Reaction of 4-hydroxycoumarin with arylglyoxals and ureas

Article abstract of DOI:10.1134/S1070428009010151

One-pot condensation of 4-hydroxycoumarin with arylglyoxals and ureas gave 4-aryl-5-(4-hydroxy-2-oxo-2H-chromen-3-yl)-1H-imidazol-2(3H)-ones. The same compounds may be obtained from aroylbis(4-hydroxy-2-oxo-2H-chromen-3-yl)methanes and urea. The reaction

Full text of DOI:10.1134/S1070428009010151

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2009, Vol. 45, No. 1, pp. 119–125. © Pleiades Publishing, Ltd., 2009.
Original Russian Text © N.N. Kolos, L.L. Gozalishvili, E.N. Sivokon’, I.V. Knyazeva, 2009, published in Zhurnal Organicheskoi Khimii, 2009, Vol. 45,
No. 1, pp. 124–129.
Reaction of 4-Hydroxycoumarin with Arylglyoxals and Ureas
N. N. Kolosa, L. L. Gozalishvilia, E. N. Sivokon’a, and I. V. Knyazevab
a Karazin Khar’kov National University, pl. Svobody 4, Khar’kov, 61077 Ukraine
e-mail: kolos@univer.kharkov.ua
b State Scientific Institution “Institute for Single Crystals,” National Academy of Sciences of Ukraine,
60 Lenin ave., Kharkov 61001, Ukraine
Received January 28, 2008
Abstract—One-pot condensation of 4-hydroxycoumarin with arylglyoxals and ureas gave 4-aryl-5-(4-hy-
droxy-2-oxo-2H-chromen-3-yl)-1H-imidazol-2(3H)-ones. The same compounds may be obtained from aroyl-
bis(4-hydroxy-2-oxo-2H-chromen-3-yl)methanes and urea. The reaction of 4-bromobenzaldehyde with 4-hy-
droxycoumarin in the presence of urea led to the formation of the corresponding Michael adduct without
participation of urea.
DOI: 10.1134/S1070428009010151
4-Hydroxycoumarin derivatives have found wide
application in medical practice as anticoagulants and
photosensitizers [1–3], inhibitors of some enzymes
[4, 5], and antibacterial and antitumor agents [6, 7].
From the synthetic viewpoint, 4-hydroxycoumarin is
a cyclic β-keto ester which can be used as a convenient
three-carbon synthon in processes accompanied by
recyclization of the chromene ring system [8–12]; it
also acts as CH acid and gives rise to bis-adducts with
aldehydes and glyoxals [12, 13]. Kidwai et al. [14]
reported on Biginelli reaction of 4-hydroxycoumarins
with aromatic aldehydes and urea or thiorea. Analo-
gous three-component condensations with participation
of arylglyoxals were almost not studied. We can note
only one publication [15] concerning one-pot synthesis
of dihydropyrimidinones from ethyl acetoacetate, urea,
and arylglyoxals.
lyzed by HCl under the conditions described in [14]
for the synthesis of chromenopyrimidines, but the yield
and purity were poorer. In addition, compounds IVa
and IVb were also synthesized (in lower yield and
with an impurity of 4-hydroxycoumarin) in an alterna-
tive way, by heating bis-adducts VIa and VIb with
urea in boiling ethanol in the presence of acetic acid as
catalyst (Scheme 1).
The IR spectra of IVa–IVl contained absorption
bands due to stretching vibrations of the lactone
(1710–1729 cm–1) and amide carbonyl groups (1669–
1
1695 cm–1). Their H NMR spectra confirmed that the
coumarin fragment was conserved during the process:
the spectra displayed a dublet from the 5-H proton (J =
7.4–8.0 Hz), a triplet from 7-H (J = 7.0–8.0 Hz), and
a multiplet from 6-H and 8-H at δ 7.32–7.45 ppm. In
the downfield region of the spectra of IVa–IVf we ob-
served one-proton singlets at δ ~10.0 and 10.5 ppm
(one singlet at δ ~10.5 ppm in the spectra of IVg–IVi)
and a broadened singlet at δ ~12.0 ppm, which disap-
peared upon addition of D2O.
The goal of the present work was to examine the
possibility for synthesizing aroyl derivatives of chrom-
eno[4,3-d]pyrimidines with the use of arylglyoxals as
carbonyl component. However, heating of a mixture of
4-hydroxycoumarin (I), arylglyoxal IIa–IIf, and urea
IIIa–IIIc in ethanol in the presence of a catalytic
amount of acetic acid for a short time (15–50 min)
resulted in the formation of colorless crystalline prod-
ucts IVa–IVl whose physical and chemical properties
were not consistent with the structure of expected
benzopyrano[4,3-d]pyrimidines V. A compound like
IV (namely IVa) was also formed in the reaction cata-
Compound IVe showed in the mass spectrum the
molecular ion peak with m/z 446. Fragmentation paths
of the molecular ion (Scheme 2) include opening of
the pyran ring with elimination of phenol molecule
[M – 98]+. and expulsion of p-iodophenyl radical
[M – 203]+; in addition, 4-hydroxycoumarin ion peak
(m/z 162) was present. The base peak was that with
m/z 121 due to 2-hydroxybenzoyl ion.
119

KOLOS et al.
120
Scheme 1.
R1
Ar
N
OH
O
O
N
R2
O
OH
O
O
IVa–IVl
O
EtOH, AcOH
H
+
+
Ar
O
R1NH
NHR2
O
O
HN
NH
I
IIa–IIf
IIIa–IIIc
Ar
O
O
O
V
Ar
O
HO
OH
EtOH, AcOH
+
IIIa
IVa, IVb
O
O
O
VIa, VIb
II, Ar = Ph (a), 4-MeC6H4 (b), 4-ClC6H4 (c), 4-BrC6H4 (d), 4-IC6H4 (e), 2-thienyl (f); III, R1 = R2 = H (a); R1 = Ph, R2 = H (b); R1 =
R2 = Me (c); IV, R1 = R2 = H; Ar = Ph (a), 4-MeC6H4 (b), 4-ClC6H4 (c), 4-BrC6H4 (d), 4-IC6H4 (e), 2-thienyl (f); R1 = R2 = Me; Ar =
Ph (g), 4-MeC6H4 (h), 4-ClC6H4 (i), R1 = Ph, R2 = H; Ar = Ph (j), 4-MeC6H4 (k), 4-ClC6H4 (l); VI, Ar = Ph (a), 4-MeC6H4 (b).
The structure of compounds IV was additionally
confirmed by their bromination and acylation. Treat-
ment of substituted dihydroimidazol-2-one IVg gave
bromo derivative VII, whereas acylation of IVd with
acetic anhydride involved three nucleophilic centers
(one oxygen and two nitrogen atoms) to afford com-
pound VIII (Scheme 3). Thus, the spectral and chem-
ical properties of compounds IVa–IVl are consistent
with the structure of 4-aryl-5-(4-hydroxy-2-oxo-2H-
chromen-3-yl)-1H-imidazol-2(3H)-ones.
Scheme 2.
+·
I
+
NH
OH
NH
OH
O
m/z 352
O
O
–C6H4I, m/z 203
–PhOH
N
H
N
H
O
O
O
m/z 243
[M]+, m/z 446
OH
O
+
O
OH
m/z 121 (100%)
O
m/z 162
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 45 No. 1 2009

REACTION OF 4-HYDROXYCOUMARIN WITH ARYLGLYOXALS AND UREAS
121
Scheme 3.
Br
Ph
Br
Ac
Ph
OH
Ac
N
N
O
O
O
O
Br2, AcOH
Ac2O
IVg
IVd
N
N
Ac
O
O
O
VII
VIII
It is known [16–18] that reactions of arylglyoxals
with ureas led to the formation of hydantoins. How-
ever, as might be expected, the reaction of preliminary
prepared hydantoin IX with 4-hydroxycoumarin under
the above conditions did not produce compound IVg.
An alternative reaction path includes formation of
Scheme 4.
Path 1
OH
O
OH
O
Ph
I
+ IIa
O
A
IIIb
OH
O
OH
O
O
Ph
HN
Ph
O
OH
O
Ph
O
N
N
NHPh
H
O
IIa + IIIb
Ph
Ph
OH
Ph
OH
Ph
N
NH
N
Ph
O
O
O
O
I
+
N
N
H
N
H
Ph
O
O
O
O
IVg
IX
Path 2
O
Ph
Ph
O
O
OH
HN
I
Ph
Ph
IIa + IIIb
N
N
N
H
H
O
O
O
B
C
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 45 No. 1 2009

KOLOS et al.
122
Scheme 5.
Br
CHO
HO
OH
I
+
IIIa
+
Br
O
O
O
Xb
XI
they do not ensure reliable identification of structure
XI or V. Our H NMR data for compound XI confirm
its structure and are consistent with those given in [1].
intermediate A (Scheme 4, path 1) which then reacts
with N-phenylurea via addition at the carbonyl group
or undergoes replacement of the side-chain hydroxy
group (in the phenacyl fragment) (Scheme 4). The first
version leads to 1,4-diphenyl-2,3-dihydro-1H-imida-
zol-2-one derivative, while the second, to regioisomer-
ic 3,4-diphenyl-substituted compound. We also cannot
rule out formation of Schiff base B (path 2), followed
by transformation into intermediate C and intramolec-
ular cyclization of the latter. Analogous intermediates
were isolated previously [19].
1
EXPERIMENTAL
The progress of reactions and the purity of products
were monitored by TLC on Silufol UV-254 plates
using toluene–ethyl acetate (1:1) as eluent (develop-
ment with iodine vapor). The IR spectra were recorded
in KBr on a Specord-75 IR spectrometer. The 1H NMR
spectra were measured on a Varian Mercury VX-200
instrument from solutions in DMSO-d6 using tetra-
methylsilane as internal reference. The mass spectra
(electron impact, 70 eV) were obtained on a Hewlett–
Packard LC/MSD 1100 instrument. The elemental
compositions were determined on a Leco CHNS-900
analyzer. The melting points were measured on
a Kofler hot stage.
To distinguish between 1,4- and 3,4-diphenyl-sub-
stituted 5-(4-hydroxy-2-oxo-2H-chromen-3-yl)-2,3-di-
hydro-1H-imidazol-2-ones, we recorded the NOE
spectrum of compound IVg. Irradiation at a frequency
corresponding to resonance of the NH proton gave no
response on protons in the ortho positions of the phen-
yl ring attached to carbon atom; therefore, compounds
IVg–IVi were assigned the structure of 3,4-diphenyl
derivatives.
Aroylbis(4-hydroxy-2-oxo-2H-chromen-3-yl)-
methanes VIa and VIb were synthesized according to
the procedure described in [12].
Our results indicated that under the above condi-
tions the electrophilic C4 atom in molecule I is not
involved in the reaction with such a weak nucleophile
as urea. On the other hand, it is known that strong nu-
cleophiles (aromatic ortho-diamines [8–11], α-amino
acid esters, α-amino ketones [20]) attack just the C4
atom. Therefore, we tried to perform one-pot reaction
of 4-hydroxycoumarin with aromatic aldehydes and
urea under the conditions reported in [14]. However,
we failed to obtain chromenopyrimidines like V.
Instead, in the reaction with 4-bromobenzaldehyde
(Xb), the product was the corresponding bis-adduct XI
(Scheme 5) whose melting point coincided with that
given in [21], while in the reaction with benzaldehyde
we isolated only unreacted 4-hydroxycoumarin; i.e., in
no case urea was involved in the process. Unfortu-
4-Aryl-5-(4-hydroxy-2-oxo-2H-chromen-3-yl)-
2,3-dihydro-1H-imidazol-2-ones IVa–IVl (general
procedure). a. (One-pot procedure). 4-Hydroxycouma-
rin (I), 1 mmol, was dissolved in 10 ml of ethanol con-
taining 3–4 drops of acetic acid, 1 mmol of the corre-
sponding aryl(hetaryl)glyoxal IIa–IIf and 1 mmol of
urea IIIa–IIIc were added, and the mixture was heated
for 15–50 min under reflux until a colorless solid sepa-
rated from the hot solution. The precipitate was filtered
off and recrystallized from ethanol.
b. A mixture of equimolar amounts of bisadduct VI
and urea III, 1 mmol each, in 10 ml of ethanol was
heated for 1.5 h. The colorless precipitate was filtered
off and recrystallized from ethanol.
1
5-(4-Hydroxy-2-oxo-2H-chromen-3-yl)-4-phenyl-
2,3-dihydro-1H-imidazol-2-one (IVa). Yield 70% (a),
nately, the H NMR spectra of compounds V given in
[14] were recorded at a frequency of 60 MHz, so that
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 45 No. 1 2009

REACTION OF 4-HYDROXYCOUMARIN WITH ARYLGLYOXALS AND UREAS
123
41% (b), mp 269–270°C. IR spectrum, ν, cm–1: 1719
(C=O, lactone), 1685 (C=O, amide), 1610 (C=C).
1H NMR spectrum, δ, ppm: 7.12–7.43 m (7H, C6H5,
6-H, 8-H), 7.68 t (1H, 7-H, J = 7.0 Hz), 7.89 d (1H,
5-H, J = 8.0 Hz), 9.97 s (1H, NH), 10.51 s (1H, NH),
12.04 br.s (1H, OH). Found, %: C 67.61; H 3.85;
N 8.67. C18H12N2O4. Calculated, %: C 67.50; H 3.78;
N 8.75.
(19), 203 (11), 188 (17), 162 (8), 128 (14), 127 (22),
121 (100), 120 (30), 92 (96), 89 (20). Found, %:
C 48.25; H 2.60; N 6.29. C18H11IN2O4. Calculated, %:
C 48.45; H 2.48; N 6.48.
5-(4-Hydroxy-2-oxo-2H-chromen-3-yl)-4-(2-thi-
enyl)-2,3-dihydro-1H-imidazol-2-one (IVf). Yield
57%, mp 277–278°C. IR spectrum, ν, cm–1: 1709
(C=O, lactone), 1670 (C=O, amide), 1609 (C=C).
1H NMR spectrum, δ, ppm: 6.94 t (1H, β-H, J =
4.0 Hz), 7.16–7.22 m (2H, α-H, β-H), 7.35–7.45 m
(2H, 6-H, 8-H), 7.70 t (1H, 7-H, J = 7.6 Hz), 7.92 d
(1H, 5-H, J = 7.8 Hz), 10.04 s (1H, NH), 10.56 s (1H,
NH), 12.09 br.s (1H, OH). Found, %: C 59.00; H 3.20;
N 8.71. C16H10N2O4S. Calculated, %: C 58.89; H 3.09;
N 8.58.
5-(4-Hydroxy-2-oxo-2H-chromen-3-yl)-4-
(4-methylphenyl)-2,3-dihydro-1H-imidazol-2-one
(IVb). Yield 68% (a), 44% (b), mp 263–264°C. IR
spectrum, ν, cm–1: 1709 (C=O, lactone), 1689 (C=O,
1
amide), 1608 (C=C). H NMR spectrum, δ, ppm:
2.19 s (3H, CH3), 7.03 d (2H, o-H, J = 7.8 Hz), 7.19 d
(2H, m-H, J = 8.2 Hz), 7.32–7.42 m (2H, 6-H, 8-H),
7.67 t (1H, 7-H, J = 7.8 Hz), 7.89 d (1H, 5-H, J =
7.6 Hz), 9.93 s (1H, NH), 10.48 s (1H, NH), 11.96 br.s
(1H, OH). Found, %: C 68.31; H 4.35; N 8.42.
C19H14N2O4. Calculated, %: C 68.26; H 4.22; N 8.38.
5-(4-Hydroxy-2-oxo-2H-chromen-3-yl)-3,4-di-
phenyl-2,3-dihydro-1H-imidazol-2-one (IVg). Yield
69%, mp 254–255°C. IR spectrum, ν, cm–1: 1720
(C=O, lactone), 1693 (C=O, amide), 1615 (C=C).
1H NMR spectrum, δ, ppm: 6.93 m (2H, p-H), 7.09–
7.14 m (4H, C6H4), 7.19–7.40 m (6H, NC6H4, 6-H,
8-H), 7.66 t (1H, 7-H, J = 7.4 Hz), 7.86 d (1H, 5-H, J =
7.4 Hz), 10.47 s (1H, NH), 12.06 br.s (1H, OH).
Found, %: C 72.59; H 4.18; N 7.21. C24H16N2O4. Cal-
culated, %: C 72.72; H 4.07; N 7.07.
4-(4-Chlorophenyl)-5-(4-hydroxy-2-oxo-2H-
chromen-3-yl)-2,3-dihydro-1H-imidazol-2-one
(IVc). Yield 69%, mp 278–279°C. IR spectrum, ν,
cm–1: 1709 (C=O, lactone), 1688 (C=O, amide), 1609
(C=C). 1H NMR spectrum, δ, ppm: 7.30 m (4H, C6H4),
7.36–7.43 m (2H, 6-H, 8-H), 7.67 t (1H, 7-H, J =
7.2 Hz), 7.89 d (1H, 5-H, J = 7.6 Hz), 10.03 s (1H,
NH), 10.56 s (1H, NH), 12.00 br.s (1H, OH). Found,
%: C 61.02; H 3.19; N 7.82. C18H11ClN2O4. Calculat-
ed, %: C 60.94; H 3.13; N 7.90.
5-(4-Hydroxy-2-oxo-2H-chromen-3-yl)-4-(4-
methylphenyl)-3-phenyl-2,3-dihydro-1H-imidazol-
2-one (IVh). Yield 55%, mp 228–230°C. IR spectrum,
ν, cm–1: 1729 (C=O, lactone), 1695 (C=O, amide),
1
1609 (C=C). H NMR spectrum, δ, ppm: 2.12 s (3H,
4-(4-Bromophenyl)-5-(4-hydroxy-2-oxo-2H-
chromen-3-yl)-2,3-dihydro-1H-imidazol-2-one
(IVd). Yield 63%, mp 274–275°C. IR spectrum, ν,
cm–1: 1708 (C=O, lactone), 1682 (C=O, amide), 1615
(C=C). 1H NMR spectrum, δ, ppm: 7.23 m (4H, C6H4),
7.36–7.43 m (2H, 6-H, 8-H), 7.69 t (1H, 7-H, J =
8.0 Hz), 7.90 d (1H, 5-H, J = 7.6 Hz), 10.03 s (1H,
NH), 10.56 s (1H, NH), 11.97 br.s (1H, OH). Found,
%: C 54.24; H 2.69; N 7.20. C18H11BrN2O4. Calculat-
ed, %: C 54.16; H 2.78; N 7.02.
CH3), 6.81 d (2H, o-H, J = 8.0 Hz), 6.91 d (2H, m-H,
J = 8.0 Hz), 7.12 d (2H, m-H, J = 7.4 Hz), 7.22–7.40 m
(5H, o-H, 6-H, 8-H, p-H), 7.66 t (1H, 7-H, J = 8.0 Hz),
7.86 d (1H, 5-H, J = 8.0 Hz), 10.43 s (1H, NH),
12.08 br.s (1H, OH). Found, %: C 73.24; H 4.28;
N 6.95. C25H18N2O4. Calculated, %: C 73.16; H 4.42;
N 6.83.
4-(4-Chlorophenyl)-5-(4-hydroxy-2-oxo-2H-
chromen-3-yl)-3-phenyl-2,3-dihydro-1H-imidazol-2-
one (IVi). Yield 58%, mp 223–224°C. IR spectrum, ν,
cm–1: 1718 (C=O, lactone), 1690 (C=O, amide), 1614
5-(4-Hydroxy-2-oxo-2H-chromen-3-yl)-4-
(4-iodophenyl)-2,3-dihydro-1H-imidazol-2-one
(IVe). Yield 63%, mp 261–262°C. IR spectrum, ν,
cm–1: 1710 (C=O, lactone), 1687 (C=O, amide), 1614
1
(C=C). H NMR spectrum, δ, ppm: 6.91 d (2H, m-H,
J = 8.4 Hz), 7.11–7.41 m (9H, o-H, C6H5, 6-H, 8-H),
7.67 t (1H, 7-H, J = 7.6 Hz), 7.86 d (1H, 5-H, J =
7.8 Hz), 10.55 s (1H, NH), 12.04 br.s (1H, OH).
Found, %: C 67.04; H 3.40; N 6.70. C24H15ClN2O4.
Calculated, %: C 66.91; H 3.51; N 6.50.
1
(C=C). H NMR spectrum, δ, ppm: 7.09 d (2H, m-H,
J = 8.6 Hz), 7.33–7.43 m (2H, 6-H, 8-H), 7.56–7.82 t
(1H, 7-H, J = 7.2 Hz), 7.59 d (2H, o-H, J = 8.6 Hz),
7.89 d (1H, 5-H, J = 7.8 Hz), 10.06 s (1H, NH),
10.56 s (1H, NH), 12.01 br.s (1H, OH). Mass spec-
trum, m/z (Irel, %): 446 [M]+ (16), 352 (6), 243 (3), 230
5-(4-Hydroxy-2-oxo-2H-chromen-3-yl)-1,3-di-
methyl-4-phenyl-2,3-dihydro-1H-imidazol-2-one
(IVj). Yield 47%, mp >300°C. IR spectrum, ν, cm–1:
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KOLOS et al.
124
1702 (C=O, lactone), 1669 (C=O, amide), 1609 (C=C).
1H NMR spectrum, δ, ppm: 2.99 s (3H, CH3), 3.12 s
(3H, CH3), 7.27–7.39 m (7H, C6H5, 6-H, 8-H), 7.64 t
(1H, 7-H, J = 7.2 Hz), 7.91 d (1H, 5-H, J = 7.4 Hz),
12.09 br.s (1H, OH). Found, %: C 69.06; H 4.40;
N 8.15. C20H16N2O4. Calculated, %: C 68.96; H 4.63;
N 8.04.
acetate (VIII). A mixture of 1 mmol of compound
IVd and 5 ml of acetic anhydride was heated for
15 min under reflux. It was then cooled and poured
onto ice, and the light yellow precipitate was filtered
off. Yield 0.36 g (72%), mp 188–190°C (from
acetone). 1H NMR spectrum, δ, ppm: 2.31 s (3H, CH3),
2.53 s (3H, NCH3), 2.69 s (3H, NCH3), 7.16 d (2H,
m-H, J = 8.2 Hz), 7.34 t (1H, 6-H, J = 7.6 Hz), 7.46 d
(2H, o-H, J = 8.2 Hz), 7.55 m (2H, 5-H, 8-H), 7.70 t
(1H, 7-H, J = 7.6 Hz). Found, %: C 54.95; H 3.35;
N 5.42. C24H17BrN2O7. Calculated, %: C 54.87;
H 3.26; N 5.33.
5-(4-Hydroxy-2-oxo-2H-chromen-3-yl)-1,3-di-
methyl-4-(4-methylphenyl)-2,3-dihydro-1H-imida-
zol-2-one (IVk). Yield 45%, mp 256–257°C. IR spec-
trum, ν, cm–1: 1702 (C=O, lactone), 1669 (C=O,
1
amide), 1609 (C=C). H NMR spectrum, δ, ppm:
2.22 s (3H, CH3), 2.97 s (3H, CH3), 3.10 s (3H, CH3),
7.13 m (4H, C6H4), 7.28–7.39 m (2H, 6-H, 8-H), 7.65 t
(1H, 7-H, J = 8.0 Hz), 7.81 d (1H, 5-H, J = 7.4 Hz),
12.02 br.s (1H, OH). Found, %: C 69.72; H 5.11;
N 7.90. C21H18N2O4. Calculated, %: C 69.60; H 5.01;
N 7.73.
3,3′-(4-Bromophenylmethylene)bis(4-hydroxy-
2H-chromen-2-one) (XI) was obtained following the
procedure described in [14]. Yield 72%, mp 240–
1
242°C; published data [21]: mp 243–244°C. H NMR
spectrum, δ, ppm: 6.24 s (1H, CH), 7.07 d (2H, o-H,
J = 8.2 Hz), 7.23–7.38 m (6H, m-H, 6-H, 8-H), 7.54 t
(2H, 7-H, J = 7.6 Hz), 7.84 d (2H, 5-H, J = 8.2 Hz).
4-(4-Chlorophenyl)-5-(4-hydroxy-2-oxo-2H-
chromen-3-yl)-1,3-dimethyl-2,3-dihydro-1H-imida-
zol-2-one (IVl). Yield 45%, mp 259–260°C. IR spec-
trum, ν, cm–1: 1710 (C=O, lactone), 1675 (C=O,
This study was performed under financial support
by the State Foundation for Basic Research of Ukraine
(project no. F 25.3/032, contract no. F25/728-2007,
September 3, 2007).
1
amide), 1608 (C=C). H NMR spectrum, δ, ppm:
2.98 s (3H, CH3), 3.12 s (3H, CH3), 7.25 d (2H, m-H,
J = 8.6 Hz), 7.33–7.41 m (4H, o-H, 6-H, 8-H), 7.66 t
(1H, 7-H, J = 7.2 Hz), 7.81 d (1H, 5-H, J = 7.4 Hz),
12.03 br.s (1H, OH). Found, %: C 62.60; H 3.90;
N 7.41. C20H15ClN2O4. Calculated, %: C 62.75;
H 3.95; N 7.32.
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