Multicomponent Synthesis of Thiazole, Selenazole, Pyrane, and Pyridine Derivatives, Initiated by the Knoevenagel Reaction

Article abstract of DOI:10.1134/S1070428019020131

(2E,2′E)-3,3′-(Propane-1,3-diyl)bis[oxy(4,1-phenylene)]bis[2-(4-aryl-1,3-thiazol-2-yl)acrylonitriles] and functionally substituted pyridines and fused pyrans containing a 3-[1,3-thi(selen)azol-2-yl]-substituent were synthesized by multicomponent condensations initiated by the Knoevenagel reaction. The structures of 2-amino-5-oxo-4-(1-phenylethyl)-4,5-dihydropyrano[3,2-c]chromene-3-carbonitrile and 2-amino-7-hexyloxy-4-cyclohexyl-4H-chromene-3-carborutrile were studied by X-ray diffraction analysis.

Full text of DOI:10.1134/S1070428019020131

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2019, Vol. 55, No. 2, pp. 215–226. © Pleiades Publishing, Ltd., 2019.
Russian Text © I.V. Dyachenko, V.D. Dyachenko, P.V. Dorovatovskii, V.N. Khrustalev, V.G. Nenaidenko, 2019, published in Zhurnal Organicheskoi Khimii,
2019, Vol. 55, No. 2, pp. 266–278.
Multicomponent Synthesis of Thiazole, Selenazole, Pyrane,
and Pyridine Derivatives, Initiated by the Knoevenagel Reaction
I. V. Dyachenkoa, V. D. Dyachenkoa, P. V. Dorovatovskiib,
V. N. Khrustalevb,c, and V. G. Nenaidenkod,*
a Taras Shevchenko Lugansk National University, Oboronnaya ul. 2, Lugansk, 91011 Ukraine
b Kurchatov Institute National Research Center, ul. Akad. Kurchatova 1, Moscow, 123182 Russia
c Russian Peoples Friendship University, ul. Miklukho-Maklaya 6, Moscow, 117198 Russia
d Lomonosov Moscow State University, Leninskie Gory 1, Stroenie 3, Moscow, 119991, Russia
*e-mail: nenajdenko@gmail.com
Received June 1, 2018; revised June 16, 2018; accepted August 14, 2018
Abstract—(2Е,2'Е)-3,3'-(Propane-1,3-diyl)bis[oxy(4,1-phenylene)]bis[2-(4-aryl-1,3-thiazol-2-yl)acrylonitriles]
and functionally substituted pyridines and fused pyrans containing a 3-[1,3-thi(selen)azol-2-yl]-substituent
were synthesized by multicomponent condensations initiated by the Knoevenagel reaction. The structures of 2-
amino-5-oxo-4-(1-phenylethyl)-4,5-dihydropyrano[3,2-c]chromene-3-carbonitrile and 2-amino-7-hexyloxy-4-
cyclohexyl-4H-chromene-3-carbonitrile were studied by X-ray diffraction analysis.
Keywords: thiazole, selenazole, pyran, pyridine, Knoevenagel reaction, X-ray structural analysis
DOI: 10.1134/S1070428019020131
Thiazole, pyran and pyridine derivatives are
widespread in nature, which explains the continuing
interest of researchers to these heterocycles. Among
synthetic substituted thiazole, compounds with
antitumor [1, 2], antiviral [3], and bactericidal [4]
properties were found. Some pyran derivatives are
effective drugs for treating cancer (caspase activators
and apoptosis inductors) [5] and neurogenerative
diseases [6].
successfully occurs in DMF at 20°С in the presence of
10% aqueous NaOH and involves intermediate
formation of Knoevenagel alkene А which then
converts into Hantzsch thiazole В. The latter is readily
alkylated with allyl bromide 4 under Williamson ether
synthesis conditions to form ether 5 (Scheme 1).
The use in this multicomponent condensation of
aromatic aldehydes 1a and 1b, phenacyl bromides 3b
and 3c, and 1,3-dibromopropane 6 allows, other
conditions being equal, synthesis of (2Е,2'Е)-3,3'-
(propane-1,3-diyl)bis[(oxy(4,1-phenylene)]bis[2-(4-
aryl-1,3-thiazol-2-yl)acrylonitriles] 7а–7с. Thus, all
reaction steps can be performed in one pot, thereby
substantially increasing molecular complexity
(Scheme 2).
Functionalized pyridines can be used to treat
seborrheic dermatitis [7], Alzheimer's disease [8], and
CNS diseases [9]. Proceeding with the research into
multicomponent condensations leading to potentially
biologically active thiazole, pyran, and pyridine
derivative [10–12], in the present work we studied the
multicomponent syntheses of previously unknown
compounds of the above classes of heterocycles,
initiated by the Knoevenagel reaction.
The reaction of 2-phenylpropanal 1с with
cyanothioacetamide 2a and 4-hydroxycoumarin 8 in
DMF in the presence of N-methylmorpholine at 20°С
unexpectedly gave chromene 9. The formation of this
product is likely to include the following steps:
1) Michael addition of СН acid 8 to Knoevenagel
alkene А; 2) intramolecular cyclization of intermediate
С to fused pyran 9 with H2S elimination.
It was shown that the condensation of 4-hydroxy-3-
ethoxy benzaldehyde 1a with cyanothiacetamide 2a, 4-
butylphenacyl bromide 3а, and allyl bromide 4 forms
(Е)-3-[4-(allyloxy)-3-ethoxyphenyl)]-2-[4-(4-butylphe-
nyl)thiazol-2-yl]acrylonitrile 5. The condensation
215

DYACHENKO et al.
216
Scheme 1.
S
NH2
CN
Bu
NH2
NC
CHO
Br
S
O
3a
2a
_H2O
_HBr, _H2O
HO
OEt
OEt
OH
1a
A
Bu
Bu
S
N
S
N
CN
Br
CN
4
OEt
O
OEt
HO
B
5
Scheme 2.
R1
R
R
OH
R
OH
Br
OH
O
_HBr, _H2O
2a
3b, 3c
R1
_H2O
H2N
OHC
N
CN
CN
1a, 1b
S
S
A
B
R1
R1
Br
Br
6
N
N
R
O
S
S
R
CN
CN
O
7a_7c
1, R = OEt (a), Н (b); 3, R1 = 4-MeC6H4 (b), 4-MeOC6H4 (с); 7, R = OEt, R1 = 4-MeC6H4 (a);
R = H, R1 = 4-MeC6H4 (b); R = H, R1 = 4-MeOC6H4 (c).
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MULTICOMPONENT SYNTHESIS OF THIAZOLE, SELENAZOLE, PYRANE, AND PYRIDINE
217
Scheme 3.
OH
O
R
S
O
O
O
NH2
2a
8
RCHO
A
C
N
OH
1c, 1d
C
Ph
Me
O
O
Ph
S
O
Ph
S
CN
O
O
NH2
O
NH2
O
NH2
O
NH2
_H2S
_2[H]
N
O
D
9
10
1, R = MeCHPh (c), Ph (d)
The same condensation with benzaldehyde 1d
formed 2,5-dioxo-4-phenyl-3,5-dihydro-2Н-chromeno-
[4,3-b]pyridine-3-carbothioamide 10. Obviously, under
the reaction conditions pyran D has underwent
Dimroth recyclization [13] (Scheme 3).
corresponding regions δ. The geometric isomerism was
determined with account for the data in [19]. Unambi-
guous structural assessment of the multicomponent con-
densation product substituted pyrano[3,2-c]chromene 9
was performed by X-ray diffraction (XRD) analysis.
The reaction of 4-ethoxybenzaldehyde 1е with a
double excess of cyanothioacetamide 2a, equimolar
amount of 3-(2-bromoacetyl)-7-hydroxy-2Н-chromen-
2-one 11, and allyl bromide 4 in DMF in the presence
of 10% aqueous NaOH yields 2-[2-(7-allyloxy-2-oxo-
2Н-chromen-3-yl)-2-oxoethylsulfanyl]-6-amino-4-(4-
ethoxyphenyl)pyridin-3,5-dicarbonitrile 12, a potential
synthon for the synthesis of ring ensembles [14–16].
The reaction scheme includes formation of the
corresponding Knoevenagel alkene А and Michael
addition of cyanothioaceamide 2a to the latter. Thus
formed adduct E chemoselectively cyclizes into
substituted pyridine-2-thiolate F, whose alkylation
with α-bromoketone 11 gives ether G. The subsequent
reaction of ether G with allyl bromine 4 in an alkaline
medium yields Williamson ether 12 (Scheme 4).
Compound 9 includes a system of fused pyran,
pyranone, and benzene rings (Fig. 1). The benzo-
pyranone fragment is nearly planar (the deviation of its
atom from the mean plane is no larger than ±0.011°),
whereas the pyran ring has a flattened boat
conformation with the bend angle along the O1···C4
line of 9.15(11)°. The N2 atom has a trigonal pyramidal
configuration [the sum of bond angles is 354(3)°].
Molecule 9 contains two asymmetric centers at C4
and C12. The crystal of compound 9 is a racemate and
comprises enantiomeric pairs having a rac-(4RS,12RS)
relative configuration of the centers. Molecules 9 form
N–H···N and N-H···O hydrogen-bonded layers parallel
to the (102¯) plane (Table 1, Fig. 2).
We also studied the multicomponent condensation
of aromatic aldehydes 1e–1h, cyanothio(seleno)-
acetamides 2a and 2b, α-bromoketones 3d–3f, and
dimedone 13. This process was performed in DMF at
20°С in the presence of morpholine. This cascade
transformation results in the formation of 2-amino-4-
The structures of all the products were confirmed
1
by spectral methods (see Experimental). The Н NMR
spectra of substituted acrylonitrile 5 contain charac-
teristic signals of the allyl substituent [17, 18] and the
spectra of ethers 7а–7с, propyl proton signals in the
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 55 No. 2 2019

DYACHENKO et al.
218
Scheme 4.
OEt
OEt
OEt
2a
2a
A
NC
S
CN
NC
CN
S
_H2S,
_2[H]
CHO
NH2
H2N
S
H2N
N
1e
E
F
O
O
Br
OH
O
11
OEt
OEt
OH
O
4 / NaOH
NC
CN
S
NC
CN
S
O
O
H2N
N
H2N
N
O
O
O
O
12
G
aryl(hetaryl)-7,7-dimethyl-3-[4-aryl(2-oxo-2H-chro-
men-3-yl)-1,3-thi(selen)azol-2-yl]-7,8-dihydro-4Н-
chromen-5(6Н)-ones 14a–14d. The reaction involves
formation of Knoevenagel alkenes A as intermediates.
After that a Hantzsch reaction occurs to form vinylthi-
(selen)azoles В. Furhter on the latter take up dimedone
13 to give adducts Н which undergo intramolecular
cyclization into final heterocyclic systems 14a–14d
C15
C16
C17
C14
C13
O5
1
C18
C19
(Scheme 5). Their Н NMR spectra display characte-
C12
ristic proton signals of the dimedone fragments with a
typical splitting and a С4Н-proton signals of the pyran
fragment as a singlet at δ 4.46–4.83 ppm [20–23].
C5
C4A
O6
N11
C4
C10B
C11
C3
C2
C6A
The condensation of cyclohexanecarbaldehyde 1i,
cyanothioacetamide 2a, resorcinol 15, and hexyl iodide
16 under the above conditions yields 2-amino-7-
hexyloxy-4-cyclohexyl-4Н-chromene-3-carbonitrile
17, a promising half-product in the design of
antimicrobial drugs Staphylococcus aureas [23]. The
probable cheme condensation scheme involves the
following steps. The first forms a Knoevenagel
product, cyclohexylidenecyanothioaceamide A. The
C7
C8
C10A
C10
O1
N2
C9
Fig. 1. Molecular structure of compound 9 (anisotropic
displacement ellipsoids are drawn at the 50% probability
level).
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 55 No. 2 2019

MULTICOMPONENT SYNTHESIS OF THIAZOLE, SELENAZOLE, PYRANE, AND PYRIDINE
Table 1. Hydrogen bonds in structures 9 and 17.
219
D-H···A
d(D-H), Å
d(H···A), Å
Compound 9
2.155(15)
2.046(16)
Compound 17
2.247(18)
2.38(2)
d(D···A), Å
Angle (DHA), deg
N2-H2A···N11a
N2-H2B···O5b
0.899(15)
0.891(16)
3.0346(17)
2.9219(15)
165.7(13)
167.5(13)
N2-H2A···N9c
N2-H2B···N9d
C6-H6···O7a
0.915(18)
0.92(2)
0.95
3.1275(19)
3.195(2)
3.413(2)
161.3(15)
148.1(17)
170.0
2.47
Symmetry codes:
–x, -y+1, –z+1;
–x+1, y-1/2, –z+3/2;
–x, –y, –z;
a
b
c
d
x+1, y, z.
subsequent Michael addition of resorcinol 15 to alkene
A to form adduct I which undergoes chemoselective
intramolecular heterocyclization into substituted pyran
K, and the latter reacts by Williamson with hexyl
iodide 16, yielding ether 17 (Scheme 5).
17 has a flattened boat conformation with the bend
angle along the O1···C4 line of 11.98(12)°. The N2
angle has a trigonal bipyramidal configuration [the
sum of bond angles is 352(4)°]. The hexyloxy
substituent is in a completely transoid (“linear”)
conformation.
Molecule 17 has one asymmetric center at C4. The
crystal of compound 17 is a racemate. Molecules 17
form N–H···N and C–H···O hydrogen-bonded layers
parallel to the (011¯) plane (Table 1, Fig. 4).
For unambiguous structural assessment of the
product of the considered multicomponent condensation,
we performed an XRD analysis of the molecular and
crystal structure of compound 17 (Figs. 3 and 4). The
pyran ring of the benzopyran fragment in compound
Fig. 2. Crystal structure of compound 9.
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DYACHENKO et al.
220
Scheme 5.
HO
OH
CN
2a, 2b
15
A
RCHO
1e_1i
HO
OH
S
NH2
I
3d_3f
_H2S
O
B
Me
O
Me
13
CN
R1
O
R
N
HO
O
NH2
K
X
Me
Me
C
N
OH
Me
I
H
16
R1
O
R
O
N
CN
X
Me
NH2
Me
O
O
NH2
Me
14a_14d
17
1, R = thiophen-2-yl (f), 4-BrC6H4 (g), 2-furyl (h), cyclohexyl (i); 2, X = Se (b); 3, R1 = coumarin-3-yl (d), Ph (e);
4-PhC6H4 (f); 14, R = 4-EtOC6H4, R1 = coumarin-3-yl, X = S (a); R = 4-BrC6H4, R1 = Ph, X = Se (b); R = 2-furyl,
R1 = 4-PhC6H4, X = Se (c); R = thiophen-2-yl, R1 = 4-PhC6H4, X = Se (d).
C12
C11
Thus, we have demonstrated the possibility of the
multicomponent synthesis of heterocycles by reactions
initiated by the Knoevenagel condensation.
C13
C14
C15
C10
C4
C5
EXPERIMENTAL
C9
N9
C6
C4A
C3
C7
The unit cell parameters and reflection intensities
for compounds 9 and 17 were measured on a Rayonix
SX165 CCD two-coordinate detector (T 100 K, λ
0.96990 Å, φ scanning with a 1.0 deg increment) at the
Belok synchrotron station, Kurchatov Institute
National Research Center. Experimental data were
processed using the iMosflm program from the CCP4
program suite [24]. The principal crystallographic data
and refinement parameters are listed in Table 2.
Absorption was included using the Scala program
[25].
C2
O7
C8A
C8
O1
N2
C16
C17
C20
C18
C19
C21
Fig. 3. Molecular structure of compound 17 (anisotropic
displacement ellipsoids are drawn at the 50% probability
level).
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MULTICOMPONENT SYNTHESIS OF THIAZOLE, SELENAZOLE, PYRANE, AND PYRIDINE
221
Fig. 4. Crystal structure of compound 17.
The structures were solved by direct methods and
refined by full-matrix least squares on F2 with aniso-
tropic displacement parameters for non-hydrogen
atoms. The hydrogen atoms of amino groups were
revealed by difference Fourier synthesis and refined
isotropically with fixed displacement parameters [Uiso(H) =
1.2Ueq(N)[. The other hydrogen atoms were placed in
geometrically calculated positions and refined riding
on their carrier atoms with isotropic displacement
parameters [Uiso(H) = 1.5Ueq(C) for CH3 groups and
Uiso(H) = 1.2Ueq(C) for the other groups]. All calcula-
tions were performed using the SHELXTL program
suite [26]. The tabulated atomic coordinates, bond
lengths, bond and torsion angles, and anisotropic
displacement parameters for compounds 9 and 17 are
deposited at the Cambridge Crystallographic Data
Center [CCDC 1862036 (9) and CCDC 1862037 (17)].
needle voltage was 3.5 kV, and the capillary
temperature was 275°С. The mass spectra were
registered in the positive (PI) and negative ion modes
with a resolution of 480000. The 2DMSO+Н+ cation
(m/z 157.03515) and dodecyl sulfate anion (m/z
265.14789) were used as internal calibrants for the
positive and negative ion modes, respectively. The
mass spectra of the other compounds were measured
on an Agilent LS/MSDLS system (matrix CH3COOH,
electron ionization at 70 eV). Elemental analysis was
performed on a Perkin Elmer CHN analyzer. The
melting points were measured on a Kofler hot stage.
The reaction progress and purity of the synthesized
compounds were monitored by TLC on Silufol UV-
254 in an acetone–hexane (3 : 5) solvent system with
development in iodine vapor and UV light.
(E)-3-(4-Allyloxy-3-ethoxyphenyl)-2-[4-(4-butyl-
phenyl)-1,3-thiazol-2-yl]acrylonitrile (5). Morpho-
line, 3 drops, was added to a stirred solution of 1.7 g
(10 mmol) 4-hydroxy-3-ethoxybenzaldehyde 1a and
1.0 g (10 mmol) cyanothioaceamide 2a in 25 mL of
DMF at 20°С. The resulting mixture was stirred for 1 h,
after which 2.6 g (10 mmol) of 4-butylphenacyl bromide
3a was added. After 3-h stirring, 4.0 mL (10 mmol) of
10% aqueous NaOH and 0.85 mL (10 mmol) of allyl
bromide 4 were added in succession, and the mixture
was stirred for 1 h, left to stand for a day, and then
diluted by half with water. The precipitate that formed
The IR spectra were obtained on an IKS-40
instrument in mineral oil. The 1H and 13C NMR spectra
were measured on a Varian VXR–400 spectrometer
(399.97 and 100 МHz, respectively) in DMSO-d6
solutions, internal standard TMS. The mass spectra of
compounds 6, 7с, 9, and 17 were obtained on a
Thermo Scientific Orbitrap Elite hybrid mass
spectrometer. The samples for high-resolution mass
spectrometry were dissolved in 1 mL of DMSO,
diluted 100 times with 1% HCOOH in CH3CN, and
infused to an ESI source at 40 µL/min. The spray
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DYACHENKO et al.
222
Table 2. Crystallographic data for compounds 9 and 17.
Parameter
9
C21H16N2O3
344.36
17
C22H30N2O2
354.48
Brutto formula
Molecular weight
Crystal dimensions, mm
0.10 × 0.10 × 0.30
Monoclinic
P21/c
0.02 × 0.10 × 0.10
Triclinic
P-1
Syngony
Space groups
a, A
8.3001(17)
15.000(3)
13.930(3)
90
6.4301(13)
9.1002(18)
17.580(4)
87.26(3)
82.39(3)
76.04(3)
989.4(4)
2
b, A
c, A
α, deg
β, deg
99.76(3)
90
γ, deg
V, A3
1709.2(6)
4
Z
dc, g/cm–3
1.338
1.190
F(000)
720
384
μ, mm–1
0.190
0.156
2θmax, deg
76.86
71.66
Measured reflections
Unique reflections (Rint)
Reflections with I > 2σ(I)
Refined parameters
R1; wR2 [for reflections with I > 2σ(I)]
R1; wR2 (for all measured reflections)
GOF on F2
15269
14541
3390 (0.053)
2820
3205 (0.061)
2834
243
244
0.042; 0.112
0.052; 0.120
1.096
0.047; 0.130
0.052; 0.134
1.096
Extinction coefficient
0.014(2)
0.940; 0.970
0.021(2)
0.975; 0.990
T
min; Tmax
was filtered off, washed with water, ethanol, and
Нarom, J 8.6 Hz), 7.26 d (2Н, Нarom, J 7.9 Hz), 7.64 d
(1Н, Нarom, J 8.6 Hz), 7.73 s (1Н, Нarom), 7.90 d (2Н,
hexane. Yield 3.2 g (72%), yellow powder, mp 63–64°С
1
(МеOH). IR spectrum, ν, cm–1: 2202 (С≡N). Н NMR
Н
arom, J 7.9 Hz), 8.12 s (1Н, Н5thiazole), 8.21 s (1Н,
spectrum, δ, ppm: 0.89 t (3H, Ме, J 7.3 Hz), 1.21–1.26
m (2Н, СН2), 1.32 t (3H, Ме, J 6.8 Hz), 1.50–1.64 m
(2Н, СН2), 2.59 t (2H, СН2, J 7.7 Hz), 4.08 q (2H,
ОСН2Ме, J 6.8 Hz), 4.67 d (2H, ОСН2СН=, J 5.0 Hz),
5.27 d (1Н, =СН2, Jcis 10.52 Hz), 5.41 d (1Н, =СН2,
Jtrans 17.3 Hz), 5.91–6.17 m (1Н, СН=), 7.14 d (1Н,
СН=ССN). 13С NMR spectrum, δ, ppm: 14.2, 15.1,
33.5, 35.1, 64.3, 69.3, 96.8, 102.0, 113.8, 114.2, 115.0,
117.6, 118.5, 125.1, 125.7, 126.6 (2С), 129.2 (2С),
131.5, 133.7, 143.3, 145.5, 148.2, 151.6, 156.3, 163.9.
HRMS (ESI), m/z: found 445.1944 [M + Н]+.
C27H28N2O2S. Calculated 445.1871.
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MULTICOMPONENT SYNTHESIS OF THIAZOLE, SELENAZOLE, PYRANE, AND PYRIDINE
223
Substituted acrylonitriles 7a–7c were synthesized
in the same way from aromatic aldehydes 1a and 1b,
and 0.5 mL (5 mmol) of 1,3-dibromopropane 6.
1.33 mL (10 mmol) of 2-phenylpropanal 1c, 1.6 g
(10 mmol) of 4-hydroxycoumarin 8, 1 g (10 mmol) of
cyanothioaceamide 2a, and 1.1 mL (10 mmol) of N-
methylmorpholine in 30 mL of DMF was stirred at
20°С for a day and lest to stand for a day. The reaction
mixture was diluted by half with water and left to stand
for 2 days. The precipitate that formed was filtered off
and successively washed with water, ethanol, and
hexane. Yield 2.6 g (75%), colorless crystals, mp 219–
221°С (i-PrOH). IR spectrum, ν, cm–1: 3488, 3252,
3196 (NH2), 2210 (С≡N), 1719 (С=О), 1643 (δNH2).
1Н NMR spectrum, δ, ppm: 1.12 d (3Н, Ме, J 7.2 Hz),
3.11–3.19 m (1Н, СНМе), 3.61 d (1Н, Н4, J 3.2 Hz),
7.13–7.25 m (5Н, Нarom), 7.26 br.s (2H, NH2), 7.44 t
(1Н, Нarom, J 7.6 Hz), 7.48 d (1Н, Нarom, J 7.9 Hz), 7.67
t (1Н, Нarom, J 8.2 Hz), 7.74 d (1Н, Нarom, J 7.9 Hz).
13С NMR spectrum, δ, ppm: 14.1, 43.2, 52.7, 104.85,
104.9, 113.4, 117.0, 119.6, 122.5, 126.9, 128.3 (2С),
128.4 (2С), 133.2, 142.8, 152.6, 155.3, 160.6, 161.3,
170.0. HRMS (ESI), m/z: found 343.1088 [M – Н]+.
C21H16N2O3. Calculated 343.1161.
(2Е,2'Е)-3,3'-(Propane-1,3-diyl)bis[oxy(2-ethoxy-
4,1-phenylene)]bis[2-{4-[(4-methylphenyl)phenyl]-
1,3-thiazol-2-yl}acrylonitrile] (7a). Yield 2.9 g
(75%), bright yellow powder, mp 192–194°С (АсOH).
IR spectrum, ν, cm–1: 2215 (С≡N). 1Н NMR spectrum,
δ, ppm: 1.38 t (6H, 2Ме, J 6.8 Hz), 2.26 t (2Н, СН2, J
6.0 Hz), 2.36 s (6H, 2Ме), 4.12 q (4Н, 2ОСН2Ме, J
6.8 Hz), 4.31 t (4H, 2СН2О, J 6.0 Hz), 7.22 d (2Н,
Н
arom, J 8.8 Hz), 7.29 d (4Н, Нarom, J 7.7 Hz), 7.68 d
(2Н, Нarom, J 8.8 Hz), 7.75 s (2Н, 2Н5thiazole), 7.91 d
(4Н, Нarom, J 7.7 Hz), 8.12 s (2Н, Нarom), 8.24 s (2Н,
2СН=ССN). Mass spectrum, m/z (Irel, %): 765.7 (100)
[M + 1]+. Found, %: C 70.50; H 5.11; N 7.23.
C45H40N4O4S2. Calculated, %: C 70.66; H 5.27; N
7.32. М 764.9.
(2Е,2'Е)-3,3'-(Propane-1,3-diyl)bis[oxy(4,1-phe-
nylene)]bis[2-{4-[(4-methylphenyl)phenyl]-1,3-
thiazol-2-yl}acrylonitrile] (7b). Yield 2.3 g (68%),
yellow powder, mp 188–190°С (АсOH). IR spectrum,
2,5-Dioxo-4-phenyl-3,5-dihydro-2Н-chromeno-
[4,3-b]pyridine-3-carbothioamide (10) was prepared
similarly to compound 9 from 1.0 mL (10 mmol) of
benzaldehyde 1d. Yield 2.3 g (77%), light yellow
powder, mp 245–247°С (dioxane). IR spectrum, ν, cm–1:
3459, 3316 (NH2), 1719 (С=О), 1634 (δNH2), 1181
(C=S). 1Н NMR spectrum, δ, ppm: 5.12 s (1Н,
Н3pyridine), 6.83 br.s (2H, NH2), 7.16 t (1Н, Нarom, J
1
ν, cm–1: 2200 (С≡N). Н NMR spectrum, δ, ppm: 2.25
t (2H, СН2, J 6.0 Hz), 2.35 s (6H, 2Ме), 4.28 t (4H,
2СН2О, J 6.0 Hz), 7.16 d (4Н, Нarom, J 8.6 Hz), 7.27 d
(4Н, Нarom, J 8.0 Hz), 7.90 d (4Н, Нarom, J 8.0 Hz), 8.04
d (4Н, Нarom, J 8.6 Hz), 8.11 s (2Н, 2Н5thiazole), 8.24 s
(2Н, 2СН=ССN). Mass spectrum, m/z (Irel, %): 677.2
(100) [M + 1]+. Found, %: C 72.61; H 4.65; N 8.15.
C41H32N4O2S2. Calculated, %: C 72.76; H 4.77; N
8.28. М 676.9.
7.1 Hz), 7.23 t (2Н, Нarom, J 7.4 Hz), 7.34 d (2Н, Нarom
J 7.4 Hz), 7.46 t (2Н, Нarom, J 8.4 Hz), 7.70 t (1Н,
arom, J 7.6 Hz), 7.99 d (1Н, Нarom, J 7.6 Hz). 13С NMR
,
Н
(2Е,2'Е)-3,3'-(Propane-1,3-diyl)bis[oxy(2-methoxy-
4,1-phenylene)]bis[2-{4-[(4-methylphenyl)phenyl]-
1,3-thiazol-2-yl}acrylonitrile] (7c). Yield 2.5 g (70%),
yellow powder, mp 173–175°С (BuOH), it fluoresces
under UV irradiation. IR spectrum, ν, cm–1: 2200
spectrum, δ, ppm: 36.7, 97.2, 105.2, 114.2, 116.9,
123.1, 125.2, 127.2, 128.4 (2С), 128.7 (2С), 133.2,
142.8, 152.5, 155.9, 157.3, 160.7, 169.7. Mass
spectrum, m/z (Irel, %): 349.0 [M + 1]+. Found, %: C
65.39; H 3.33; N 7.96. C19H12N2O3S. Calculated, %: C
65.51; H 3.47; N 8.04. М 348.4.
1
(С≡N). Н NMR spectrum, δ, ppm: 2.23 t (2H, СН2, J
6.0 Hz), 3.79 s (6Н, 2МеО), 4.25 t (4H, 2СН2О, J
6.0 Hz), 7.01 d (4Н, Нarom, J 8.8 Hz), 7.15 d (4Н,
2-[2-(7-Allyloxy-2-oxo-2Н-chromen-3-yl)-2-oxo-
ethylsulfanyl]-6-amino-4-(4-ethoxyphenyl)pyridine-
3,5-dicarbonitrile (12). A mixture of 1.4 mL (10 mmol)
of 4-ethoxybenzaldehyde 1e, 2 g (20 mmol) of cyano-
thioaceamide 2a, and 3 drops of N-methylmorpholine
in 30 mL DMF was stirred at 20°С for 30 min, after
which 4.0 mL (10 mmol) of 10% aqueous NaOH and
2.8 g (10 mmol) of 7-hydroxy-3-(2-bromoacetyl)
coumarin 11 were added in succession. The reaction
mixture was stirred for 3 h, left to stand for a day, and
diluted by half with water. The precipitate that formed
was washed with water, ethanol, and hexane. Yield 4.3 g
Нarom, J 8.7 Hz), 7.93 d (4Н, Нarom, J 8.7 Hz), 8.02 d
(4Н, Нarom, J 8.8 Hz), 8.04 s (2Н, 2Н5thiazole), 8.22 s (2Н,
2СН=ССN). 13С NMR spectrum, δ, ppm: 28.8, 55.7
(2С), 65.1 (2С), 102.1 (2С), 113.8 (2С), 114.7 (4С),
115.7 (4С), 117.5 (2С), 125.6 (2С), 126.7 (2С), 128.1 (4С),
132.6 (4С), 145.0 (2С), 155.6 (2С), 160.0 (2С), 161.9
(2С), 163.2 (2С). HRMS (ESI), m/z: found 709.1940
[M + Н]+. C41H32N4O4S2. Calculated 709.1865.
2-Amino-5-oxo-4-(1-phenylethyl)-4,5-dihydropy-
rano[3,2-c]chromene-3-carbonitrile (9). A mixture of
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 55 No. 2 2019

DYACHENKO et al.
224
(80%), yellow powder, mp 243–245°С (BuOH). IR
spectrum, ν, cm–1: 3445, 3318, 3197 (NH2), 2223 sh
(С≡N), 1717, 1695 (С=О), 1644 (δNH2). Н NMR
196.1. Mass spectrum, m/z (Irel, %): 541.2 (100) [M +
1]+. Found, %: C 68.75; H 5.14; N 5.80. C31H28N2O5S.
Calculated, %: C 68.87; H 5.22; N 5.93. М 540.6.
1
spectrum, δ, ppm: 1.38 t (3Н, Ме, J 6.8 Hz), 4.12 q
(2Н, ОСН2Ме, J 6.8 Hz), 4.68–4.74 m (4H, SCH2 +
OCH2CH=), 5.32 d (1Н, =СН2, Jcis 10.6 Hz), 5.45 d (1Н,
=СН2, Jtrans 17.3 Hz), 6.01–6.15 m (1Н, СН=СН2),
7.03–7.16 m (4Н, Нarom), 7.50 d (2Н, Нarom, J 8.4 Hz),
7.83 br.s (2H, NH2), 7.93 d (1Н, Нarom, J 8.4 Hz), 8.67
s (1Н, Н4coumarin). 13С NMR spectrum, δ, ppm: 15.1,
41.0, 63.8, 69.7, 86.3, 93.7, 101.6, 112.7, 114.4, 115.0
(2С), 115.9, 116.1, 118.9, 120.2, 126.1, 130.7 (2С),
132.9, 133.1, 149.0, 157.7, 158.4, 159.6, 160.0, 160.7,
164.4, 166.5, 190.0. Mass spectrum, m/z (Irel, %):
539.0 [M + 1]+. Found, %: C 64.52; H 3.97; N 10.32.
C29H22N4O5S. Calculated, %: C 64.67; H 4.12; N
10.40. М 538.6.
2-Amino-4-(4-bromophenyl)-7,7-dimethyl-3-(4-
phenyl-1,3-selenazol-2-yl)-7,8-dihydro-4Н-chromen-
5(6Н)-one (14b). Yield 4.4 g (79%), yellow powder,
mp 115–117°С (EtOH). IR spectrum, ν, cm–1: 3200–
1
3455 (NH2), 1657 (С=О), 1619 (δNH2). Н NMR
spectrum (CHCl3), δ, ppm: 0.96 s (3Н, Ме), 1.12 s
2
(3Н, Ме), 2.20 d (1Н, С8Н2, J 16.4 Hz), 2.27 d (1Н,
2
С8Н2, J 16.4 Hz), 2.47 s (2Н, С6Н2), 4.66 s (1Н,
Н4pyran), 6.75 br.s (2H, NH2), 7.25–7.48 m (7Н, Нarom),
7.75 s (1Н, Н5selenazole), 7.80 d (2Н, Нarom, J 7.3 Hz). 13С
NMR spectrum, δ, ppm: 26.8, 29.1, 32.3, 50.4, 84.8,
91.3, 114.2, 115.0, 120.0, 126.6 (2С), 128.1, 129.2
(2С), 131.0 (2С), 131.3 (2С), 135.5, 144.0, 152.4,
154.1, 162.2, 162.8, 173.6, 196.2. Mass spectrum, m/z
(Irel, %): 555.0 (100) [M + 1]+. Found, %: C 56.22; H
4.05; N 4.93. C26H23BrN2O2Se. Calculated, %: C
56.34; H 4.18; N 5.05. М 554.4.
2-Amino-4-aryl(hetaryl)-7,7-dimethyl-3-[4-aryl-
(coumarin-3-yl)-1,3-thi(selen)azol-2-yl]-7,8-dihydro-
4Н-chromen-5(6Н)-ones (14a–14d) (general proce-
dure). Morpholine, 3 drops, was added to a stirred
mixture of 10 mmol of aldehyde 1e–1h and cyanothio-
(seleno)acetamide 2a and 2b in 30 mL DMF (with
compound 2b, under argon) at 20°С. The resulting
mixture was stirred for 30 min, after which 10 mmol of
α-bromoketone 3d–3f was added. After 2-h stirring,
1.4 g (10 mmol) of dimedone 13 and 0.87 mL (10 mmol)
of morpholine were added, stirring was continued for
an additional 1 h, and the mixture was left to stand for
a day, diluted by half with water, and left to stand for
2 days. The precipitate that formed was filtered off and
washed with water, ethanol, and hexane.
2-Amino-3-[4-(4-phenylphenyl)-1,3-selenazol-2-
yl]-4-(furan-2-yl)-7,7-dimethyl-7,8-dihydro-4Н-
chromen-5(6Н)-one (14c). Yield 4.2 g (78%), dark red
powder, mp 183–185°С (dioxane). IR spectrum, ν, cm–1:
3222–3450 (NH2), 1655 (С=О), 1623 (δNH2). 1Н
NMR spectrum, δ, ppm: 0.96 s (3Н, Ме), 1.07 s (3Н,
2
Ме), 2.18 d (1Н, С8Н2, J 16.1 Hz), 2.34 d (1Н, С8Н2,
2J 16.1 Hz), 2.52 d (1Н, С6Н2, 2J 17.6 Hz), 2.60 d (1Н,
2
С6Н2, J 17.6 Hz), 4.63 s (1Н, Н4pyran), 6.21 s (1Н,
Н3furan), 6.28 s (1Н, Н4furan), 7.37 t (1Н, Нarom, J 6.8 Hz),
7.42 s (1Н, Н5selenazole), 7.47 t (2Н, Нarom, J 7.44 Hz),
7.72 t (4Н, Нarom, J 8.6 Hz), 7.95 d (2Н, Нarom, J
8.0 Hz), 8.14 br.s (2H, NH2), 8.26 s (1Н, Н5furan). 13С
NMR spectrum, δ, ppm: 26.8, 29.2, 32.4 (2С), 32.9,
50.4, 82.9, 107.6, 110.8, 112.5, 114.3, 127.0 (4С),
127.1 (2С), 128.0, 129.4 (2С), 134.6, 139.7, 140.1,
142.0, 152.6, 153.7, 155.3, 163.3, 173.7, 195.9. Mass
spectrum, m/z (Irel, %): 543.2 (100) [M+1]+. Found, %:
C 66.33; H 4.70; N 4.97. C30H26N2O3Se. Calculated,
%: C 66.42; H 4.83; N 5.16. М 542.5.
3-[2-(2-Amino-4-(4-ethoxyphenyl)-7,7-dimethyl-
5-oxo-5,6,7,8-tetrahydro-4Н-chromen-3-yl)-1,3-
thiazol-4-yl]-2Н-chromen-2-one (14a). Yield 4.4 g
(82%), bright yellow powder, mp 186–188°С (BuOH).
IR spectrum, ν, cm–1: 3366, 3140, 2977 (NH2), 1708,
1661 (С=О), 1607 (δNH2). 1Н NMR spectrum, δ, ppm:
0.86 s (3Н, Ме), 1.05 s (3Н, Ме), 1.25 t (3Н, Ме, J
2
6.8 Hz), 2.08 d (1Н, С8Н2, J 16.2 Hz), 2.29 d (1Н,
С8Н2, 2J 16.2 Hz), 2.45 d (1Н, С6Н2, 2J 17.6 Hz), 2.59
d (1Н, С6Н2, 2J 17.6 Hz), 3.90 q (2Н, ОСН2, J 6.8 Hz),
4.46 s (1Н, Н4pyran), 6.76 d (2Н, Нarom, J 8.3 Hz), 7.18 d
(2Н, Нarom, J 8.3 Hz), 7.26–7.49 m (2Н, Нarom), 7.58 t
2-Amino-3-[4-(4-phenylphenyl)-1,3-selenazol-2-
yl]-7,7-dimethyl-4-(thiophen-2-yl)-7,8-dihydro-4Н-
chromen-5(6Н)-one (14d). Yield 4.3 g (77%), light
yellow log-like crystals, mp 189–191°С (dioxane). IR
spectrum, ν, cm–1: 3280–3444 (NH2), 1652 (С=О),
(1Н, Нarom, J 7.4 Hz), 7.77–7.95 m (3H, NH2 and
13
Н
arom), 8.03 s (1Н, Н5thiazole), 8.76 s (1Н, Н4coumarin). С
1
NMR spectrum, δ, ppm: 15.2, 26.7, 29.3, 32.3, 36.9,
50.5, 63.3, 82.1, 114.2 (2С), 115.0, 115.5, 115.6, 116.3,
119.7, 120.4, 125.1, 129.4, 129.6 (2С), 132.1, 132.7,
136.6, 139.4, 146.7, 152.7, 157.5, 159.3, 161.8, 168.3,
1621 (δNH2). Н NMR spectrum, δ, ppm: 0.91 s (3Н,
2
Ме), 1.06 s (3Н, Ме), 2.17 d (1Н, С8Н2, J 16.2 Hz),
2
2
2.34 d (1Н, С8Н2, J 16.2 Hz), 2.46 d (1Н, С6Н2, J
17.6 Hz), 2.59 d (1Н, С6Н2, J 17.6 Hz), 4.83 s (1Н,
2
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 55 No. 2 2019

MULTICOMPONENT SYNTHESIS OF THIAZOLE, SELENAZOLE, PYRANE, AND PYRIDINE
225
Н4pyran), 6.84 t (1Н, Н4thiophene, J 4.0 Hz), 6.97 d (1Н,
Н3thiophene, J 3.0 Hz), 7.24 d (1Н, Н5thiophene, J 5.0 Hz),
7.39 t (1Н, Нarom, J 7.3 Hz), 7.48 t (2Н, Нarom, J 7.3 Hz),
7.71 d (2Н, Нarom, J 8.6 Hz), 7.74 d (2Н, Нarom, J 8.6 Hz),
7.96 d (2Н, Нarom, J 8.2 Hz), 8.18 br.s (2H, NH2), 8.26
s (1Н, Н5selenazole). 13С NMR spectrum, δ, ppm: 26.7, 29.2,
32.4, 34.2, 50.4, 85.4, 114.5, 115.3, 125.0, 126.1, 126.9
(3С), 127.0, 127.1, 127.5 (2С), 128.0, 129.4 (3С), 134.2,
139.9, 140.0, 149.2, 152.4, 153.7, 162.4, 173.9, 196.1.
Mass spectrum, m/z (Irel, %): 559.0 (100) [M + 2]+.
Found, %: C 64.49; H 4.62; N 4.93. C30H26N2O2SSe.
Calculated, %: C 64.62; H 4.70; N 5.02. М 557.6.
2. Sanner, M.A., Helal, С.J., and Cooper, C.B., US Patent
no. 6720427, 2004; Ref. Zh., Khim., 2005, no. 05.04-
19O.172P.
3. Bender, W., Betz, U., Kleymann, G., Baumeister, J.,
Eckenberg, P., Fischer, R., Handke-Ergueden, G.,
Hendrix, M., Henninger, K., Jensen, A., Keldenich, J.,
Reefschlöger, J., Schmidf, T., Schneider, U., and
Weber, O., FRG Patent Appl. no. 10210319, 2003; Ref.
Zh., Khim., 2004, no. 04.22-19O.114P.
4. Haap, W., Hölzl, W., Ochs, D., Puchtler, K., and
Schnyder, M., EP Patent Appl. no. 1103180, 2001; Ref.
Zh., Khim., 2001, no. 01.17-19O.327P.
5. Drewe, J.A., Xiong, C.S., and Wang, Y., US Patent
no. 6906203, 2005; Ref. Zh., Khim., 2006, no. 06.14-
19O.57P.
6. Konkay, C.S., Fick, D.B., Cai, S.X., Lan, N.C., and
Keana, J.F.W., US Patent no. 6800657, 2004; Ref. Zh.,
Khim., 2005, no. 05.18-19O.110P.
7. Khekhst, A., Bon, M., Kromer, K.T., and Markus, S.A.,
RF Patent Appl. no. 99108756, 2001; Ref. Zh., Khim.,
2001, no. 01.14-19O.100P.
8. Darvesh, S., Magee, D., Valenta, Z., and Martin, E., US
Patent no. 6436972, 2002; Ref. Zh., Khim., 2003,
no. 03.07-19O.87P.
9. Crooks, P.A., Dull, G.M., Caldwell, W.S., Bhatti, B.S.,
Deo, N.M., and Ravard, A., US Patent no. 6624173,
2003; Ref. Zh., Khim., 2004, no. 04.11-19O.86P.
10. Dyachenko, I.V. and Dyachenko, V.D., Russ. J. Org.
Chem., 2016, vol. 52, p. 32. doi 10.1134/
S1070428016010061
2-Amino-7-(hexyloxy)-4-cyclohexyl-4Н-chrome-
ne-3-carbonitrile (17) was prepared similarly to
compounds 14 from 1.21 mL (10 mmol) of
cyclohexanecarbaldehyde 1i, 1.0 g (10 mmol) of
cyanothioaceamide 2a, 1.1 g (10 mmol) of resorcinol
15, and 1.48 mL (10 mmol) of hexyl iodide 16. Yield
2.5 g (71%), colorless crystals, mp 135–137°С
(АсОН). IR spectrum, ν, cm–1: 3215–3446 (NH2),
2212 (С≡N), 1633 (δNH2). 1Н NMR spectrum, δ, ppm:
0.83 t (3Н, Ме, J 7.1 Hz), 0.87–1.18 m (4Н, Нaliph),
1.22–1.32 m (8Н, Нaliph), 1.49–1.68 m (5Н, Нaliph), 2.44
–2.48 m (2Н, Нaliph), 3.22 d (1Н, Н4pyran, J 3.4 Hz), 3.89
t (2Н, OCН2, J 6.5 Hz), 6.44 s (1Н, С8Н), 6.66 d (1Н,
С6Н, J 8.5 Hz), 6.79 br.s (2H, NH2), 7.02 d (1Н, С5Н,
J 8.5 Hz). 13С NMR spectrum, δ, ppm: 14.4, 22.5 (2С),
25.6 (2С), 26.2, 26.4 (2С), 29.0, 29.4, 31.4, 47.2, 53.0,
68.1, 101.5, 111.4, 115.8, 122.1, 129.6, 151.1, 158.5,
162.7. HRMS (ESI), m/z: found 355.2380 [M + Н]+.
C22H30N2O2. Calculated 355.2307.
11. Dyachenko, I.V. and Dyachenko, V.D., Russ. J. Org.
Chem., 2015, vol. 51, p. 1293. doi 10.1134/
S1070428015090146
12. Dyachenko, V.D. and Pugach, Yu.Yu., Russ. J. Gen.
Chem., 2013, vol. 83, p. 979. doi 10.1134/
S1070363213050162
FUNDING
13. Dimrot, K., Wolf, K., and Kroke, H., J. Lie. Ann. Chem.,
1964, vol. 678, p. 181. doi 10.1002/jlac.19646780119
14. Dyachenko, V.D., Dyachenko, I.V., and Nenaidenko, V.G.,
Russ. Chem. Rev., 2018, vol. 87, p. 1. doi 10.1070/
RCR4760
The work was financially supported by the 5-100
Russian Academic Excellence Project and Russian
Foundation for Basic Research (project nos. 18-53-
06006 Az_a and 16-29-10669 ofi_m). X-ray diffraction
measurements were performed at the Kurchatov
synchrotron radiation source funded by the Ministry of
Education and Science of the Russian Federation
(project identifier RFMEFI61917X0007).
15. Antipin, I.S., Kazymova, M.A., Kuznetsov, M.A.,
Vasilyev, A.V., Ishchenko, M.A., Kiryushkin, A.A.,
Kuznetsova, L.M., Makarenko, S.V., Ostrovskii, V.A.,
Petrov, M.L., Solod, O.V., Trishin, Yu.G., Yakovlev, I.P.,
Nenaidenko, V.G., Beloglazkina, E.K., Beletskaya, I.P.,
Ustynyuk, Yu.A., Solov’ev, P.A., Ivanov, I.V.,
Malina, E.V., Sivova, N.V., Negrebetskii, V.V.,
Baukov, Yu.I., Pozharskaya, N.A., Traven’, V.F.,
Shchekotikhin, A.E., Varlamov, A.V., Borisova T.N.,
Lesina, Yu.A., Krasnokutskaya, E.A., Rogozhni-
kov, S.I., Shurov, S.N., Kustova, T.P., Klyuev, M.V.,
Khelevina, O.G., Stuzhin, P.A., Fedorov, A.Yu.,
Gushchin, A.V., Dodonov, V.A., Kolobov, A.V.,
Plakhtinskii, V.V., Orlov, V.Yu., Kriven’ko, A.P.,
CONFLICT OF INTEREST
The authors declare no conflict of interest.
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RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 55 No. 2 2019

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