Cyanoselenoacetamide in a new synthesis of propane-bis(thioamide), the promising reagent for heterocyclizations

Article abstract of DOI:10.1134/S1070363213090168

Cyanoselenoacetamide reacts with hydrogen sulfide to form propane-bis(thioamide), which can be used to produce thiazoles (the Hantzsch synthesis) and 3-thioxo-1-phenyl-2,3,5,6,7,8-hexahydroisoquinoline-4- carbonitrile. From the latter compound, 2-alkylsul

Full text of DOI:10.1134/S1070363213090168

ISSN 1070-3632, Russian Journal of General Chemistry, 2013, Vol. 83, No. 9, pp. 1724–1728. © Pleiades Publishing, Ltd., 2013.
Original Russian Text © I.V. Dyachenko, M.V. Vovk, 2013, published in Zhurnal Obshchei Khimii, 2013, Vol. 83, No. 9, pp. 1504–1508.
Cyanoselenoacetamide in a New Synthesis
of Propane-bis(thioamide), the Promising Reagent
for Heterocyclizations
I. V. Dyachenkoa and M. V. Vovkb
a Taras Shevchenko Luhansk National University, ul. Oboronnaya 2, Luhansk, 91011 Ukraine
e-mail: ivladya87@e-mail.ua
b Institute of Organic Chemistry, National Academy of Sciences of Ukraine,
ul. Murmanskaya 5, Kiev, 02660 Ukraine
e-mail: mvovk@i.com.ua
Received September 3, 2012
Abstract—Cyanoselenoacetamide reacts with hydrogen sulfide to form propane-bis(thioamide), which can be
used to produce thiazoles (the Hantzsch synthesis) and 3-thioxo-1-phenyl-2,3,5,6,7,8-hexahydroisoquinoline-4-
carbonitrile. From the latter compound, 2-alkylsulfanyl-1-phenyl-5,6,7,8-tetrahydroisoquinoline-4-carbonitriles
and 1-amino-N-(4-bromophenyl)-5-phenyl-6,7,8,9-tetrahydrothieno[2,3-c]isoquinoline-2-carboxamide can be
prepared.
DOI: 10.1134/S1070363213090168
Cyanoselenoacetamide (I), first prepared via the
reaction of hydrogen selenide with malononitrile [1],
readily undergoes dimerization to form 4,6-diamino-2-
selenoxo-1,2-dihydronicotinenitrile. In spite of this, it
can be used in the synthesis of various 2-selenoxo-1,2-
dihydronicotinenitriles [3–6]. Selenoazoles are smoothly
prepared from I derivatives, aryl(hetaryl)methylidene-
cyanoselenoacetamides [7].
The studied reaction could be considered as a new
approach to preparation of the promising polyfunc-
tional propane-bis(thioamide) II. Previously, for its
synthesis the amidation of diethyl tetrathiomalonate [9]
or thionation of malonamide [10, 11] were used.
The use of dithioamide II for synthesis of the
transition metal complexes [12] and II application as a
nucleophilic substrate for preparation of 1,3-dithiyne
[13], 1,2,3-thiadiazole [10], and naphthothiazole [14]
have been described. To date, the Hantzsch condensa-
tion of II with α-halogenated carbonyl compounds has
been limited to a few examples [15, 16], although it
seems to be an efficient approach to prepare methylene-
bis(thiazoles), the unusual ligands for complexation
[12]. Using the reaction of II with two-fold excess of
α-bromoketones IIIa–IIIc in DMF we demonstrated
the general nature of that approach allowing to prepare
dithiazolylmetanes IVa–IVc with yield of 71–82%.
Searching for synthetic selenium blocks capable of
heterocyclization is a topical issue due to high
biological activity of organoselenium compounds [8].
One of the promising candidates is 3-amino-3-selen-
oxopropanetioamide A, not yet described in the
literature. In this work, we aimed to prepare this
compound in the reaction of cyanoselenoacetamide I
with hydrogen sulfide at room temperature in pyridine
in the presence of equimolar amount of triethylamine.
However, instead of A, its dithio analogue, propan-bis
(thioamide) II, was formed in that reaction.
Apparently, even under those mild conditions, the
interaction did not stop at the stage of nitrile group
conversion to thioamide, but further addition of
hydrogen sulfide to the C=Se group occurred to form
intermediate B, which was stabilized by hydrogen
selenide elimination.
Another synthetic application of II, a CH-acidic
component in heterocyclizations, was demonstrated by
the condensation with enaminoketone V. That reaction
proceeded smoothly in anhydrous ethanol at 20ºC in
the presence of sodium ethylate and gave 3-thioxo-1-
phenyl-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile
1724

CYANOSELENOACETAMIDE IN A NEW SYNTHESIS OF PROPANE-BIS(THIOAMIDE)
1725
VI. Most likely, it proceeded via nucleophilic vinyl
substitution (SNVin) [17–19] through formation of
intermediate C that further underwent cyclization
accompanied by elimination of hydrogen sulfide from
the exocyclic thioamide group.
tion of VI with α-bromocyclohexanone VII in DMF in
alkaline medium resulted in the corresponding thio-
ester VIII. With alkylating agent being N-(4-bromo-
phenyl)-2-chloroacetamide IX, under similar condi-
tions S-alkylation occurred as well [21, 22], leading to
N-(4-bromophenyl)-2-(1-phenyl-4-cyano-5,6,7,8-tetra-
hydroisoquinoline-3-yl)acetamide X. Given the fact
that 3-alkylsulfanyl-4-cyano-5,6,7,8-tetrahydroisoquino-
line derivatives exhibit neurotropic [23] and anti-
bacterial properties [24], compounds VIII and X are
promising for the design of new bioactive substances.
The structure of VI was confirmed by comparing
its physical, chemical, and spectral characteristics with
those of the reaction of 2-benzoylcyclohexanone with
cyanothioacetamide product [20], as well as by studies
of VI chemical transformations. In particular, alkyla-
SH
Se
Se
S
HSe
H2S
H2S
S
CN
NH2
NH2
NH2
NH2
NH2
B
I
А
Br
2
O
S
R
IIIа−IIIc
S
S
S
N
N
−H2Se
−2HBr,
−2H2O
NH2
NH2
R
R
II
IVа−IVc
N
O
−
O
NH
Ph
O
V
Br
O
S
CN
CN
S
VII
NH2
−H2O,
−H2S
−HBr
Ph
S
Ph
N
H
N
H2N
O
Ph
S
O
C
VIII
VI
H
N
IX/2KOH
Cl
O
b
Br
IX
CN
NH2
KOH
O
O
Ph
S
а
N
S
Ph
N
HN
HN
XI
X
Br
Br
III, IV, R = Ph (a), 4-MeC6H4 (b), and coumarin-3-yl (c).
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 83 No. 9 2013

1726
DYACHENKO, VOVK
Treating of X with equimolar amount of potassium
was used as eluent, and color developers were iodine
vapor and UV radiation.
hydroxide led to the formation of the product con-
taining thiophene cycle, 1-amino-N-(4-bromophenyl)-
5-phenyl-6,7,8,9-tetrahydrothieno[2,3-c]isoquinoline-2-
carboxamide XI, (method a). That product could be
potentially used to create antitumor [25] and analeptic
(corazolum type) [26] drugs. A one-pot variant of XI
preparation was a reaction of isoquinolinethione VI
with chloroacetanilide IX in the presence of a double
excess of alkali (method b).
Propane-bis(thioamide) (II). 14 ml (0.1 mol) of
triethylamine was added to a solution of 14.7 g
(0.1 mol) of cyanoselenoacetamide I in 50 ml of
pyridine at 20ºC, and a moderate flow of hydrogen
sulfide was bubbled during 4 h under argon. Then, the
reactor was sealed and left in the refrigerator for 24 h.
Next day, the reaction mixture was diluted with an
equal volume of water and left in the refrigerator for
5 days. The resulting precipitate was filtered off,
washed with water (20 ml), ethanol (20 ml), and
hexane (20 ml), then dried and crystallized from
ethanol. Yield 8.86 g (66%), yellow powder, mp 188–
190°C (published [9]: 190°C). Elemental analysis, IR
spectrum and 13C NMR spectrum were in agreement
IR spectrum of X contained characteristic absorp-
tion bands assigned to stretching vibrations of con-
jugated cyano group 2218 cm–1) and amide fragment
(1680 cm–1). In the IR spectrum of XI, the absorption
band of cyano group stretching vibrations disappeared,
and the bands assigned to stretching (3195–3412 cm–1)
and bending (1646 cm–1) vibrations of the amino group
appeared. In the 1H NMR spectrum of X, in addition to
the signals of the protons of tetramethylene fragment,
aromatic substituents, and NH group, there was a
singlet of SCH2 protons at 4.14 ppm. The latter signal
disappeared in the spectrum of XI, instead, the signal
of amino protons appeared as a broad singlet at
7.18 ppm. 13C NMR spectra of substituted tetrahydro-
isoquinolines VIII, X, and XI contained signals of all
carbon atoms with the respective chemical shifts. Mass
spectrum of dithiazolyl-substituted methane IVb
contained a peak of [M + 2]+, indicating the presence
of sulfur atoms in the molecule [27], while the signal
[M]+ was in accordance with the nitrogen rule [28].
1
with the published ones [9]. H NMR spectrum, δ,
ppm: 3.79 s (2H, CH2), 9.32 br.s (2H, NH2), 9.62 br.s
(2H, NH2). Mass spectrum, m/z (Irel, %): 136 (8)
[M + 2]+, 135 (5) [M + 1]+, 134 (100) [M]+, 133 (6)
[M – 1]+, 117 (2) [M – NH3]+, 101 (14) 75 (10) 60 (44)
42 (38) 30 (15). C3H6N2S2. M 134.222.
Bis(4-phenylthiazol-2-yl)methane (IVa). A mix-
ture of 1.34 g (10 mmol) of malonic dithioamide II
and 4.0 g (20 mmol) phenacyl bromide IIIa in 25 ml
of DMF was stirred for 5 h, left overnight at room
temperature and diluted with an equal volume of water.
The resulting precipitate was filtered off, washed with
water (20 ml), ethanol (20 ml), and hexane (20 ml),
then dried and crystallized from methanol. Yield 2.57 g
(77%), yellow powder, mp 117–118°C (published
1
EXPERIMENTAL
[16]: 119–120°C). H NMR spectrum, δ, ppm: 4.92 s
(2H, CH2), 7.15–7.64 m (6H, Harom), 7.82–8.23 m (6H,
H
Found, %: C 68.11, H 4.17, N 8.33. C19H14N2S2.
Calculated, %: C 68.23, H 4.22, N 8.38. M 334.465.
1H NMR spectra were recorded with Varian
Mercury 400 spectrometer (399.97 MHz) in DMSO-d6,
with TMS as internal reference. 13C NMR spectra were
recorded with Varian VXR-300 spectrometer (125.74
MHz) in DMSO-d6, with TMS as internal reference.
Mass spectra were recorded with Kratos MS-890
spectrometer (70 eV) using a direct inlet of the
material into the ion source (compounds II, IVb) and
with Crommas GC/MS (Hewlett-Packard) 5890/5972
instrument, with HP-5MS (70 eV) column, in CH2Cl2
(compounds IVa, IVc, VIII, X, and XI). IR spectra of
the KBr pellets were recorded with “SPEKTRUM
ONE” (Perkin Elmer) spectrometer. Elemental analysis
was performed with Perkin-Elmer C,H,N-analyzer.
Melting points were determined with a Kofler bench.
The reaction course and the purity of the individual
compounds were monitored by thin-layer chromato-
graphy with Silufol UV-254 plates, acetone-hexane 3:5
arom). Mass spectrum, m/z (Irel, %): 335 (100) [M + 1]+.
Bis(4-p-tolylthiazol-2-yl)methane (IVb) was prepared
similarly to IVa using 4.26 g (20 mmol) of α-bromo-
ketone IIIb. Yield 2.97 g (82%), yellow powder, mp
1
132–133°C (MeOH). H NMR spectrum, δ, ppm: 2.34
s (6H, 2Me), 4.83 s (2H, CH2), 7.22 d (4H, Harom, J
7.72 Hz), 7.82 d (4H, Harom, J 7.72 Hz), 7.88 s (2H,
thiazole). Mass spectrum, m/z (Irel, %): 364 (10) [M + 2]+,
363 (23) [M + 1]+, 362 (100) [M]+, 181 (31), 149 (15)
148 (63), 147 (82), 115 (26), 104 (14), 91 (28) [MeC6H4]+,
77 (10) [Ph]+, 69 (8), 45 (10), 39 (6). Found, %: C
69.41, H 4.97, N 7.63. C21H18N2S2. Calculated, %: C
69.58, H 5.00, N 7.73. M 362.518.
3,3'-[2,2'-Methylene-bis(thiazol-4,2-diyl)]-bis(2H-
chromen-2-one) (IVc) was prepared similarly to IVa
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 83 No. 9 2013

CYANOSELENOACETAMIDE IN A NEW SYNTHESIS OF PROPANE-BIS(THIOAMIDE)
1727
using 5.34 g (20 mmol) of α-bromoketone IIIc. Yield
3.1 g (71%), yellow crystals, mp 183–185°C (BuOH).
IR spectrum, ν, cm–1: 1714 (C=O). 1H NMR spectrum,
δ, ppm: 4.91 s (2H, CH2), 7.33–7.49 m (4H, Harom),
7.58–7.72 m (2H, Harom), 7.85 d (2H, Harom, J 7.42 Hz),
8.37 s (2H, thiazole), 8.80 s (2H, H4, coumarine). Mass
spectrum, m/z (Irel, %): 439 (100) [M + 1]+. Found, %:
C 68.30, H 3.15, N 6.26. C25H14N2O4S. Calculated, %:
C 68.48, H 3.22, N 6.39. M 438.466.
(1H, SCH), 7.39–7.58 m (5H, Ph). 13C NMR spectrum,
δC, ppm: 21.37, 22.34, 25.12, 27.13, 27.34, 28.52,
34.47, 41.68, 54.19, 105.71, 115.25, 127.69, 128.55 (2C),
129.36 (2C), 129.42, 139.04, 152.62, 156.93, 160.22,
205.41. Mass spectrum, m/z (Irel, %): 363 (100) [M +
1]+. Found, %: C 72.83, H 6.02, N 7.69. C22H22N2OS.
Calculated, %: C 72.90, H 6.12, N 7.73. M 362.496.
N-(4-Bromophenyl)-2-(1-phenyl-4-cyano-5,6,7,8-
tetrahydroisoquinolin-3-ylthio)acetamide (X). 5.6 ml
(10 mmol) of 10% aqueous KOH solution and 2.48 g
(10 mmol) of IX were added sequentially to a stirred
solution of 2.66 g (10 mmol) of VI in 15 ml of DMF.
The mixture was stirred for 4 h and left for a day. The
reaction mixture was diluted with an equal volume of
water and the resulting precipitate was filtered off,
washed with water (20 ml), ethanol (20 ml), and
hexane (20 ml), and recrystallized from butanol. Yield
3.68 g (77%), colorless crystals, mp 194–196°C. IR
spectrum, ν, cm–1: 3312 (NH), 2218 (C≡N), 1680
3-Thioxo-1-phenyl-2,3,5,6,7,8-hexahydroquino-
line-4-carbonitrile (VI). A solution prepared of 0.23 g
(10 mmol) of sodium and 10 ml of absolute ethanol
was added to a stirred mixture of 2.71 g (10 mmol) of
V and 1.34 g of II in 15 ml of absolute ethanol at 20°C.
The mixture was stirred for 4 h and left for 24 h. The
reaction mixture was diluted with 10% hydrochloric
acid to pH 5 and left for 2 days. The resulting
precipitate was filtered off, washed with water (20 ml),
ethanol (20 ml), and hexane (20 ml), and then
recrystallized from glacial acetic acid. Yield 1.84 g
(68%), yellow powder, mp 248–250°C (at 195°C
sublimates) (published [20]: 259–262°C). IR spectrum,
1
(CONH). H NMR spectrum, δ, ppm: 1.53–1.65 m
(2H, CH2), 1.72–1.80 m (2H, CH2), 2.53–2.69 m (2H,
CH2), 2.81–2.93 m (2H, CH2), 4.14 s (2H, SCH2),
7.18–7.26 m (2H, Harom), 7.38 t (1H, Ph), 7.39–7.59 m
(6H, Harom), 10.36 h. with (NH). 13C NMR spectrum,
δC, ppm: 21.35, 22.34, 27.32, 28.49, 35.25, 105.17,
115.23, 115.29, 121.28 (2C), 127.85, 128.37 (2C),
129.36, 129.61 (2C), 132.00 (2C), 138.85, 138.97,
152.71, 157.49, 160.40, 166.55. Mass spectrum, m/z
(Irel, %): 479 (100) [M + 1]+. Found, %: C 60.15, H
4.11, N 8.69. C24H20BrN3OS. Calculated, %: C 60.26,
H 4.23, N 8.78. M 478.414.
1
ν, cm–1: 3348 (NH), 2222 (C≡N), 1195 (C=S). H
NMR spectrum, δ, ppm: 1.58–1.65 m (2H, CH2), 1.75–
1.84 m (2H, CH2), 2.32 t (2H, CH2, J 4.5 Hz), 2.87 t
(2H, CH2, J 6.0 Hz), 7.42 d (2H, Ph, J 7.0 Hz), 7.51–
7.56 m (3H, Ph), 13.94 br.s (1H, NH). 13C NMR
spectrum, δC, ppm: 20.65, 20.90, 25.19, 28.86, 114.85,
115.84, 121.10, 128.22 (2C), 128.83 (2C), 129.95,
131.45, 151.24, 156.69, 174.74. Mass spectrum, m/z
(Irel, %): 267 (100) [M + 1]+. Found, %: C 71.98, H
5.22, N 10.39. C16H14N2S. Calculated, %: C 72.15, H
5.30, N 10.52. M 266.365.
1-Amino-N-(4-Bromophenyl)-5-phenyl-5,6,7,8-
tetrahydrothieno[2,3-c]isoquinoline-2-carboxamide
(XI). a. 5.6 ml (10 mmol) of 10% aqueous KOH
solution was added to a stirred solution of 4.8 g
(10 mmol) of X in 20 ml of DMF, the mixture was
stirred for 4 h and then diluted with an equal volume of
water. Tar product was separated by decantation and
rubbed up in 20 ml of MeOH. The resulting precipitate
was separated and washed with water (20 ml),
methanol (20 ml), and hexane (20 ml), and then
crystallized from methanol. Yield 3.3 g (69%), yellow
powder, mp 269–272°C. IR spectrum, ν, cm–1: 3195–
3-(2-Oxocyclohexylthio)-1-phenyl-5,6,7,8-tetra-
hydroisoquinoline-4-carbonitrile (VIII). 5.6 ml
(10 mmol) of 10% aqueous KOH solution and 1.77 g
(10 mmol) of VII were added sequentially to a stirred
solution of 2.66 g (10 mmol) of VI in 15 ml of DMF.
The mixture was stirred for 4 h and left for a day. The
reaction mixture was diluted with an equal volume of
water; tar product was separated by decantation and
rubbed up in 20 ml of MeOH. The precipitate formed
was separated and washed with water (20 ml),
methanol (20 ml), and hexane (20 ml), and recrystal-
lized from butanol. Yield 2.43 g (67%), colorless
crystals, mp 124–126°C. IR spectrum, ν, cm–1: 2219
(C≡N), 1714 (C=O). 1H NMR spectrum, δ, ppm: 1.51–
1.65 m (3H, CH2), 1.68–1.84 m (5H, CH2), 1.89–2.02
m (1H, CH2), 2.29–2.48 m (3H, CH2) , 2.55–2.64 m
(2H, CH2), 2.81–2.96 m (2H, CH2C=O), 4.68–4.77 m
1
3412 (NH2, NH), 1677 (CONH), 1646 [δ(NH2)]. H
NMR spectrum, δ, ppm: 1.54–1.69 m (2H, CH2), 1.76–
1.81 m (2H, CH2), 2.64–2.73 m (2H, CH2), 3.39–3.45
m (2H, CH2), 7.18 br.s (2H, NH2), 7.31–7.73 m (9H,
H
arom), 10.77 br.s (CONH). 13C NMR spectrum, δC,
ppm: 21.94, 22.13, 27.04, 28.37, 79.67, 115.30, 123.66
(2C), 123.99, 126.95, 128.50 (2C), 128.63, 129.28
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 83 No. 9 2013

1728
DYACHENKO, VOVK
and Lopyrev, V.A., Chem. Heterocycl. Comp. 2002,
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14. Katritzki, A.R. and Fan, W-Q., J. Het. Chem., 1988,
(2C), 131.59 (2C), 139.50 , 140.43, 145.27, 149.78,
156.71, 160.04, 164.94. Mass spectrum, m/z (Irel, %):
479 (100) [M + 1]+. Found, %: C 60.19, H 4.17, N
8.72. C24H20BrN3OS. Calculated, %: C 60.26, H 4.23,
N 8.78. M 478.414.
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b. 5.6 ml (10 mmol) of 10% aqueous KOH solution
and 2.48 g (10 mmol) of IX were added sequentially to
a stirred solution of 2.66 g (10 mmol) of VI in 15 ml
of DMF. The mixture was stirred for 4 h, and 5.6 ml
(10 mmol) of 10% aqueous KOH solution was added
once again. The reaction mixture was diluted with an
equal volume of water; tar product was separated by
decantation and rubbed up in 20 ml of MeOH. The
resulting precipitate was separated and washed with
water (20 ml), methanol (20 ml), and hexane (20 ml),
and then recrystallized from methanol. 3.54 g (74%) of
compound XI was obtained, identical (as from mp and
chromatography data) to the synthesized via the
method a.
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