Five-membered 2.3-dioxo heterocycles: LXVIII. Three pathways in the reaction of methyl 3-aroyl-1-aryl-4,5-dioxo-4,5-dihydro-1H-pyrrole-2- carboxylates with 3-amino-5,5-dimethylcyclohex-2-en-1-one

Article abstract of DOI:10.1134/S1070428010030152

Methyl 3-aroyl-1-aryl-4,5-dioxo-4,5-dihydro-1H-pyrrole-2-carboxylates reacted with 3-amino-5,5-dimethylcyclohex-2-en-1-one having no substituent on the nitrogen atom to give 3-aroyl-4-arylamino-6′,6′-dimethyl- 6′,7′-dihydro-5H-spiro[furan-2,3′-indole]-2′,

Full text of DOI:10.1134/S1070428010030152

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2010, Vol. 46, No. 3, pp. 389–393. © Pleiades Publishing, Ltd., 2010.
Original Russian Text © E.S. Denislamova, A.N. Maslivets, 2010, published in Zhurnal Organicheskoi Khimii, 2010, Vol. 46, No. 3, pp. 396–400.
Five-Membered 2.3-Dioxo Heterocycles:
LXVIII.* Three Pathways in the Reaction of Methyl
3-Aroyl-1-aryl-4,5-dioxo-4,5-dihydro-1H-pyrrole-2-carboxylates
with 3-Amino-5,5-dimethylcyclohex-2-en-1-one
E. S. Denislamovaa and A. N. Maslivetsb
a Institute of Technical Chemistry, Ural Division, Russian Academy of Sciences
b Perm State University, ul. Bukireva 15, Perm, 614990 Russia
e-mail: koh2@psu.ru
Received May 4, 2009
Abstract—Methyl 3-aroyl-1-aryl-4,5-dioxo-4,5-dihydro-1H-pyrrole-2-carboxylates reacted with 3-amino-5,5-
dimethylcyclohex-2-en-1-one having no substituent on the nitrogen atom to give 3-aroyl-4-arylamino-6′,6′-
dimethyl-6′,7′-dihydro-5H-spiro[furan-2,3′-indole]-2′,4′,5′(1′H,5′H)-triones or methyl 12-aroyl-11-aryl-9-hy-
droxy-5,5-dimethyl-3,10-dioxo-8,11-diazatricyclo[7.2.1.02,7]dodec-2(7)-ene-1-carboxylates. The latter under-
went thermal recyclization to 3′-aroyl-1′-aryl-4′-hydroxy-6,6-dimethyl-6,7-dihydrospiro[indole-3,2′-pyrrole]-
2,4,5′(1H,1′H,5H)-triones.
DOI: 10.1134/S1070428010030152
Monocyclic 1H-pyrrole-2,3-diones are known to
react with difunctional nucleophiles to form various
five-, six-, and seven-membered aza heterocycles, as
well as fused and spiro heterocyclic systems [2, 3]. We
previously showed that methyl 3-aroyl-1-aryl-4,5-di-
oxo-4,5-dihydro-1H-pyrrole-2-carboxylates react with
N-alkyl- and N-aryl-substituted acyclic, carbocyclic,
and heterocyclic enamino ketones (ethyl 3-anilinobut-
2-enoates [4], 3-alkylamino- and 3-arylamino-5,5-di-
methylcyclohex-2-en-1-ones [5], and 1-methyl-3,4-di-
hydrobenzo[f]isoquinolines [6]) as with 1,3-C,N-bi-
nucleophiles via initial attack by the β-CH group in the
enamino fragment of enamino ketone at C2 of pyrrole-
dione and subsequent closure of new pyrrole ring as
a result of intramolecular attack by the NH group in
the enamino fragment on the ester carbonyl carbon
atom and elimination of methanol. These reactions
lead to the formation of spiro heterocyclic systems
such as 1,7-diazaspiro[4.4]nona-3,8-dienes [4], spiro-
[indole-3,2′-pyrroles] [5], and spiro[benzo[h]-pyrrolo-
[2,1-a]isoquinoline-2,2′-pyrroles] [6].
work we examined reactions of methyl 3-aroyl-1-aryl-
4,5-dioxo-4,5-dihydro-1H-pyrrole-2-carboxylates Ia–
Id with 3-amino-5,5-dimethylcyclohex-2-en-1-one
(II), which is a potential 1,3-C,N-binucleophile (cyclic
enamino ketone). Pyrrolediones Ia–Id reacted with
an equimolar amount of enamino ketone II on heating
in boiling anhydrous benzene or chloroform over
a period of 1–10 min (until intense red color typical of
initial pyrrolediones disappeared) to give methyl
12-aroyl-11-aryl-9-hydroxy-5,5-dimethyl-3,10-dioxo-
8,11-diazatricyclo[7.2.1.02,7]dodec-2(7)-ene-1-carbox-
ylates IIIa–IIIc** and 3-aroyl-4-arylamino-6′,6′-di-
methyl-6′,7′-dihydro-5H-spiro[furan-2,3′-indole]-
2′,4′,5′(1′H,5H)-triones IVa and IVb (Scheme 1).
Compounds IIIa–IIIc were isolated as colorless or
light yellow high-melting crystalline substances that
are readily soluble in DMSO and DMF, poorly sol-
uble in other common organic solvents, and insoluble
in water and saturated hydrocarbons. Compounds
IIIa–IIIc showed a negative color test for enolic
hydroxy goup with an alcoholic solution of FeCl3.
In continuation of our studies on chemical trans-
formations of monocyclic 1H-pyrrole-2,3-diones by
the action of difunctional nucleophiles, in the present
The IR spectra of IIIa–IIIc contained absorption
bands due to stretching vibrations of the NH group at
3330–3384 cm–1, OH group at 3090–3130 cm–1 (broad
* For communication LXVII, see [1].
** For preliminary communication, see [7].
389

DENISLAMOVA, MASLIVETS
390
Scheme 1.
H2N
7
MeO
Ar2
O
Me
H
N
1
Me
Me
7a
6
Me
Δ
O
N
Ar2
2
3
5
–MeOH
3a
N
2'
4
O
O
1'
3'
COAr1
O
COAr1
5'
4'
O
OH
OH
Va, Vb
a2
H2N
O
6
H8
HO
Me
O
MeO
Ar2
9
N
7
2
5
Me
Me
O
Ar2
10
Me
OMe
Ar1
O
12
4
N
N
Ar1
1
3
+
N
11
O
O
Me
Me
O
a1
O
O
Ar2
MeO
COAr1
O
NH2
O
O
OH
Ia–Id
II
IIIa–IIIc
b
7'
Me
H
N
1'
Me
Me
O
O
H
6'
N
H
Me
Me
N
O
Ar1CO
Ar1
Ar2
Me
5'
O
Ar1CO
2'
3'
2
4'
O1
5
3
O
N
H
O
OH
COOMe
O
4
Ar2NH
Ar2NH
COOMe
O
O
IVa, IVb
I, Ar1 = Ar2 = Ph (a); Ar1 = Ph, Ar2 = C6H4Me-4 (b); Ar1 = Ph, Ar2 = C6H4Cl-4 (c); Ar1 = C6H4OEt-4, Ar2 = C6H4Me-4 (d); III, Ar1 =
Ar2 = Ph (a), C6H4Me-4 (b), C6H4Cl-4 (c); IV, Ar1 = Ph, Ar2 = C6H4Cl-4 (a); Ar1 = C6H4OEt-4, Ar2 = C6H4Me-4 (b); V, Ar1 = Ar2 =
Ph (a); Ar1 = Ph, Ar2 = C6H4Me-4 (b).
band), lactam carbonyl C10=O at 1748–1756 cm–1,
ester carbonyl at 1726–1732 cm–1, and enone carbonyl
group C3=O in the dimedone fragment and ketone
(aroyl) carbonyl group in the region 1623–1665 cm–1.
16,16-dimethyl-3-phenyl-3,10,13-triazapentacyclo-
[10.7.1.01,10.04,9.014,19]eicosa-4,6,8,14(19)-tetraene-
2,11,18-trione whose structure was proved by X-ray
analysis [8].
1
In the H NMR spectra of IIIa–IIIc we observed
Compounds IVa and IVb are yellow high-melting
crystalline substances; they are readily soluble in
DMSO and DMF, difficultly soluble in other organic
solvents, and insoluble in water and saturated hydro-
carbons. They showed a negative color test for enolic
hydroxy group with an alcoholic solution of iron(III)
chloride. Compounds IVa and IVb displayed in the IR
spectra absorption bands due to stretching vibrations
of the NH group (a broad band in the region 3380–
3200 cm–1), lactone carbonyl group C5=O in the furan
ring and lactam carbonyl group C2′=O in the indole
fragment (1786–1730 cm–1), and enone carbonyl group
C4′=O in the dimedone fragment and ketone carbonyl
signals from protons in aromatic rings and substituents
attached thereto, two singlets from protons in two non-
equivalent methyl groups (δ 0.72–0.89 ppm), two
doublets of doublets from protons in two nonequiv-
alent methylene groups in the cyclohexene fragment
(δ 1.90–2.30 ppm), a singlet from the methoxycar-
bonyl group (δ 3.78–3.79 ppm), a singlet from 12-H
(δ 5.11–5.15 ppm), a singlet from the hydroxy proton
(δ 6.71–6.81 ppm), and a singlet from the NH proton at
δ 7.27–7.47 ppm. The spectral parameters of bridged
compounds IIIa–IIIc are very similar to those of
model 13-allyl-20-(4-bromobenzoyl)-12-hydroxy-
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FIVE-MEMBERED 2.3-DIOXO HETEROCYCLES: LXVIII.
391
group in the aroyl fragment (1670–1630 cm–1). The
1H NMR spectra of IVa and IVb contained signals
from protons in the aromatic rings and substituents
attached thereto, two singlets from protons in two
nonequivalent methyl groups (δ 0.78–1.05 ppm), two
doublets of doublets from protons in two nonequiv-
alent methylene groups in the cyclohexene fragment
(δ 1.90–2.69 ppm), and two singlets from the NH
protons in the lactam and secondary amine fragments
at δ 8.97–9.30 and 11.24–11.35 ppm, respectively. The
spectral parameters of spiro compounds IVa and IVb
are very similar to those of model 4-arylamino-3-
aroyl-1′-(4-methoxyphenyl)-6′,6′-dimethyl-2,2′,3′,4′,-
5,5′,6′,7′-octahydro-1′H-spiro[furan-2,3′-indole]-
2′,4′,5-trione whose structure was proved by X-ray
analysis [9].
In the IR spectra of Va and Vb, absorption bands
due to stretching vibrations of the NH and OH groups
were located in the region 3495–3090 cm–1, lactam
carbonyl group C2=O in the indole fragment and C5′=O
group in the pyrrole fragment gave rise to absorption
band at 1748–1709 cm–1, and stretching vibrations of
the enone (C4=O) and benzoyl carbonyl groups had
1
a frequency of 1665–1625 cm–1. The H NMR spectra
of Va and Vb contained signals from protons in the
aromatic rings and substituents attached thereto, two
singlets from protons in two nonequivalent methyl
groups (δ 0.60–0.86 ppm), two doublets of doublets
from protons in two nonequivalent methylene groups
in the cyclohexene fragment (δ 1.95–2.06 ppm), and
two singlets from the NH and OH protons at δ 11.08–
11.14 and 12.42–12.45 ppm, respectively. The spectral
parameters of compounds Va and Vb are very similar
to those of model 3′-benzoyl-1-cyclohexyl-4′-hydroxy-
6,6-dimethyl-1′-phenyl-1′,2,3,4,5,5′,6,7-octahydro-
1H,2′H-spiro[indole-3,2′-pyrrole]-2,4,5′-trione [5] and
3′-benzoyl-4′-hydroxy-11,11-dimethyl-1′-phenyl-
1,2,2′,5′,10,11-hexahydrospiro[benzo[h]pyrrolo[2,1-a]
isoquinoline-2,2′-pyrrole]-1,5′-dione [6] whose struc-
ture was proved by X-ray analysis.
Bridged compounds IIIa–IIIc are likely to be
formed via initial orbital-controlled [2, 3, 10–12] ad-
dition of the β-CH group in the enamino fragment of II
at the C2 carbon atom of dioxo ester Ia–Ic (path a) and
subsequent attack by the amino group on C4 (path a1;
Scheme 1). No compounds analogous to III were
detected previously in the reactions of pyrrolediones I
with N-substituted enamino ketones, presumably due
to increased steric hindrances at the substituted nitro-
gen atom.
Presumably, compounds IIIa and IIIb in solution
undergo thermally induced cleavage of the hemiaminal
NH–C(OH) bond and closure of new pyrrole ring via
intramolecular attack by the primary amino group in
the enamino fragment on the ester carbonyl group
(path a2) with elimination of methanol (Scheme 1).
Analogous scheme of reaction of pyrrolediones like I
with N-alkyl- and N-aryl-substituted acyclic, cyclic,
and heterocyclic enamino ketones was observed by us
most frequently [4–6].
Path b leading to formation of compounds IVa and
IVb involves initial charge-controlled [2, 3, 12] addi-
tion of the amino nitrogen atom in enamine II at the C5
carbon atom in pyrrolediones Ic and Id. Next follows
opening of the pyrrole ring at the N1–C5 bond and
intramolecular closure of new pyrrole ring via nucleo-
philic addition of the β-CH group in the enamino
fragment to the ketone carbonyl group. Hemiacetal
hydroxy group thus formed attacks the ester carbonyl
carbon atom, leading to closure of furan ring with
elimination of methanol. Analogous reaction scheme
was observed previously as side process [9].
Thus we have revealed three different pathways in
the reactions of methyl 3-aroyl-1-aryl-4,5-dioxo-4,5-
dihydro-1H-pyrrole-2-carboxylates with 3-amino-5,5-
dimethylcyclohex-2-en-1-one.
On heating in boiling 1,2-dichloroethane over
a period of 10–12 min, bridged compounds IIIa and
IIIb underwent recyclization to 3′-aroyl-1′-aryl-4′-hy-
droxy-6,6-dimethyl-6,7-dihydrospiro[indole-3,2′-pyr-
role]-2,4,5′(1H,1′H,5H)-triones Va and Vb (Scheme 1).
Spiro compounds Va and Vb were isolated as colorless
high-melting crystalline substances that are readily
soluble in DMSO and DMF, poorly soluble in other
organic solvents, and insoluble in water and saturated
hydrocarbons; they showed a positive color test for
enolic hydroxy group with an alcoholic solution of
iron(III) chloride.
EXPERIMENTAL
The IR spectra were recorded on FSM-1201 and
Bruker IFS-66 spectrometers from samples dispersed
1
in mineral oil. The H and 13C NMR spectra were
measured on a Bruker AM-400 spectrometer (at
400 MHz for H) from solutions in DMSO-d6 using
1
tetramethylsilane as internal reference. The purity of
the products was checked by TLC on Silufol plates
using ethyl acetate or ethyl acetate–benzene (1:5) as
eluent; chromatograms were developed by treatment
with iodine vapor.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 46 No. 3 2010

DENISLAMOVA, MASLIVETS
C27H25ClN2O6. Calculated, %: C 63.72; H 4.95;
392
Methyl 12-benzoyl-9-hydroxy-5,5-dimethyl-3,10-
dioxo-11-phenyl-8,11-diazatricyclo[7.2.1.02,7]dodec-
2(7)-ene-1-carboxylate (IIIa). A solution of 1.0 mmol
of compound Ia and 1.0 mmol of enamine II in 10 ml
of anhydrous benzene was heated for 1 min under
reflux. The mixture was cooled, and the precipitate
was filtered off. Yield 3.75 g (79%), mp 178–180°C
(decomp., from ethyl acetate). IR spectrum, ν, cm–1:
3384 (NH), 3090 br (OH), 1751 (C10=O), 1732
Cl 6.97; N 5.50.
3-Benzoyl-4-(4-chlorophenylamino)-6′,6′-di-
methyl-6′,7′-dihydro-5H-spiro[furan-2,3′-indole]-
2′,4′,5(1′H,5′H)-trione (IVa). A solution of 1.0 mmol
of compound Ic and 1.0 mmol of enamino ketone II in
10 ml of anhydrous benzene was heated for 10 min
under reflux. The mixture was cooled, and the precip-
itate was filtered off. Yield 54%, mp 182–185°C
(decomp., from ethyl acetate). IR spectrum, ν, cm–1:
3200 br (NH), 1786 (C5=O), 1765 (C2′=O), 1638
(C4′=O, COPh). 1H NMR spectrum, δ, ppm: 0.80 s and
1.05 s (3H each, Me), 1.93 d.d and 2.27 d.d (1H each,
7-H, J = 16.0 Hz), 2.41 d.d and 2.69 d.d (1H each,
5-H, J = 18.1 Hz), 6.65–7.38 m (9H, Harom), 9.30 s
(1H, 1′-H), 11.35 s (1H, 4-NH). Found, %: C 65.49;
H 4.24; Cl 7.61; N 5.68. C26H21ClN2O5. Calculated, %:
C 65.48; H 4.44; Cl 7.43; N 5.87.
1
(COOMe), 1663, 1630 (C3=O, COPh). H NMR spec-
trum, δ, ppm: 0.73 s and 0.86 s (3H each, Me),
1.91 d.d and 1.98 d.d (1H each, 6-H, J = 16.1 Hz),
2.18 d.d and 2.29 d.d (1H each, 4-H, J = 16.5 Hz),
3.79 s (3H, OMe), 5.15 s (1H, 12-H), 6.75 s (1H, OH),
7.44 s (1H, NH), 7.12–7.82 m (10H, Harom). Found, %:
C 68.38; H 5.50; N 5.92. C27H26N2O6. Calculated, %:
C 68.34; H 5.52; N 5.90.
Compounds IIIb and IIIc were synthesized in
6′,6′-Dimethyl-4-(4-methylphenylamino)-3-
(4-ethoxybenzoyl)-6′,7′-dihydro-5H-spiro[furan-
2,3′-indole]-2′,4′,5(1′H,5′H)-trione (IVb) was syn-
thesized in a similar way. Yield 67%, mp 198–200°C
(decomp., from ethyl acetate). IR spectrum, ν, cm–1:
3380 (NH), 1730 (C5=O, C2′=O), 1670, 1630 (C4′=O,
a similar way.
Methyl 12-benzoyl-9-hydroxy-5,5-dimethyl-
11-(4-methylphenyl)-3,10-dioxo-8,11-diazatricyclo-
[7.2.1.02,7]dodec-2(7)-ene-1-carboxylate (IIIb). Yield
37%, mp 173–175°C (decomp., from ethyl acetate). IR
spectrum, ν, cm–1: 3365 (NH), 3110 br (OH), 1748
(C10=O), 1730 (COOMe), 1665, 1626 (C3=O, COPh).
1H NMR spectrum, δ, ppm: 0.73 s and 0.89 s (3H each,
Me), 1.92 d.d and 1.99 d.d (1H each, 6-H, J =
16.0 Hz), 2.18 d.d and 2.30 d.d (1H each, 4-H, J =
16.4 Hz), 2.33 s (3H, C6H4Me), 3.79 s (3H, OMe),
5.14 s (1H, 12-H), 6.71 s (1H, OH), 7.27 s (1H, NH),
6.98–7.82 m (9H, Harom). 13C NMR spectrum, δC, ppm:
20.60 (CH3C6H4), 27.37 (5-CH3), 32.18 (C5), 42.04
(C6), 49.55 (C4), 54.09 (CH3O), 57.30 (C12), 59.65
(C1), 100.62 (C9), 115.85 (C2), 125.33–138.23 (Carom),
158.84 (C7), 164.70 (MeOCO), 167.82 (C10), 187.66
(PhCO), 195.46 (C3). Found, %: C 68.99; H 5.66;
N 5.92. C28H28N2O6. Calculated, %: C 68.84; H 5.78;
N 5.73.
1
COAr). H NMR spectrum, δ, ppm: 0.78 s and 1.04 s
(3H each, Me), 1.28 t (3H, CH3CH2, J = 7.0 Hz),
1.90 d.d and 2.24 d.d (1H each, 7-H, J = 16.1 Hz),
2.06 s (3H, C6H4CH3), 2.39 d.d and 2.66 d.d (1H each,
5-H, J = 18.4 Hz), 4.00 q (2H, OCH2, J = 7.1 Hz),
6.57–8.21 m (8H, Harom), 8.97 s (1H, 1′-H), 11.24 s
(1H, 4-NH). 13C NMR spectrum, δC, ppm: 14.41
(CH3), 20.56 (CH3C6H4), 27.34 (5-CH3), 32.17 (C6′),
42.00 (C7′), 49.55 (C5′), 63.49 (CH2O), 77.55 (C2, C3′),
113.85 (C3a′), 126.48–131.40 (Carom), 130.71 (C3),
138.15 (C4), 158.77 (C5), 164.66 (C2′), 167.72 (C7a′),
186.16 (C6H4CO), 195.44 (C4′). Found, %: C 69.53;
H 5.64; N 5.43. C29H28N2O6. Calculated, %: C 69.59;
H 5.64; N 5.60.
3′-Benzoyl-4′-hydroxy-6,6-dimethyl-1′-phen-
yl-6,7-dihydrospiro[indole-3,2′-pyrrole]-
2,4,5′(1H,1′H,5H)-trione (Va). A solution of
1.0 mmol of compound Ia and 1.0 mmol of enamine II
in 10 ml of anhydrous benzene was heated for 10 min
under reflux. The mixture was cooled, and the pre-
cipitate was filtered off. Yield 54%, mp 185–187°C
(decomp., from ethyl acetate). IR spectrum, ν, cm–1:
3383, 3247 br (NH, OH), 1732, 1715 (C2=O, C5′=O),
1665, 1628 (C4=O, COPh). 1H NMR spectrum, δ, ppm:
0.60 s and 0.86 s (3H each, Me), 1.94 d.d and 2.05 d.d
(1H each, 7-H, J = 16.1 Hz), 2.21 d.d and 2.42 d.d (1H
each, 5-H, J = 18.0 Hz), 7.03–7.87 m (9H, Harom),
Methyl 12-benzoyl-11-(4-chlorophenyl)-9-hy-
droxy-5,5-dimethyl-3,10-dioxo-8,11-diazatricyclo-
[7.2.1.02,7]dodec-2(7)-ene-1-carboxylate (IIIc). Yield
25%, mp 182–184°C (decomp., from methanol). IR
spectrum, ν, cm–1: 3330 (NH), 3130 br (OH), 1756
(C10=O), 1726 (COOMe), 1659, 1623 (C3=O, COPh).
1H NMR spectrum, δ, ppm: 0.72 s and 0.85 s (3H each,
Me), 1.90 d.d and 1.98 d.d (1H each, 6-H, J =
16.3 Hz), 2.18 d.d and 2.30 d.d (1H each, 4-H, J =
16.7 Hz), 3.78 s (3H, OMe), 5.11 s (1H, 12-H), 6.81 s
(1H, OH), 7.47 s (1H, NH), 7.16–7.82 m (9H, Harom).
Found, %: C 63.77; H 4.91; Cl 6.99; N 5.54.
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FIVE-MEMBERED 2.3-DIOXO HETEROCYCLES: LXVIII.
393
and Shurov, S.N., Khimiya pyatichlennykh 2,3-diokso-
geterotsiklov (Chemistry of Five-Membered 2,3-Dioxo
Heterocycles), Perm’: Perm. Gos. Univ., 1994, p. 91.
11.14 s (1H, NH), 12.42 s (1H, OH). Found, %:
C 70.41; H 5.06; N 6.19. C26H22N2O5. Calculated, %:
C 70.58; H 5.01; N 6.33.
3. Maslivets, A.N. and Mashevskaya, I.V., 2,3-Digidro-
2,3-pirroldiony (2,3-Dihydropyrrole-2,3-diones), Perm’:
Perm. Gos. Univ., 2005, p. 63.
3′-Benzoyl-4′-hydroxy-6,6-dimethyl-1′-(4-meth-
ylphenyl)-6,7-dihydrospiro[indole-3,2′-pyrrole]-
2,4,5′(1H,1′H,5H)-trione (Vb). Yield 67%, mp 253–
255°C (decomp., ethyl acetate). IR spectrum, ν, cm–1:
3495, 3090 br (NH, OH), 1748, 1709 (C2=O, C5′=O),
1662, 1625 (C4=O, COPh). 1H NMR spectrum, δ, ppm:
0.66 s and 0.86 s (3H each, Me), 1.95 d.d and 2.06 d.d
(1H each, 7-H, J = 16.1 Hz), 2.29 s (3H, C6H4CH3),
2.21 d.d and 2.41 d.d (2H, 5-H, J = 18.4 Hz), 6.89–
7.23 m (4H, C6H4), 7.46–7.66 m (5H, C6H5), 11.08 s
(1H, NH), 12.45 s (1H, OH). Found, %: C 71.16;
H 5.10; N 6.16. C27H24N2O5. Calculated, %: C 71.04;
H 5.30; N 6.14.
4. Bannikova, Yu.N., Sedegova, E.A., Khalturina, V.V.,
and Maslivets, A.N., Russ. J. Org. Chem., 2007, vol. 43,
p. 1338.
5. Bannikova, Yu.N., Maslivets, A.N., and Aliev, Z.G.,
Russ. J. Org. Chem., 2004, vol. 40, p. 1791.
6. Bannikova, Yu.N., Maslivets, A.N., Rozhkova, Yu.S.,
Shklyaev, Yu.V., and Aliev, Z.G., Mendeleev Commun.,
2005, p. 158.
7. Denislamova, E.S., Bannikova, Yu.N., and Masli-
vets, A.N., Russ. J. Org. Chem., 2008, vol. 44, p. 772.
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deleev Commun., 2005, p. 163.
This study was performed under financial support
by the Russian Foundation for Basic Research (project
no. 07-03-96036).
9. Bannikova, Yu.N. and Maslivets, A.N., Russ. J. Org.
Chem., 2006, vol. 42, p. 772.
10. Andreichikov, Yu.S., Maslivets, A.N., Smirnova, L.I.,
Krasnykh, O.P., Kozlov, A.P., and Perevozchikov, L.A.,
Zh. Org. Khim., 1987, vol. 23, p. 1534.
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RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 46 No. 3 2010