Synthesis of 2-(4′-morpholin-4″-yl-5-chromeno-[2,3-d]pyrimidin- 2′-yl)phenol from salicylaldehyde and substituted acrylonitriles

Article abstract of DOI:10.1134/S1070363212050209

The synthesis of 2-(4′-morpholin-4″-yl-5-chromeno[2,3-d] pyrimidin-2′-yl)phenol was performed via the reaction of salicylaldehyde with the substituted acrylonitriles. Its structure was confirmed by the X-ray analysis.

Full text of DOI:10.1134/S1070363212050209

ISSN 1070-3632, Russian Journal of General Chemistry, 2012, Vol. 82, No. 5, pp. 921–926. © Pleiades Publishing, Ltd., 2012.
Original Russian Text © V.D. Dyachenko, Yu.Yu. Pugach, 2012, published in Zhurnal Obshchei Khimii, 2012, Vol. 82, No. 5, pp. 844–849.
Synthesis of 2-(4'-Morpholin-4''-yl-5Н-chromeno-
[2,3-d]pyrimidin-2'-yl)phenol from Salicylaldehyde
and Substituted Acrylonitriles
V. D. Dyachenko and Yu. Yu. Pugach
Taras Shevchenko Lugansk National University, ul. Oboronnaya, 2, Lugansk, 91011 Ukraine
e-mail: dvd_lug@online.lg.ua
Received March 10, 2011
Abstract—The synthesis of 2-(4'-morpholin-4''-yl-5Н-chromeno[2,3-d]pyrimidin-2′-yl)phenol was performed
via the reaction of salicylaldehyde with the substituted acrylonitriles. Its structure was confirmed by the X-ray
analysis.
DOI: 10.1134/S1070363212050209
Some of the fused pyrimidine derivatives are biolo-
gically active compounds. In particular, they exhibit
anticancer, antimicrobial, anticoagulation [1–3], neuro-
protective [4], antiviral [5] and fungicidal [6] activity.
In this regard, developing simple and efficient
synthetic approach to the compounds of this class is
promising.
In this work we studied the condensation of
salicylaldehyde Ia with cyclohexylidene malononitrile
Scheme 1.
_
O
O
+
CN
IІ, III
O
NC CN
OH
NC CN
OH
а
CN
OH
OH
Iа
V
VI
VII
O
Ph
EtO
NC
b
c
_PhCHO
_EtOH
NC
CN
XI
CN
XII
O
O
N
O
N
N
III
Iа
_H2O
CN
NH
N
OH
N
OH
O
N
NH
NH
O
O
N
O
IX
IV
X
VIII
921

922
DYACHENKO, PUGACH
Table 1. Bond lengths (Å) in structure IV
II and morpholine III at 20°C in ethanol resulting in 2-
(4'-morpholin-4''-yl-5Н-chromeno[2,3-d]pyrimidin-2'-
yl)phenol (method a, Scheme 1). Compound IV has
been obtained earlier via the three-component
condensation of salicylaldehyde, malonodinitrile and
morpholine in ethanol in the presence of LiClO4 [7], as
well as under microwave irradiation using the same
reagents at 100°C for 3–6 min [8].
Bond
A
B
O1–C9
O1–C6
O2–C13
O3–C19
O3–C20
N1–C9
N1–C10
N2–C10
N2–C11
N3–C11
N3–C21
N3–C18
C1–C2
1.358(3)
1.381(3)
1.341(4)
1.407(4)
1.411(3)
1.332(3)
1.333(3)
1.327(3)
1.342(3)
1.384(3)
1.457(3)
1.468(3)
1.376(4)
1.384(3)
1.495(3)
1.380(4)
1.371(4)
1.368(4)
1.382(3)
1.500(3)
1.385(3)
1.412(3)
1.476(4)
1.394(4)
1.408(4)
1.375(4)
1.367(5)
1.373(5)
1.378(4)
1.473(4)
1.445(4)
1.361(3)
1.392(3)
1.343(3)
1.418(4)
1.398(3)
1.331(3)
1.337(3)
1.335(3)
1.345(3)
1.368(3)
1.450(3)
1.465(3)
1.384(4)
1.386(4)
1.500(3)
1.378(4)
1.374(4)
1.366(4)
1.383(4)
1.508(4)
1.385(3)
1.409(3)
1.478(4)
1.402(4)
1.396(3)
1.375(4)
1.361(4)
1.377(4)
1.371(4)
1.485(4)
1.505(4)
The formation of heterocyclic ring system IV
proceeds probably through the forming adduct V and
oxetane VI. The latter is converted into alkene VII
with cyclohexanone elimination followed by the intra-
molecular cyclization into 2-iminobenzopyran VIII.
Further a nucleophilic addition occurs of morpholine
to the nitrile group and the formation of derivative IX,
which reacts with salicylaldehyde Ia to give a tricyclic
system X. Under the reaction conditions the latter
undergoes a prototropic tautomerisation with the aro-
matization of the pyrimidine ring to afford heterocyclic
system IV. The replacement of cyclohexylidene
malononitrile II with benzalmalononitrile XI (method
b) or with ethoxymethylene malononitrile XII (method
c) does not change the condensation direction:
compound IV is formed. The reaction proceeds ap-
parently similar to that in the method a.
C1–C6
C1–C7
C2–C3
C3–C4
C4–C5
C5–C6
C7–C8
C8–C9
C8–C11
C10–C12
C12–C17
C12–C13
C13–C14
C14–C15
C15–C16
C16–C17
C18–C19
C20–C21
The structure of compound IV was established by
the X-ray diffraction analysis (see the figure, Tables
1, 2). The symmetrically independent part of the unit
cell contains two molecules A and B of compound IV.
They differ by the 4H-pyran ring conformation and the
orientation of the morpholine moiety relative to the
tricyclic fragment. In the molecule A the pyran ring is
flat, while in the molecule B this ring has a flattened
boat conformation with a deviation of the O1 and C7
atoms from the plane of other atoms in the ring by
0.117(4) and 0.142(4) Å respectively. The nitrogen
atom N3 of morpholine ring in both molecules have a
pyramidal conformation [sum of the bond angles
centered on the atom are 350.6(2) and 355.1(2)° in the
A and B molecules, respectively]. In the A molecule
the tricyclic fragment (N3–C11 bond) has an equatorial
orientation relative to the morpholine ring, and in the B
molecule, axial orientation [torsion angle C19C18N3C11
is 162.6(3)° in the A molecule and –103.0(3)° in the B
molecule). A lesser degree of the N3 atom pyramidality
in the B molecule results in a shorter N3–C11 bond,
1.368(3) Å [in the A molecule this bond length is
1.384(3) Å]. In both molecules there is a much
General view of the molecule of IV according to the X-ray
diffraction data.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 82 No. 5 2012

SYNTHESIS OF 2-(4'-MORPHOLIN-4''-YL-5Н-CHROMENO[2,3-d]PYRIMIDIN-2'-YL)PHENOL
923
shortened intramolecular C21–H···H–C7 contact {1.88 Å
Table 2. Bond angles (deg) in structure IV
(A), 1.99 Å (B), the sum of the van der Waals radii is
Angle
А
В
2.32 Å [9]}. The resulting steric strain is compensated
by the conjugation between the lone electrons pair of
the N3 atom and π-system of the pyridine ring [torsion
angle LpN3N3C11C8 –65° (A), –59° (B), where LpN3 is
an idealized location of the lone electrons pair of the
N3 atom]. Apparently, the difference in the relative
orientation of the tricyclic fragment of morpholine ring
causes the 4H-pyran ring nonplanarity in the B
molecule. The high conformational flexibility of the
heterocycle [10], especially in the polycyclic systems
[11], can reduce the steric strain in the molecule due to
the ring bending, as evidenced by the significantly
greater C21–H···H–C7 distance in the B molecule.
C9O1C6
119.75(19)
109.3(2)
115.7(2)
118.3(2)
123.9(2)
117.0(2)
109.7(2)
117.1(2)
121.1(2)
121.7(2)
121.5(3)
120.1(3)
119.8(3)
119.4(3)
116.3(2)
121.7(2)
122.0(3)
113.0(2)
113.7(2)
120.0(2)
126.3(2)
110.7(2)
125.4(2)
123.9(2)
125.2(2)
117.2(2)
117.6(2)
114.2(2)
121.7(2)
124.1(2)
118.0(3)
119.7(3)
122.2(3)
117.6(3)
122.5(3)
119.9(3)
121.2(3)
119.7(3)
120.5(4)
120.7(3)
111.6(3)
113.9(3)
113.6(3)
113.2(3)
118.85(19)
109.4(2)
116.0(2)
117.9(2)
124.5(2)
119.9(2)
110.7(2)
117.2(2)
121.5(2)
121.2(3)
121.6(3)
119.7(3)
120.3(3)
119.5(3)
116.4(2)
121.9(2)
121.8(3)
112.3(2)
114.0(2)
120.2(2)
125.4(2)
111.4(2)
125.1(2)
123.5(2)
124.9(2)
117.2(2)
117.9(2)
115.3(2)
121.9(2)
122.6(2)
117.8(3)
122.4(3)
119.9(2)
116.4(3)
122.9(3)
120.7(3)
120.4(3)
120.5(3)
119.9(3)
120.8(3)
111.7(3)
110.9(3)
113.0(3)
109.7(3)
C19O3C20
C9N1C10
C10N2C11
C11N3C21
C11N3C18
C21N3C18
C2C1C6
C2C1C7
C6C1C7
C1C2C3
C4C3C2
C5C4C3
C4C5C6
O1C6C5
O1C6C1
C5C6C1
C1C7C8
C9C8C11
C9C8C7
o-Hydroxyphenyl moiety is virtually coplanar with
the pyrimidine ring [the torsion angle N1C10C12C13 is –
4.6(4)° and 6. (4)° in molecules A and B, respectively]
due to the formation of intramolecular hydrogen O2–
H···N1 bond [H···N 1.86 (A), 1.87 Å (B), O–H···N
147°]. In this regard, there is also some shortening of
the C13–O2 bond to 1.341(4) (A) and 1.343(3) Å (B)
compared with the average value (1.36 Å) [12].
The quantum chemical calculations of the isolated
A and B molecules by a B3LYP/def2-TZVP method
revealed that both orientations of the morpholine
substituent in the molecule of IV correspond to
minima on the potential energy surface. In general, the
geometric parameters of the molecules obtained from
the calculations are close to those observed in the
crystal. However, in both conformers of the isolated
compound IV there is a significant and almost equal
flattening of the 4H-pyran ring – the deviations of the
O1 and C7 atoms from the plane of the remaining ring
atoms are 0.18 and 0.23 Å, respectively. The mor-
pholine moiety orientation does not essentially differ
from that found experimentally (the sum of bond
angles centered on the N1 atom differ by less than 3°,
and torsion angles LpN3N3C11C8 by less than 15°),
which also leads to the formation of the greatly
shortened C21–H···H–C7 contacts in the A conformer
(2.00 Å) and B conformer (1.96 Å). Thus, we can
conclude that the 4H-pyran ring flattening and the
formation of the strongly shortened H···N contacts are
due the intramolecular interactions rather than the
packing effects in the crystal. According to the
calculations the A conformer is more preferable by
0.24 J mol–1.
C11C8C7
N1C9O1
N1C9C8
O1C9C8
N2C10N1
N2C10C12
N1C10C12
N2C11N3
N2C11C8
N3C11C8
C17C12C13
C17C12C10
C13C12C10
O2C13C14
O2C13C12
C14C13C12
C15C14C13
C14C15C16
C15C16C17
C16C17C12
N3C18C19
O3C19C18
O3C20C21
C20C21N3
In the crystal the molecules form AB type dimers
due to the stacking interactions between the tricyclic
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 82 No. 5 2012

924
DYACHENKO, PUGACH
systems (the shortest C9A···C2B' distance [1 – x, 0.5 + y,
0.5 – z] is 3.35 Å, the angle between the planes of the
pyrimidine and benzene rings is 12°). The adjacent
dimers are linked by the C–H···π hydrogen bonds
C16A–H···C4A' [–1 + x, 0.5 – y, 0.5 + z] (H···C 2.86 Å,
C–H···C 15°).
compound XIVa with p-chlorophenacyl bromide XVI
in DMF at 20°C results in the Hantzsch thiazole XVII
(method a), which is synthesized also in the reaction of
saliylcylaldehyde Ia with CH-acid XIII (method b). In
the reaction the corresponding Knoevenagel adduct
XIX probably forms, which undergoes the intra-
molecular cyclization into substituted 3-[4'-(4''-chloro-
The condensation of o-hydroxy substituted aro-
matic aldehydes Ia, Ib with CH-acids XIIa, XIIb in
ethanol at 20°C in the presence of morpholine III is
completed at the stage of the formation of coumarin
derivatives XIVa, XIVb. The reaction occurs probably
via the formation of product XV of Knoevenagel
condensation followed by the intramolecular acylation
to give chromene system XIV. The condensation of
phenyl)thiazol-2'-yl]-2H-chromen-2-one
XVII
(Scheme 2).
The condensation of salicylaldehyde Ia with cyano-
selenoacetamide XX under Knoevenagel reaction
conditions did not stop at the stage of the formation of
corresponding alkene XXI, and the pyran ring closure
proceeds to give 2-oxo-2H-chromeno-3-carboselen-
Scheme 2.
R1
NH2
S
NH2
Se
R1
NH2
S
R
R
_EtOH or
H2O
OH R2
O
OH
O
Y
N
XIVа, XIVb
Cl
XXI
XV
NH2
Se
NH2
S
а
_H2O
III,
CN
_H2O,
XX
R2
O
Br
_H2O
_HBr
XIIIа, XIIIb
O
XVI
R1
NH2
Se
Cl
R
O
N
Cl
OH
O
NH
S
Iа, Ib
XXII
III,
O
O
Ph
б
S
XVII
N
Ph
b
а
N
O
_H2O,
_NH3
_HBr,
S
_H2O
_H2S,
_NH3
Se
_H2O
Br
XXIII
NH2
XVIII
CN
XXVI
Cl
N
Ph
N
Ph
N
H2O/H+
_NH3
S
Se
Se
OH H2N
XIX
S
O
O
O
NH
XXIV
XXV
I, R = R1 = H (a), R = R1 = CH=CH–CH=CH (b); XIII, R2 = OEt (a), NH2 (b); XIV, R = R1 = H, Y = O (a), R = R1 = CH=CH–
CH=CH, Y = NH (b).
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SYNTHESIS OF 2-(4'-MORPHOLIN-4''-YL-5Н-CHROMENO[2,3-d]PYRIMIDIN-2'-YL)PHENOL
925
amide XXII. The latter enters easily into the Hantzsch
condensation with phenacyl bromide XXIII in DMF at
20°C to form the corresponding 3-selenazolyl-sub-
stituted 2-iminocoumarin XXIV. We failed to be
identify the latter due to its rapid hydrolysis under the
reaction conditions to give 3-(4-phenyl-1,3-selenazol-
2-yl)-2H-chromen-2-one XXV (method a). It is also
formed by the condensation of salicylaldehyde Ia with
a substituted selenazole XXVI (method b).
2-(4'-Morpholin-4''-yl-5H-chromeno[2,3-d]pyri-
midin-2'-yl)phenol (IV). a. A mixture of 2.14 ml
(20 mmol) of salicylaldehyde Ia, 0.87 ml (10 mmol) of
morpholine IІІ, and 1.46 g (10 mmol) of cyclo-
hexylidene malonitrile II in 20 ml of ethanol at 20°C
was stirred for 1 h and left standing for 48 h. The
resulting precipitate was filtered off, washed with
ethanol and hexane. Yield 2.6 g (72%), yellow
crystals, mp 205–208°C (EtOH) (210°C [8]). IR spec-
1
trum, ν, cm–1: 3445 (OH). H NMR spectrum, δ, ppm:
EXPERIMENTAL
3.52 t (4Н, СН2NCH2, J 4.0 Hz), 3.80 t (4Н,
СН2ОСН2, J 4.0 Hz), 4.01 s (2Н, СН2), 6.93 t (2Н,
НAr, J 8.0 Hz), 7.11–7.20 m (2Н, НAr), 7.27 t (1Н, НAr,
J 8.0 Hz), 7.33–7.41 m (2Н, НAr), 8.27 d (1Н, НAr, J
8.0 Hz), 13.11 br. s (1Н, OH). 13С NMR spectrum, δС,
ppm: 24.99, 48.01, 65.88, 97.56, 116.24, 117.30,
117.99, 118.78, 119.82, 124.52, 128.05, 128.59,
128.96, 132.84, 159.69, 160.49, 163.98. Mass spec-
trum, m/z (Irel, %): 361 (100) [M]+, 304 (28), 275 (14),
248 (5), 155 (11), 128 (13), 86 (24) [morpholinyl]+.
Found, %: C 69.68; H 5.24; N 11.52. C21H19N3O3.
Calculated, %: C 69.79; H 5.30; N 11.63.
The crystals of IV are monoclinic, C21H19N3O3, at
298 K: a 17.9785(6), b 9.9722(4), c 20.5412(7) Å, β
106.126(4)°, V 3537.8(2) Å3, M 361.39, Z 8, space
group P21/c, dcalc 1.36 g cm–3, μ(MoKα) 0.093 mm–1,
F(000) 1520. The unit cell parameters and intensities
of 33782 reflections (6217 independent, Rint 0.049)
were measured on a Xcalibur 3 four-circle automatic
diffractometer (MoKα, graphite monochromator, CCD-
detector, ω-scanning, 2θmax 50°).
The structure of IV was solved by the direct
method using SHELX-97 software [13]. The positions
of hydrogen atoms were found from a difference
synthesis of electron density and refined by a rider
model with Uiso = nUeq of the carrier atom (n = 1.5 for
the hydroxy groups and n = 1.2 for the remaining
hydrogen atoms). The structure was refined with
respect to F2 by the full-matrix least-squares method in
the anisotropic approximation for the non-hydrogen
atoms to wR2 0.172 for 6217 reflections (R1 0.056 for
3633 reflections with F > 4σ(F), S 1.03). The bond
lengths and angles are given in Tables 1 and 2.
b. Similarly to the method a using 1.54 g (10 mmol)
of compound IX. Yield 2.78 g (77%).
c. Similarly to the method a using 1.5 g (10 mmol)
of compound XII. Yield 2.67 g (74%).
2-Oxo-2H-chromene-3-carbothioamide (XIVa).
A mixture of 1.1 ml (10 mmol) of salicylaldehyde Ia
and 1.47 g (10 mmol) of CH-acid XIIIa in 15 ml of
DMF at 20°C was stirred for 5 h, kept for 48 h, diluted
with 10% hydrochloric acid to pH 5, and allowed to
stand for 1 day. The resulting precipitate was filtered
off, washed with ethanol and hexane. Yield 1.58 g
(77%), mp 242–244°C (AcOH) (240°C [15]). Mass
spectrum, m/z (Irel, %): 205 (82) [M]+, 172 (100) [M –
SH]+, 88 (15), 63 (12), 45 (4), 39 (7). When CH-acid
XIIIb was used instead of compound XIIIa, the yield
was 1.46 g (71%).
The optimization of the geometrical parameters of
the isolated conformers by a B3LYP/def2-TZVP
method was performed using an Orca 2.8.0 program
package [14].
The melting points were determined on a Koeffler
block. The IR spectra were obtained on a FIR
Spectrum One (Perkin-Elmer) instrument from KBr
pellets. The 1H and 13C NMR spectra were recorded on
a Bruker Avance II 400 instrument (399.9601 MHz) in
DMSO-d6 relative to internal TMS. The mass spectra
were registered on a MX-1321 spectrometer (70 eV)
using the direct injection of a sample into the ion
source. The reaction progress and the compounds
purity were monitored by the TLC method on Silufol
UV-254 plates eluting with an acetone–hexane mixture
(3:5) and detecting with iodine vapor and UV
irradiation.
3-Imino-3H-benzo[f]chromene-2-carbothioamide
(XIVb). A mixture of 1.72 g (10 mmol) of β-hyd-
roxynaphthalene-3-carbaldehyde Ib, 1.47 g (10 mmol)
of CH-acid XIIIa and 3 drops of morpholine III in
20 ml of ethanol was stirred for 3 h and kept for 1 day.
The resulting precipitate was filtered off, washed with
ethanol and hexane. Yield 8.2 g (82%), mp 183–184°C
1
(DMF). IR spectrum, ν, cm–1: 3290, 3341 (NH). H
NMR spectrum, δ, ppm: 7.41 d (1Н, НAr, J 7.9 Hz),
7.52 t (1Н, НAr, J 8.2 Hz), 7.71 t (1Н, НAr, J 8.2 Hz),
7.99 d (1Н, НAr, J 8.1 Hz), 8.14 d (1Н, НAr, J 7.9 Hz),
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 82 No. 5 2012

926
DYACHENKO, PUGACH
8.29 d (1Н, НAr, J 8.1 Hz), 9.21 s (1Н, С4Н), 9.55 s
and 10.41 s (2Н, NH2), 11.72 br. s (1Н, NH). Found,
%: С 66.01; Н 3.84; N 10.95. С14Н10N2ОS. Calculated,
%: С 66.12; Н 3.96; N 11.02.
8.79 s (1Н, С5Нselenazole), 9.09 s (1Н, С4Н). Found, %:
С 61.22; Н 3.03; N 3.81. С18Н11N2ОSе. Calculated, %:
С 61.38; Н 3.15; N 3.98.
b. A mixture of 2.5 g (10 mmol) of the substituted
selenazole XXVI, 1.07 ml (10 mmol) of salicyl-
aldehyde Ia in 15 ml of DMF was stirred for 3 h under
argon and diluted with an equal volume of water. The
resulting precipitate was filtered off, washed with
water, ethanol, and hexane. Yield 2.64 g (75%).
3-[4'-(4''-Chlorophenyl)thiazol-2'-yl]-2H-chromen-
2-one (XVII). a. A mixture of 2.05 g (10 mmol) of the
substituted coumarin XIVa and 2.33 g (10 mmol) of p-
chlorophenacyl bromide XVI in 15 ml of DMF was
stirred for 3 h and diluted with an equal volume of
water. The resulting precipitate was filtered off,
washed with ethanol and hexane. Yield 2.78 g (82%),
mp 208–212°C (AcOH). IR spectrum, ν, cm–1: 1718
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1. Bilov, І.E., Kovalenko, S.M., and Chernikh, V.P.,
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(C=O). H NMR spectrum, δ, ppm: 7.46 t (1Н, НAr, J
8.0 Hz), 7.55 m (3Н, НAr), 7.72 t (1Н, НAr, J 8.0 Hz),
8.04 d (1Н, НAr, J 8.0 Hz), 8.15 d (2Н, НAr, J 8.02 Hz),
8.38 s (1Н, С5Нthiazole), 9.14 s (1Н, С4Н). Mass spec-
trum, m/z (Irel, %): 339 (100) [М]+, 275 (8), 168 (81),
133 (42), 89 (24). Found, %: С 63.52; Н 2.85; N 4.01.
С18Н10ClNО2S. Calculated, %: С 63.63; Н 2.97; N 4.12.
b. A mixture of 1.07 ml (10 mmol) of sali-
cylaldehyde Ia and 2.7 g (10 mmol) of the substituted
thiazole XVIII and 0.87 ml (10 mmol) of morpholine
III in 20 ml of ethanol was stirred at 20°C for 5 h and
kept for 48 h. The resulting precipitate was filtered off,
washed with ethanol and hexane. Yield 2.3 g (68%).
5. Nasr, M.N. and Gineinah, M.M., Arch. Pharm. Pharm.
Med. Chem., 2002, vol. 335, no. 6, p. 289.
6. Papalardo, M.S., Vittorio, F., Pasquinucci, L., and
2-Imino-2H-chromene-2-carboselenoamide (XXII).
A mixture of 7.1 ml (10 mmol) of salicylaldehyde Ia,
1.47 g (10 mmol) of cyanoselenoacetamide XX, and
1 drop of N-methylmorpholine in 15 ml of anhydrous
ethanol was stirred for 1 h under argon. After 1 day the
formed precipitate was filtered off, washed with
ethanol and hexane. Yield 1.9 g (75%), mp 125–127°C
(EtOH). IR spectrum, ν, cm–1: 3315–3411 (NH, NH2).
1H NMR spectrum, δ, ppm: 6.96–8.00 m (4Н, НAr),
8.42 s (1Н, С4Н), 11.21 br.s and 10.14 br.s (1Н, NH2),
12.37 br. s (1Н, NH). Found, %: С 48.01; Н 3.50; N
10.89. С10Н8N2ОSе. Calculated, %: С 47.82; Н 3.31;
N 11.15.
Bousquet, E., Farmaco, 1989, vol. 44, p. 483.
7. Ghahremanzadeh, R., Amanpour, T., and Bazgir, A.,
Tetrahedron Lett., 2010, vol. 51, no. 31, p. 4202.
8. Zonouzi, A., Biniaz, M., Mirzazadeh, R., Talebi, M.,
and Ng, S.W., Heterocycles, 2010, vol. 81, no. 5, p. 1271.
9. Zefirov, Yu.V. and Zorkii, P.M., Usp. Khim., 1989,
vol. 58, no. 5, p. 713.
10. Shishkin, O.V., J. Mol. Struct., 1997, vol. 412, no. 3,
p. 115.
11. Shishkin, O.V., Kovalevskii, A.Yu., and Dekaprile-
vich, M.O., Izv. Akad. Nauk, Ser. Khim., 1998, no. 3,
p. 388.
12. Burgi, H.-B. and Dunitz, J.D., Structure Correlation,
3-(4-Phenyl-1,3-selenazol-2-yl)-2H-chromen-2-one
(XXV). a. A mixture of 2.5 g (10 mmol) of compound
XXII and 2.0 g (10 mmol) of phenacyl bromide XXIII
in 15 ml of DMF was stirred for 3 h under argon,
diluted with an equal volume of water, and kept for
48 h. The resulting precipitate was filtered off, washed
with water, ethanol and hexane. Yield 2.53 g (72%),
mp 211–213°C (BuOH). IR spectrum, ν, cm–1: 1719
1994, vol. 2, p. 741.
13. Sheldrick, G., Acta Cryst. (A), 2008, vol. 64, no. 1,
p. 112.
14. Neese, F., Becker, U., Ganyushin, D., Hansen, A.,
Liakos, D.G., Kollmar, C., Kossmann, S., Petrenko, T.,
Reimann, C., Riplinger, C., Sivalingam, K., Valeev, E.,
Wezisla, B., and Wennmohs, F., ORCA 2.8.0,
University of Bonn, Bonn, Germany, 2010.
1
15. Brunskill, J.S.A., De, A., Elagbar, Z., Jeffrey, H., and
(C=O). H NMR spectrum, δ, ppm: 7.29–7.58 m (5Н,
НAr), 7.71 t (1Н, НAr, J 6.95 Hz), 8.04 m (3Н, НAr),
Ewing, D.F., Synth. Commun., 1978, vol. 8, no. 8, p. 533.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 82 No. 5 2012