Five-membered 2,3-dioxoheterocycles: LXXXVI. spiro-heterocyclization of 1-aryl-4-aroyl-5-methoxycarbonyl-1H-pyrrole-2,3-diones under the action of 3-arylamino-1H-inden-1-ones. Crystal and molecular structure of 4′-hydroxy-3′-(2,4-dimethylbenzoyl)-1,1′-diphenyl-1H- spiro[indeno[1,2-b]pyrrole-3,2′-pyrrole]-2,4,5′(1′H)-trione

Article abstract of DOI:10.1134/S1070428012050119

1-Aryl-4-aroyl-5-methoxycarbonyl-1H-pyrrole-2,3-diones react with 3-arylamino-1H-inden-1-ones affording 1,1′-diaryl-3′-aroyl-4′- hydroxy-1H-spiro[indeno[1,2-b]pyrrole-3,2′-pyrrole]-2,4, 5′(1′H)-triones. The crystal and molecular structure of 4′-hydroxy-3′-(2,4-dimethylbenzoyl)-1,1′-diphenyl-1H- spiro[indeno[1,2-b] pyrrole-3,2′-pyrrole]-2,4,5′(1′H)-trione.

Full text of DOI:10.1134/S1070428012050119

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2012, Vol. 48, No. 5, pp. 694−698. © Pleiades Publishing, Ltd., 2012.
Original Russian Text © N.V. Bubnov, E.S. Denislamova, P.S. Silaichev, P.A. Slepukhin, A.N. Maslivets, 2012, published in Zhurnal Organicheskoi Khimii,
2012, Vol. 48, No. 5, pp. 697−700.
Five-Membered 2,3-Dioxoheterocycles: LXXXVI.*
Spiro-Heterocyclization of 1-Aryl-4-aroyl-5-methoxycarbonyl-
1H-pyrrole-2,3-diones under the Action
of 3-Arylamino-1H-inden-1-ones. Crystal and Molecular
Structure of 4'-Hydroxy-3'-(2,4-dimethylbenzoyl)-1,1'-
diphenyl-1H-spiro[indeno[1,2-b]pyrrole-3,2'-pyrrole]-
2,4,5'(1'H)-trione
N. V. Bubnov a, E. S. Denislamova b, P. S. Silaichev a,b, P. A. Slepukhin c, and A. N. Maslivetsa,b
aInstitute of Natural Sciences at Perm State University, Perm, 614990 Russia
e-mail: koh2@psu.ru
bPerm State University, Perm, Russia
cPostovskii Institute of Organic Synthesis, Ural Division, Russian Academy of Sciences, Yekaterinburg, Russia
Received June 29, 2011
Abstract—1-Aryl-4-aroyl-5-methoxycarbonyl-1H-pyrrole-2,3-diones react with 3-arylamino-1H-inden-1-ones
affording 1,1'-diaryl-3'-aroyl-4'-hydroxy-1H-spiro[indeno[1,2-b]pyrrole-3,2'-pyrrole]-2,4,5'(1'H)-triones. The
crystal and molecular structure of 4'-hydroxy-3'-(2,4-dimethylbenzoyl)-1,1'-diphenyl-1H-spiro[indeno[1,2-b]
pyrrole-3,2'-pyrrole]-2,4,5'(1'H)-trione.
DOI: 10.1134/S1070428012050119
with two molecules of aminoindenones followed by the
intramolecular cyclization [5]. Reactions of the other
monocyclic 1H-pyrrole-2,3-diones with substituted
1H-inden-1-ones were not investigated.
Nucleophilic heterocyclizations and recyclizations
of monocyclic 1H-pyrrole-2,3-diones under treatment
with binucleophilic reagents is a convenient synthetic
procedure for preparation of versatile five-, six-, and
seven-membered azaheterocycles, fused, bridged, and
spirobisheterocyclic systems [2, 3].
At boiling 1-aryl-4-aroyl-5-methoxycarbonyl-1H-
pyrrole-2,3-diones Ia–Ig with 3-(arylamino)-1H-inden-
1-ones IIa–IId in the ratio 1 : 1 in anhydrous toluene
for 1.5–2 h (TLC monitoring) we obtained 1,1'-diaryl-
3'-aroyl-4'-hydroxy-1H-spiro[indeno[1,2-b]pyrrole-3,2'-
pyrrole]-2,4,5'(1'H)-triones IIIa–IIIn (see the scheme)
whose structure was proved by XRD analysis by an
example of compound IIIc.
Formerly a spiro-heterocyclization was described of
5-phenyl-4-ethoxycarbonyl-1H-pyrrole-2,3-diones under
the action of 3-arylamino-1H-inden-1-ones involved
into reactions in the ratios 1 : 1 and 1 : 2 that resulted
in spiro[indeno[1,2-b]quinoline-10,3'-pyrroles] [4] and
spiro[diindeno[1,2-b:2',1'-e]pyridine-11,3'-pyrroles]
respectively [5]. In the reaction at the ratio 1:1 the
successive addition occurs of the activated ortho-group
CH of the aryl substituent and the β-CH group of the
enamino fragment to the carbon atom of the carbonyl
group in the position 3 of pyrrolediones [4]. In the
reaction at the ratio 1 : 2 the carbonyl group in the
Compounds IIIa–IIIn are red or orange crystalline
substances readily soluble in DMSO and DMF, sparingly
soluble in common organic solvents, insoluble in water
and alkanes.
IR spectra of compounds IIIa–IIIn contain absorption
bands of stretching vibrations of OH group (3111–3180
cm–1), two lactam carbonyl groups C2=O and C5'=O
(1703–1724, 1757–1778 cm–1), keto carbonyl group
position 3 of pyrrolediones enters into the condensation
______________
* For communication LXXXVI, see [1].
694

FIVE-MEMBERED 2,3-DIOXOHETEROCYCLES: LXXXVI.
695
Scheme.
O
Ar1CO
Ar1CO
O
H3C
OH
O
OH
O
4-YC6Н4
ArCO
O
4-YC6Н4
NH
С6H4Y-4
N
IIа_г
_MeOH
NH
O
N
O
O
N
O
_MeOH
MeOOC
O
N
С6H4X-4
С6H4X-4
C6H4X-4
Ia_Ig
IIIa_IIIn
I, Ar = 4-MeC6H4, X = H (a); Ar = 2,4-Me2C6H3, X = Me (b), H (c); Ar = Ph, X = H (d), Cl (e), Br (f), Me (g); II, Y = H (a), Me (b),
OMe (c), Cl (d); III, Ar = 4-MeC6H4: X = Y = H (a); X = H, Y = Me (j); Ar = 2,4-Me2C6H3: X = Me, Y = H (b); X = Y = H (c), Me (h);
X = Me, Y = OMe (i); Ar = Ph: X = Y = H (d); X = Cl, Y = Me (e); X = Br, Y = Me (f); X = Cl, Y = OMe (g); X = H, Y = OMe (k); X =
Cl, Y = H (l); X = Me, Y = H (m); X = Me, Y = Cl (n).
C4=O (1663–1690 cm–1), and aroyl carbonyl group
(1607–1630 cm–1).
the planes of the heterocycles at the spiro-node amounts
to 89.3 deg. The most significant feature of the crystal
packing is the formation of dimers at the expense of
intermolecular HB O2–H2⋯O3 [–x + 1, –y, –z] [O2–H2
0.90(2), H2–O3 1.72(2), O2–O3 2.560(3) Å, angle O2H2O3
154.1(14)°]. The position of OH group with respect to
the carbonyl group C12=O3 suggests also the formation of
intramolecular HB, but too small observed angle of bond-
ing O–H⋯O (104°) and the large interatomic distance
H⋯O (2.55 Å) does not allow a conclusion on the actual
existence of this intramolecular HB in the crystal state.
1
In the H NMR spectra of compounds IIIa–IIIn
alongside the signals of the protons of aromatic rings
and of substituents attached to them a doublet is
observed upfield belonging to the proton H8 shielded
by the π-electrons of the benzene ring at the atom N1
(6.38–6.43 ppm), and a broadened singlet of the proton
of OH group at 12.20–12.51 ppm.
In the 13C NMR spectrum of compound IIIc
beside the signals of carbon atoms of the phenyl rings,
2,4-dimethylbenzoyl substituent, and indeno[1,2-b]-
pyrrole fragment signals are observed of the carbon atom
of the lactam carbonyl group C5’=O (165.31 ppm), atoms
C4’ (176.77 ppm), C3’ (117.39 ppm), and spiro-carbon
atom (68.60 ppm). The chemical shifts of the signals from
the mentioned atoms are well consistent with he chemical
shifts in the spectrum of methyl 4’-hydroxy-6,6-dimethyl-
1'-(4-tolyl)-1-phenyl-2,4,5'-trioxo-1,1',2,4,5,5',6,7-
octahydrospiro[indole-3,2'-pyrrole]-3'-carboxylate
[C5'=O (165.04 ppm), C4' (174.45 ppm), C3' (107.94 ppm),
and Cspiro (68.31 ppm)] [6]. The considerable shift of
the signal of atom C3’ (by 9.45 ppm) may be ascribed to
the stronger acceptor properties of 2,4-dimethylbenzoyl
substituent compared to the methoxycarbonyl group.
The formation of compounds IIIa–IIIn occurs ap-
parently due to the addition of the β-CH group of the
enamino fragment of indenones IIa–IId to the atom C5
According to XRD study compound IIIc crystallized
in the centrosymmetric space group as a solvate with
a toluene molecule, 1 : 1. The general appearance of
the molecule and the numbering of atoms used in the
structural experiment are given in the figure.
Molecular structure of 4'-hydroxy-3'-(2,4-dimethylbenzoyl)-
1,1'-diphenyl-1H-spiro[indeno[1,2-b]pyrrole-3,2'-pyrrole]-
Bond lengths and bond angles in compound IIIc are
2,4,5'(1'H)-trione (IIIc).
close to standard values. The measured angle between
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BUBNOV et al.
696
diphenyl-1H-spiro[indeno[1,2-b]pyrrole-3,2'-pyrrole]-
2,4,5'(1'H)-trione (IIIc). Yield 84%, mp 255–256°C
(from toluene). IR spectrum, cm–1: 3120 br (OH), 1773
(C2=O), 1703 (C5'=O), 1674 (C4=O), 1611 (COC6H3).
1H NMR spectrum, δ, ppm: 2.26 s (3H, Me), 2.31 s
(3H, Me), 6.39 d (1H, H8, J 7.1 Hz), 7.08–7.69 group
of signals (16H, 2Ph + 2C6H3), 12.30 br.s (1H, OH).
13C NMR spectrum, δ, ppm: 18.83 (Me), 20.86 (Me),
68.60 (Cspiro), 108.02 (C3a), 117.39 (C3'), 120.64–140.60
(CAr), 153.95(C8b) 165.31 (C5'=O), 171.56 (C2=O),
176.77 (C4’), 183.84 (C4=O), 190.45 (ArCO). Found,
%: C 76.17; H 4.34; N 5.06. C35H24N2O5. Calculated,
%: C 76.10; H 4.39; N 5.09.
of pyrrolediones Ia–Ig followed by the closure of the
pyrrole ring through the intramolecular attack of amino
group of indenones IIa–IId on the ester carbonyl group
in the position 5 of pyrroledione with simultaneous elimi-
nation of methanol.
The reported reaction is a new way of building up a dif-
ficultly accessible heterocyclic system spiro[indeno[1,2-
b]pyrrole-3,2'-pyrrole], and also an example of direct
spiroheterocyclization of monocyclic 1H-pyrrole-2,3-
diones under the treatment with enaminoketones.
EXPERIMENTAL
XRD analysis of compound IIIc was carried out
on an automatic four-circle diffractometer Xcalibur 3
equipped with a CCD-detector using the standard pro-
cedure [T 150(2) K, λ(MoKα) 0.71073 Å, ω-scanning
with a step 1°). Data array was collected and processed
by the standard procedure [7], no correction for ex-
tinction was made. The crystal triclinic, space group
P-1, a 10.0516(11), b 12.6108(15), c 14.2748(9) Å, α
89.071(7), β 81.788(7), γ 69.813(10)°, μ 0.084 mm–1.
Within the angles 52.79 < θ < 28.28° 9778 reflections
were collected, 8063 among them were independent
(Rint 0.0265), 3677 with I > 2σ(I). Completeness for θ <
28.29° 96.5%. The structure was solved and refined us-
ing SHELX software [8]. The refinement was performed
in full-matrix least-mean-square method with respect to
F2 in the anisotropic approximation for all nonhydrogen
atoms. Hydrogen atoms of the C–H bonds were placed
geometrically and were included into the refinement in
the isotropic approximation using the rider model with
thermal parameters depending on the attached C atom, the
position of hydrogen atom of OH group was refined in-
dependently in the isotropic approximation. Final results
of the refinement are as follows: R1 0.0427, wR2 0.1005
[for reflections with I > 2σ(I)], R1 0.1033, wR2 0.1056
(for all reflections) at the reliability factor S 1.018. The
peaks of maximum and minimum of the residual electron
density are 0.319 and –0.322 ē·A-3. The results of XRD
experiments were deposited in the Cambridge Crystal-
lographic Data Center (CCDC no. 876974). These data
are in a free access and can be obtained at the address
www.ccdc.cam.ac.uk/data_request/cif.
IR spectra of compounds obtained were recorded on
a spectrophotometer FSM-1201 from mulls in mineral
oil. NMR spectra were registered on a spectrometer
BrukerAM-400 [operating frequencies 400 (1H) and 100
(13C) MHz] in DMSO-d6, internal reference TMS. The
homogeneity of compounds obtained was confirmed by
TLC on Silufol plates, eluent benzene–ethyl acetate, 5:1,
development in iodine vapor.
4'-Hydroxy-3'-(4-toluoyl)-1',1-diphenyl-1H-spiro-
[indeno[1,2-b]pyrrole-3,2'-pyrrole]-2,4,5'(1'H)-trione
(IIIa). Asolution of 1 mmol of compound Ia and 1 mmol
of compound IIa in 10 ml of anhydrous toluene was
boiled for 2 h, cooled, and the separated precipitate was
filtered off. Yield 82%, mp 249–250°C (from toluene).
IR spectrum, cm–1: 3180 br (OH), 1763 (C2=O), 1715
(C5'=O), 1688 (C4=O), 1615 br (COC6H4). 1H NMR
spectrum, δ, ppm: 2.38 s (3H, Me), 6.38 d (1H, H8,
J 7.1 Hz), 7.15–7.69 group of signals (17H, 2Ph + C6H4 +
C6H3), 12.20 br.s (1H, OH). Found, %: C 75.88; H 4.14;
N 5.25. C34H22N2O5. Calculated, %: C 75.83; H 4.12;
N 5.20.
Compounds IIIb–IIIn were obtained in the similar
way.
4'-Hydroxy-3'-(2,4-dimethylbenzoyl)-1'-(4-tolyl)-1-
phenyl-1H-spiro[indeno[1,2-b]pyrrole-3,2'-pyrrole]-
2,4,5’(1’H)-trione (IIIb). Yield 87%, mp 260–261°C
(from 1,2-dichloroethane). IR spectrum, cm–1: 3119
br (OH), 1771 (C2=O), 1704 (C5’=O), 1667 (C4=O),
1619 (COC6H3). 1H NMR spectrum, δ, ppm: 2.25 s
(3H, Me), 2.29 s (3H, Me), 2.31 s (3H, Me), 6.39 d (1H,
H8, J 7.1 Hz), 7.01–7.62 group of signals (15H, Ph +
C6H4 + 2C6H3), 12.40 br.s (1H, OH). Found, %: C 76.35;
H 4.67; N 4.96. C36H26N2O5. Calculated, %: C 76.31;
H 4.63; N 4.94.
3'-Benzoyl-4'-hydroxy-1,1'-diphenyl-1H-spiro-
[indeno[1,2-b]pyrrole-3,2'-pyrrole]-2,4,5'(1'H)-trione
(IIId). Yield 74%, mp 232–233°C (from toluene). IR
spectrum, cm–1: 3111 br (OH), 1766 (C2=O), 1712
4'-Hydroxy-3'-(2,4-dimethylbenzoyl)-1,1'-
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FIVE-MEMBERED 2,3-DIOXOHETEROCYCLES: LXXXVI.
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(C5'=O), 1671 (C4=O), 1622 (COC6H5). 1H NMR spec-
trum, δ, ppm: 6.38 d (1H, H8, J 7.1 Hz), 7.16–7.78 group
of signals (18H, 3Ph + C6H3), 12.50 br.s (1H, OH). Found,
%: C 75.56; H 4.38; N 5.34. C33H20N2O5. Calculated, %:
C 75.58; H 4.34; N 5.36.
methoxyphenyl)-1'-(4-tolyl)-1H-spiro[indeno-[1,2-b]
pyrrole-3,2'-pyrrole]-2,4,5'(1'H)-trione (IIIi). Yield
83%, mp 239–240°C (from toluene). IR spectrum, cm–1:
3138 br (OH), 1763 (C2=O), 1703 (C5’=O), 1667 (C4=O),
1
1618 (COC6H3). H NMR spectrum, δ, ppm: 2.25 s (3H,
Me), 2.29 s (3H, Me), 2.31 s (3H, Me), 3.85 s (3H, Me),
6.40 d (1H, H8, J 7.1 Hz), 7.01–7.41 group of signals
(14H, 2C6H4 + 2C6H3), 12.20 br.s (1H, OH). Found, %:
C 74.50; H 4.70; N 4.71. C37H28N2O6. Calculated, %:
C 74.48; H 4.73; N 4.70.
3'-Benzoyl-4'-hydroxy-1-(4-tolyl)-1'-(4-chloro-
phenyl)-1H-spiro[indeno[1,2-b]pyrrole-3,2'-pyrrole]-
2,4,5'(1'H)-trione (IIIe). Yield 85%, mp 223–224°C
(from toluene). IR spectrum, ν, cm–1: 3180 br (OH), 1777
(C2=O), 1724 (C5’=O), 1688 (C4=O), 1615 (COC6H5).
1H NMR spectrum, δ, ppm: 2.44 s (3H, Me), 6.43 d (1H,
H8, J 7.1 Hz), 7.13–7.76 group of signals (16H, Ph +
2C6H4 + C6H3), 12.20 br.s (1H, OH). Found, %: C 71.47;
H 3.65; Cl 6.13; N 4.69. C34H21ClN2O5. Calculated, %:
C 71.27; H 3.69; Cl 6.19; N 4.89.
4'-Hydroxy-1-(4-tolyl)-3'-(4-toluoyl)-1'-phenyl-1H-
spiro[indeno[1,2-b]pyrrole-3,2'-pyrrole]-2,4,5'(1'H)-
trione (IIIj). Yield 76%, mp 242–243°C (from toluene).
IR spectrum, cm–1: 3152 br (OH), 1757 (C2=O), 1715
(C5'=O), 1684 (C4=O), 1619 (COC6H4). 1H NMR spec-
trum, δ, ppm: 2.38 s (3H, Me), 2.43 s (3H, Me), 6.40 d
(1H, H8, J 7.1 Hz), 7.13–7.68 group of signals (16H, Ph +
2C6H4 + C6H3), 12.40 br.s (1H, OH). Found, %: C 73.97;
H 4.20; N 4.94. C35H24N2O6. Calculated, %: C 73.93;
H 4.25; N 4.93.
3'-Benzoyl-1'-(4-bromophenyl)-4'-hydroxy-1-(4-
tolyl)-1H-spiro[indeno[1,2-b]pyrrole-3,2'-pyrrole]-
2,4,5’(1’H)-trione (IIIf). Yield 69%, mp 210–211°C
(from toluene). IR spectrum, cm–1: 3152 br (OH), 1769
(C2=O), 1703 (C5'=O), 1663 (C4=O), 1630 (COC6H4).
1H NMR spectrum, δ, ppm: 2.44 s (3H, Me), 6.43 d (1H,
H8, J 7.1 Hz), 7.12–7.76 group of signals (12H, Ph +
C6H4 + C6H3), 12.30 br.s (1H, OH). Found, %: C 66.10;
H 3.45; Br 12.98; N 4.53. C34H21BrN2O5. Calculated, %:
C 66.14; H 3.43; Br 12.94; N 4.54.
3'-Benzoyl-4'-hydroxy-1-(4-methoxyphenyl)-1'-
phenyl-1H-spiro[indeno[1,2-b]pyrrole-3,2'-pyrrole]-
2,4,5'(1'H)-trione (IIIk). Yield 84%, mp 240–241°C
(from toluene). IR spectrum, cm–1: 3166 br (OH), 1769
(C2=O), 1721 (C5'=O), 1690 (C4=O), 1623 (COC6H5).
1H NMR spectrum, δ, ppm: 3.86 s (3H, Me), 6.39 d (1H,
H8, J 7.1 Hz), 7.16–7.77 group of signals (17H, 2Ph +
C6H4 + C6H3), 12.30 br.s (1H, OH). Found, %: C 73.59;
H 4.02; N 5.09. C34H22N2O6. Calculated, %: C 73.64;
H 4.00; N 5.05.
3'-Benzoyl-4'-hydroxy-1-(4-methoxyphenyl)-1'-
(4-chlorophenyl)-1H-spiro[indeno[1,2-b]pyrrole-
3,2'-pyrrole]-2,4,5'(1'H)-trione (IIIg). Yield 90%, mp
213–214°C (from toluene). IR spectrum, cm–1: 3138 br
(OH), 1763 (C2=O), 1715 (C5’=O), 1672 (C4=O), 1618
1
(COC6H5). H NMR spectrum, δ, ppm: 3.87 s (3H, Me),
3'-Benzoyl-1'-(4-chlorophenyl)-4'-hydroxy-1-
phenyl-1H-spiro[indeno[1,2-b]pyrrole-3,2'-pyrrole]-
2,4,5'(1'H)-trione (IIIl). Yield 83%, mp 229–230°C
(from toluene). IR spectrum, cm–1: 3150 br (OH), 1778
(C2=O), 1711 (C5’=O), 1676 (C4=O), 1607 (COC6H5).
1H NMR spectrum, δ, ppm: 6.42 d (1H, H8, J 7.1 Hz),
7.13–8.29 group of signals (17H, 2Ph + C6H4 + C6H3),
12.37 br.s (1H, OH). Found, %: C 70.88; H 3.44; Cl 6.36;
N 5.00. C33H19ClN2O5. Calculated, %: C 70.91; H 3.43;
Cl 6.34; N 5.01.
6.42 d (1H, H8, J 7.1 Hz), 7.00–7.45 group of signals
(16H, Ph + 2C6H4 + C6H3), 12.20 br.s (1H, OH). Found,
%: C 69.33; H 3.59; Cl 6.02; N 4.76. C34H21ClN2O5.
Calculated, %: C 69.35; H 3.60; Cl 6.03;N 4.70.
4'-Hydroxy-3'-(2,4-dimethylbenzoyl)-1,1'-di(4-
tolyl)-1H-spiro[indeno[1,2-b]pyrrole-3,2'-pyrrole]-
2,4,5'(1'H)-trione (IIIh). Yield 90%, mp 253–254°C
(from toluene). IR spectrum, cm–1: 3152 br (OH), 1770
(C2=O), 1710 (C5’=O), 1672 (C4=O), 1624 (COC6H3).
1H NMR spectrum, δ, ppm: 2.27 s (3H, Me), 2.29 s (3H,
Me), 2.44 s (3H, Me), 2.52 s (3H, Me), 6.42 d (1H, H8,
J 7.1 Hz), 7.03–7.48 group of signals (14H, 2C6H4 +
2C6H3), 12.30 br.s (1H, OH). Found, %: C 76.56; H 4.61;
N 4.80. C37H28N2O5. Calculated, %: C 76.54; H 4.59;
N 4.82.
3'-Benzoyl-4'-hydroxy-1'-(4-tolyl)-1-phenyl-
1H-spiro[indeno[1,2-b]pyrrole-3,2'-pyrrole]-
2,4,5'(1'H)-trione (IIIm). Yield 81%, mp 224–225°C
(from toluene). IR spectrum, cm–1: 3160 br (OH),
1774 (C2=O), 1707 (C5’=O), 1680 (C4=O), 1611
1
(COC6H5). H, δ, ppm: 2.33 C (3H, Me), 6.41 d (1H,
H8, J 7.1 Hz), 7.07–8.17 group of signals (17H, 2Ph +
4'-Hydroxy-3'-(2,4-dimethylbenzoyl)-1-(4-
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BUBNOV et al.
698
C6H4 + C6H3), 12.51 br.s (1H, OH). Found, %: C 75.89;
H 4.10; N 5.17. C34H22N2O5. Calculated, %: C 75.83;
H 4.12; N 5.20.
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Maslivets, A.N., Zh. Org. Khim., 2011, vol. 47, p. 309.
5. Dmitriev, M.V., Silaichev, P.S., Aliev, Z.G., and
Maslivets, A.N., Zh. Org. Khim., 2011, vol. 47, p. 1866.
6. Silaichev, P.S., Chudinova, M.A., Slepukhin, P.A.,
Maslivets, A.N., Zh. Org. Khim., 2011, vol. 47, p. 1682.
7. CrysAlis SSD, Version 1.171.29.9, release 23-03-2006:
Oxford, Diffraction Ltd., 2006.
3'-Benzoyl-4'-hydroxy-1'-(4-tolyl)-1-(4-chloro-
phenyl)-1H-spiro[indeno[1,2-b]pyrrole-3,2'-pyrrole]-
2,4,5'(1'H)-trione (IIIn). Yield 88%, mp 214–215°C
(from toluene). IR spectrum, cm–1: 3155 br (OH), 1775
(C2=O), 1707 (C5'=O), 1680 (C4=O), 1607 (COC6H5).
1H NMR spectrum, δ, ppm: 2.33 s (3H, Me), 6.40 (1H,
H8, J 7.1 Hz), 7.09–8.26 group of signals (16H, Ph +
2C6H4 + C6H3), 12.43 br.s (1H, OH). Found, %: C 71.21;
H 3.71; Cl 6.24; N 4.87. C34H21ClN2O5. Calculated, %:
C 71.27; H 3.69; Cl 6.19; N 4.89.
ACKNOWLEDGMENTS
The study was carried out under the financial support
of the Ministry of Education and Science of the Russian
Federation (project 2.19.10) and the Russian Foundation
for Basic Research (grant no. 12-03-00696).
8. Sheldrick, G.M., Acta Cryst. A, 2008, vol. 64, p. 112.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 48 No. 5 2012