Reactions of 4-acyl-1-alkoxyaryl-5-aryl-3-hydroxy-2,5-dihydro-1H-pyrrol-2- ones with nucleophilic reagents

Article abstract of DOI:10.1134/S1070428011010118

4-Acetyl-1-alkoxyaryl-5-aryl-3-hydroxy-2,5-dihydro-1H-pyrrol-2-ones reacted with amines to give 1-alkoxyaryl-5-aryl-4-(1-R-aminoethylidene)pyrrolidine-2,3- diones. Reactions of amines with 4-benzoyl-substituted analogs involve nucleophilic attack on the C³ atom in the heteroring to produce the corresponding 3-R-amino-1-alkoxyaryl-5-aryl-4-benzoyl-2,5-dihydro-1H-pyrrol-2- ones. Reactions of the title compounds with hydrazine hydrate, regardless on the substituent on C⁴, afforded 4-aryl-3-methyl(phenyl)-5-[2(4)- methoxyphenyl]-4,6-dihydropyrrolo[3,4-c]pyrazol-6-ones.

Full text of DOI:10.1134/S1070428011010118

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2011, Vol. 47, No. 1, pp. 95–99. © Pleiades Publishing, Ltd., 2011.
Original Russian Text © V.L. Gein, N.L. Fedorova, E.B. Levandovskaya, M.I. Vakhrin, 2011, published in Zhurnal Organicheskoi Khimii, 2011, Vol. 47,
No. 1, pp. 97–100.
Reactions of 4-Acyl-1-alkoxyaryl-5-aryl-3-hydroxy-2,5-dihydro-
1H-pyrrol-2-ones with Nucleophilic Reagents
V. L. Gein, N. L. Fedorova, E. B. Levandovskaya, and M. I. Vakhrin
Perm State Pharmaceutical Academy, ul. Lenina 48, Perm, 614990 Russia
e-mail: geinvl48@mail.ru
Received March 30, 2010
Abstract—4-Acetyl-1-alkoxyaryl-5-aryl-3-hydroxy-2,5-dihydro-1H-pyrrol-2-ones reacted with amines to give
1-alkoxyaryl-5-aryl-4-(1-R-aminoethylidene)pyrrolidine-2,3-diones. Reactions of amines with 4-benzoyl-sub-
stituted analogs involve nucleophilic attack on the C3 atom in the heteroring to produce the corresponding
3-R-amino-1-alkoxyaryl-5-aryl-4-benzoyl-2,5-dihydro-1H-pyrrol-2-ones. Reactions of the title compounds
with hydrazine hydrate, regardless on the substituent on C4, afforded 4-aryl-3-methyl(phenyl)-5-[2(4)-methoxy-
phenyl]-4,6-dihydropyrrolo[3,4-c]pyrazol-6-ones.
DOI: 10.1134/S1070428011010118
It is known that 4-aroyl-1,5-diphenyltetrahydro-1H-
pyrrole-2,3-diones do not react with aromatic amines
because of their stabilization due to enolization and
formation of intra- and intermolecular hydrogen bonds;
more nucleophilic aliphatic amines, such as butyl-
amine and 2-aminoethanol, give rise to 3-R-amino-4-
aroyl-1,5-diphenyl-2,5-dihydro-1H-pyrrol-2-ones,
while the reaction with hydrazine hydrate leads to the
formation of fused pyrrolo[3,4-c]pyrazole system [1].
at C3, yielding the corresponding 1-alkoxyaryl-5-aryl-
4-benzoyl-3-butylamino-2,5-dihydro-1H-pyrrol-2-one
III (Scheme 1).
Compounds IIa, IIb, and III were isolated as color-
less crystalline substances which are soluble in com-
mon organic solvents and insoluble in water. The
1H NMR spectra of IIa, IIb, and III contained signals
from aromatic protons, a three-proton multiplet from
the methyl group in the butylamine residue (δ 0.90–
1.00 ppm), a four-proton multiplet from two methylene
groups (2′-H and 3′-H; δ 1.42–1.51 ppm), a two-proton
multiplet from the NHCH2 group (δ 3.29–3.51 ppm),
a singlet from the NH proton (IIa, IIb, δ 11.04–
11.07 ppm; III, δ 8.41 ppm), and a singlet from the
5-H proton in the pyrrolidine ring (δ 5.56–5.91 ppm);
the latter signal was displaced upfield relative to the
corresponding signal of initial compounds I. Com-
With a view to estimate the effect of alkoxyaryl
substituent in position 1 of the heteroring on the reac-
tivity of 2,5-dihydro-1H-pyrrol-2-ones we synthesized
4-acyl-1-alkoxyaryl-5-aryl-3-hydroxy-2,5-dihydro-1H-
pyrrol-2-ones [2] and examined their reactions with
aliphatic and aromatic amines and hydrazine hydrate.
The reactions of 4-acetyl(benzoyl)-1-alkoxyaryl-5-
aryl-3-hydroxy-2,5-dihydro-1H-pyrrol-2-ones I with
butylamine were carried out by heating the reactants at
a ratio of 1:2 in glacial acetic acid under reflux (over
a period of 2 h) or by fusion under solvent-free con-
ditions. The reaction direction depended on the substit-
uent nature in position 4 of the heteroring. If that sub-
stituent was an acetyl group (which is more reactive
than benzoyl group due to the lack of conjugation
with aromatic ring), the reaction of I with aliphatic
amines occurred at the side-chain (acetyl) carbonyl
group to form 1-alkoxyaryl-5-aryl-4-(1-butylamino-
ethylidene)pyrrolidine-2,3-diones IIa and IIb, while
4-benzoyl-substituted analog reacted with butylamine
1
pounds IIa and IIb also displayed in the H NMR
spectra signals from methyl protons in the ethylidene
fragment (δ 1.75–1.84 ppm), which were also dis-
placed upfield relative to the signal from acetyl methyl
1
group in compounds I. The H NMR data and color
test with an alcoholic solution of iron(III) chloride
indicated that compounds IIa and IIb have dicarbonyl
structure and that compound III exists as enamine
tautomer.
Reactions of compounds I with aromatic amines
that are weaker nucleophiles [3] than aliphatic amines
also followed two pathways. By heating compounds I
95

GEIN et al.
96
Scheme 1.
NHR4
O
Me
O
R1 = Me
N
R2
O
N
N
R1
NH
R1
OH
R3
NH2NH2
R4NH2
O
O
N
IIa, IIb, IVa–IVc
R2
R2
O
NHR4
O
Ph
R3
R3
VIa–VIe
I
R1 = Ph
N
R2
R3
III, Va–Ve
II, R4 = Bu: R2 = H, R3 = Me (a); R2 = 4-MeO, R3 = 2-MeO (b); III, R2 = 4-Cl, R3 = 2-Me, R4 = Bu; IV, R2 = H, R3 = 4-Me, R4 =
Ph (a), 4-MeC6H4 (b); R2 = 3-O2N, R3 = 2-MeO, R4 = 4-MeOC6H4 (c); V, R2 = H, R3 = 4-MeO, R4 = Ph (a), 4-MeC6H4 (b),
4-MeOC6H4 (c); R3 = 2-MeO, R4 = 4-MeOC6H4, R2 = 3-O2N (d), 4-Cl (e); VI, R1 = Me: R2 = H, R3 = 4-MeO (a); R2 = 3-O2N, R3 =
2-MeO (b); R2 = 4-MeO, R3 = 2-MeO (c); R1 = Ph: R2 = H, R3 = 4-MeO (d); R2 = 4-Cl, R3 = 2-MeO (e).
with aniline, p-anisidine, and p-toluidine in boiling
glacial acetic acid at a reactant ratio of (1:2) (reaction
time 2–4 h) we obtained in good yields 1-alkoxyaryl-5-
aryl-4-(1-arylaminoethylidene)pyrrolidine-2,3-diones
IVa–IVc or 1-alkoxyaryl-5-aryl-3-arylamino-4-ben-
zoyl-2,5-dihydro-1H-pyrrol-2-ones Va–Ve (Scheme 1).
The IR spectra of Va–Vc contained strong absorp-
tion bands belonging to stretching vibrations of the NH
bond (3296–3304 cm–1), lactam carbonyl group (1664–
1692 cm–1), and exocyclic ketone (benzoyl) carbonyl
1
group (1632–1664 cm–1). In the H NMR spectra of
Va–Ve we observed multiplet signals from aromatic
and methoxy protons, the 5-H signal appeared at
δ 6.04–6.30 ppm, and the NH proton resonated at
δ 8.67–8.89 ppm. In keeping with the IR and NMR
data and negative color test for enolic hydroxy group,
compounds V were assigned enamine structure.
Compounds IVa–IVc and Va–Ve are yellow crys-
talline substances that are soluble in common organic
solvents and insoluble in water. The IR spectra of IVa–
IVc contained strong absorption bands due to stretch-
ing vibrations of the NH bond (3380–3400 cm–1),
lactam carbonyl group (1696–1700 cm–1), and ketone
Compound I reacted with hydrazine hydrate
(1.1 equiv) on heating in boiling acetic acid or 1,4-di-
oxane over a period of 1–2 h to produce the corre-
sponding 4-aryl-3-methyl(phenyl)-5-[2(4)-methoxy-
phenyl]-4,6-dihydropyrrolo[3,4-c]pyrazol-6-ones VIa–
VIe, regardless of the substituent nature on C4. Com-
pounds VIa–VIe were isolated as colorless or yellow-
ish crystalline substances which are soluble in DMF,
DMSO, acetone, and hot ethanol and propan-2-ol and
1
carbonyl group (1604–1632 cm–1). In the H NMR
spectra of these compounds, methyl protons in the
ethylidene fragment resonated as a singlet at δ 1.82–
1.90 ppm, methoxy group in the phenyl substituent on
C1 gave a singlet at δ 3.65–3.75 ppm, the 5-H proton
resonated as a singlet at δ 5.96–6.00 ppm, aromatic
protons appeared as a multiplet in the region δ 6.67–
7.99 ppm, and the NH signal was a singlet located at
δ 12.54–12.59 ppm. Compounds IVa–IVc displayed
a negative color test (no cherry color) with a solution
of iron(III) chloride, and their spectral parameters were
also consistent with the dicarbonyl structure.
1
insoluble in water. According to the H NMR data, in
some cases the reaction was accompanied by forma-
tion of acetylacetohydrazide as by-product which was
removed by treatment with hot water.
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REACTIONS OF 4-ACYL-1-ALKOXYARYL-5-ARYL-3-HYDROXY-2,5-DIHYDRO...
97
7.31 m (9H, Harom), 11.04 s (1H, NH). Found, %:
C 72.94; H 6.89; N 7.44. C23H26N2O3. Calculated, %:
C 72.99; H 6.92; N 7.40.
The IR spectra of compounds VIa–VIe contained
absorption bands typical of stretching vibrations of NH
bond (3236–3400 cm–1) and lactam carbonyl (1676–
1
1708 cm–1). In the H NMR spectra of these com-
4-(1-Butylaminoethylidene)-1-(2-methoxyphen-
yl)-5-(4-methoxyphenyl)pyrrolidine-2,3-dione (IIb).
Yield 1.71 g (57%) (a), 1.45 g (49%) (b); mp 210–
212°C. 1H NMR spectrum, δ, ppm: 1.00 m (3H, CH3),
1.51 m (4H, CH2CH2CH3), 1.75 s (3H, =CCH3),
3.36 m (2H, NHCH2), 3.64 s (3H, 2-CH3O), 3.72 s
(3H, 4-CH3O), 5.56 s (1H, 5-H), 6.58–7.10 m (8H,
Harom), 11.07 s (1H, NH). Found, %: C 70.64; H 6.88;
N 6.92. C24H28N2O4. Calculated, %: C 70.57; H 6.91;
N 6.86.
pounds, signals from aromatic protons, and protons
in the methoxy group, a singlet from 4-H (δ 5.68–
6.64 ppm), a singlet from the NH proton (δ 13.11–
14.06 ppm), and a singlet from the 3-Me group (VIa–
VIc; δ 2.00–2.08 ppm) were present. Compound VId
showed in the mass spectrum the molecular ion peak
[M]+ with m/z 381 (23.3%) and the following fragment
ion peaks, m/z (Irel, %): 232 (13.2) [M – MeOC6H4-
NC=O]+, 77 (56.4) [Ph]+.
Thus the presence of an acetyl or benzoyl group in
position 4 of the pyrrole ring in 1-alkoxyaryl-5-aryl-3-
hydroxy-2,5-dihydro-1H-pyrrol-2-ones I almost does
not affect the direction of their reaction with hydrazine
hydrate: in both cases, the corresponding 4,6-dihydro-
pyrrolo[3,4-c]pyrazol-6-one derivatives were formed.
4-Benzoyl-3-butylamino-5-(4-chlorophenyl)-
1-(2-methoxyphenyl)-2,5-dihydro-1H-pyrrol-2-one
(IIIa). Yield 0.82 g (24%) (a), 0.61 g (18%) (b);
1
mp 99–101°C. H NMR spectrum, δ, ppm: 0.90 m
(3H, CH3), 1.42 m (4H, CH2CH2CH3), 3.54 m (2H,
NHCH2), 3.71 s (3H, CH3O), 5.91 s (1H, 5-H), 6.63–
7.24 m (13H, Harom), 8.41 s (1H, NH). Found, %:
C 70.86; H 5.68; Cl 7.50; N 5.94. C28H27ClN2O3. Cal-
culated, %: C 70.80; H 5.73; Cl 7.46; N 5.90.
EXPERIMENTAL
The IR spectra were recorded from samples dis-
persed in mineral oil on a Specord-85 spectrometer.
Compounds IVa–IVc and Va–Ve (general proce-
dure). A mixture of 0.001 or 0.002 mol of compound I
and 0.002 or 0.004 mol of the corresponding aromatic
amine in glacial acetic acid was heated for 2–4 h under
reflux. The mixture was cooled, and the precipitate
was filtered off and recrystallized from ethanol or
propan-2-ol.
1
The H NMR spectra were measured on Bruker AM-
300 and AM-500 instruments (300 and 500 MHz, re-
spectively) using DMSO-d6 as solvent and tetramethyl-
silane as internal reference. The mass spectra (electron
impact, 70 eV) were obtained on a Finnigan MAT
INCOS 50 mass spectrometer.
1-(4-Methoxyphenyl)-5-phenyl-4-(1-phenyl-
Compounds IIa, IIb, and III (general procedure).
a. A mixture of 0.005 mol of 4-acetyl(benzoyl)-1-
alkoxyaryl-5-aryl-3-hydroxy-2,5-dihydro-1H-pyrrol-2-
one I and 0.01 mol of butylamine in glacial acetic acid
was heated for 2 h under reflux. The mixture was
cooled, and the precipitate was filtered off and recrys-
tallized from ethanol.
aminoethylidene)pyrrolidine-2,3-dione (IVa). Yield
1
0.70 g (58%), mp 237–238°C. H NMR spectrum, δ,
ppm: 1.90 s (3H, =CCH3), 3.66 s (3H, CH3O), 6.00 s
(1H, 5-H), 6.68–7.49 m (14H, Harom), 12.59 s (1H,
NH). Found, %: C 75.30; H 5.61; N 6.99. C25H22N2O3.
Calculated, %: C 75.36; H 5.57; N 7.03.
1-(4-Methoxyphenyl)-4-[1-(4-methylphenyl-
amino)ethylidene]-5-phenylpyrrolidine-2,3-dione
(IVb). Yield 0.20 g (34%), mp 257–258°C. IR spec-
trum, ν, cm–1: 3400 (NH), 1700 (C2=O), 1632 (C3=O).
1H NMR spectrum, δ, ppm: 1.87 s (3H, =CCH3), 2.31 s
(3H, CH3C6H4), 3.65 s (3H, CH3O), 5.99 s (1H, 5-H),
6.67–7.34 m (13H, Harom), 12.56 s (1H, NH). Found,
%: C 75.68; H 5.91; N 6.73. C26H24N2O3. Calculated,
%: C 75.71; H 5.86; N 6.79.
b. A mixture of 0.005 mmol of compound I and
0.01 mol of butylamine was fused at 150–250°C by
heating on a metal bath until gaseous products no
longer evolved. The melt was cooled and treated with
ethanol, and the precipitate was filtered off and recrys-
tallized from ethanol.
4-(1-Butylaminoethylidene)-1-(4-methoxyphen-
yl)-5-phenylpyrrolidine-2,3-dione (IIa). Yield 1.60 g
(57%) (a), 0.70 g (25%) (b); mp 159–161°C. 1H NMR
spectrum, δ, ppm: 0.93 m (3H, CH3), 1.49 m (4H,
CH2CH2CH3), 1.84 s (3H, =CCH3), 3.29 m (2H,
NHCH2), 3.65 s (3H, CH3O), 5.89 s (1H, 5-H), 6.66–
1-(2-Methoxyphenyl)-4-[1-(4-methoxyphenyl-
amino)ethylidene]-5-(3-nitrophenyl)pyrrolidine-2,3-
dione (IVc). Yield 0.98 g (70%), mp 239–241°C. IR
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GEIN et al.
98
spectrum, ν, cm–1: 3380 (NH), 1696 (C2=O), 1604
Compounds VIa–VIe (general procedure). Hydra-
zine hydrate, 3.3 mmol, was added to a mixture of
3 mmol of 4-acyl-1-alkoxyaryl-5-aryl-3-hydroxy-2,5-
dihydro-1H-pyrrol-2-one and 15 ml of acetic acid or
1,4-dioxane. The mixture was heated for 3 h under
reflux and cooled, and the precipitate was filtered off
and recrystallized from ethanol.
1
(C3=O). H NMR spectrum, δ, ppm: 1.82 s (3H,
=CCH3), 3.75 s (6H, CH3O), 5.96 s (1H, 5-H), 6.73–
7.99 m (12H, Harom), 12.54 s (1H, NH). Found, %:
C 65.90; H 4.94; N 8.81. C26H23N3O6. Calculated, %:
C 65.95; H 4.90; N 8.87.
4-Benzoyl-1-(4-methoxyphenyl)-5-phenyl-
3-phenylamino-2,5-dihydro-1H-pyrrol-2-one (Va).
Yield 1.22 g (87%), mp 194–196°C. IR spectrum, ν,
cm–1: 3304 (NH), 1692 (C2=O), 1648 (C=O). 1H NMR
spectrum, δ, ppm: 3.65 s (3H, CH3), 6.20 s (1H, 5-H),
6.64–7.42 m (19H, Harom), 8.71 s (1H, NH). Found, %:
C 78.19; H 5.29; N 6.12. C30H24N2O3. Calculated, %:
C 78.24; H 5.25; N 6.08.
5-(4-Methoxyphenyl)-3-methyl-4-phenyl-4,5-di-
hydropyrrolo[3,4-c]pyrazol-6(1H)-one (VIa). Yield
0.69 g (73%), mp 211–213°C. IR spectrum, ν, cm–1:
1
3360 (NH), 1696 (C=O). H NMR spectrum, δ, ppm:
2.00 s (3H, 3-CH3), 3.64 s (3H, CH3O), 6.22 s (1H,
4-H), 6.72–7.36 m (9H, Harom), 13.11 s (1H, NH).
Found, %: C 71.38; H 5.31; N 13.19. C19H17N3O2. Cal-
culated, %: C 71.46; H 5.37; N 13.16.
4-Benzoyl-1-(4-methoxyphenyl)-3-(4-methyl-
phenylamino)-5-phenyl-2,5-dihydro-1H-pyrrol-
2-one (Vb). Yield 0.70 g (50%), mp 241–242°C. IR
spectrum, ν, cm–1: 3296 (NH), 1680 (C2=O), 1664
5-(2-Methoxyphenyl)-3-methyl-4-(3-nitrophen-
yl)-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one
(VIb). Yield 0.73 g (66%), mp 146–148°C. IR spec-
trum, ν, cm–1: 3248 (NH), 1696 (C=O). 1H NMR spec-
trum, δ, ppm: 2.08 s (3H, 3-CH3), 3.76 s (3H, CH3O),
6.13 s (1H, 4-H), 6.69–7.92 m (8H, Harom). Found, %:
C 62.57; H 4.40; N 15.31. C19H16N4O4. Calculated, %:
C 62.63; H 4.43; N 15.38.
1
(C=O). H NMR spectrum, δ, ppm: 2.12 s (3H, CH3),
3.66 s (3H, CH3O), 6.17 s (1H, 5-H), 6.68–7.41 m
(18H, Harom), 8.67 s (1H, NH). Found, %: C 78.51;
H 5.49; N 5.86. C31H26N2O3. Calculated, %: C 78.46;
H 5.52; N 5.90.
4-Benzoyl-1-(4-methoxyphenyl)-3-(4-methoxy-
phenylamino)-5-phenyl-2,5-dihydro-1H-pyrrol-
2-one (Vc). Yield 1.23 g (84%), mp 221–223°C. IR
spectrum, ν, cm–1: 3296 (NH), 1664 (C2=O), 1632
5-(2-Methoxyphenyl)-4-(4-methoxyphenyl)-3-
methyl-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one
(VIc). Yield 0.15 g (15%), mp 175–177°C. IR spec-
trum, ν, cm–1: 3400 (NH), 1708 (C=O). 1H NMR spec-
trum, δ, ppm: 2.03 s (3H, 3-CH3), 3.63 s (3H,
4-CH3O), 3.72 s (3H, 2-CH3O), 5.68 s (1H, 4-H),
6.69–7.09 m (8H, Harom), 13.42 s (1H, NH). Found, %:
C 68.70; H 5.53; N 12.00. C20H19N3O3. Calculated, %:
C 68.75; H 5.48; N 12.03.
1
(C=O). H NMR spectrum, δ, ppm: 3.62 s and 3.69 s
(3H each, CH3O), 6.30 s (1H, 5-H), 6.56–7.49 m (18H,
Harom), 8.80 s (1H, NH). Found, %: C 75.82; H 5.29;
N 5.78. C31H26N2O4. Calculated, %: C 75.90; H 5.34;
N 5.71.
4-Benzoyl-1-(2-methoxyphenyl)-3-(4-methoxy-
phenylamino)-5-(3-nitrophenyl)-2,5-dihydro-1H-
pyrrol-2-one (Vd). Yield 0.91 g (57%), mp 147–
5-(4-Methoxyphenyl)-3,4-diphenyl-4,5-dihydro-
pyrrolo[3,4-c]pyrazol-6(1H)-one (VId). Yield 0.70 g
(62%), mp 246–248°C. IR spectrum, ν, cm–1: 3248
1
1
149°C. H NMR spectrum, δ, ppm: 3.59 s (3H,
(NH), 1676 (C=O). H NMR spectrum, δ, ppm: 3.70 s
4-CH3O), 3.78 s (3H, 2-CH3O), 6.20 s (1H, 5-H),
6.38–7.82 m (17H, Harom), 8.89 s (1H, NH). Found, %:
C 69.59; H 4.76; N 7.80. C31H25N3O6. Calculated, %:
C 69.52; H 4.71; N 7.85.
(3H, CH3O), 6.64 s (1H, 4-H), 6.88–7.55 m (14H,
Harom), 14.06 s (1H, NH). Mass spectrum, m/z (Irel, %):
381 (23.32) [M]+, 350 (13.71) [M – OCH3]+, 232
(13.21) [M – CH3OC6H4NC=O]+, 149 (28.03)
[CH3OC6H4NC=O]+, 107 (5.41) [C6H4OCH3]+, 77
(56.36) [Ph]+. Found, %: C 75.51; H 4.98; N 11.08.
C24H19N3O2. Calculated, %: C 75.57; H 5.02; N 11.02.
4-Benzoyl-5-(4-chlorophenyl)-1-(2-methoxy-
phenyl)-3-(4-methoxyphenylamino)-2,5-dihydro-
1H-pyrrol-2-one (Ve). Yield 0.67 g (43%), mp 165–
1
166°C. H NMR spectrum, δ, ppm: 3.58 s (3H,
4-(4-Chlorophenyl)-5-(2-methoxyphenyl)-3-
phenyl-4,6-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one
(VIe). Yield 0.83 g (68%), mp 123–125°C. IR spec-
trum, ν, cm–1: 3236 (NH), 1700 (C=O). 1H NMR spec-
trum, δ, ppm: 3.76 s (3H, CH3O), 6.21 s (1H, 4-H),
4-CH3O), 3.78 s (3H, 2-CH3O), 6.04 s (1H, 5-H),
6.38–7.28 m (17H, Harom), 8.72 s (1H, NH). Found, %:
C 70.86; H 4.87; Cl 6.69; N 5.30. C31H25ClN2O4. Cal-
culated, %: C 70.92; H 4.80; Cl 6.75; N 5.34.
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REACTIONS OF 4-ACYL-1-ALKOXYARYL-5-ARYL-3-HYDROXY-2,5-DIHYDRO...
99
sovremennoi nauki i obrazovaniya. Biologicheskie nauki:
materialy Vserossiiskoi nauchno-prakticheskoi konferen-
tsii s mezhdunarodnym uchastiem (Current Problems of
Science and Education. Biological Sciences: Proc. All-
Russian Scientific–Practical Conf. with International
Participation), Ufa: Redakts.-Izd. Tsentr Bashkir. Gos.
Univ., 2010, vol. 2, p. 457.
6.74–7.34 m (13H, Harom), 13.88 s (1H, NH). Found,
%: C 69.35; H 4.40; Cl 8.49; N 10.06. C24H18ClN3O2.
Calculated, %: C 69.31; H 4.36; Cl 8.52; N 10.10.
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