophthalamide III and p-toluidine resulted in
formation of diimine XIII in virtually quantitative yield
(Scheme 4). Chromatographic monitoring of the reaction
progress showed that in the first minutes of the process
formed two products, and then one of them disappeared.
Presumably we succeeded in observing the formation
of a product of monosubstitution of the aryloxy group in
compound III, suggesting that the photoisomerisantion in
the molecule with two photoactive centers was sequential.
For the sake of comparison we carried out the photo-
lysis of 1,4- and 1,5-di(4-tert-butylphenoxy)-9,10-
anthraquinones (XIV and XV) in the presence of p-tolui-
dine. These compounds also contain two aryl groups
capable of migration under irradiation, but unlike compound
III both groups are attached to the same anthraquinone
framework.
Presumably in compounds XIV and XV both groups
could take part in the sequential migration to give diimino
derivatives, but the corresponding experiments yielded
only the monosubstituted products: 1-hydroxy-4- and 5(4-
tert-butylphenoxy)-9,10-anthraquinone 9-imines (XVI and
XVII).
In the study of the photochemical activity of the
polyfunctional compounds obtained a reasonable problem
arises whether all the photoactive fragments of 1-aryloxy-
9,10-anthraquinone present take part in the photoinduced
isomerization, and also whether the process occurs by
stages. To clear the problem we carried out a photholysis
of compound III in the presence of an equiv amount
of p-toluidine. The reaction with amines was used as
a certain test on ana-quinoid structure formation in the
course of photomigration of aryl group. We showed
The reason of this difference is probably the presence
in compounds XVI and XVII of a chromophoric quinone
imine system that governs the position of the longwave
maximum in the electron absorption spectra (442 nm).
Therefore at further irradiation no redistribution of electron
Scheme 4.
Me
Me
NH2
Me
HO
N
O
N
O
OH
hv
III +
NHC
O
CNH
O
NO2
XIII
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 42 No. 11 2006

SYNTHESIS OF PHOTOACTIVE POLYFUNCTIONAL MOLECULES
1693
Scheme 5.
Me
O
OAr
R
N
O
OH
R
hv
hv
4-NH2C6H4Me
R'
O
R'
XVI, XVII
XIV, XV
XIV, XVI, R = OAr, R' = H; XV, XVII, R = H, R' =OAr;Ar = 4-t-BuC6H4.
combining the filters UFS-2 and ZhS-3. TLC analysis
was carried out on Silufol UV-254 plates, eluent a mixture
toluene–ethanol, 9:1. For column chromatograpy silica
gel was used (140–350 µm). The solvents were dried
before use.
density on quinone oxygens occurs that is required for
the migration of the second aryl group (cf. [13]). Whereas
the experiments with dendrones III, V, IX, and XI suggest
that the irradiation with light causes presumably a sequen-
tial isomerization in all photoactive centers present in the
molecule.
Initial compounds I, X, XI, XIV, and XV were
synthesized by a protocol from [14], compound II, by
procedure [15], VI, by [16].
Thus we have developed a convenient preparation
method for a wide range of photochromic dendrones
containing alongside the photoactive groups crown ether
fragments capable of complexing. Compounds obtained
can be used for designing photoactive dendrimers.
N,N'-Bis[1-(4-tert-butylphenoxy)-9,10-anthra-
quinone-2-yl]-5-nitroisophthalamide (III). A mixture
of 0.37 g (1 mmol) of compound I and 0.15 g (0.6 mmol)
of compound II was boiled in 20 ml of toluene for 30 min
(TLC monitoring). The reaction mixture was evaporated
to a volume of 3–4 ml, and ethyl ether was added. The
precipitate was filtered off, washed with ethyl ether, and
subjected to column chromatography on SiO2 (eluent
CHCl3).Yield 0.75 g (85%), mp 326–328°C. IR spectrum,
ν, cm–1: 3412 (N–H), 2963, 2928 (C–H), 1675 (C=O), 1590
(C=C). Electron absorption spectrum, λmax, nm (log ε):
EXPERIMENTAL
IR spectra were recorded on a spectrophotometer
Bruker Vector-22 from KBr pellets, electron absorption
spectra were taken on a spectrophotometer Hewlett-
PackardAgilent-8453 from ethanol solutions (10–4 mol/l).
1H NMR spectra were registered on a spectrometer
Βrukεr WP-200SY, internal reference SiMe4. Mass
spectra (electron impact) were measured on Finnigan
MAT-8200 instrument; the m/z values for molecular ion
[M]+ are presented. Mass spectrometric analysis of
compounds with a molecular mass >500 was carried out
using a liquid chromatograph with a mass-selective
detector Agilent (1100 Series LC/MSD). The samples
admission mode directly into the flow of liquid (FIA) was
used. The samples ionization was performed by electro-
static atomization (API-ES). The scanning of positive or
negative ions was performed in the range m/z 350–1500
at three values of voltage on the atomizer: 40, 70, and
100 V. Photolysis was carried out using DRSh-500 lamp
with a filter UFS-1 (280–400 nm), and also with the total
light of the mercury lamp. The desired spectral intervals
were separated by standard filters: UFS-2, ZhS-3, SS-5,
OS-11 (State Standard GOST 9411-66). The 313 nm line
was isolated from the spectrum of the mercury lamp
1
262 (4.71), 372 (3.98). H NMR spectrum (CDCl3), δ,
ppm: 1.23 s [18H, 2C(CH3)3], 6.91 d (4H, H2',6', J 9 Hz),
7.35 d (4H, H3',5', J 9 Hz), 7.75 m (4H, H6,7), 8.21 m (4H,
H5,8), 8.40 d (2H, H3, J 8.5 Hz), 8.51, 8.66, 8.90 br.s (3H,
C6H3), 9.05 d (2H, H4, J 8.5 Hz), 9.08 m (2H, NH).
Found, %: C 73.36; H 4.66; N 4.50. [M]+ 917.
C56H43N3O10. Calculated, %: C 73.28; H 4.69; N 4.58.
M 917.98.
5-Amino-N,N'-bis[1-(4-tert-butylphenoxy)-9,10-
anthraquinon-2-yl]isophthalamide (IV). To a mixture
of 0.92 g (1 mmol) of compound III and 0.02 g of moist
Pd/C in 50 ml of ethanol was added dropwise 2 ml of
hydrazine hydrate within 20 min. The mixture was boiled
for 1 h and on cooling was subjected to column
chromatography onAl2O3 (eluent CHCl3), separating the
main yellow zone. Eluate was evaporated, hexane was
added, the separated precipitate was filtered off, and
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 42 No. 11 2006

KLIMENKO et al.
1694
dried. Yield 0.53 g (60%), mp 271–274°C. IR spectrum,
in 30 ml of ethanol. Yield 0.30 g (75%), mp 198–202°C.
IR spectrum, ν, cm–1: 3470, 3415 (NH2), 2962, 2910 (C–
H), 1675 (C=O), 1587 (C=C). Electron absorption
spectrum, λmax, nm (lgε): 256 (4.37), 380 (3.82). Found,
%: C 69.53; H 5.51; N 5.35. C46H45N3O10. Calculated,
%: C 69.09; H 5.63; N 5.26.
ν, cm–1: 3425, 3375 (NH2), 2960, 2868 (C–H), 1674
(C=O), 1564 (C=O). Electron absorption spectrum, λmax
,
nm (log ε): 268 (4.84), 388 (4.07). Found [M]+ 887.
C56H45N3O8. Calculated M 887.99.
N,N'-Bis{N,N'-di[1-(4-tert-butylphenoxy)-9,10-
anthraquinon-2-yl]-5-isophthalamido}-5-nitro-
isophthalamide (V) was prepared similarly to compound
III from 0.45 g (0.5 mmol) of compound IV and 0.08 g
(0.3 mmol) of 5-nitroisophthaloyl dichloride. Yield 0.35 g
(72%), mp 308–312°C. IR spectrum,ν,cm–1: 3420 (N–
H), 2962, 2903 (C–H), 1676 (C=O), 1585 (C=O). Electron
absorption spectrum, λmax, nm(logε):266(5.28),378 (4.41).
Found, %: C 73.33; H 4.51; N 4.56. C120H91N7O20.
Calculated, %: C 73.88; H 4.67; N 5.03.
N,N'-Bis{N-[1-(4-tert-butylphenoxy)-9,10-
anthraquinone-2-yl]-N'-(2,3,5,6,8,9,11,12-
octahydrobenzo[b][1,4,7,10,13]pentaoxacyclo-
pentadecen-15-yl)-5-isophthalamido}-5-nitroiso-
phthalamide (IX) was prepared in the same way as
compound III from 0.40 g (0.5 mmol) of compound VIII,
and 0.08 g (0.3 mmol) of compound II.Yield 0.35 g (72%),
mp 238−241°C. IR spectrum, ν, cm–1: 3420 (N–H), 2960,
2930 (C–H), 1675 (C=O), 1585 (C=C). Electron
absorption spectrum, λmax, nm (log ε): 266 (4.83), 376
(4.09). Found, %: C 67.30; H 5.11; N 5.65. C100H89N7O24.
Calculated, %: C 67.76; H 5.03; N 5.53.
N-[1-(4-tert-butylphenoxy)-9,10-anthraquinon-2-
yl]-N'-(2,3,5,6,8,9,11,12-octahydrobenzo[b][1,4,7,
10,13]pentaoxacyclopentadecen-15-yl)-5-nitroiso-
phthalamide (VII). To a solution of 0.5 g (2.1 mmol) of
compound II in 20 ml of anhydrous benzene at 0°C was
added dropwise within 30 min at stirring a solution of
0.74 g (2 mmol) of compound I in 15 ml of benzene
containing several drops of pyridine (TLC monitoring).
The reaction mixture was kept at room temperature in
the dark for 5 h. Then 0.6 g (2.1 mmol) of 4-aminobenzo-
15-crown-5 in 15 ml of THF containing several drops of
pyridine was added, the mixture was heated at 40°C for
1 h. The reaction mixture was evaporated to a volume of
3–4 ml, and ethyl ether was added. The precipitate was
filtered off, washed with ethyl ether, and subjected to
column chromatography on SiO2 (eluent CHCl3). Yield
1.1 g (67%), mp 220–223°C. IR spectrum, ν, cm–1: 3421
(N–H), 3071, 2956, 2870 (C–H), 1673 (C=O), 1590
(C=C). Electron absorption spectrum, λmax, nm (log ε):
N,N',N''-Tri[1-(4-tert-butylphenoxy)-9,10-anthra-
quinon-2-yl]-2,4,6-amino-1,3,5-triazine (XI). A mix-
ture of 1.1 g (3 mmol) of compound I, 0.2 g (1 mmol) of
cyanuric chloride (X), and 5 g of phenol was heated at
stirring to 200°C for 40 min (TLC monitoring). The
reaction mixture was cooled, and 50 ml of 10% water
solution of KOH was added. The precipitate was filtered
off, washed with hot water, and dried. Then it was
subjected to column chromatography on Al2O3 (eluent
CHCl3), separating the main yellow zone. Eluate was
evaporated, hexane was added, the separated precipitate
was filtered off, and dried. Yield 0.91 g (76%), mp 236–
238°C. IR spectrum, ν, cm–1: 3406 (N–H), 2962 (C–H),
1676 (C=O), 1593 (C=C). Electron absorption spectrum
λ
max, nm (log ε): 255 (5.06), 395 (4.27). Found, %:
C 75.33; H 5.03; N 7.11. C75H60N6O9. Calculated, %:
C 75.76; H 5.05; N 7.07.
1
256 (4.38), 370 (3.80). H NMR spectrum (CDCl3), δ,
ppm: 1.23 s [9H, C(CH3)3], 3.79–4.08 m (16H,
OCH2CH2), 6.83 d (2H, H2',6', J 9 Hz), 6.97 d (1H, H6ê,
J 9 Hz), 7.21 d (2H, H3',5', J 9 Hz), 7.36 d.d (1H, H5ê, J1
9, J2 2 Hz), 7.47 d (1H, H3ê, J 2 Hz), 7.89 m (2H, H6,7),
8.13 m (2H, H5,8), 8.27 d (1H, H3, J 8.5 Hz), 8.41 d (2H,
H4, J 8.5 Hz), 8.51, 8.66, 8.89 br.s (3H, C6H3), 10.50,
10.65 br.s (2H, 2NH). Found [M]+ 829. C46H43N3O12.
Calculated M 829.87.
Synthesis of compounds XIII, XVI, and XVII. In
0.5 liter of anhydrous benzene was dissolved 1 mmol of
initial compound III, XIV, or XV, 2 mmol of p-toluidine
was added, and the reaction mixture was subjected to
the radiation of a mercury lamp SVD-120A for 3–4 h or
to the sunlight for 10–12 h. Photholysis was carried out
at 20–25°C till disappearance of the initial compound
(TLC monitoring). The solvent was distilled off in
a vacuum to dryness at 30°C, the residue was washed
with hexane, filtered off, purified by column chromato-
graphy (eluent CHCl3), and recrystallized from a mixture
benzene–ethanol, 1:1.
5-Amino-N-[1-(4-tert-butylphenoxy)-9,10-
anthraquinon-2-yl]-N'-(2,3,5,6,8,9,11,12-octahydro-
benzo[b][1,4,7,10,13]pentaoxacyclopentadecen-15-
yl)isophthalamide (VIII) was prepared in the same way
as compound IV from 0.42 g (0.5 mmol) of compound
VII, 0.01 g of moist Pd/C, and 1 ml of hydrazine hydrate
N,N'-Bis[1-hydroxy-9-(4-methylphenyl)imine-
9,10-anthraquinon-2-yl]-5-nitroisophthalamide
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 42 No. 11 2006

SYNTHESIS OF PHOTOACTIVE POLYFUNCTIONAL MOLECULES
1695
REFERENCES
(XIII). From 0.92 g of compound III and 0.22 g of
p-toluidine we obtained 0.76 g (92%) of compound XIII,
mp 215–218°C. IR spectrum, ν, cm–1: 3432 (N–H), 3067,
2962 (C–H), 1676, 1630 (C=O, C=N), 1593 (C=C).
Electron absorption spectrum, λmax, nm (log ε): 260 (4.78),
432 (4.04). 1H NMR spectrum (CDCl3), δ, ppm: 2.39 s
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Zh. Org. Khim., 1998, vol. 34, p. 1581.
1-Hydroxy-4-(4-tert-butylphenoxy)-9-(4-
tolylimino)-9,10-anthraquinone (XVI). From 0.5 g of
compound XIV and 0.22 g of p-toluidine we obtained
0.41 g (90%) of compound XVI, mp 157–158°C. IR spec-
trum, ν, cm–1: 3431 (O–H), 3068, 2926, 2864 (C–H), 1671,
1636 (C=N, C=O), 1592 (C=C). Electron absorption
spectrum, λmax, nm (log ε): 268 (4.46), 442 (3.86).
1H NMR spectrum (CDCl3), δ, ppm: 1.28 s [9H,
C(CH3)3], 2.34 s (3H, CH3), 6.83 d (2H, H2',6', J 9 Hz),
7.00 d (2H, H2''6'', J 9 Hz), 7.15 d (2H, H3',5', J 9 Hz),
7.24 d (2H, H3'',5'', J 9 Hz), 7.34 m (2H, H6,7), 7.44 d (1H,
H3, J 8.5), 8.10 d.d (1H, H8, J1 9, J2 2 Hz), 8.35 d.d (1H,
H5, J1 9, J2 2 Hz), 8.95 d (1H, H2, J 8.5 Hz), 15.20 br.s
(1H, OH). Found, %: C 80.18; H 5.65; N 3.00.
C31H27NO3. Calculated, %: C 80.69; H 5.86; N 3.04.
1-Hydroxy-5-(4-tert-butylphenoxy)-9-(4-tolyl-
imino)-9,10-anthraquinone (XVII). From 0.5 g of
compound XV and 0.22 g of p-toluidine we isolated
0.40 g (87%) of compound XVII, mp 180–182°C. IR
spectrum, ν, cm–1: 3423 (O–H), 3073, 2926, 2872 (C–
H), 1670, 1635 (C=N, C=O), 1591 (C=C). Electron
absorption spectrum, λmax, nm (log ε): 278 (4.48), 440
(3.87). 1H NMR spectrum (CDCl3), δ, ppm: 1.28 s [9H,
C(CH3)3], 2.34 s (3H, CH3), 6.90 d (2H, H2',6', J 9 Hz),
7.05 d (2H, H2'',6'', J 9 Hz), 7.12 d (2H, H3',5', J 9 Hz),
7.20 d (2H, H3'',5'', J 9 Hz), 7.32 m (1H, H7), 7.38 m (1H,
H6), 7.41 d (1H, H3, J 8.5 Hz), 8.10 m (1H, H8), 8.79 d
(1H, H2, J 8.5 Hz), 15.12 br.s (1H, OH). Found, %:
C 80.51; H 5.76; N 3.09. C31H27NO3. Calculated, %:
C 80.69; H 5.86; N 3.04.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 42 No. 11 2006