Synthesis of nitrogen heterocycles underlain by application of 3-(4-acetyl[phenyl)-2h-coumarin

Article abstract of DOI:10.1134/S1070428013110158

3-(4-Acetylphenyl)-2H-chromen-2-one was obtained from 4- acetylphenyldiazonium chloride in the conditions of Meerwein reaction. Reactions of 3-[4-(2-bromoacetyl)phenyl]-2H-chromen-2-one with pyridine, 4-methylpyridine, quinoline, benzo[f]quinoline, and triphenylphosphine afforded quaternary salts, and with thioacetamide, thiourea, 2-aminopyridine, 2-aminopyrimidine, and 6-aminopurine provided the corresponding derivatives of thiazole, imidazo[1,2-a]pyridine, imidazo[1,2-a]pyrimidine, imidazo[2,1-i] purine. In the reaction of the same bromo derivative with thiosemicarbazide and aromatic aldehydes a thiazole ring is built and the corresponding hydrazones are formed. Pleiades Publishing, Ltd., 2013.

Full text of DOI:10.1134/S1070428013110158

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2013, Vol. 49, No. 11, pp. 1655−1660. © Pleiades Publishing, Ltd., 2013.
Original English Text © O.V. Skripskaya, N.O. Feilo, A.O. Neshchadin, O.V. Elenich, R.Z. Lytvyn, N.D. Obushak, P.I. Yagodinets, 2013, published in Zhurnal
Organicheskoi Khimii, 2013, Vol. 49, No. 11, pp. 1673−1678.
Synthesis of Nitrogen Heterocycles Underlain by Application
of 3-(4-Acetyl[phenyl)-2H-coumarin
O. V. Skripskayaa, N. O. Feiloa, A. O. Neshchadinb, O. V. Elenicha,
R. Z. Lytvynb, N. D. Obushakb, and P. I. Yagodinetsa
aYurii Fed’kovich Chernivtsi National University, Chernivtsi, Ukraine
bIvan Franko Lviv National University, Lviv, 79005 Ukraine
e-mail: obushak@in.lviv.ua
Received June 7, 2013
Abstract—3-(4-Acetylphenyl)-2H-chromen-2-one was obtained from 4-acetylphenyldiazonium chloride in the
conditions of Meerwein reaction. Reactions of 3-[4-(2-bromoacetyl)phenyl]-2H-chromen-2-one with pyridine,
4-methylpyridine, quinoline, benzo[f]quinoline, and triphenylphosphine afforded quaternary salts, and with
thioacetamide, thiourea, 2-aminopyridine, 2-aminopyrimidine, and 6-aminopurine provided the corresponding
derivatives of thiazole, imidazo[1,2-а]pyridine, imidazo[1,2-а]pyrimidine, imidazo[2,1-i]purine. In the reaction
of the same bromo derivative with thiosemicarbazide and aromatic aldehydes a thiazole ring is built and the
corresponding hydrazones are formed.
DOI: 10.1134/S1070428013110158
The interest in the chemistry of coumarins
(2Н-benzopyran-2-ones) is to a large extent due to the
wide range of biological actions exhibited by this class
compounds [1, 2], and also by their applications as laser
dyes and luminescent indicators [3]. In many of these
compounds the coumarin scaffold is combined with a het-
erocyclic or onium fragment. The synthesis of such com-
pounds often utilizes the reactions of 3-(ω-bromo-acetyl)
coumarins with nucleophilic reagents [4–7], substituted
2-hydroxybenzaldehydes with 2-hetaryl-acetonitriles [8],
and also the recyclization of 2-iminocoumarins under the
treatment with binucleophilic reagents [9].
pounds with arenediazonium salts (Meerwein reaction)
[10]. Coumarin (I) reacts with 4-acetylphenyldiazonium
chloride (II) in the presence of copper(II) chloride giv-
ing 3-(4-acetylphenyl)-2H-chromen-2-one (III) in 40%
yield. The bromination of the latter at heating in acetic
acid furnished compound IV (Scheme 1).
3-[4-(2-Bromoacetyl)phenyl]-2H-chromen-2-one
(IV) at heating in toluene with heterocyclic bases (pyri-
dine, 4-methylpyridine, quinoline, benzo[f]quinoline),
and also with triphenylphosphine readily forms quater-
nary salts V–IX (Scheme 2).
At treating the solution of phosphonium salt IX in
DMF with water solution of potassium carbonate tri-
phenylphosphorylide X was formed which at boiling in
In this research we used for the molecular design of
coumarin derivatives the arylation of unsaturated com-
Scheme 1.
O
O
N2Cl
Br
CuCl2
Br
2
+
AcOH
O
O
O
O
O
O
O
IIII
III
IV
II
1655

SKRIPSKAYA et al.
1656
Scheme 2.
R
O
O
N+
Br
N+
_
_
Br
O
O
O
O
V, VI
VII
O
O
+
N+
_
PPh3
_
Br
Br
O
O
O
O
VIII
IX
R = H (V), Me (VI).
Scheme 3.
O
O
O
PPh3
NO
K2CO3
2
IX
NO2
O
O
O
O
XI
X
toluene with 4-nitrobenzaldehyde afforded ketone XI
(Scheme 3).
and the vinyl groups [13]. In the region of 980–990 cm–1
an absorption band is observed originating from the
bending =С–Н vibrations of the trans-substituted vinyl
group [14].
In the IR spectra of salts V–VIII the absorption band
of the carbonyl group of the fragment СОСН2 appears
in the region 1660–1680 cm–1, the vibrations of the С–N
bond give rise to the band at 3400 cm–1 [11], the absorp-
tion band of the carbonyl group of the chromenone ring
is observed in the region 1715–1725 cm–1 [12]. The IR
spectrum of phosphonium salt IX contains the absorption
band of the С=О bond of the oxo group at 1670 cm–1. In
going to phosphorylide X a strong shift to low frequen-
cies occurs in the absorption of this bond, and it appears
as two bands at 1565 and 1605 cm–1. The Р=С bond of
compound X is characterized by two absorption bands
at 1385 and 880 cm–1.
We used the bromoacetyl group of compound IV for
designing nitrogen heterocycles. The attention directed
to the synthesis of compounds containing a coumarin
fragment and nitrogen heterocycles originates from the
presence among them of substances possessing high bio-
logical activity [15, 16]. We investigated cyclocondensa-
tions of 3-[4-(2-bromoacetyl)phenyl]-2H-chromen-2-one
(IV) with thioacetamide, thiourea, 2-aminopyridine,
2-aminopyrimidine, and 6-aminopurine and obtained
derivatives of thiazole XII, XIII, imidazo[1,2-а]pyri-
dine XIV, imidazo[1,2-а]pyrimidine XV, imidazo[2,1-i]
purine XVI (Scheme 4).
The absorption bands in the IR spectrum of compound
XI at 1610 and 1665 cm–1 belong to the stretching vibra-
tions of the aliphatic double bond and of carbonyl group,
respectively. The intensity of the absorption band of the
carbonyl group is considerably less than that of the С=С
bond indicating the mutual s-cis-position of the carbonyl
Bromo derivative IV reacted with thiosemicarbazide
in ethanol at heating with the formation of a thiazole
ring. The subsequent addition to the reaction mixture
of 4-nitro- or 4-dimethylaminobenzaldehyde led to
the formation of compounds XVII, XVIII. The same
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 49 No. 11 2013

SYNTHESIS OF NITROGEN HETEROCYCLES
1657
Scheme 4.
S
R
N
R
NH
2
S
O
O
O
O
XII, XIII
XIV, XV
XVI
X
NH
N
2
N
IV
N
N
X
NH
2
O
O
N
N
N
N
N
N
N
N
R = Me (XII), NH2 (XIII); X = CH (XIV), N (XV).
Scheme 5.
S
H
N
N
H N
2
NHNH
O
2
N
IV
S
O
R
O
R
XVII, XVIII
H
N
H N
2
N
S
R
XIX, XX
R = NO2 (XVII, XIX), NMe2 (XVIII, XX).
compounds were obtained at heating reagent IV with
the thiosemicarbazones of the corresponding aldehydes
XIX, XX (Scheme 5).
(400 MHz) in DMSO-d6, internal reference TMS. Melting
points were measured on Boёtius heating block.
4-Acetylphenyldiazonium chloride (II). A mixture
of 3.8 g (0.028 mol) of 4-aminoacetophenone, 18 mL of
conc. HCl, and 10 mL of water was heated to boiling.
The obtained solution was cooled to 0–5°C and kept
for 5 min. To the formed slurry of aminoacetophenone
hydrochloride at efficient cooling was added dropwise
while stirring 2.4 g (0.034 mol) of NaNO2 in 10 mL of
water. On completing the addition the reaction mixture
was left standing for 15 min in an ice bath. The obtained
solution of diazonium salt was filtered, the filtrate was
The thiazole ring in the IR spectra of compounds XII,
XIII, XVII, XVIII gives rise to the absorption bands at
1535–1560 cm–1.
EXPERIMENTAL
IR spectra were recorded on a spectrophotometer
1
Specord 75IR from pellets with KBr. H NMR spectra
were registered on a spectrometer Varian Mercury 400
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 49 No. 11 2013

SKRIPSKAYA et al.
1658
neutralized by portions of 20–30 mL with saturated
7.41 t (1Н, coumarin, J 7.4 Hz), 7.46 d (1Н, couma-
rin, J 8.2 Hz), 7.67 t (1Н, coumarin, J 7.4 Hz), 7.86 d
(1Н, coumarin, J 7.8 Hz), 8.03 d (2Нarom, J 8.2 Hz),
8.10–8.21 m (4Н), 8.51 s (1Н, coumarin), 8.94 d (2НPy,
J 5.9 Hz). Found, %: С 63.46; Н 4.28; N 3.47.
C23H18BrNO3. Calculated, %: С 63.32; Н 4.16; N 3.21.
sodium acetate solution to pH 6.
3-(4-Acetylphenyl)-2H-chromen-2-one (III). To
a mixture of 4.1 g (0.028 mol) of coumarin I, 0.36 g
(2.1 mol) of CuCl2·2H2O, and 35 mL of acetone
was added at stirring dropwise a cooled solution of
4-acetylphenyldiazonium chloride at a rate 1–2 drop per
second. After the end of nitrogen liberation (~2 h) the
formed precipitate was filtered off, washed with water,
dried, and recrystallized from a mixture ethanol–DMF.
Yield 2.96 g (40%), mp 225–227°C. 1H NMR spectrum,
δ, ppm: 2.62 s (3H, CH3), 7.36–7.47 m (2HHt), 7.66 t
1-{2-Oxo-2-[4-(2-oxo-2H-chromen-3-yl)-phenyl]
ethyl}quinolinium bromide (VII). Yield 0.34 g
1
(71%), mp 248–250°С (aqueous ethanol). Н NMR
spectrum, δ, ppm: 7.09 с (2Н, СН2), 7.44 t (1Н, cou-
marin, J 7.4 Hz), 7.50 d (1Н, coumarin, J 8.2 Hz),
7.70 t (1Н, coumarin, J 7.4 Hz), 7.89 d (1Н, coumarin,
J 7.8 Hz), 8.05–8.09 m (3Нarom), 8.23–8.28 m (3Нarom),
8.36 d.d (1Нquin., J 8.2, 5.9 Hz), 8.49–8.52 m (2Нarom),
8.58 d (1Нquin, J 8.2 Hz), 9.48 d (1Нquin, J 8.2 Hz),
9.58 d (1Нquin, J 5.9 Hz). Found, %: С 66.41; Н 3.72;
N 3.11. C26H18BrNO3. Calculated, %: С 66.12; Н 3.84;
N 2.97.
(1HHt, J 8.2 Hz), 7.81 d (1ÍHt, J 7.6 Hz), 7.89 d (2Harom
,
J 8.2 Hz), 8.04 d (2Harom, J 8.2 Hz), 8.38 s (1HHt).
Found, %: C 77.08; H 4.31. C17H12O3. Calculated, %:
C 77.26; H 4.58.
3-[4-(2-Bromoacetyl)phenyl]-2H-chromen-2-one
(IV). To a solution of 2.64 g (0.01 mol) of reagent III in
120 mL of acetic acid at 85–90°С was added dropwise
0.52 mL (0.01 mol) of bromine. Then the solution was
cooled, the crystalline precipitate was filtered off, washed
with water, dried, and recrystallized from aqueous DMF.
Yield 2.61 g (76%), mp 175–177°С. 1H NMR spectrum,
δ, ppm: 5.64 s (2Н, СН2), 7.40 t (1НHt, J 7.4 Hz), 7.45 d
(1НHt, J 8.2 Hz), 7.65 t (1НHt, J 7.4 Hz), 7.81 d (1НHt,
4-{2-Oxo-2-[4-(2-oxo-2H-chromen-3-yl)-phenyl]
ethyl}benzo[f]quinolinium bromide (VIII). Yield
1
0.45 g (86%), mp 204–206°С (CH3СООН). Н NMR
spectrum, δ, ppm: 7.18 s (2Н, СН2), 7.42 t (1Н, cou-
marin, J 7.4 Hz), 7.47 d (1Н, coumarin, J 8.2 Hz),
7.67 t (1Н, coumarin, J 7.8 Hz), 7.86 d (1Н, coumarin,
J 7.0 Hz), 7.97 t (1Н, С13H9N, J 7.4 Hz), 8.01–8.08 m
(3Нarom), 8.24–8.29 m (3Нarom), 8.35 d (1Н, С13H9N,
J 8.6 Hz), 8.47–8.51 m (2Нarom), 8.63 d (1Н, С13H9N,
J 8.6 Hz), 9.15 d (1Н, С13H9N, J 7.4 Hz), 9.57 br.s (1Н,
С13H9N), 10.26 d (1Н, С13H9N, J 6.7 Hz). Found, %:
С 69.20; Н 4.10; N 2.81. C30H20BrNO3. Calculated, %:
С 68.98; Н 3.86; N 2.68.
J 7.4 Hz), 7.96 d (2Нarom, J 8.6 Hz), 8.05 d (2Нarom
,
J 8.6 Hz), 8.40 s (1НHt). Found, %: С 59.63; Н 3.38;
Br 23.05. C17H11BrO3. Calculated, %: С 59.50; Н 3.23;
Br 23.28.
Quaternary salts V–IX. A mixture of equimolar
amounts (1 mmol) of compound IV and an appropriate
heterocyclic base (or triphenylphosphine) was boiled in
15–20 mL of anhydrous toluene for 1–1.5 h. The formed
precipitates of salts V–IX were filtered off and dried.
{2-Oxo-2-[4-(2-oxo-2H-chromen-3-yl)phenyl]-eth-
yl}triphenylphosphonium bromide (IX). Yield 0.58 g
(95%), mp 163–165°С (ethanol). 1Н NMR spectrum, δ,
ppm: 6.39 d (2Н, JPH 12.9 Hz), 7.40 t (1Н, coumarin,
J 7.4 Hz), 7.44 d (1Н, coumarin, J 8.2 Hz), 7.64 t (1Н,
coumarin, J 7.0 Hz), 7.78–8.03 m (17Нarom), 8.20 d
(2Н, С6Н4, J 8.2 Hz), 8.47 s (1Н, coumarin). Found, %:
С 69.25; Н 4.12. C35H26BrO3Р. Calculated, %: С 69.43;
Н 4.33.
1-{2-Oxo-2-[4-(2-oxo-2H-chromen-3-yl)phenyl]
ethyl}pyridinium bromide (V). Yield 0.37 g (88%), mp
>262°С (CH3СООН). 1Н NMR spectrum, δ, ppm: 6.59 s
(2Н, СН2), 7.44 t (1Н, coumarin, J 7.4 Hz), 7.49 d (1Н,
coumarin, J 8.2 Hz), 7.69 t (1Н, coumarin, J 7.4 Hz),
7.87 d (1Н, coumarin, J 7.0 Hz), 8.05 d (2Нarom, J 8.2 Hz),
8.17 d (2Нarom, J 8.2 Hz), 8.32 t (2НPy, J 6.7 Hz),
8.51 s (1Н, coumarin), 8.77 t (1НPy, J 7.4 Hz), 9.08 d
(2НPy, J 5.9 Hz). Found, %: С 62.69; Н 4.03; N 3.41.
C22H16BrNO3. Calculated, %: С 62.58; Н 3.82; N 3.32.
1-[4-(2-Oxo-2H-chromen-3-yl)phenyl]-2-triphenyl-
λ5-phosphanylidene-1-ethanone (X). To a solution of
0.6 g (1 mmol) of phosphonium salt IX in 15 mLof DMF
was added at stirring 25 mL of 10% water solution of
K2СО3. The formed precipitate was filtered off, washed
with water, and dried. Yield 0.42 g (81%), mp 192–194°С
(toluene). 1Н NMR spectrum, δ, ppm: 7.37–7.47 m (3Н),
7.78–8.03 m (15Н), 7.81 d (2Н, J 7.8 Hz), 7.89 d (1Н,
4-Methyl-1-{2-oxo-2-[4-(2-oxo-2H-chromen-3-yl)
phenyl]ethyl}pyridinium bromide (VI). Yield 0.40
1
g (92%), mp 260–262ºС (toluene–С2Н5ОН). Н NMR
spectrum, δ, ppm: 2.68 s (3Н, СН3), 6.57 s (2Н, СН2),
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 49 No. 11 2013

SYNTHESIS OF NITROGEN HETEROCYCLES
1659
J 7.8 Hz), 7.96 d (2Н, J 7.4 Hz), 8.03 d (1Н, J 7.4 Hz),
8.30 s (1Н, coumarin). Found, %: С 80.31; Н 4.67.
C35H25O3Р. Calculated, %: С 80.14; Н 4.80.
8.63 d (1Н, imidazopyridine, J 6.7 Hz). Found, %:
C 77.84; Н 3.92; N 8.25. C22H14N2O2. Calculated, %:
C 78.09; Н 4.17; N 8.28.
3-(4-Nitrophenyl)-1-[4-(2-oxo-2H-chromen-3-yl)
phenyl]prop-2-en-1-one (XI). To a solution of 0.26 g
(0.5 mmol) of compound X in 20 mL of anhydrous
toluene was added 0.08 g (0.5 mmol) of 4-nitrobenz-
aldehyde, and the mixture was boiled for 2 h. The formed
precipitate was filtered off, washed with ether. Yield
3-(4-Imidazo[1,2-a]pyrimidin-2-ylphenyl)-2H-
chromen-2-one (XV). Yield 0.24 g (71%), mp 166–
168°С (aqueous DMF). Н NMR spectrum, δ, ppm:
7.40–7.47 m (2Н), 7.66 t (1Н, coumarin, J 7.4 Hz),
7.81 d (1Н, coumarin, J 6.7 Hz), 7.88 t (1Н, coumarin,
J 7.8 Hz), 7.93–8.17 m (6Н), 8.41–8.46 m (2Н). Found,
%: C 74.15; Н 3.81; N 12.56. C21H13N3O2. Calculated,
%: C 74.33; Н 3.86; N 12.38.
1
1
0.15 g (75%), mp >260°С (DMF). H NMR spectrum,
δ, ppm: 7.43 t (1Н, coumarin, J 7.8 Hz), 7.49 d (1Н,
coumarin, J 8.2 Hz), 7.68 t (1Н, coumarin, J 7.4 Hz),
7.85 d (1Н, coumarin, J 7.8 Hz), 7.88 d (1Н, СН,
J 15.7 Hz), 7.98 d (2Н, С6Н4, J 8.2 Hz), 8.19–8.33 m
(6Нarom + 1НСН), 8.46 s (1Н, coumarin). Found, %:
C 72.38; Н 3.59; N 3.76. C24H15NO5. Calculated, %:
C 72.54; Н 3.80; N 3.52.
3-{4-(1H-Imidazo[2,1-i]purin-8-yl)phenyl}-
2H-chromen-2-one (XVI). Yield 0.33 g (87%), mp
218–221°С (precipitated by water from DMF). 1Н NMR
spectrum, δ, ppm: 7.42–7.49 m (2Н), 7.68 t (1Н, cou-
marin, J 7.4 Hz), 7.81–8.22 m (8Н), 8.37 s (1Н), 8.46 s
(1Н, coumarin). Found, %: C 69.56; Н 3.27; N 18.22.
C22H13N5O2. Calculated, %: C 69.65; Н 3.45; N 18.46.
Heterocyclic derivatives XII–XVI. General proce-
dure. To 0.34 g (1 mmol) of bromoketone IV in 15 mL of
ethanol was added an equimolar quantity of an appropri-
ate reagent (thioacetamide, thiourea, 2-aminopyridine,
2-aminopyrimidine, 6-aminopurine). The reaction mix-
ture was boiled for 1 h. The precipitate was filtered off,
washed with ether.
4-Nitrobenzaldehyde {4-[4-(2-oxo-2H-chromen-3-
yl)phenyl]thiazol-2-yl}hydrazone (XVII). Amixture of
0.68 g (2 mmol) of compound IV, 0.18 g (2 mmol) of
thiosemicarbazide in 50 mL of anhydrous ethanol was
boiled for 10 min. To the reaction mixture 0.3 g (2 mmol)
of 4-nitrobenzaldehyde was added, and the mixture was
boiled for another 15 min. The formed precipitate was
filtered off, washed with ether. Yield 0.87 g (93%), mp
3-[4-(2-Methyl-1,3-thiazol-4-yl)phenyl]-2H-
chromen-2-one (XII). Yield 0.29 g (91%), mp 228–
230°С (aqueous DMF). 1Н NMR spectrum, δ, ppm: 2.74 s
(3Н, СН3), 7.39 t (1Н, coumarin, J 7.4 Hz), 7.45 d (1Н,
coumarin, J 8.2 Hz), 7.63 t (1Н, coumarin, J 7.8 Hz),
7.79–7.84 m (3Н), 8.01–8.05 m (3Нarom), 8.34 s (1Н, cou-
marin). Found, %: C 71.29; Н 4.18; N 4.14. C19H13NO2S.
Calculated, %: C 71.45; Н 4.10; N 4.39.
1
>260°С (precipitation by water from DMF). Н NMR
spectrum, δ, ppm: 7.37 t (1Н, coumarin, J 7.4 Hz), 7.44 d
(1Н, coumarin, J 8.2 Hz), 7.63 t (1Н, coumarin, J 7.8 Hz),
7.79–7.84 m (2Н), 7.90 d (2Н, С6Н4, J 8.2 Hz), 8.04 d
(2Н, С6Н4, J 8.2 Hz), 8.11 d (2Н, С6Н4NO2, J 8.8 Hz),
8.21 d (2Н, С6Н4NO2, J 8.8 Hz), 8.28 s (1Н, CH), 8.38 s
(1Н, coumarin), 11.72 s (1Н, NH). Found, %: C 64.24;
Н 3.61; N 11.78. C25H16N4O4S. Calculated, %: C 64.09;
Н 3.44; N 11.96.
3-[4-(2-Amino-1,3-thiazol-4-yl)phenyl]-2H-chro-
men-2-one (XIII). Yield 0.26 g (81%), mp 256–258°С
(aqueous DMF). 1Н NMR spectrum, δ, ppm: 7.12 s (1Н,
thiazole), 7.16 br.s (2Н, NН2), 7.37 t (1Н, coumarin,
J 7.4 Hz), 7.43 d (1Н, coumarin, J 8.2 Hz), 7.61 t (1Н,
coumarin, J 7.4 Hz), 7.74–7.80 m (3Н, Ar), 7.88 d (2Н,
С6Н4, J 8.2 Hz), 8.29 s (1Н, coumarin). Found, %:
C 67.37; Н 3.61; N 8.42. C18H12N2O2S. Calculated, %:
C 67.48; Н 3.78; N 8.74.
4-Dimethylaminobenzaldehyde {4-[4-(2-oxo-2H-
chromen-3-yl)phenyl]thiazole-2-yl}hydrazone (XVIII)
was obtained similarly. Yield 0.6 g (64%), mp >260°С
(precipitation by water from DMF). 1Н NMR spectrum,
δ, ppm: 2.95 s (6Н, СН3), 6.73 d (2Н, С6Н4, J 8.6 Hz),
7.36–7.99 m (12Н), 8.31–8.35 m (1Н), 11.63 s (1Н, NH).
Found, %: C 69.27; Н 4.60; N 11.87. C27H22N4O2S. Cal-
culated, %: C 69.51; Н 4.75; N 12.01.
3-(4-Imidazo[1,2-a]pyridin-2-ylphenyl)-2H-chro-
men-2-one (XIV). Yield 0.22 g (65%), mp 229–231°С
(aqueous DMF). 1Н NMR spectrum, δ, ppm: 7.05 t (1Н,
imidazopyridine, J 6.7 Hz), 7.38–7.47 m (3Н), 7.64 t (1Н,
J 7.0 Hz), 7.69 d (1Н, J 9.0 Hz), 7.81 d (1Н, J 7.8 Hz),
7.88 d (2Н, С6Н4, J 8.2 Hz), 8.07 d (2Н, С6Н4, J 8.2 Hz),
8.36 s (1Н, coumarin), 8.58 s (1Н, imidazopyridine),
ACKNOWLEDGMENTS
The study was carried out under the financial support
by the State Foundation for Fundamental Research of
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 49 No. 11 2013

SKRIPSKAYA et al.
no. 3, p. 52; Kovalenko, S.N., Orlenko, I.V., Vlasov, S.V.,
1660
Ukraine (grant no. F54.3/004).
and Chernykh, V.P., Zh. Org. Farm. Fhim., 2005, vol. 3,
no, 4, p. 30; Belokon’, Ya.V., Kovalenko, S.N., Silin,A.V.,
and Nikitchenko, V.M., Khim. Geterotsikl. Soedin., 1997,
p. 1345.
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