Five-membred 2,3-dioxoheterocycles: LXXXI. Reactions of 4,5-bis(methoxycarbonyl)-1H-pyrrole-2,3-diones with N-substituted 3-amino-5,5-dimethyl-2-cyclohex-2-en-1-ones. crystal and molecular structure of methyl 4′-hydroxy-6,6-dimethyl-1,1′-bis(4-methylpheny

Article abstract of DOI:10.1134/S107042801111011X

1-Aryl-4,5-bis(methoxycarbonyl)-1H-pyrrole-2,3-diones react with N-substituted 3-amino-5,5-dimethylcyclohex-2-en-1-ones affording methyl 1,1′-diaryl-4′-hydroxy-6,6-dimethyl-2,4,5′-trioxo-1,1′, 2,4,5,5′,6,7-octahydrospiro[indole-3,2′-pyrrole]-3′- carboxyla

Full text of DOI:10.1134/S107042801111011X

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2011, Vol. 47, No. 11, pp. 1718−1722. © Pleiades Publishing, Ltd., 2011.
Original Russian Text © P.S. Silaichev, M.A. Chudinova, P.A. Slepukhin, A.N. Maslivets, 2011, published in Zhurnal Organicheskoi Khimii, 2011, Vol. 47,
No. 11, pp. 1682−1686.
Five-Membred 2,3-Dioxoheterocycles: LXXXI.*
Reactions of 4,5-Bis(methoxycarbonyl)-1H-pyrrole-2,3-diones
with N-Substituted 3-Amino-5,5-dimethyl-2-cyclohex-2-en-1-ones.
Crystal and Molecular Structure of Methyl 4'-Hydroxy-6,6-di-
methyl-1,1’-bis(4-methylphenyl)-2,4,5'-trioxo-1,1',2,4,5,5',6,7-
octahydrospiro[indole-3,2'-pyrrole]-3'-carboxylate
P. S. Silaichev a, M. A. Chudinova b, P. A. Slepukhin c, and A. N. Maslivetsa,b
a Institute of Natural Sciences at Perm’State University, Perm, 614990 Russia
e-mail: koh2@psu.ru
b Perm’State University, Perm, 614990 Russia
cPostovsky Institute of Organic Synthesis,
Ural Division, Russian Academy of Sciences, Yekaterinburg, Russia
Received March 22, 2011
Abstract—1-Aryl-4,5-bis(methoxycarbonyl)-1Н-pyrrole-2,3-diones react with N-substituted 3-amino-5,5-
dimethylcyclohex-2-en-1-ones affording methyl 1,1'-diaryl-4'-hydroxy-6,6-dimethyl-2,4,5'-trioxo-1,1',2,4,5,5',6,7-
octahydrospiro[indole-3,2'-pyrrole]-3'-carboxylates whose structure was proved by XRD analysis.
DOI: 10.1134/S107042801111011X
and СООMe group in the position 5 of the heterocycle.
The third, minor, direction is the addition of NH and β-СН
groups of the enamine fragment to atoms С2 and С3 of
the pyrrolediones with the cleavage of the pyrroledione
ring and the subsequent cyclization [5].
It was shown formerly that the direction of the reac-
tion between monocyclic 1Н-pyrrole-2,3-diones with
enamines was governed by the structure of the substitu-
ents in the pyrroledione ring [2–5].
The reaction of 1-alkyl-5-phenyl-4-ethoxycarbonyl-
1Н-pyrrole-2,3-diones with N-aryl-substituted enamines
proceeds as a successive addition of the groups of the
ortho-СН of aryl substituent and β-СН of the enamine
fragment to the С3 atom of pyrrolediones [2, 3].
4-Isopropoxalyl-1,5-diphenyl-1Н-pyrrole-2,3-dione re-
acted with enamine adding the NH and β-СН groups of
the enamine fragment to atoms С2 and С3 of pyrroledione
followed by the cleavage of the pyrroledione ring and by
subsequent cyclization [4]. In the reaction of 1-aryl-4-
aroyl-5-methoxycarbonyl-1Н-pyrrole-2,3-diones with
enamines the process proceeds along three directions.
Firstly, successive addition occurs of β-СН and NH
groups of the enamine fragment to atoms С5 and С3 of the
pyrrolediones, secondly, the similar addition to atom С5
__________________
In order to investigate the effect on the reactiv-
ity of 1Н-pyrrole-2,3-diones of introduction of two
methoxycarbonyl fragments into the positions 4 and 5 we
studied the reactions of 1-aryl-4,5-bis(methoxycarbonyl)-
1Н-pyrrole-2,3-diones Iа–Ic with 1,3-CH,NH-
binucleophiles, 3-arylamino-5,5-di-methyl-2-cyclohex-
2-en-1-ones IIа–IIf. N-Substituted dimedone imines
IIа–IIf existing in the enamine form were chosen as
CH,NH-binucleophiles due to their preparative avail-
ability [6] and the ease of the variation of substituents at
the nitrogen atom. These cyclic enaminoketones exist in
the form of (Е)-isomers with the location of β-СН and
NH groups of the enamine fragment on the same side of
the double bond favoring their participation in reactions
as binucleophiles. The wide range of electron-donor and
electron-acceptor substituents at the nitrogen atom in
* For communication LXXX, see [1].
1718

FIVE-MEMBRED 2,3-DIOXOHETEROCYCLES: LXXXI.
1719
Scheme.
O
MeOOC
O
Me
Me
MeOOC
OH
OH
NHR2
MeOOC
H
R2
MeOOC
MeOOC
O
IIа_IIf
N
R2
N
O
O
N
N
R1
_MeOH
O
N
R1
O
R1
O
Me
Me
Me
Me
Iа_Ic
IVа_IVj
IIIа_IIIj
I, R1 = Ph (а), C6H4Mе-4 (b), C6H4ОMе-4 (c); II, R2 = CH2=CH–CH2 (а), Ph (b), C6H4Mе-4 (c), C6H4ОMе-4 (d), C6H4Br-4
(e), 1-naphthyl (f); III, R1 = Ph, R2 = 1-naphthyl (а); R1 = C6H4Mе-4: R2 = CH2=CH–CH2 (b), Ph (c), C6H4ОMе-4 (e),
C6H4Br-4 (f); R1 = R2 = C6H4Mе-4 (d); C6H4ОMе-4 (i); R1 = C6H4ОMе-4, R2 = Ph (g), C6H4Mе-4 (h), 1-naphthyl (j).
enaminoketones IIа–IIf was used in order to estimate
their effect on the reaction course.
ton of the enol hydroxy group (12.40–12.69 ppm). In
the 1Н NMR spectrum of compound IIIb alongside the
above mentioned signals the proton signals of the allyl
substituent are observed in the region 4.18–5.72 ppm.
In the spectra of 1-(α-naphthyl) derivatives IIIa, IIIj
a double set of signals appears from the protons of methyl,
methylene, and methoxycarbonyl groups apparently due
to the existence of these compounds as a mixture of two
relatively stable conformers because of the hindrance to
The reaction of pyrrolediones Iа–Ic with en-
amines IIа–IIf in equimolar ratio at boiling
the reagents solution in anhydrous toluene over
2–4 h furnished in good yields methyl 1,1'-diaryl-4'-
hydroxy-6,6-dimethyl-2,4,5'-trioxo-1,1',2,4,5,5',6,7-
octahydrospiro[indole-3,2'-pyrrole]-3'-carboxylates
IIIа–IIIj (see the scheme) whose structure was proved
by XRD analysis of compound IIId.
Compounds IIIа–IIIj are colorless crystalline
substances of high melting points, easily soluble in DMF
and DMSO, sparingly soluble in the common organic
solvents, insoluble in alkanes and water, with a positive
test (cherry color) for the presence of an enol hydroxy
group with the alcohol solution of iron(III) chloride.
The IR spectra of compounds IIIа–IIIj contain char-
acteristic absorption bands of the stretching vibrations of
the enol hydroxy group in the region 3130–3280 cm–1,of
the methoxycarbonyl group at 1750–1759 cm–1, of two
lactam and of a ketone carbonyl groups in the region
1701–1732 and 1613–1634 cm–1 respectively.
1
In the Н NMR spectra of compounds IIIа–IIIj
alongside the proton signals of the aromatic rings and
the groups attached to them two six-proton singlets
appear corresponding to two nonequivalent methyl
groups in the position 6 of the cyclohexenone fragment
(0.56–0.93 ppm) and four four-proton doublets belonging
to two nonequivalent methylene groups in the positions
5 and 7 of the cyclohexenone fragment (1.79–2.38 ppm),
a three-proton singlet from the methoxycarbonyl group
(3.63–3.78 ppm), and a broadened singlet from the pro-
General appearance of the molecule of methyl 4'-hydroxy-
6,6-dimethyl-1,1'-bis-(4-methylphenyl)-2,4,5'-trioxo-
1,1',2,4,5,5',6,7-octahydrospiro-[indole-3,2'-pyrrole]-3'-
carboxylate (IIId) shown in thermal ellipsoids of 50% prob-
ability according to XRD data.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 47 No. 11 2011

SILAICHEV et al.
1720
the free rotation of the bulky naphthyl substituent around
the С–N bond.
by TLC of Silufol plates, eluent benzene–ethyl acetate,
5 : 1, development in iodine vapor.
In the 13С NMR spectrum of compound IIIc along-
side the carbon signals from the atoms of the aromatic
and aliphatic substituents the signals are present from
the carbon atom of the keto (С4=О), two lactam (С5′=О
and С2=О) and ester carbonyl groups at 190.56, 165.04,
155.04, and 161.99 ppm respectively, and also the signal
from the spirocarbon atom at 68.31 ppm.
Methyl 4'-hydroxy-6,6-dimethyl-1-naphthyl-
2,4,5'-trioxo-1'-phenyl-1,1',2,4,5,5',6,7-octahydro-
spiro[indole-3,2’-pyrrole]-3’-carboxylate (IIIа).
A olution of 1.0 mmol of pyrroledione Iа and 1.0 mmol
of enamine IIf in 20 mi of anhydrous toluene was boiled
over 4 h (TLC monitoring) and cooled. The separated pre-
cipitate was filtered off and recrystallized from toluene.
Yield 76%, mp 190–192°С (toluene). IR spectrum, ν,
cm–1: 3150 (ОН), 1744 (СООMе), 1719 (С2=О, С5'=О),
According to XRD data compound IIId (see the figure)
crystallized from acetone as a solvate in the ratio 1:1 in a
centrosymmetric space group of symmetry. The ОН group
of the hydroxypyrrolone fragment is involved into an
intramolecular hydrogen bond with the methoxycarbonyl
group [O4–H4 86(2), H4⋯O2 2.21(2), O4⋯O2 2.838(2) Å,
angle O4H4O2 130(1)°] and an intermolecular hydrogen
bond with the keto group of the cyclohexenone fragment
(H4⋯O1 [–x, –y + 1, –z + 1] 2.02(2), O4⋯O1 [–x, –y +
1, –z + 1] 2.743(2) Å, angle O4H4O2 140(1)° Å). By the
hydrogen bonds the molecules are joined into dimers.
1
1636 (С4=О). Н NMR spectrum, δ, ppm: 0.73 s (3H,
Me), 0.92 s (3H, Me), 1.79 d (1H, С7H2, J 15.8 Hz),
2.18–2.30 group of signals (3Н, С7H2, С5H2), 3.78 s (3H,
OMe), 6.47–8.14 group of signals (11H, C6H4, С10Н7),
12.69 br.s (1H, OH); 0.51 c (3H, Me), 088 s (3H, Me),
2.03 d (1H, С7H2, J 15.8 Hz), 2.16–2.30 group of signals
(3Н, С7H2, С5H2), 3.82 s (3H, OMe), 6.47–8.14 group of
signals (12H, Рh, С10Н7), 12.69 br.s (1H, OH). Found,
%: C 71.21; H 5.06; N 5.39. С30H26N2О6. Calculated, %:
C 71.25; H 5.02; N 5.36.
The formation of compounds IIIа–IIIj proceeds
along the scheme similar to that described in [5]. As
a result of the initial addition of the activated β-СН
group of the enamine fragment of compounds IIа–IIf to
the carbon atom in the position 5 of pyrrolediones Iа–Ic
with the formation of intermediate compounds IVа–IVj
followed by the intramolecular closure of a pyrrole ring
due to the nucleophilic attack of the amino group of the
enamine fragment on the carbonyl of the ester substituent
in the position 5 of pyrrolediones and methanol elimina-
tion compounds IIIа–IIIj are obtained. The reaction
of pyrroledione Ib with N-alkyl-substituted enamine
IIа proceeded notably faster as showed the TLC moni-
toring of the reaction mixture than the reactions with
N-aryl-substituted enamines IIb–IIf. At the same time
the introduction of electron-donor or electron-acceptor
substituents into the aryl ring attached to the nitrogen of
N-aryl-substituted enamines IIb–IIf did not affect the
rate of their reaction with pyrrolediones Iа–Ic.
Compounds IIIb–IIIj were obtained similarly.
Methyl 1-allyl-4'-hydroxy-6,6-dimethyl-1'-
(4-methylphenyl)-2,4,5'-trioxo-1,1',2,4,5,5',6,7-
octahydrospiro[indole-3,2'-pyrrole]-3'-carboxylate
(IIIb). Yield 77%, mp 243–244°С (toluene). IR spectrum,
ν, cm–1: 3175 (ОН), 1746, 1701 (С2=О, С5'=О, СООMе),
1641 (С4=О). 1Н NMR spectrum, δ, ppm: 0.70 s (3H,
Me), 0.99 s (3H, Me), 2.04 d (1H, С7H2, J 16.4 Hz), 2.14 d
(1H, С5H2, J 18.3 Hz), 2.28 s (3H, Me), 2.34 d (1H, С7H2,
J 16.4 Hz), 2.54 d (1H, С5H2, J 18.3 Hz), 3.63 s (3H,
OMe), 4.18 s (2Н, –СН2–), 4.79 d (1Н, =СН2, J 17.3 Hz
), 5.04 d (1Н, =СН2, J 10.6 Hz), 5.72 m (1Н, –СН2=),
6.80 d (2Нarom, J 8.0 Hz), 7.19 d (2Нarom, J 8.0 Hz),
12.40 br.s (1H, OH). Found, %: C 69.15; H 5.34; N 5.77.
С24H26N2О6. Calculated, %: C 69.12; H 5.39; N 5.76.
Methyl 4'-hydroxy-6,6-dimethyl-1'-(4-
methylphenyl)-2,4,5'-trioxo-1-phenyl-1,1',2,4,5,5',6,7-
octahydrospiro[indole-3,2'-pyrrole]-3'-carboxylate
(IIIc). Yield 75%, mp 240–241°С (toluene). IR spectrum,
ν, cm–1: 3170 (ОН), 1750, 1701 (С2=О, С5'=О, СООMе),
EXPERIMENTAL
1
1628 (С4=О). Н NMR spectrum, δ, ppm: 0.55 s (3H,
IR spectra of compounds synthesized were recorded
on a spectrophotometer FSM-1201 from mulls in min-
eral oil. NMR spectra were registered on a spectrom-
eter Bruker AM-400 [operating frequencies 400 (1H),
100 MHz (13С)] in DMSO-d6, internal reference TMS.
The homogeneity of compounds obtained was confirmed
Me), 0.93 s (3H, Me), 2.00 d (1H, С7H2, J 16.3 Hz), 2.11 d
(1H, С5H2, J 18.5 Hz), 2.18 d (1H, С7H2, J 16.3 Hz),
2.30 s (3H, Me), 2.38 d (1H, С5H2, J 18.5 Hz), 3.70 s
(3H, OMe), 6.94–7.60 group of signals (9H, Ph, C6H4),
12.08 br.s (1H, OH). 13С NMR spectrum, δ, ppm: 20.63
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 47 No. 11 2011

FIVE-MEMBRED 2,3-DIOXOHETEROCYCLES: LXXXI.
1721
(Me), 26.51 (C6Me), 27.85 (C6Me), 33.82 (C6), 35.86
(C7), 50.48 (C5), 51.56 (OMe), 68.31 (C3), 107.94 (C3a),
109.52 (C3'), 125.26–138.03 (Сarom), 155.05 (C2), 161.99
(CОО), 165.04 (C5'), 174.45 (C4'), 190.56 (C4). Found,
%: C 69.15; H 5.34; N 5.77. С28H26N2О6. Calculated, %:
C 69.12; H 5.39; N 5.76.
Methyl 4'-hydroxy-6,6-dimethyl-1'-(4-
methylphenyl)-1-(4-methoxyphenyl)-2,4,5'-trioxo-
1,1',2,4,5,5',6,7-octahydrospiro[indole-3,2'-pyrrole]-
3’-carboxylate (IIIe). Yield 76%, mp 236–238°С
(toluene). IR spectrum, ν, cm–1: 3205 (ОН), 1753, 1721
1
(С2=О, С5'=О, СООMе), 1620 (С4=О). Н NMR spec-
trum, δ, ppm: 0.56 s (3H, Me), 0.93 s (3H, Me), 1.99 d
(1H, С7H2, J 16.1 Hz), 2.08 d (1H, С5H2, J 17.9 Hz), 2.17
d (1H, С7H2, J 16.1 Hz), 2.30 s (3H, Me), 2.32 d (1H,
С5H2, J 16.1 Hz), 3.70 s (3H, OOMe), 3.81 s (3H, OMe),
6.92–7.26 group of signals (8H, 2C6H4), 12.54 br.s (1H,
OH). Found, %: C 67.45; H 5.42; N 5.39. С29H28N2О7.
Calculated, %: C 67.43; H 5.46; N 5.42.
Methyl 4'-hydroxy-6,6-dimethyl-1,1'-bis(4-
methylphenyl)-2,4,5'-trioxo-1,1',2,4,5,5',6,7-
octahydrospiro[indole-3,2'-pyrrole]-3'-carboxylate
(IIId). Yield 78%, mp 234–236°С (toluene). IR spectrum,
ν, cm–1: 3280 (ОН), 1759, 1719 (С2=О, С5'=О, СООMе),
1
1613 (С4=О). Н NMR spectrum, δ, ppm: 0.56 s (3H,
Me), 0.93 s (3H, Me), 2.00 d (1H, С7H2, J 16.2 Hz), 2.10 d
(1H, С5H2, J 18.0 Hz), 2.17 d (1H, С7H2, J 16.2 Hz),
2.30 s (3H, Me), 2.34 d (1H, С5H2, J 18.0 Hz), 2.37 s
(3H, Me), 3.70 s (3H, OMe), 6.93–7.37 group of signals
(8H, 2C6H4), 12.53 br.s (1H, OH). Found, %: C 69.60;
H 5.61; N 5.66. С29H28N2О6. Calculated, %: C 69.59;
H 5.64; N 5.60.
Methyl 1-(4-bromophenyl)-4’-hydroxy-6,6-dimeth-
yl-1'-(4-methylphenyl)-2,4,5'-trioxo-1,1',2,4,5,5',6,7-
octahydrospiro[indole-3,2'-pyrrole]-3'-carboxylate
(IIIf). Yield 76%, mp 236–238°С (toluene). IR spectrum,
ν, cm–1: 3209 (ОН), 1757, 1719 (С2=О, С5'=О, СООMе),
1619 (С4=О). 1Н NMR spectrum, δ, ppm: 0.56 s (3H,
Me), 0.93 s (3H, Me), 2.00 d (1H, С7H2, J 16.1 Hz), 2.17 d
(1H, С5H2, J 18.1 Hz), 2.19 d (1H, С7H2, J 16.1 Hz),
2.30 s (3H, Me), 2.40 d (1H, С5H2, J 18.1 Hz), 3.70 s
XRD analysis of compound IIId was carried
out on a diffractometer Xcalibur-3 with a CCD de-
tector [λ(MoKα) 0.71073, graphite monochromator,
ω-scanning, scanning step 1°, T 295(2) K]. The analysis
was performed using a fragment of a colorless crystal
of the size 0.25 × 0.20 × 0.15 mm. The correction for
extinction was not applied due to its negligible value
(μ 0.088 mm–1). The structure was solved by the direct
method using SHELXS-97 software and it was refined
using SHELXL-97 program [7]. The positions and
thermal parameters of nonhydrogen atoms were refined
first in isotropic and then in nonisotropic approximation
by the full-matrix least-squares method. The hydrogen
atoms were localized from the electron density maxima
and included into the refinement in the rider model. The
main data of the structural experiment: crystal triclinic,
space group Р-1, a 9.8911(9), b 10.9834(6), c 13.8528(10)
Å, α 83.825(6), β 88.581(7), γ 88.163(6) deg, dcalc 1.241
g cm–3, V 1495.09(19) Å3, Z 2. At scanning angles 2.82
< θ < 28.28° 8857 reflections were collected, among
them 7108 independent (Rint 0.0202), 3788 at I > 2σ(I).
Completeness for θ 26.00° 97.2%. The final parameters
of refinement: R1 0.0419, wR2 0.1006 [for I > 2σ(I)], R1
0.0897, wR2 0.1082 (for all reflections) at S 1.006, maxi-
mum and minimum peaks of the spatial electron density
0.221, –0.226 ē/Å3.
(3H, OOMe), 6.92 d (2Нarom, J 8.1 Hz), 7.18 d (2Нarom
J 8.8 Hz), 7.25 d (2Нarom, J 8.1 Hz), 7.78 d (2Нarom
,
,
J 8.8 Hz), 12.62 br.s (1H, OH). Found, %: C 57.45;
H 5.42; Br 10.14; N 5.39. С29H28BrN2О7. Calculated, %:
C 57.43; H 5.46; Br 10.17; N 5.42.
Methyl 4'-hydroxy-6,6-dimethyl-1'-(4-methoxy-
phenyl)-2,4,5'-trioxo-1-phenyl-1,1',2,4,5,5',6,7-
octahydrospiro[indole-3,2'-pyrrole]-3'-carboxylate
(IIIg). Yield 78%, mp 236–237°С (toluene). IR spectrum,
ν, cm–1: 3130 (ОН), 1754, 1727 (С2=О, С5'=О, СООMе),
1636 (С4=О). 1Н NMR spectrum, δ, ppm: 0.59 s (3H,
Me), 0.94 s (3H, Me), 2.02 d (1H, С7H2, J 15.7 Hz), 2.10 d
(1H, С5H2, J 18.0 Hz), 2.20 d (1H, С7H2, J 15.7 Hz),
2.38 s (1H, С5H2, J 18.0 Hz), 3.70 c (3H, OOMe),
6.96–7.59 group of signals (9H, Ph, C6H4), 12.57 br.s (1H,
OH). Found, %: C 68.01; H 3.94; N 10.11. С28H26N2О7.
Calculated, %: C 68.05; H 3.90; N 10.15.
Methyl 4'-hydroxy-6,6-dimethyl-1-(4-methyl-
phenyl)-1'-(4-methoxyphenyl)-2,4,5'-trioxo-
1,1',2,4,5,5',6,7-octahydrospiro[indole-3,2'-pyrrole]-
3’-carboxylate (IIIh). Yield 79%, mp 236–238°С
(toluene). IR spectrum, ν, cm–1: 3254 (ОН), 1759, 1725
1
(С2=О, С5'=О, СООMе), 1626 (С4=О). Н NMR spec-
The XRD results were deposited into the Cambridge
Cristallographic Datacenter under the number CCDC
846265. These materials are available at the address www.
ccdc.cam.ac.uk/data_request/cif.
trum, δ, ppm: 0.59 s (3H, Me), 0.93 s (3H, Me), 2.02 d
(1H, С7H2, J 15.9 Hz), 2.09 d (1H, С5H2, J 17.4 Hz),
2.18 d (1H, С7H2, J 15.9 Hz), 2.30 (С5H2, J 17.4 Hz),
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 47 No. 11 2011

SILAICHEV et al.
1722
2.37 s (3H, Me), 3.70 s (3H, OMe), 3.75 s (3H, OMe),
6.94–7.36 group of signals (8H, 2C6H4), 12.54 br.s (1H,
OH). Found, %: C 67.41; H 5.42; N 5.47. С29H28N2О7.
Calculated, %: C 67.43; H 5.46; N 5.42.
С10Н7), 12.61 br.s (1H, OH); 0.59 s (3H, Me), 0.90 s (3H,
Me), 1.79 d (1H, С7H2, J 16.2 Hz), 2.16–2.30 group of
signals (3Н, С7H2, С5H2), 3.80 s (3H, OMe), 3.81 s (3H,
OMe), 6.98–8.15 group of signals (12H, Ph, С10Н7),
12.61 br.s (1H, OH). Found, %: C 69.60; H 5.29; N 5.01.
С31H28N2О7. Calculated, %: C 69.56; H 5.11; N 5.07.
Methyl 4'-hydroxy-6,6-dimethyl-1,1'-bis(4-
methoxyphenyl)-2,4,5'-trioxo-1,1',2,4,5,5',6,7-
octahydrospiro[indole-3,2'-pyrrole]-3'-carboxylate
(IIIi). Yield 71%, mp 246–248°С (toluene). IR spectrum,
ν, cm–1: 3200 (ОН), 1752, 1727 (С2=О, С5'=О, СООMе),
ACKNOWLEDGMENTS
1
1631 (С4=О). Н NMR spectrum, δ, ppm: 0.59 s (3H,
The study was carried out under the financial support
of the Ministry of Education and Science of the Russian
Federation (project no. 2.19.10).
Me), 0.94 s (3H, Me), 2.01 d (1H, С7H2, J 15.9 Hz), 2.09 d
(1H, С5H2, J 17.9 Hz), 2.18 d (1H, С7H2, J 15.9 Hz),
2.33 s (С5H2, J 17.9 Hz), 3.70 s (3H, OMe), 3.75 s (3H,
OMe), 3.81s (3H, ОOMe), 6.94–7.16 group of signals
(8H, 2C6H4), 12.54 br.s (1H, OH). Found, %: C 65.60;
H 5.19; N 5.41. С29H28N2О8. Calculated, %: C 65.41;
H 5.30; N 5.26.
REFERENCES
1. Denislamova, E.S., Bubnov, N.V., Aliev Z.G.,and Masli-
vets, A.N., Zh. Org. Khim., 2011, vol. 47, p. 1341.
2. Silaichev, P.S., Aliev, Z.G., and Maslivets, A.N., Zh. Org.
Khim., 2009, vol. 45, p. 1125.
3. Silaichev, P.S., Dmitriev, M.V., Aliev, Z.G., and Masli-
vets, A.N., Zh. Org. Khim., 2010, vol. 46, p. 1173.
4. Silaichev, P.S., Aliev, Z.G., and Maslivets, A.N., Zh. Org.
Khim., 2009, vol. 45, p. 130.
5. Denislamova, E.S. and Maslivets, A.N., Zh. Org. Khim.,
2010, vol. 46, p. 396.
6. Jirkovsky, I., Canad. J. Chem., 1974, vol. 52, p. 55.
7. Sheldrick, G.M., Acta. Cryst., 2008, vol. A64, p. 112.
Methyl 4'-hydroxy-6,6-dimethyl-1-naphthyl-1'-
(4-methoxyphenyl)-2,4,5'-trioxo-1,1',2,4,5,5',6,7-
octahydrospiro[indole-3,2'-pyrrole]-3'-carboxylate
(IIIj). Yield 72%, mp 229–231°С (toluene). IR spectrum,
ν, cm–1: 3195 (ОН), 1759, 1719 (С2=О, С5'=О, СООMе),
1634 (С4=О). 1Н NMR spectrum, δ, ppm: 0.78 s (3H,
Me), 0.93 s (3H, Me), 1.91 d (1H, С7H2, J 16.4 Hz), 2.16–
2.30 group of signals (3Н, С7H2, С5H2), 3.77 s (3H, OMe),
3.87 (3H, OMe), 6.46–8.15 group of signals (11H, C6H4,
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 47 No. 11 2011