Five-membered 2,3-dioxoheterocycles: XCVI.*reactions of 3-aroylpyrrolo[1,2-a]quinoxaline-1,2,4(5H)-triones with substituted 1,3,3-trimethyl-2-azaspiro[4.5]dec-1-enes

Article abstract of DOI:10.1134/S1070428013110171

3-Aroylpyrrolo[1,2-a]quinoxaline-1,2,4(5H)-triones react with 1,3,3,7,9-pentamethyl-2-azaspiro-[4.5] deca-1,6,9-trien-8-one and 2',5',5'-trimethyl-4',5'-dihydro-4H-spiro[naphthalene-1,3'-pyrrol]-4-one providing 3-aroyl-2-hydroxy-3a-{(3,3,7,9-tetramethyl-8-oxo-2-azaspiro[4.5]deca- 1,6,9-trien-1-yl)methyl}pyrrolo[1,2-a] quinoxaline-1,4(3aH,5H)-diones and 3-aroyl-2-hydroxy-3a-{(5',5'-dimethyl-4-oxo-4',5'-dihydro-4H- spiro[naphthalene-1,3'-pyrrol]-2'-yl)methyl}pyrrolo[1,2-a]-quinoxaline-1,4(3aH, 5H)-diones. Pleiades Publishing, Ltd., 2013.

Full text of DOI:10.1134/S1070428013110171

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2013, Vol. 49, No. 11, pp. 1666−1669. © Pleiades Publishing, Ltd., 2013.
Original English Text © V.V. Konovalova, K.A. Galataa, Yu.V. Shklyaev, A.N. Maslivets, 2013, published in Zhurnal Organicheskoi Khimii, 2013, Vol. 49,
No. 11, pp. 1683−1686.
Five-Membered 2,3-Dioxoheterocycles: XCVI.* Reactions
of 3-Aroylpyrrolo[1,2-а]quinoxaline-1,2,4(5H)-triones
with Substituted 1,3,3-trimethyl-2-azaspiro[4.5]dec-1-enes
V. V. Konovalovaa, K. A. Galataa, Yu. V. Shklyaeva, and A. N. Maslivetsb
aInstitute of Technical Chemistry, Ural Branch, Russian Academy of Sciences,Perm, Russia
bPerm State National Research University, Perm, 614990 Russia
e-mail: koh2@psu.ru
Received June 25, 2012
Abstract—3-Aroylpyrrolo[1,2-а]quinoxaline-1,2,4(5Н)-triones react with 1,3,3,7,9-pentamethyl-2-azaspiro-[4.5]
deca-1,6,9-trien-8-one and 2',5',5'-trimethyl-4',5'-dihydro-4H-spiro[naphthalene-1,3'-pyrrol]-4-one providing
3-aroyl-2-hydroxy-3а-{(3,3,7,9-tetramethyl-8-oxo-2-azaspiro[4.5]deca-1,6,9-trien-1-yl)methyl}pyrrolo[1,2-а]
quinoxaline-1,4(3аН,5Н)-diones and 3-aroyl-2-hydroxy-3а-{(5',5'-dimethyl-4-oxo-4',5'-dihydro-4Н-
spiro[naphthalene-1,3'-pyrrol]-2'-yl)methyl}pyrrolo[1,2-а]-quinoxaline-1,4(3аН,5Н)-diones.
DOI: 10.1134/S1070428013110171
Recyclization and heterocyclization reactions under
the action of binucleophilic reagents of substituted 4-acyl-
1Н-pyrrole-2,3-diones, in particular, those fused with
azaheterocycles at the [е] side, are a convenient method
of building up a wide range of fused heterocycles and
spirobisheterocyclic systems [2, 3].
The reactions of 3-aroylpyrrolo[1,2-а]quinoxaline-
1,2,4(5Н)-triones Iа–Ie with substituted 1,3,3-trimethyl-
2-azaspiro[4.5]dec-1-enes IIа, IIb [5, 6] in a ratio 1 : 1 at
boiling in anhydrous acetonitrile for 10–30 min (till the
disappearance of the bright violet color of initial pyrrolo-
quinoxalinetriones) afforded in high yields the products
of addition of the activated β-CH group of the tautomeric
enamino form А of compounds IIа, IIb to the carbon
atom in the position 3а of pyrroloquinoxalinetriones Iа–
Ie, 3-aroyl-2-hydroxy-3а-{(3,3,7,9-tetramethyl-8-oxo-
2-azaspiro[4.5]deca-1,6,9-trien-1-yl)methyl}- IIIа–IIIe
and 3-aroyl-2-hydroxy-3а-{(5',5'-dimethyl-4-oxo-4',5'-
dihydro-4Н-spiro[naphthalene-1,3'-pyrrol]-2'-yl)methyl}
pyrrolo[1,2-а]quinoxaline-1,4(3аН,5Н)-diones IIIf–IIIj.
We showed formerly that 4-acyl-1Н-pyrrole-
2,3-diones fused with 1,4-benzoxazinone fragment
(3-aroylpyrrolo[2,1-с][1,4]benzoxazine-1,2,4-
triones) reacted with a spiroheterocyclic enamine
(2',5',5'-trimethyl-4',5'-dihydro-4H-spiro[naphthalene-
1,3'-pyrrol]-4-one) as with a 1,3-СН,NH-binucleophile
along the scheme with a successive attack of groups β-СН
and NH on the enamino fragment of the enamino form
of the spironaphthalenepyrrolone at the carbon atoms
in the positions 3а and 4 of pyrrolobenzoxazinetriones,
respectively, with the cleavage of the С4–О5 bond of
the oxazine ring of pyrrolobenzoxazinetriones and the
formation of substituted dispiro[azol-2,2'-(azolo[1,2-а]
azol)-7',1''-(dihydronaphthalenes)] [4]. In extension
of the investigation of this process we studied the
reaction of 4-acyl-1Н-pyrrole-2,3-diones fused with
1,4-quinoxalinone fragment {3-aroylpyrrolo[1,2-а]
Compounds IIIа–IIIj are colorless crystalline sub-
stances of high melting points (melting with decompo-
sition), readily soluble in DMSO and DMF, sparingly
soluble in alcohols and haloalkanes, insoluble in water
and alkanes, showing a positive test (cherry-red color) for
the presence of enol hydroxyl with the alcohol solution
of iron(III) chloride.
IR spectra of compounds IIIа–IIIj contain the
absorption of the stretching vibrations of the enol ОН
group as a broad band in the region 3216–3230 cm–1, a
broad band of the NH group at 3155–3169 cm–1, bands
of two lactam carbonyl groups C1=O and C4=O in the
quinoxaline-1,2,4(5Н)-triones} with spiropyrrolines.
______________
* For communication XCV, see [1].
1666

FIVE-MEMBERED 2,3-DIOXOHETEROCYCLES: XCVI.
1667
Ar = Ph (а, f), 4-MeС6H4 (b, g), 4-MeОС6H4 (c, h), 4-СlС6H4 (d, i), 4-BrС6H4 (e, j).
region 1689–1692 cm–1, of aroyl carbonyl group, of the
carbonyl group of the cyclohexadiene fragment С8=О
(for compounds IIIа–IIIe) or of the naphthalenone
fragment С4=О (for compounds IIIf–IIIj) in the region
1641–1659 cm–1.
compounds IIIа–IIIj exists in the imine form, although
formerly only its presence in the enamine form [7],
has been observed, apparently because of the lack in
compounds IIIа–IIIj of intramolecular hydrogen bonds,
which may stabilize the enamine form.
1
In the Н NMRspectra of compounds IIIа–IIIj in
Further intramolecular cyclization of substituted
3а-(pyrrolylmethyl)pyrroloquinoxalinediones IIIа–IIIj,
which has been observed for 3а-(pyrrolylmethyl)pyrrolo-
benzoxazinediones [4] does not occur with the former
compounds evidently due to the decreased electrophi-
licity of the carbonyl carbon atom of the С4=О group as
compared to the electrophilicity of the ester carbon atom.
DMSO-d6 alongside with the proton signals from the
aromatic rings and the groups attached to them two
singlets are present of the protons of two methyl groups
in the position 3 (for compounds IIIа–IIIe) or 5' (for
compounds IIIf–IIIj) of the pyrrolidine fragment in
the region 1.16–1.33 and 1.22–1.40 ppm, a doublet of
doublets of the С4Н2 group of the pyrrolidine fragment
(for compounds IIIа–IIIe) in the region 1.83–2.12 ppm
and the С4'Н2 group of the pyrrolidine fragment (2.03–
2.31 ppm for compounds IIIf–IIIj), a doublet of doublets
of the CH2 group in the region 3.32–3.37 (for compounds
IIIа–IIIe) and 1.82–3.17 ppm (for compounds IIIf–IIIj),
a singlet from the proton of NН group in the region
10.67–10.84 ppm, and a broadened singlet of the proton
of enol ОН group in the region 11.41–11.80 ppm.
We attempted to modify the structure of initial
1,3,3-trimethyl-2-azaspiro-[4.5]dec-1-enes in order to
change the regiodirection of their reaction with pyr-
roloquinoxalinetriones. It turned out that the reaction
of 3-aroylpyrrolo[1,2-а]quinoxaline-1,2,4(5Н)-triones
Iа–Ie with 1,3,3-trimethyl-2-azaspiro[4.5]dec-1-enes IIc,
IId containing an additional ester group under analogous
reaction conditions did not occur due to increased steric
hindrances at the reaction site caused by the additional
functional group.
The spiropyrroline fragment in the synthesized
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 49 No. 11 2013

KONOVALOVA et al.
1668
2-Hydroxy-3-(4-methoxybenzoyl)-3а-{(3,3,7,9-
EXPERIMENTAL
tetramethyl-8-oxo-2-azaspiro[4.5]deca-1,6,9-trien-
1-yl)methyl}pyrrolo[1,2-а]quinoxaline-1,4(3аН,5Н)-
dione (IIIc). Yield 92%, mp 186–187°С (ethyl acetate).
IR spectrum, cm–1: 3229 br (OH), 3168 br (NH), 1691
(C1=O, C4=O), 1648 (СОС6Н4ОMе-4, С8=Оcyclohex.).
1Н NMRspectrum, δ, ppm: 1.20 s, 1.27 s (6H, 2Mе),
1.52 s (3H, Mе), 1.87 s (3H, Mе), 1.87, 2.12 d.d (2H,
С4Н2, J 16.8 Hz), 3.34, 3.37 d.d (2H, СН2, J 6.3 Hz),
3.41 s (3H, 4-MеОС6Н4), 6.05 s (1H, H6), 6.54 s (1H,
H10), 7.08–7.87 group of signals (8H, 2C6H4), 10.84 s
(1Н, NH), 11.80 br.s (1Н, ОH). Found, %: С 70.01;
H 5.52; N 7.26. С33Н31N3O6. Calculated, %: С 70.07;
H 5.52; N 7.43.
IR spectra were recorded on an IR Fourier spectro-
photometer IFS 66 (Bruker) from mulls in mineral oil.
1Н and 13С NMRspectra were registered on a spectrom-
eter Mercury-300BB (operating frequency 300 MHz) in
DMSO-d6, internal reference HMDS. The homogeneity of
compounds synthesized was confirmed by TLC on Sorbfil
plates, eluents ethyl acetate–benzene, 1 : 5, ethyl acetate;
spots visualized with 0.5% chloranil solution in toluene.
3-Benzoyl-2-hydroxy-3а-{(3,3,7,9-tetramethyl-
8-oxo-2-azaspiro[4.5]deca-1,6,9-trien-1-yl)methyl}
pyrrolo[1,2-а]quinoxaline-1,4(3аН,5Н)-dione (IIIа).
A solution of 1.0 mmol of reagent Ia and 1.0 mmol of
spirocompound IIа in 20 mL of anhydrous acetonitrile
was boiled for 20 min, cooled, the separated precipitate
was filtered off. Yield 97%, mp 242–243°С (ethyl ac-
etate). IR spectrum, cm–1: 3220 br (OH), 3161 br (NH),
1691 (C1=O, C4=O), 1643 (СОPh, С8=Оcyclohex.).
1Н NMRspectrum, δ, ppm: 1.16 s, 1.23 s (6H, 2Mе),
1.47 s (3H, Mе), 1.83 s (3H, Mе), 1.83, 2.09 d.d (2H,
С4Н2, J 16.5 Hz), 3.33, 3.36 d.d (2H, СН2, J 6.3 Hz),
6.00 s (1H, H6), 6.50 s (1H, H10), 7.04–7.83 group of
signals (9H, Ph, C6H4), 10.79 s (1Н, NH), 11.57 br.s (1Н,
ОH). Found, %: С 71.61; H 5.58; N 7.66. С32Н29N3O5.
Calculated, %: С 71.76; H 5.46; N 7.85.
2-Hydroxy-3а-{(3,3,7,9-tetramethyl-8-oxo-2-
azaspiro[4.5]deca-1,6,9-trien-1-yl)methyl}-
3-(4-chlorobenzoyl)pyrrolo[1,2-а]quinoxaline-
1,4(3аН,5Н)-dione (IIId). Yield 96%, mp 260–261°С
(ethyl acetate). IR spectrum, cm–1: 3230 br (OH), 3168
br (NH), 1690 (C1=O, C4=O), 1647 (СОС6Н4Cl-4,
С8=Оcyclohex.). 1Н NMR spectrum, δ, ppm: 1.20 s, 1.27 s
(6H, 2Mе), 1.51 s (3H, Mе), 1.87 s (3H, Mе), 1.87,
2.12 d.d (2H, С4Н2, J 16.7 Hz), 3.34, 3.37 d.d (2H,
СН2, J 6.3 Hz), 6.05 s (1H, H6), 6.53 s (1H, H10), 7.08–
7.87 group of signals (8H, 2C6H4), 10.83 s (1Н, NH),
11.74 br.s (1Н, ОH). Found, %: С 67.31; H 5.00; N 7.23.
С32Н28ClN3O5. Calculated, %: С 67.42; H 4.95; N 7.37.
Compounds IIIb–IIIj were similarly obtained.
3-(4-Bromobenzoyl)-2-hydroxy-3а-{(3,3,7,9-
tetramethyl-8-oxo-2-azaspiro[4.5]deca-1,6,9-trien-
1-yl)methyl}pyrrolo[1,2-а]quinoxaline-1,4(3аН,5Н)-
dione (IIIe). Yield 94%, mp 272–273°С (dichloroethane).
IR spectrum, cm–1: 3229 br (OH), 3169 br (NH), 1692
(C1=O, C4=O), 1641 (СОС6Н4Br-4, С8=Оcyclohex.).
1Н NMRspectrum, δ, ppm: 1.16 s, 1.22 s (6H, 2Mе),
1.47 s (3H, Mе), 1.82 s (3H, Mе), 1.83, 2.12 d.d (2H,
С4Н2, J 16.7 Hz), 3.32, 3.37 d.d (2H, СН2, J 6.4 Hz),
6.01 s (1H, H6), 6.48 s (1H, H10), 7.04–7.82 group of
signals (8H, 2C6H4), 10.77 s (1Н, NH), 11.71 br.s (1Н,
ОH). Found, %: С 62.43; H 4.79; N 6.82. С32Н28BrN3O5.
Calculated, %: С 62.55; H 4.59; N 6.84.
2-Hydroxy-3а-{(3,3,7,9-tetramethyl-8-oxo-2-
azaspiro[4.5]deca-1,6,9-trien-1-yl)methyl}-3-(4-
toluoyl)pyrrolo[1,2-а]quinoxaline-1,4(3аН,5Н)-dione
(IIIb). Yield 96%, mp 187–188°С (dichloroethane).
IR spectrum, cm–1: 3221 br (OH), 3162 br (NH), 1690
(C1=O, C4=O), 1651 (СОС6Н4Mе-4, С8=Оcyclohex.).
1Н NMRspectrum, δ, ppm: 1.16 s, 1.23 s (6H, 2Mе),
1.49 s (3H, Mе), 1.83 s (3H, Mе), 1.83, 2.12 d.d (2H,
С4Н2, J 16.8 Hz), 2.37 s (3H, 4-MеС6Н4), 3.32, 3.37 d.d
(2H, СН2, J 6.4 Hz), 6.00 s (1H, H6), 6.49 s (1H, H10),
7.04–7.83 group of signals (8H, 2C6H4), 10.75 s (1Н,
NH), 11.41 br.s (1Н, ОH). 13С NMRspectrum, δ, ppm:
15.72, 15.89 (7-Mе, 9-Mе), 21.24 (4-MеС6Н4), 29.92
(СН2), 30.42, 30.72 (С3Mе2), 45.53 (2H, С4Н2), 63.80
(С3Mе2), 65.08 (С3а), 74.59 (С5spiro), 115.84 (С3COAr),
120.90–135.81 (СAr), 134.40, 134.74 (С7,9cyclohex.),
145.07, 145.73 (С6Н, С10Нcyclohex.), 151.62 (С2ОН),
162.76 (С1), 163.85, 164.96 (С1=О, С4=О), 185.41
(С8cyclohex.), 190.68 (СОAr). Found, %: С 72.10; H 5.89;
N 7.47. С33Н31N3O5. Calculated, %: С 72.11; H 5.69; N
7.65.
3-Benzoyl-2-hydroxy-3а-{(5',5'-dimethyl-4-oxo-
4',5'-dihydro-4Н-spiro[naphthalene-1,3'-pyrrol]-2'-
yl)methyl}pyrrolo[1,2-а]quinoxaline-1,4(3аН,5Н)-
dione (IIIе). Yield 96%, mp 236–237°С (dichloroethane).
IR spectrum, cm–1: 3219 br (OH), 3161 br (NH), 1689
(C1=O, C4=O), 1653 (СОPh, С4=Оnaphth.). 1Н NMRspec-
trum, δ, ppm: 1.29 s, 1.36 s (6H, 2Mе), 2.04, 2.27 d.d (2H,
С4'Н2, J 14.3 Hz), 1.83, 3.16 d.d (2H, СН2, J 16.7 Hz),
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 49 No. 11 2013

FIVE-MEMBERED 2,3-DIOXOHETEROCYCLES: XCVI.
1669
5.76 s (1H, C3Hnaphth.), 6.28 s (1H, C2Hnaphth.), 7.01–7.98
group of signals (13H, Ph, 2C6H4), 10.70 s (1Н, NH),
11.54 br.s (1Н, ОH). Found, %: С 73.16; H 4.96; N 7.53.
С34Н27N3O5. Calculated, %: С 73.24; H 4.88; N 7.54.
3-(4-Bromobenzoyl)-2-hydroxy-3а-{(5',5'-
dimethyl-4-oxo-4',5'-dihydro-4Н-spiro[naphthalene-
1,3'-pyrrol]-2'-yl)methyl}pyrrolo[1,2-а]-quinoxaline-
1,4(3аН,5Н)-dione (IIIj). Yield 96%, mp 230–231°С
(dichloroethane). IR spectrum, cm–1: 3219 br (OH),
3156 br (NH), 1691 (C1=O, C4=O), 1656 (СОС6Н4Br-4,
2-Hydroxy-3а-{(5',5'-dimethyl-4-oxo-4',5'-
dihydro-4Н-spiro[naphthalene-1,3'-pyrrol]-2'-
yl)methyl}-3-(4-tolyl)pyrrolo[1,2-а]quinoxaline-
1,4(3аН,5Н)-dione (IIIg). Yield 97%, mp 220–222°С
(dichloroethane). IR spectrum, cm–1: 3223 br (OH),
3158 br (NH), 1690 (C1=O, C4=O), 1659 (СОС6Н4Mе-4,
С4=Оnaphth). 1Н NMRspectrum, δ, ppm: 1.29 s, 1.35 s (6H,
2Mе), 2.03, 2.26 d.d (2H, С4'Н2, J 14.0 Hz), 2.37 s (3H,
4-MеС6Н4), 1.83, 3.16 d.d (2H, СН2, J 17.0 Hz), 5.76 s
(1H, C3Hnaphth.), 6.27 s (1H, C2Hnaphth.), 7.00–7.97 group of
signals (12H, 3C6H4), 10.67 s (1Н, NH), 11.41 br.s (1Н,
ОH). Found, %: С 73.53; H 5.22; N 7.24. С35Н29N3O5.
Calculated, %: С 73.54; H 5.11; N 7.35.
1
С4=Оnaphth.). Н NMRspectrum, δ, ppm: 1.29 s, 1.36 s
(6H, 2Mе), 2.03, 2.27 d.d (2H, С4'Н2, J 14.1 Hz), 1.82,
3.12 d.d (2H, СН2, J 16.8 Hz), 5.77 s (1H, C3Hnaphth.),
6.29 s (1H, C2Hnaphth.), 7.01–7.98 group of signals (12H,
3C6H4), 10.71 s (1Н, NH), 11.72 br.s (1Н, ОH). Found,
%: С 64.02; H 4.25; N 6.60. С34Н26N3O5Br. Calculated,
%: С 64.16; H 4.12; N 6.60.
ACKNOWLEDGMENTS
The study was carried out under the financial support
of the Russian Foundation for Basic Research (grants
nos. 12-03-00146, 12-03-00696, 12-03-33135) and of the
Council of grants of the President of the Russian Federa-
tion (MQ-2998.2011.3).
2-Hydroxy-3а-{(5',5'-dimethyl-4-oxo-4',5'-
dihydro-4Н-spiro[naphthalene-1,3'-pyrrol]-2'-
yl)methyl}-3-(4-methoxybenzoyl)pyrrolo[1,2-а]
quinoxaline-1,4(3аН,5Н)-dione (IIIh). Yield 91%,
mp 233–234°С (dichloroethane). IR spectrum, cm–1:
3216 br (OH), 3155 br (NH), 1691 (C1=O, C4=O), 1655
REFERENCES
1
(СОС6Н4ОMе-4, С4=Оnaphth). Н NMRspectrum, δ,
1. Konovalova, V.V., Shklyaev, Yu.V., Slepukhin, P.A., and
Maslivets,A.N., Russ. J. Org. Khim., 2013, vol. 49, p. 1480.
2. Maslivets, A.N. and Mashevskaya, I.V., 2,3-Digidro-2,3-
pirrol-2,3-diony (2,3-Dihydro-2,3-pyrrol-2,3-diones),
Perm’: Izd. Perm. Gos. Univ., 2005.
3. Mashevskaya, I.V. and Maslivets, A.N., 2,3-Digidro-
2,3-pirrol-2,3-diony, kondensirovannye s razlichnymi
geterotsiklami storonoi [a] i ikh benzo[b]analogi: sintez
khimicheskie svoistva, prakticheskoe primenenie (2,3-Di-
hydro-2,3-pyrrol-2,3-diones Condenced with Various
Heterocycles by Syde [a] and Their Benzo[b] Analogs),
Perm: Izd. PGSKhA, 2003.
4. Konovalova, V.V., Shklyaev, Yu.V., and Maslivets, A.N.,
Russ. J. Org. Khim., 2012, vol. 48, p. 1257.
5. Rozhkova, Yu.S., Khmelevskaya, K.A., Shklyaev, Yu.V.,
Ezhikova, M.A., and Kodess, M.I., Russ. J. Org. Khim.,
2012, vol. 48, p. 69.
ppm: 1.33 s, 1.40 s (6H, 2Mе), 2.08, 2.31 d.d (2H, С4'Н2,
J 14.3 Hz), 1.85, 3.17 d.d (2H, СН2, J 16.5 Hz), 3.39 с
(3H, 4-MеОС6Н4), 5.80 s (1H, C3Hnaphth.), 6.33 s (1H,
C2Hnaphth.), 7.05–8.01 group of signals (12H, 3C6H4),
10.77 s (1Н, NH), 11.78 br.s (1Н, ОH). Found, %: С
71.44; H 5.05; N 7.05. С35Н29N3O6. Calculated, %: С
71.54; H 4.97; N 7.15.
2-Hydroxy-3а-{(5',5'-dimethyl-4-oxo-4',5'-
dihydro-4Н-spiro[naphthalene-1,3'-pyrrol]-2'-
yl)methyl}-3-(4-chlorobenzoyl)pyrrolo[1,2-а]
quinoxaline-1,4(3аН,5Н)-dione (IIIi). Yield 92%,
mp 233–234°С (dichloroethane). IR spectrum, cm–1:
3217 br (OH), 3156 br (NH), 1690 (C1=O, C4=O), 1657
(СОС6Н4Cl-4, С4=Оnaphth.). 1Н NMRspectrum, δ, ppm:
1.28 s, 1.35 s (6H, 2Mе), 2.03, 2.26 d.d (2H, С4'Н2,
J 13.8 Hz), 1.82, 3.13 d.d (2H, СН2, J 16.5 Hz), 5.76 s
(1H, C3Hnaphth.), 6.29 s (1H, C2Hnaphth.), 7.01–7.97 group
of signals (12H, 3C6H4), 10.71 с (1Н, NH), 11.71 br.s (1Н,
ОH). Found, %: С 68.91; H 4.51; N 6.99. С34Н26ClN3O5.
Calculated, %: С 68.98; H 4.43; N 7.10.
6. Nifontov, Yu.V., Glushkov, V.A., and Shklyaev, Yu.V. Izv.
Akad. Nauk, Ser. Khim., 2003, vol. 2, p. 418.
7. Konovalova, V.V., Shklyaev, Yu.V., and Maslivets, A.N.,
Russ. J. Org. Khim., 2011, vol. 47, p. 1062.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 49 No. 11 2013