Three-component synthesis of alkyl-substituted functionalized 4H-thiopyrans, 1,2- and 1,4-dihydropyridines, 2-alkylsulfanylpyridines, thieno[2,3-b]pyridines, and cyclohexa-1,3-diene

Article abstract of DOI:10.1134/S1070363215050102

Three-component condensation of aliphatic aldehydes with CH-acids has afforded functionalized alkylsubstituted 4H-thiopyrans, 1,2- and 1,4-dihydropyridines, 2-alkylsulfanylpyridines, thieno[2,3-b]pyridines, and cyclohexa-1,3-diene.

Full text of DOI:10.1134/S1070363215050102

ISSN 1070-3632, Russian Journal of General Chemistry, 2015, Vol. 85, No. 5, pp. 1063–1068. © Pleiades Publishing, Ltd., 2015.
Original Russian Text © I.V. Dyachenko, E.N. Karpov, V.D. Dyachenko, 2015, published in Zhurnal Obshchei Khimii, 2015, Vol. 85, No. 5, pp. 765–770.
Three-Component Synthesis of Alkyl-Substituted
Functionalized 4H-Thiopyrans, 1,2- and 1,4-Dihydropyridines,
2-Alkylsulfanylpyridines, Thieno[2,3-b]pyridines,
and Cyclohexa-1,3-diene
I. V. Dyachenko, E. N. Karpov, and V. D. Dyachenko
Shevchenko Lugansk National University, ul. Oboronnaya 2, Lugansk, 91011 Ukraine
e-mail: dyachvd@mail.ru
Received January 19, 2015
Abstract—Three-component condensation of aliphatic aldehydes with CH-acids has afforded functionalized alkyl-
substituted 4H-thiopyrans, 1,2- and 1,4-dihydropyridines, 2-alkylsulfanylpyridines, thieno[2,3-b]pyridines, and
cyclohexa-1,3-diene.
Keywords: aliphatic aldehyde, CH-acid, 4H-thiopyran, 1,4-dihydropyridine, thieno[2,3-b]pyridine, cyclohexa-1,3-
diene
DOI: 10.1134/S1070363215050102
Multicomponent synthesis of heterocyclic compounds
has recently become increasingly important [1–3]. This
method is particularly relevant to obtain scarcely
studied alkyl-substituted carbo- and heterocyclic
compounds starting from aliphatic aldehydes, since the
latter are known for high toxicity, flammability, and
ability to readily isomerize and dimerize [4] as
compared with the aromatic analogs.
form the substituted 1,4-dihydropyridine IV. In the
case of Alk = (Me)2CHCH2, the reaction stopped at the
stage of formation of the corresponding 1,4-dihydro-
pyridine IV due to oxidation of the hydrosulfide group
with air oxygen into organic disulfide V. On top of
that, the reaction was accompanied with aromatization
of the dihydropyridine core (Scheme 1).
In the case of the Knöevenagel condensation
involving 2-phenylpropionaldehyde Ic and malono-
nitrile VI in the presence of morpholine as a catalyst,
the formed alkene C was capable of the Michael-type
dimerization under the reaction conditions. The adduct
D underwent intramolecular cyclization into the
substituted 1,3-cyclohexadiene VII.
Extending the earlier research on synthesis of alkyl-
substituted carbo- and heterocyclic compounds via a
multicomponent condensation [5–7], we investigated
new possibilities of three-component interaction of
aliphatic aldehydes Ia–Ij with a number of CH-acids
and organic bases under conditions of the Knöevenagel
reaction. It was found that condensation of aliphatic
aldehydes Ia and Ib with cyanothioacetamide II and
ethyl 3-amino-3-thioxopropanoate III in anhydrous
ethanol at 20°C in the presence of sodium ethylate
resulted in ethyl 2-amino-4-isopropyl-6-mercapto-5-
cyano-3-carboxylate IV and diethyl 6,6'-disulfandi-
ylbis(2-amino-4-isobutyl-5-cyanonicotinate V. Apparently,
the reaction proceeded through formation of alkene A
followed by addition of the CH-acid III to give the
adduct B. The latter intermediate [Alk = (Me)2CH]
underwent chemoselective intramolecular cyclization
accompanied with hydrogen sulfide elimination to
Three-component condensation of aliphatic alde-
hydes I with cyanothioacetamide II and malononitrile
VI in the presence of morpholine in anhydrous ethanol
at 20°C resulted in the formation of 4-alkyl-2,6-
diamino-3,5-dicyano-4H-thiopyrans VIIIc, VIIIh,
VIIIi, and VIIIj. At the same time, the same reaction
in ethanol medium under reflux allowed preparation of
4-substituted 6-amino-2-thioxo-3,5-dicyano-1,2-dihyd-
ropyridines IXd and IXg, similarly to the analogous
condensation involving aromatic aldehydes [8–10].
Thiopyrans VIII, the kinetic control products,
underwent ring-opening via formation of intermediates
1063

1064
DYACHENKO et al.
Scheme 1.
Alk
EtOOC
CN
S
EtOOC
H2N
CN
SH
EtOOC
CN
S
O2
−H2S
−2H2O,
−H2S
H2N
N
N
H2N
S
H2N
2
H
O
IV
B
V
EtO
H2N
, EtONa
S
III
Ph
O
CN
CN
Alk
N
H
,
CN
S
CN
H2N
S
VI
II
AlkCHO
−H2O
−H2O
NC
CN
Iа−Ij
H2N
C
А
Ph
Alk
Alk
S
Ph
NC
CN
NC
CN
C
NC
CN
C
CN
H2N
NH2
S
NH2
N
N
D
E
VIIIc, VIIIh, VIIIi, VIIIj
Ph
Alk
CN
Alk
NC
Ph
NC
CN
−2[H]
H
H
+
N
C
N
H2N
N
S−
NC
NC
CN
H2N
SH
G
NH2
O
Cl
NH2
F
VII
Hlg
Z
H+
XIа−XId
O
NC
XII
Alk
Alk
Alk
NH2
NC
CN
S
NC
CN
S
NH2
S
O
H2N
N
H
H2N
N
H2N
N
Z
IXd, IXg
Xа−Xd
XIIIа, XIIIb
I, VIII, IX, XIII, Alk = (Me)2CH (a), (Me)2CHCH2 (b), Me(Ph)CH (c), Me(Ph)CHCH2 (d), cyclohex-2-enyl (e), Ме(СН2)10
(f), Ph(CH2)2 (g), Ме(СН2)6 (h), PhCH2 (i), Ме(СН2)5 (j); X, XI, Hlg = Cl, Z = Ph, Alk = cyclohex-2-enyl (a); Hlg = Br, Z =
4-ClC6H4CO, Alk = Me(CH2)10 (b); Hlg = Br, Z = 4-NO2C6H4CO, Alk = PhCH2 (c); Hlg = I, Z = H, Alk = CH2Ph (d).
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THREE-COMPONENT SYNTHESIS OF ALKYL-SUBSTITUTED
1065
Table 1. Yields, melting points and elemental analysis data for compounds IV–X and XIII
Found, %
Calculated, %
H N
Comp.
no.
Yield,
%
mp, °С
Formula
C
H
N
C
IV
65
69
72
80
75
77
70
66
68
71
89
73
82
78
65
197–199 (EtOH)
53.84
6.29
5.63
6.02
4.89
7.15
4.43
6.60
4.68
4.21
5.18
6.32
3.46
4.22
4.68
5.15
15.65
14.92
14.15
19.76
20.12
20.76
20.71
18.95
19.86
16.02
11.49
16.22
19.86
25.30
24.03
C12H17N3O2S
C26H32N6O4S2
C26H24N4
53.91
56.10
79.48
63.81
60.84
62.66
57.97
65.28
64.26
69.34
64.65
61.53
64.26
52.35
53.96
6.41
5.79
6.22
5.00
7.29
4.51
6.74
4.79
4.32
5.24
6.47
3.52
4.31
4.76
5.23
15.72
15.10
14.30
19.84
20.27
20.88
20.80
19.03
19.98
16.17
11.60
16.31
19.98
25.44
24.20
V
263–265 (AcOH) 55.98
VII
218–220 (PrOH)
206–208 (EtOH)
165–167 (EtOH)
183–185 (EtOH)
159–161 (PrOH)
233–235 (EtOH)
79.44
63.72
60.70
62.58
57.84
65.19
VIIIc
VIIIh
VIIIi
VIIIj
IХd
IXg
C15H14N4S
C14H20N4S
C14H12N4S
C13H18N4S
C16H14N4S
C15H12N4S
C20H18N4S
C26H31ClN4OS
C22H15N5O3S
C15H12N4S
C12H13N5OS
C13H15N5OS
118–120 (MeOH) 64.18
162–163 (AcOH) 69.28
188–190 (AcOH) 64.58
203–205 (BuOH) 61.48
241–243 (AcOH) 64.11
281–282 (AcOH) 52.26
289–290 (BuOH) 53.86
Xаа
Xb
Xc
Xd
XIIIаb
XIIIbа
a Fluoresced under UV irradiation. b Sublimated at 200°C.
E and F to yield the substituted morpholinium
pyridine-2-thiolates G. They were stabilized into
pyridinethiones IX in acidic medium. Formation of the
salts G was confirmed by formation of thioethers X
when alkyl halides XIa–XId were introduced in the
reaction, in accordance with fundamentals of pyridi-
nethiones chemistry [11–13]. Noteworthily, com-
pounds Xa–Xd are promising building blocks to create
drugs for treatment of inflammatory processes [14] and
cardiovascular diseases [15].
In particular, IR spectra of the obtained compounds
contained the expected characteristic absorption bands
of NH2 (3099–3450 cm–1), C≡N (1706–1724 cm–1),
and C=O (2172–2252 cm–1) groups stretching. GC–
MS spectra revealed the presence of the [M + 1]+
molecular ion peak. Mass spectrum of compound IXg
contained the molecular ion peak and peaks of other
fragments including the [M + 2]+ peak confirming the
presence of one sulfur atom in the molecule [21]. The
1H NMR spectra contained the signals of all the
expected structural fragments.
When α-chloroacetamide XII was used as
alkylating agent in the presence of equimolar amount
of 10% aqueous KOH, the reaction led to formation of
4-alkylthieno[2,3-b]pyridines VIIIa and VIIIb, show-
ing potential antiviral [16, 17] and antitumor [18, 19]
activity. Apparently, the reaction intermediates were
the corresponding thioesters X, undergoing intra-
molecular cyclization in alkaline medium to form
compounds XIII. 2-Alkylthio-3-cyanopyridine are
convenient starting reagents for thieno[2,3-b]pyridines
synthesis [20].
EXPERIMENTAL
IR spectra were recorded with a Perkin Elmer
Spectrum One spectrophotometer (KBr pellets). H
1
NMR spectra were obtained using a Bruker Avanse II
(400.13 MHz) spectrometer (solutions in DMSO-d6)
relative to TMS as internal reference. Mass spectra
were registered with a Chrommass GC/MC (Hewlett
Packard) 5890/5972 mass spectrometer [column HP-5
MS (70 eV)] (in the cases of CH2Cl2 solutions) and
with a Kratos MS-890 spectrometer (70 eV) with the
direct specimen injection the ion source (VII, IXb,
Spectral and physico-chemical properties of the
synthesized compounds are shown in Tables 1 and 2.
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DYACHENKO et al.
Table 2. IR and 1H NMR spectral data for compounds IV–X and XIII
Comp.
ν, cm–1
no.
δH, ppm, (J, Hz)
IV
3411, 3320, 3312, 3099 (NH, 0.89 d (6H, 2Me, J 6.6), 1.18 t (3H, CH2CH3, J 7.0), 1.51–1.66 m (1H,
NH2), 2172 (C≡N), 1724 (C=O), CHMe2), 3.93 d (1H, C4H, J 4.3), 4.14 q (2H, OCH2, J 7.0), 6.17 br. s (2H,
1642 [δ(NH2)]
NH2), 11.71 br. s (1H, NH); the signal of SH proton was not observed pre-
sumably due to the rapid deuterium exchange
V
3435, 3351, 3221 (NH2), 2215 0.89 d (12H, 4Me, J 6.2), 1.35 t (6H, 2MeCH2, J 6.6), 1.76–1.92 m (2H,
(C≡N), 1706 (C=O), 1632 [δ(NH2)] 2CHMe2), 2.79 d (2H, 2CH2CH, J 6.8), 4.36 q (4H, 2OCH2, J 6.6), 7.20 br. s
(4H, 2NH2)
VII
3450, 3340, 3215 (NH2), 2252, 1.19 d (3H, Me, J 6.6), 1.33 d (3H, Me, J 6.5), 1.71–1.83 m (1H, CHMe), 2.18
2200 (C≡N), 1644 [δ(NH2)]
q (1H, CHMe, J 6.5), 2.87 d (2H, CH2CH, J 6.7), 3.38 t (1H, C6H, J 6.8), 6.05
s (1H, C4H), 6.82–6.99 m (2H, Ph), 7.06–7.19 m (3H, Ph), 7.23–7.38 m (3H,
Ph), 7.42 t (2H, Ph, J 8.1), 7.55 br. s (2H, NH2)
VIIIc
VIIIh
VIIIi
VIIIj
IXd
3444, 3314, 3210 (NH2), 2202 1.28 d (3H, Me, J 6.9), 2.81–3.04 m (1H, CHMe), 3.05 d (1H, C4H, J 5.8),
(C≡N), 1647 [δ(NH2)]
3440, 3295, 3202 (NH2), 2204 0.86 t (3H, Me, J 7.1), 1.08–1.55 m (10H, 5CH2), 2.99 t (1H, C4H, J 6.9), 6.75
(C≡N), 1643 [δ(NH2)] br. s (4H, 2NH2)
3435, 3302, 3215 (NH2), 2200 2.73 d (2H, CH2, J 6.4), 3.38 t (1H, C4H, J 6.4), 6.75 br. s (4H, 2NH2), 7.02–
(C≡N), 1642 [δ(NH2)] 7.46 m (5H, Ph)
3401, 3333, 3219 (NH2), 2199 1.92 t (3H, Me, J 6.8), 1.18–1.42 m (8H, 4CH2), 1.48–1.64 m (2H, CH2), 2.93
(C≡N), 1649 [δ(NH2)]
t (1H, C4H, J 7.2), 6.53 br. s (4H, 2NH2)
3418, 3311, 3209 (NH, NH2), 1.31 d (3H, Me, J 7.2), 3.92–3.51 m (1H, CHMe), 3.61–4.01 m (2H, CH2),
2216 (C≡N), 1640 [δ(NH2)] 7.02–7.43 m (5H, Ph), 10.02 br. s (2H, NH2), 11.82 br. s (1H, NH)
3402, 3300, 3196 (NH, NH2), 2.71–3.11 m (4H, 2CH2), 7.04–7.48 m (5H, Ph), 7.81 br. s (2H, NH2), 12.71
2217 (C≡N), 1647 [δ(NH2)] br. s (1H, NH)
6.70 br. s (2H, NH2), 6.85 br. s (2H, NH2), 7.11–7.43 m (5H, Ph)
IXg
Xа
3446, 3334, 3216 (NH2), 2214 1.65–1.82 m (1H, C6H, cyclohexene), 2.04–2.33 m (5H, cyclohexene), 3.01–
(C≡N), 1624 [δ(NH2)]
3.14 m (1H, C1H, cyclohexene), 4.45 s (2H, SCH2), 5.66–5.79 m (2H,
CH=CH), 7.23 d (1H, Ph, J 6.9), 7.29 t (2H, Ph, J 6.9), 7.47 d (2H, Ph, J 7.1),
7.94 br. s (2H, NH2)
Xb
3435, 3312, 3198 (NH2), 2219 0.87 t (3H, Me, J 7.1), 1.06–1.52 m (16H, 8CH2), 1.55–1.78 m (2H, CH2), 2.72
(C≡N), 1714 (C=O), 1648 [δ(NH2)] t (2H, CH2, J 7.7), 4.83 s (2H, SCH2), 7.53 d (2H, Ar, J 8.6), 7.64 br. s (2H,
NH2), 8.05 d (2H, Ar, J 8.6)
Хc
3430, 3318, 3206 (NH2), 2220 4.11 s (2H, CH2), 4.99 s (2H, SCH2), 7.16–7.43 m (5H, Ph), 7.81 br. s (2H,
(C≡N), 1706 (C=O), 1641 [δ(NH2)] NH2), 8.22 d (2H, C6H4, J 8.4), 8.38 d (2H, C6H4, J 8.4)
3438, 3302, 3190 (NH2), 2222 2.54 s (3H, Me), 4.07 s (2H, CH2), 7.14–7.46 m (5H, Ph), 7.96 br. s (2H, NH2)
(C≡N), 1643 [δ(NH2)]
Xd
XIIIa
3398, 3326, 3174 (NH2), 2216 1.02 d (6H, 2Me, J 5.3), 2.08–2.19 m (1H, CHMe2), 6.58 s (2H, NH2), 6.66 s
(C≡N), 1662 (CONH), 1634
[δ(NH2)]
(2H, NH2), 6.75 s (2H, NH2)
XIIIb
3390, 3338, 3206 (NH2), 2219 1.12 d (6H, 2Me, J 5.8), 2.06–2.24 m (1H, CHMe2), 2.93 d (2H, CH2, J 6.3),
(C≡N), 1670 (CONH), 1641
[δ(NH2)]
6.58 s (2H, NH2), 6.63 s (2H, NH2), 6.76 s (2H, NH2)
IXg, and Xb). Melting points were determined with a
Kofler device. The reaction progress was monitored
with TLC on Silufol UV-254 plates, eluting with an
acetone–hexane mixture (3 : 5) and developing with
iodine vapor or UV irradiation.
Ethyl 2-amino-4-isopropyl-6-thio-5-cyano-1,4-di-
hydropyridine-3-carboxylate (IV). 1.0 g (10 mmol)
of cyanothioacetamide II and a solution of sodium
ethylate prepared from 0.23 g (10 mmol) of sodium
and 15 mL of anhydrous ethanol were added to a
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THREE-COMPONENT SYNTHESIS OF ALKYL-SUBSTITUTED
1067
solution of 0.91 mL (10 mmol) of isobutyral Ia in
15 mL of anhydrous ethanol at 20°C. The reaction
mixture was stirred during 5 min, then 1.5 g (10 mmol)
of CH-acid III was added, and the mixture was stirred
during 30 min and incubated during 48 h. Next, the
mixture was diluted with 10% hydrochloric acid to pH
5 upon stirring and incubated at room temperature
during 48 h. The formed precipitate was filtered off
and washed sequentially with water, ethanol, and
hexane (Tables 1 and 2). Mass spectrum, m/z (Irel, %):
266 (100) [M – 1]+.
2,6-Diamino-4-hexyl-4H-thiopyran-3,5-dicarbo-
nitrile (VIIIj). Mass spectrum, m/z (Irel, %): 270 (100)
[M + 1]+.
4-Alkyl-6-amino-2-thioxo-3,5-dicyano-1,2-dihyd-
ropyridines (IХd, IXg) (general procedure). 0.9 mL
(10 mmol) of morpholine was added to a mixture of
10 mmol of the appropriate aldehyde I and 1.0 g
(10 mmol) of cyanothioacetamide II in 20 mL of
anhydrous ethanol at 20°C. The mixture was stirred
during 30 min, and then 0.66 g (10 mmol) of malo-
nonitrile VI was added. The mixture was refluxed
during 1 h, cooled, diluted with 10% hydrochloric acid
to pH 5, and incubated during 48 h. The formed
precipitate was filtered off and washed with ethanol
and hexane (Tables 1 and 2).
Diethyl 6,6'-disulfanediylbis(2-amino-4-isobutyl-
5-cyanonicotinate) (V) was prepared similarly from
1.1 mL (10 mmol) of isovaleric aldehyde Ib. Mass
spectrum, m/z (Irel, %): 557 (100) [M + 1]+.
6-Amino-2-thioxo-4-(2-phenylpropyl)-1,2-dihyd-
ropyridine-3,5-dicarbonitrile (IХd). Mass spectrum,
m/z (Irel, %): 294 (8) [M]+, 234 (11), 178 (9), 105 (100)
[M – PhCHMe]+, 91 (14) [PhCH2]+, 77 (22) [Ph]+, 51
(12), 43 (24).
2-Amino-6-(2-phenylpropyl)-5-(1-phenylethyl)-
cyclohexa-2,4-diene-1,1,3-tricarbonitrile (VII). 3 drops
of morpholine were added to a solution of 1.5 mL
(10 mmol) of 3-phenylbutyral Id and 0.66 g (10 mmol)
of malononitrile VI in 20 mL of anhydrous ethanol at
20°C. The reaction mixture was stirred during 1 h and
incubated during 48 h. The formed precipitate was
filtered off and washed with ethanol and hexane. Mass
spectrum, m/z (Irel, %): 394 (5) [M + 2]+, 393 (18)
[M + 1]+, 392 (39) [M]+, 287 (13) [M – PhCHMe]+,
246 (12), 232 (11), 143 (18), 131 (10), 118 (32), 106
(49) [PhCH2Me]+, 105 (100) [PhCHMe]+, 91 (54)
[PhCH2]+, 79 (47) [C6H6+1]+, 58 (42).
6-Amino-2-thioxo-4-(2-phenylethyl)-1,2-dihyd-
ropyridine-3,5-dicarbonitrile (IХg). Mass spectrum,
m/z (Irel, %): 282 (4) [M + 2]+, 281 (6) [M + 1]+, 280
(29) [M]+, 279 (9) [M – 1]+, 203 (3), 162 (4), 91 (100)
[PhCH2]+, 77 (4) [Ph]+, 65 (11), 51 (3), 39 (3).
4-Alkyl-6-amino-2-alkylsulfanyl-3,5-dicyano-
pyridines (Xa–Xd) were prepared similarly from the
appropriate alkyl halides Xa–Xd instead of hydro-
chloric acid.
4-Alkyl-2,6-diamino-3,5-dicyano-4H-thiopyrans
(VIIIc, VIIIh, VIIIi, VIIIj) (general procedure).
3 drops of morpholine were added to a mixture of
10 mmol of the appropriate aldehyde I and 1.0 g
(10 mmol) of cyanothioacetamide II in 20 mL of
anhydrous ethanol at 20°C. The mixture was stirred
during 1 h, and then 0.66 g (10 mmol) of malononitrile
VI was added. The resulting mixture was stirred
during 30 min and incubated during 24 h. The formed
precipitate was filtered off and washed with ethanol
and hexane (Tables 1 and 2).
2-Amino-6-benzylsulfanyl-4-(cyclohex-3-en-1-yl)-
pyridine-3,5-dicarbonitrile (Xa). Mass spectrum, m/z
(Irel, %): 345 (100) [M – 1]+.
6-Amino-4-undecyl-2-(4-chlorobenzoylmethyl-
sulfanyl)pyridine-3,5-dicarbonitrile (Хb). Mass spec-
trum, m/z (Irel, %): 484 (3) [M + 1]+, 483 (4) [M]+, 482
(5) [M – 1]+, 343 (6), 139 (100), [4-ClC6H4CO]+, 125
(6), 111 (18), 43 (14).
6-Amino-4-benzyl-2-(4-nitrobenzoylmethylsul-
fanyl)pyridine-3,5-dicarbonitrile (Хc). Mass spec-
trum, m/z (Irel, %): 430 (100) [M + 1]+.
2,6-Diamino-4-(1-phenylethyl)-4H-thiopyran-3,5-
dicarbonitrile (VIIIc). Mass spectrum, m/z (Irel, %):
283 (100) [M + 1]+.
6-Amino-4-benzyl-2-methylsulfanylpyridine-3,5-
dicarbonitrile (Xd). Mass spectrum, m/z (Irel, %): 281
(100) [M + 1]+.
2,6-Diamino-4-heptyl-4H-thiopyran-3,5-dicarbo-
nitrile (VIIIh). Mass spectrum, m/z (Irel, %): 277 (100)
[M + 1]+.
Substituted thieno[2,3-b]pyridines (XIIIa, XIIIb)
were prepared similarly using 5.6 mL (10 mmol) of
10% aqueous solution of KOH and 0.94 g (10 mmol)
of α-chloroacetamide XII instead of hydrochloric acid.
2,6-Diamino-4-benzyl-4H-thiopyran-3,5-dicarbo-
nitrile (VIIIi). Mass spectrum, m/z (Irel, %): 269 (100)
[M + 1]+.
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DYACHENKO et al.
Nesterov, V.N., Melenchuk, S.N., Shklover, V.E., and
3,6-Diamino-4-isopropyl-5-cyanothieno[2,3-b]-
pyridine-2-carboxamide (ХIIIa). Mass spectrum, m/z
(Irel, %): 276 (100) [M + 1]+.
Struchkov, Yu.T., Zh. Org. Khim., 1989, vol. 25, no. 3,
p. 622.
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