Multicomponent synthesis of 2-(alkylsulfanyl)-4-[furan-2-yl-(or thiophen-2-yl)]-5,6,7,8-tetrahydroquinoline-3-carbonitriles

Article abstract of DOI:10.1134/S1070428015060081

Abstract Substituted 2-(alkylsulfanyl)-4-[furan-2-yl(or thiophen-2-yl)]-5,6,7,8-tetrahydroquinoline-3-carbonitriles were synthesized by condensation of furfural or thiophene-2-carbaldehyde with 2-cyanoethanethioamide, 1-(cyclohex-1-en-1-yl)pyrrolidine, and alkyl halides. The structure of methyl 2-{[3-cyano-4-(thiophen-2-yl)-5,6,7,8-tetrahydroquinolin-2-yl]sulfanyl}acetate was determined by X-ray analysis.

Full text of DOI:10.1134/S1070428015060081

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2015, Vol. 51, No. 6, pp. 864–868. © Pleiades Publishing, Ltd., 2015.
Original Russian Text © V.D. Dyachenko, V.N. Nesterov, S.V. Dyachenko, A.V. Chernykh, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51,
No. 6, pp. 880–884.
Multicomponent Synthesis of 2-(Alkylsulfanyl)-4-[furan-2-yl-
(or thiophen-2-yl)]-5,6,7,8-tetrahydroquinoline-3-carbonitriles
V. D. Dyachenkoa, V. N. Nesterovb, S. V. Dyachenkoa, and A. V. Chernykhc
a Taras Shevchenko Lugansk National University, ul.Oboronnaya 2, Lugansk, 91011 Ukraine
e-mail: dyachvd@mail.ru
b University of North Texas, 1155 Union Circle #311277, Denton, Texas 76203-5017, USA
c Institute of Organic Chemistry, National Academy of Sciences of Ukraine,
ul. Murmanskaya 5, Kiev, 02660 Ukraine
Received January 14, 2015
Abstract—Substituted 2-(alkylsulfanyl)-4-[furan-2-yl(or thiophen-2-yl)]-5,6,7,8-tetrahydroquinoline-3-carbo-
nitriles were synthesized by condensation of furfural or thiophene-2-carbaldehyde with 2-cyanoethanethio-
amide, 1-(cyclohex-1-en-1-yl)pyrrolidine, and alkyl halides. The structure of methyl 2-{[3-cyano-4-(thiophen-
2-yl)-5,6,7,8-tetrahydroquinolin-2-yl]sulfanyl}acetate was determined by X-ray analysis.
DOI: 10.1134/S1070428015060081
Multicomponent syntheses have become more and
more popular among synthetic organic chemists due to
the possibility of using this methodology for the pre-
paration of both fairly simple compounds and fused
heterocyclic systems [1–3]. Such reactions offer
a number of advantages as compared to multistep syn-
theses, in particular simple experimental procedures,
quantitative yields of the final products, and environ-
mental safety [4, 5]. We previously synthesized in this
way functionalized pyridines [6, 7], spiro 1,4-dihydro-
pyridines [8, 9], and functionally substituted 1,4-di-
hydro-1,6-naphthyridines [10, 11] and pyrido[2,3-d]-
pyrimidine [12].
We now report a multicomponent synthesis of 2-al-
kylsulfanyl-4-[furan-2-yl(or thiophen-2-yl)]-5,6,7,8-
tetrahydroquinoline-3-carbonitriles 1a–1h that are
potential intermediate products for the preparation of
calcium channel blockers [13], eukaryotic elongation
factor-2 kinase (eEF-2K) inhibitors [14], and drugs for
the treatment of atherosclerosis [15], inflammations
[16], and other human diseases [17]. The reaction of
heteroaromatic aldehyde 2a or 2b with 2-cyanoethane-
thioamide (3), 1-(cyclohex-1-en-1-yl)pyrrolidine (4),
and alkyl halides 5a–5g in ethanol at 20°C afforded
substituted 5,6,7,8-tetrahydroquinolines 1a–1h
(Scheme 1). This reaction is likely to involve inter-
mediate formation of 2-cyano-2-[furan-2-yl(or thio-
phen-2-yl)methylidene]ethanethioamide A which
alkylates enamine 4 according to Stork [18], yielding
adduct B. Intramolecular transamination [19] of the
latter gives pyrrolidinium salt C, and the subsequent
alkylation with alkyl halides 5a–5g leads to final
sulfides 1a–1h. When α,ω-dibromoalkanes 6a and 6b
(0.5 equiv) were added instead of alkyl halides 5, the
products were substituted bis(5,6,7,8-tetrahydroquino-
lin-2-ylsulfanyl)alkanes 7a–7c.
The structure of compounds 1a–1h and 7a–7c was
confirmed by spectral data. Their IR spectra contained
an absorption band at 2215–2224 cm–1 due to stretch-
ing vibrations of the conjugated cyano group and
carbonyl band at 1674–1714 cm–1. The number and
position of signals in the 13C NMR spectra of 1a, 1h,
and 7b were consistent with the assumed structures. In
the mass spectra of the synthesized compounds we
observed the molecular ion peaks [M + 1]+. Signals
from protons in the tetramethylene fragment, hetero-
aromatic substituents, and alkyl groups were present in
1
the H NMR spectra. The SCH2 protons characteris-
tically resonated as a singlet at δ 2.60–4.46 ppm [6–9].
The structure of methyl 2-{[3-cyano-4-(thiophen-2-
yl)-5,6,7,8-tetrahydroquinolin-2-yl]sulfanyl}acetate
(1a) was determined by X-ray analysis (see figure).
The planar thiophene ring in molecule 1a is almost
orthogonal to the pyridine ring [the corresponding
864

MULTICOMPONENT SYNTHESIS OF 2-(ALKYLSULFANYL)-4-[FURAN-2-YL-...
865
Scheme 1.
NC
S
NH2
NC
+
+
CHO
2a, 2b
–H2O
X
N
H
NH2
S
X
3
A
X
X
N
CN
4
H
CN
S
H
N
H2N
N
H
S–
N
B
C
X
ZCH2Hlg (5a–5g)
CN
S
–2[H]
N
Z
1a–1h
X
X
Br(CH2)nBr (6a, 6b)
CN NC
( )n
–2[H]
N
S
S
N
7a–7c
1, X = S, Z = COOMe (a), CN (b); X = O, Z = CONH2 (c), cyclopropylcarbonyl (d); X = S, Z = H (e), cyclopropylcarbonyl (f),
Ph (g); X = O, Z = 2-oxochromen-3-ylcarbonyl (h); 2, X = O (a), S (b); 5, Hlg = Cl, Z = COOMe (a), CN (b), CONH2 (c); Hlg = Br,
Z = cyclopropylcarbonyl (d); Hlg = I, Z = H (e); Hlg = Cl, Z = Ph (f); Hlg = Br, Z = 2-oxochromen-3-ylcarbonyl (g); 6, n = 2 (a),
3 (b); 7, X = S, n = 2 (a); X = O, n = 3 (b); X = S, n = 3 (c).
dihedral angle is 88.6(1)°]. The other geometric
parameters of molecule 1a were consistent with refer-
ence values [20].
stage. The progress of reactions and the purity of
products were monitored by TLC on Silufol UV254
plates using acetone–hexane (3:5) as eluent; spots
were developed by treatment with iodine vapor or
under UV light.
EXPERIMENTAL
X-Ray diffraction data for compound 1a.
C17H16N2O2S2 (M 344.44); monoclinic crystal system;
unit cell parameters (at 100 K): a = 10.9844(4), b =
8.8673(4), c = 16.4879(7) Å; β = 91.318(1)°; V =
The IR spectra were recorded in KBr on a Perkin
1
Elmer Spectrum One spectrometer. The H and
13C NMR spectra were measured on a Bruker DRX
500 spectrometer at 499.95 and 125.74 MHz, respec-
tively, using DMSO-d6 as solvent and tetramethyl-
silane as internal standard. The mass spectra were ob-
tained on an Agilent MSDSL mass-selective detector
(electron impact; samples were introduced in a tri-
fluoroacetic acid matrix). The elemental compositions
were determined on a Perkin Elmer CHN analyzer.
The melting points were measured on a Kofler hot
1605.5(1) Å3; space group P21/n; Z = 4; dcalc
=
1.425 g/cm3. Total of 14539 reflection intensities were
measured on a Bruker SMART APEX diffractometer
[21] at 100 K (λMoKα radiation, 2θmax = 54.20°) from
a 0.21×0.19×0.17 mm single crystal of 1a. Averaging
of equivalent reflections left 3509 independent reflec-
tions (Rint = 0.0218) which were used for the structure
solution and refinement. A correction for absorption
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 51 No. 6 2015

DYACHENKO et al.
866
2.8 g (82%), light yellow crystals, mp 124–125°C
C14
S2
C13
C12
(from EtOH) [24]. 13C NMR spectrum, δC, ppm: 21.59,
21.87, 26.50, 32.15, 32.98, 52.38, 104.51, 115.08,
127.82, 128.02, 129.33, 129.86, 133.66, 146.78,
157.04, 161.63, 169.20. Mass spectrum: m/z 345
(Irel 100%) [M + 1]+. Calculated: M 344.457.
C11
C4
N2
C1
2-[(Cyanomethyl)sulfanyl]-4-(thiophen-2-yl)-
5,6,7,8-tetrahydroquinoline-3-carbonitrile (1b).
Yield 2.3 g (75%), yellow powder, mp 158–160°C
(from AcOH). IR spectrum, ν, cm–1: 2222, 2249
C5
C3
C2
C6
C7
C8
C10
C9
S1
C15
O1
1
N1
(C≡N). H NMR spectrum, δ, ppm: 1.51–1.96 m (4H,
CH2), 2.56 t (2H, CH2, J = 5.5 Hz), 2.98 t (2H, CH2,
J = 6.3 Hz), 4.23 s (2H, SCH2), 7.01–7.19 m (2H, 3′-H,
4′-H), 7.77 d (1H, 5′-H, J = 3.7Hz). Mass spectrum:
m/z 312 (Irel 100%) [M + 1]+. Found, %: C 61.65;
H 4.12; N 13.32. C16H13N3S2. Calculated, %: C 61.71;
H 4.21; N 13.49. M 311.431.
C16
O2
C17
Structure of the molecule of methyl 2-{[3-cyano-4-(thio-
phen-2-yl)-5,6,7,8-tetrahydroquinolin-2-yl]sulfanyl}acetate
(1a) according to the X-ray diffraction data.
2-{[3-Cyano-4-(furan-2-yl)-5,6,7,8-tetrahydro-
quinolin-2-yl]sulfanyl}acetamide (1c). Yield 2.1 g
(68%), yellow powder, mp 195–197°C (from
1-BuOH). IR spectrum, ν, cm–1: 3380, 3260, 3205
(μ 0.342 mm–1) was applied, the transmission factors
being determined by SADABS [22], Tmax = 0.944,
Tmin = 0.932. The structure was solved by the direct
method; all non-hydrogen atoms were localized by the
difference syntheses of electron density and were
refined against F2hkl in anisotropic approximation. All
hydrogen atoms were placed into geometrically calcu-
lated positions which were refined according to the
riding model [U(H) = 1.2 or 1.5U(C), where U(C) is
the equivalent temperature factor of the corresponding
carbon atom]. Final divergence factors: R1 = 0.0376
[Fhkl; 3180 reflections with I > 2σ(I)], wR2 = 0.1063
(F2hkl; 3509 reflections); goodness of fit 1.017. All
calculations were performed using SHELXTL software
package [23].
2-(Alkylsulfanyl)-4-hetaryl-5,6,7,8-tetrahydro-
quinolin-3-carbonitriles 1a–1h (general procedure).
Three drops of pyrrolidine were added under stirring at
20°C to a mixture of 10 mmol of aldehyde 2a or 2b
and 1.0 g (10 mmol) of 2-cyanoethanethioamide (3) in
20 mL of ethanol. The mixture was stirred for 15 min,
1.5 g (10 mmol) of enamine 4 was added, the mixture
was stirred for 30 min, a solution of 10 mmol of alkyl
halide 5a–5g in 15 mL of DMF was added, and the
mixture was stirred for 1 h and left to stand for 24 h.
The mixture was then diluted with an equal volume of
water, and the precipitate was filtered off and washed
with water, ethanol, and hexane.
1
(NH2), 2218 (C≡N), 1674 (C=O). H NMR spectrum,
δ, ppm: 1.68–1.80 m (2H, CH2), 1.82–1.94 m (2H,
CH2), 2.70 t (2H, 5-H, J = 6.1 Hz), 2.93 t (2H, 8-H, J =
6.6 Hz), 3.87 s (2H, SCH2), 6.68 d (1H, 3′-H, J =
1.8 Hz), 6.97 d.d (1H, 4′-H, J = 3.5 Hz), 7.06 br.s and
7.43 br.s (1H each, NH2), 7.88 d (1H, 5′-H, J =
1.8 Hz). Mass spectrum: m/z 314 (Irel 100%) [M + 1]+.
Found, %: C 61.28; H 4.71; N 13.33. C16H15N3O2S.
Calculated, %: C 61.40; H 4.83; N 13.41. M 313.379.
2-[(2-Cyclopropyl-2-oxoethyl)sulfanyl]-4-(furan-
2-yl)-5,6,7,8-tetrahydroquinoline-3-carbonitrile
(1d). Yield 2.4 g (71%), yellow powder, mp 142–
144°C (from EtOH). IR spectrum, ν, cm–1: 2224
(C≡N), 1702 (C=O). 1H NMR spectrum, δ, ppm: 0.83–
0.96 m (4H, CH2, cyclopropane), 1.68–1.75 m (2H,
CH2), 1.77–1.82 m (2H, CH2), 2.19–2.32 m (1H, CH,
cyclopropane), 2.72 t (2H, 5-H, J = 6.0 Hz), 2.88 t
(2H, 8-H, J = 6.2 Hz), 4.21 s (2H, SCH2), 6.68 d (1H,
3′-H, J = 4.8 Hz), 6.93–7.02 m (1H, 4′-H), 7.88 d (1H,
5′-H, J = 1.2 Hz). Mass spectrum: m/z 339 (Irel 100%)
[M + 1]+. Found, %: C 67.31; H 5.22; N 8.16.
C19H18N2O2S. Calculated, %: C 67.43; H 5.36; N 8.28.
M 338.431.
2-(Methylsulfanyl)-4-(thiophen-2-yl)-5,6,7,8-
tetrahydroquinoline-3-carbonitrile (1e). Yield 2.2 g
(79%), yellow crystals, mp 135–137°C (from AcOH).
1
IR spectrum: ν 2219 cm–1 (C≡N). H NMR spectrum,
Methyl 2-{[3-cyano-4-(thiophen-2-yl)-5,6,7,8-
tetrahydroquinolin-2-yl]sulfanyl}acetate (1a). Yield
δ, ppm: 1.55–1.66 m (2H, CH2), 1.73–1.82 m (2H,
CH2), 2.60 s (3H, Me), 2.82–2.93 m (4H, CH2), 7.18–
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 51 No. 6 2015

MULTICOMPONENT SYNTHESIS OF 2-(ALKYLSULFANYL)-4-[FURAN-2-YL-...
867
7.29 m (2H, 3′-H, 4′-H), 7.83 d (1H, 5′-H, J = 4.2 Hz).
13C NMR spectrum, δC, ppm: 13.20, 22.12, 22.33,
26.90, 33.60, 115.66, 127.72, 128.16, 129.56, 130.08,
134.23, 146.94, 159.12, 162.06. Mass spectrum:
m/z 287 (Irel 100%) [M + 1]+. Found, %: C 62.78;
H 4.80; N 9.66. C15H14N2S2. Calculated, %: C 62.90;
H 4.93; N 9.78. M 286.418.
(Irel 100%) [M + 1]+. Found, %: C 67.71; H 3.96;
N 6.25. C25H18N2O4S. Calculated, %: C 67.86; H 4.10;
N 6.33. M 442.490.
Substituted bis(5,6,7,8-tetrahydroquinolin-2-ylsul-
fanyl)alkanes 7a–7c were synthesized following the
general procedure but using 5 mmol of α,ω-dibromo-
alkane 6a or 6b.
2-[(2-Cyclopropyl-2-oxoethyl)sulfanyl]-4-(thio-
phen-2-yl)-5,6,7,8-tetrahydroquinoline-3-carboni-
trile (1f). Yield 2.4 g (68%), yellow crystals, mp 141–
143°C (from EtOH). IR spectrum, ν, cm–1: 2217
(C≡N), 1704 (C=O). 1H NMR spectrum, δ, ppm: 0.87–
1.12 m (4H, CH2, cyclopropane), 1.62–1.73 m (2H,
CH2), 1.79–1.88 m (2H, CH2), 2.21–2.34 m (1H, CH,
cyclopropane), 2.54 t (2H, CH2, J = 5.4 Hz), 2.88 t
(2H, CH2, J = 6.5 Hz), 4.22 s (2H, SCH2), 7.16–7.24 m
(2H, 3′-H, 4′-H), 7.75 d (1H, 5′-H, J = 3.7 Hz). Mass
spectrum: m/z 355 (Irel 100%) [M + 1]+. Found, %:
C 64.25; H 5.00; N 7.78. C19H18N2OS2. Calculated, %:
C 64.38; H 5.12; N 7.90. M 354.495.
2,2′-[Ethane-1,2-diylbis(sulfanediyl)]bis[4-(thio-
phen-2-yl)-5,6,7,8-tetrahydroquinoline-3-carboni-
trile] (7a). Yield 2.0 g (70%), yellow finely crystalline
powder, mp 272–274°C (from 1-BuOH). IR spectrum:
1
ν 2217 cm–1 (C≡N). H NMR spectrum, δ, ppm: 1.61–
1.73 m (4H, CH2), 1.76–1.84 m (4H, CH2), 2.52 t (4H,
CH2, J = 5.6 Hz), 2.86 t (4H, CH2, J = 5.9 Hz), 3.67 s
(4H, SCH2), 7.21–7.26 m (4H, 3′-H, 4′-H), 7.82 d (2H,
5′-H, J = 2.7 Hz). Mass spectrum: m/z 571 (Irel 100%)
[M + 1]+. Found, %: C 62.98; H 4.44; N 9.75.
C30H26N4S4. Calculated, %: C 63.13; H 4.59; N 9.82.
M 570.825.
2,2′-[Propane-1,3-diylbis(sulfanediyl)]bis[4-(fur-
an-2-yl)-5,6,7,8-tetrahydroquinoline-3-carbonitrile]
(7b). Yield 2.0 g (75%), light yellow powder fluoresc-
ing under UV irradiation, mp 177–179°C (from
2-(Benzylsulfanyl)-4-(thiophen-2-yl)-5,6,7,8-
tetrahydroquinoline-3-carbonitrile (1g). Yield 3.1 g
(85%), yellow powder, mp 122–124°C (from AcOH).
1
IR spectrum: ν 2223 cm–1 (C≡N). H NMR spectrum,
1
1-BuOH). IR spectrum: ν 2215 cm–1 (C≡N). H NMR
δ, ppm: 1.69–1.79 m (2H, CH2), 1.81–1.96 m (2H,
CH2), 2.70 t (2H, CH2, J = 6.5 Hz), 2.99 t (2H, CH2,
J = 5.9 Hz), 4.46 s (2H, SCH2), 6.67 d (1H, 3′-H, J =
4.5 Hz), 6.94 d.d (1H, 4′-H, J = 5.2 Hz), 7.22 t (1H,
Ph, J = 7.1 Hz), 7.27 t (2H, Ph, J = 7.1 Hz), 7.40 d
(2H, Ph, J = 7.2 Hz), 7.84 d (1H, 5′-H, J = 3.6 Hz).
Mass spectrum: m/z 363 (Irel 100%) [M + 1]+. Found,
%: C 69.45; H 4.88; N 7.60. C21H18N2S2. Calculated,
%: C 69.58; H 5.00; N 7.73. M 362.518.
spectrum, δ, ppm: 1.54–1.68 m (4H, CH2), 1.72–
1.82 m (4H, CH2), 2.03–2.14 m (2H, CH2CH2S), 2.59–
2.64 m (4H, CH2), 2.73–2.85 m (4H, CH2), 3.34–
3.46 m (4H, SCH2), 6.75 br.s (2H, 3′-H), 7.02 br.s (2H,
4′-H), 7.98 br.s (2H, 5′-H). 13C NMR spectrum, δC,
ppm: 21.59 (2C), 21.96 (2C), 26.58 (2C), 28.30 (2C),
28.48, 33.22 (2C), 101.80 (2C), 112.10 (2C), 115.22
(2C), 115.65 (2C), 125.84 (2C), 140.77 (2C), 145.38
(2C), 146.12 (2C), 158.71 (2C), 161.77 (2C). Mass
spectrum: m/z 553 (Irel 100%) [M + 1]+. Found, %:
C 63.19; H 4.98; N 9.97. C31H28N4O2S2. Calculated,
%: C 67.37; H 5.11; N 10.14. M 552.720.
4-(Furan-2-yl)-2-{[2-oxo-2-(2-oxo-2H-chromen-
3-yl)ethyl]sulfanyl}-5,6,7,8-tetrahydroquinoline-3-
carbonitrile (1h). Yield 3.3 g (75%), yellow finely
crystalline powder, mp 235–237°C (from 1-BuOH). IR
spectrum, ν, cm–1: 2219 (C≡N); 1714, 1692 (C=O).
1H NMR spectrum, δ, ppm: 1.54–1.73 m (4H, CH2),
2.65 t (2H, CH2, J = 5.3 Hz), 3.36–3.44 t (2H, CH2, J =
6.2 Hz), 4.77 s (2H, SCH2), 6.77 d (1H, 3′-H, J =
2.6 Hz), 7.06 d.d (1H, 4′-H, J = 2.3 Hz), 7.45 t (1H,
Harom, J = 7.4 Hz), 7.51 d (1H, Harom, J = 8.3 Hz),
7.78 t (1H, Harom, J = 8.3 Hz), 7.96 d (1H, Harom, J =
7.8 Hz), 8.00 d (1H, 5′-H, J = 1.2 Hz), 8.77 s (1H,
5″-H). 13C NMR spectrum, δC, ppm: 21.47, 21.87,
26.52, 32.89, 36.32, 101.34, 112.19, 115.46, 116.33,
118.21, 124.22, 125.24, 126.32, 130.91, 134.87,
140.84, 145.53, 145.98, 147.93, 154.65, 157.81,
158.51, 161.81, 191.41. Mass spectrum: m/z 443
2,2′-[Propane-1,3-diylbis(sulfanediyl)]bis[4-(thio-
phen-2-yl)-5,6,7,8-tetrahydroquinoline-3-carboni-
trile] (7c). Yield 1.9 g (65%), yellow powder, mp 135–
137°C (from AcOH). IR spectrum: ν 2216 cm–1 (C≡N).
1H NMR spectrum, δ, ppm: 1.63–1.72 m (4H, CH2),
1.76–1.88 m (4H, CH2), 2.12 t (2H, CH2CH2S, J =
6.8 Hz), 2.55 t (4H, CH2, J = 5.9 Hz), 2.89 t (4H, CH2,
J = 6.0 Hz), 3.38 t (4H, SCH2, J = 6.8 Hz), 7.16 d (2H,
3′-H, J = 2.0 Hz), 7.21 d.d (2H, 4′-H, J = 4.2 Hz),
7.75 d (2H, 5′-H, J = 4.0 Hz). Mass spectrum: m/z 585
(Irel 100%) [M + 1]+. Found, %: C 63.54; H 4.73;
N 9.42. C31H28N4S4. Calculated, %: C 63.66; H 4.82;
N 9.58. M 584.853.
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DYACHENKO et al.
14. Lockman, J.W., Reeder, M.D., Suzuki, K., Ostamin, K.,
868
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