Uncommon reaction of 2-bromomethyl-1,3-thiaselenole with pyridine and its derivatives

Article abstract of DOI:10.1134/S1070428017110148

Regioselective reaction of 2-bromomethyl-1,3-thiaselenole with pyridine and its derivatives is followed by rearrangement with ring expansion and the formation of a bond between a nitrogen atom and a carbon in the position 2. A set of derivatives of 2,3-dihydro-1,4-thiaselenine was obtained, substituted in the position 2 by a pyridinium residue functionalized by pharmacophoric groups.

Full text of DOI:10.1134/S1070428017110148

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2017, Vol. 53, No. 11, pp. 1691–1695. © Pleiades Publishing, Ltd., 2017.
Original Russian Text © S.V. Amosova, M.V. Penzik, Yu.I. Rykunova, V.А. Potapov, А.I. Albanov, 2017, published in Zhurnal Organicheskoi Khimii, 2017,
Vol. 53, No. 11, pp. 1655–1658.
Uncommon Reaction of 2-Bromomethyl-1,3-thiaselenole
with Pyridine and Its Derivatives
S. V. Amosova,* M. V. Penzik, Yu. I. Rykunova, V. А. Potapov, and А. I. Albanov
Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences,
ul. Favorskogo 1, Irkutsk, 664033 Russia
*e-mail: amosova@irioch.irk.ru
Received July 6, 2017
Abstract―Regioselective reaction of 2-bromomethyl-1,3-thiaselenole with pyridine and its derivatives is
followed by rearrangement with ring expansion and the formation of a bond between a nitrogen atom and a
carbon in the position 2. A set of derivatives of 2,3-dihydro-1,4-thiaselenine was obtained, substituted in the
position 2 by a pyridinium residue functionalized by pharmacophoric groups.
DOI: 10.1134/S1070428017110148
N- and Se-heterocycles possess a wide spectrum of
biological activity [1–3]. Compounds, where are
simultaneously present selenium and nitrogen
heterocycles, are described in [4–15]. Some
representatives of such systems possess various types
of bioactivity [7–10]. Combining useful properties of
N- and Se-heterocycles in one molecule may result in
creation of compounds with important biological
properties, so the search for methods of synthesis of
such heterocyclic systems is an actual task.
sion. The reaction with pyridine 2а results in the
formation of 1-(2,3-dihydro-1,4-thiaselenin-2-yl)pyri-
dinium bromide 3a in 85% yield. The reaction product
is a yellow powder easily soluble in water and alcohol,
sparingly soluble in chloroform.
Reaction proceeds regioselectively with the
formation of a bond of the nitrogen atom not with the
carbon atom of CH2Br group, but with the carbon atom
in position 2 of the generated 2,3-dihydro-1,4-
thiaselenine ring. A product of reaction with the
preservation of the five-membered ring is not formed
even in traces. It may be assumed that in the reaction
of nucleophilic substitution in 2-bromomethyl-1,3-
thiaselenole with pyridine in bipolar aprotic solvent
(acetonitrile) a seleniranium cation intermediately
forms with subsequent nucleophilic attack on the nodal
carbon atom of seleniranium cation. As a result a ring
expansion occurs with the formation of 2,3-dihydro-
1,4-thiaselenine substituted in position 2 (Scheme 1).
We developed a one-pot method for the preparation
of 2-bromomethyl-1,3-thiaselenole 1 based on the
reaction of selenium dibromide with divinyl sulfide [16,
17]. Compound 1 shows unusual reactivity in reactions
of nucleophilic substitution with nucleophiles of diverse
origin. The reactions proceed regioselectively at several
centers of intermediate seleniranium cation [17–21].
We found a reaction of nucleophile substitution to
occur in 2-bromomethyl-1,3-thiaselenole with pyridine
and its derivatives in acetonitrile at room temperature
which is followed by rearrangement with a ring expan-
Similar reaction with pyridine-3- and
-4-carbaldehydes 2b and 2c (Scheme 2) after 3 h led to
Scheme 1.
N
2a
S
N
Br
S
S
Br
N
Br
S
MeCN,
20_25oC, 1 h
Br
Se
Se
Se
Se
1
3a
1691

AMOSOVA et al.
1692
Scheme 2.
Scheme 4.
O
S
N
S
N
Br
Br
S
S
MeCN
MeCN
O
Br
Br
20_25oC, 2 h
20_25oC, 3 h
Se
Se
Se
N
N
Se
1
2f
3f
2b, 2c
3b, 3c
1
S
N
Br
S
the formation of bromides 1-(2,3-dihydro-1,4-thiase-
lenin-2-yl)-3-formylpyridinium and -4-formylpyridi-
nium 3b and 3c in yields 97 and 96% respectively. The
reaction with pyridine-2-carbaldehyde in these
conditions does not occur, evidently, as a result of
steric hindrances and deactivation of pyridine nitrogen
atom by the electron-acceptor aldehyde group.
MeCN
Br
20_25oC, 4 h
Se
N
Se
1
2g
3g
cycle are shifted downfield (6.52‒8.60 ppm) due to the
presence of a positive charge on the nitrogen atom.
The formation of six-membered ring is confirmed by
the direct spin-spin coupling constant between the
atoms of selenium and carbon of the CH2 group in the
fine structure 13С and 77Se NMR spectra. The values of
coupling constants 71.1‒72.3 Hz are in the range
typical of direct constants 1JSe,C [22].
The reaction of 2-bromomethyl-1,3-thiaselenole
with 3- and 4-(1,3-dioxolan-2-yl)pyridines 2d and 2e
proceeds in MeCN at room temperature during 3 h
(Scheme 3). The reaction with compound 2d occurs
regioselectively with the formation of 1-(2,3-dihydro-
1,4-thiaselenin-2-yl)-3-(1,3-dioxolan-2-yl)pyridinium
bromide 3d in 84% yield. From compound 2е 1-(2,3-
dihydro-1,4-thiaselenin-2-yl)-4-(1,3-dioxolan-2-yl)-
pyridinium bromide 3e was obtained in 94% yield.
Compounds 3b and 3c are poorly soluble in water
and DMSO. At registration of NMR spectra in D2O
compounds 3b and 3c fully transform into
dihydroxymethyl derivatives as a result of hydration of
the aldehyde group. However in the IR spectrum of
compounds 3b and 3c typical bands of absorption of
carbonyl group at 1706‒1710 cm–1 are observed.
Scheme 3.
O
O
O
S
N
Br
S
O
MeCN
Br
Hence applying a new regioselective reaction of
2-bromomethyl-1,3-thiaselenole with pyridine and its
derivatives we obtained in high yields a set of
previously unknown derivatives of 2,3-dihydro-1,4-
thiaselenine, functionalized with pharmacophoric
groups containing a pyridine ring. Compounds 3a–3g
probably possess bioactivity.
20_25oC, 3 h
Se
Se
N
1
2d, 2e
3d, 3e
In reaction of compound 1 with 4-ethenylpyridine
2f 1-(2,3-dihydro-1,4-thiaselenin-2-yl)-4-ethenyl-
pyridinium bromide 3f was obtained in 92% yield.
Compound 3f is interesting as a potential monomer.
The reaction with quinoline 2g occurs in acetonitrile at
room temperature and results in 1-(2,3-dihydro-1,4-
thiaselenin-2-yl)quinolinium bromide 3g in 92% yield
(Scheme 4).
EXPERIMENTAL
IR spectra were registered on a spectrophotometer
1
13
15
Bruker Vertex 70 from pellets with KBr. H, C, N,
and 77Se NMR spectra were obtained on a spectro-
meter Bruker DPX-400 (400.13, 100.61, 40.56, and
76.30 MHz respectively). Elemental analysis was
carried out on a CHNS-analyzer Thermo Scientific
Flash 2000. 2-Bromomethyl-1,3-thiaselenole 1 was
obtained by method [17].
The structure of compounds 3a–3g was confirmed
by multinuclear NMR spectroscopy (1H, 13C, 15N,
77Se), the composition was confirmed by the data of
1
elemental analysis. In H NMR spectra of compounds
3а–3g signals of protons of CH2Se groups were
observed as two doublets at 3.22‒3.99 ppm. Signals of
protons of SCH group of 2,3-dihydro-1,4-thiaselenine
3-(1,3-Dioxolan-2-yl)pyridine (2d). To a solution
of 2.14 g (0.02 mol) of pyridine-3-carbaldehyde cooled
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 53 No. 11 2017

UNCOMMON REACTION OF 2-BROMOMETHYL-1,3-THIASELENOLE WITH PYRIDINE
1693
3
3
to 0°С and 2.3 g of ethylene glycol in 30 mL of
toluene was added dropwise while stirring 1 mL of
concentrated sulfur acid. The mixture was heated for
2 h to boiling, water was distilled with toluene from
the reactive flask. Then the mixture was cooled to 0°С
and 10% solution of NaOH was added dropwise to
neutralize sulfur acid till weak alkaline reaction. The
reaction products were extracted with ethyl acetate, the
organic solution was dried with Na2SO4, the solvent
was distilled off on a rotary evaporator. Yield 2.36 g
(78%).
6.53 d.d (1Н, SСНN+, J 5.1, J 2.1 Hz), 6.61 d (1Н,
3
3
2
SCH=, J 10.4 Hz), 6.64 d (1Н, SeCH=, J 10.4, JSe,H
47.2 Hz), 8.02 d.d (1Н, Н5, C5H4N, 3J 6.1, 3J
8.1 Hz), 8.58 d (1Н, Н4, C5H4N, J 8.1 Hz), 8.91 d
3
(1Н, Н6, C5H4N, J 6.1 Hz), 8.99 s (1Н, Н2, C5H4N).
3
13С NMR spectrum (D2O), δ, ppm: 24.13 (CH2Se),
65.81 (SCHN+), 86.54 (ОСНО), 111.15 (=СНSe),
116.23 (=СНS), 127.33 (С5, C5H4N), 140.95 (C2,
C5H4N), 142.35 (C3, C5H4N), 142.84 (C6, C5H4N),
144.31 (C4, C5H4N). 15N NMR spectrum (D2O), δ,
ppm: ‒156.0. 77Se NMR spectrum (D2O), δ, ppm: 81.1.
Found, %: C 33.94; H 2.80; N 4.21. C10H10BrNOSSe.
Calculated, %: C 34.21; H 2.87; N 3.99.
4-(1,3-Dioxolan-2-yl)pyridine (2e) was obtained
similary in 80% yield.
1-(2,3-Dihydro-1,4-thiaselenin)-4-formylpyridi-
nium bromide (3c). Reaction time 3 h. Yield 0.674 g
(96%). Brown oily substance. IR spectrum, ν, cm–1:
1710 (С=О). In D2O it is present as 1-(2,3-dihydro-1,4
-thiaselenin)-4-(dihydroxymethyl)pyridinium bro-
mide. 1Н NMR spectrum (D2O), δ, ppm: 3.22 d.d (1H,
Compounds 3a–3g. General procedure. To a
solution of 0.488 g (2.00 mmol) of 2-bromomethyl-1,3
-thiaselenole 1 in 5 mL of acetonitrile was added 2.00
mmol of compound 2a–2g, and the mixture was
intensively stirred at room temperature for 1‒4 h. The
precipitate was filtered off, washed with acetonitrile,
and dried in a vacuum. Liquid products of reaction 3с
and 3е were dried in a vacuum after distillation of
acetonitrile.
2
3
2
SeCH2, J 13.5, J 5.3 Hz), 3.57 d.d (1Н, SeCH2, J
3
13.5, J 2.1 Hz), 6.11 s (1H, OCHO, J 17.7, 10.8 Hz),
6.52 br.d.d (1H, SCHN+, 3J 5.3, 3J 2.1 Hz), 6.59 d (1Н,
3
3
SCH=СНSe, J 10.4 Hz), 6.61 d (1Н, SCH=СНSe, J
10.4, J=CH-Se 47.0 Hz), 8.06 d (2Н, Н3,5, C5H4N, J
6.7 Hz), 8.92 d (2Н, Н2,6, C5H4N, 3J 6.7 Hz). 13С NMR
spectrum (D2O), δ, ppm: 25.40 (CH2Se), 66.62
(SCHN+), 88.58 (OCHO), 112.47 (=СНSe), 117.48
(=СНS), 125.90 (С3,5, C5H4N), 144.59 (C2,6, C5H4N),
162.00 (C4, C5H4N). 15N NMR spectrum (D2O), δ,
ppm: ‒156.6. 77Se NMR spectrum (D2O), δ, ppm: 82.3.
Found, %: С 33.94; Н 2.80; N 4.21. С10H10BrNOSSe.
Calculated, %: С 34.21; Н 2.87; N 3.99.
2
3
1-(2,3-Dihydro-1,4-thiaselenin-2-yl)pyridinium
bromide (3a). Reaction time 1 h. Yield 0.549 g (85%).
Yellow-brown powder, mp 135‒137°С (with
1
decomposition). Н NMR spectrum (CD3OD), δ, ppm:
3.50 d.d (1H, SeCH2, 2J 13.6, 3J 5.3 Hz), 3.68 d.d (1Н,
2
3
3
SeCH2, J 13.6, J 2.2 Hz), 6.86 d.d (1H, SCHN+, J
5.3, 3J 2.2 Hz), 6.78 d (1Н, SCH=СНSe, 3J 10.0, 3JH,Se
3
2
21.0 Hz), 6.78 d (1Н, SCH=СНSe, J 10.0, J=CH–Se
52.0 Hz), 8.21 d.d (2Н, Н3,5, C5H54N, 3J 7.5, 3J 6.9 Hz),
8.71 t.t (1Н, Н4, C5H5N, J 7.5, J 1.2 Hz), 9.18 d.d
3
1-(2,3-Dihydro-1,4-thiaselenin-2-yl)-3-(1,3-dioxo-
lan-2-yl)pyridinium bromide (3d). Reaction time 3 h.
Yield 0.664 g (84%). Red-orange powder, mp 138‒
139°С. 1Н NMR spectrum (D2O), δ, ppm: 3.56 narrow
m (2H, SeCH2), 4.05 m (4Н, ОСН2СН2О), 6.15 s (1Н,
(2Н, Н2,6, C5H5N, J 6.9, J 1.2 Hz). 13С NMR
3
4
spectrum (CD3OD), δ, ppm: 25.67 (CH2Se), 67.35
1
(SCHN+), 112.62 (=СНSe, JC-Se 114.6 Hz), 117.72
(=СНS), 129.00 (C3,5, C5H5N), 144.89 (C2,6, C5H5N),
15
148.11 (C4, C5H5N). N NMR spectrum (CD3OD), δ,
3
ОСНО), 6.96 t (1Н, SСНN+, J 3.0 Hz), 6.84 d (2Н,
ppm: ‒169.7. 77Se NMR spectrum (CD3OD), δ, ppm:
85.1. Found, %: C 33.42; H 3.11; N 4.21; S 9.91.
С9H10BrNSSe. Calculated, %: C 33.46; H 3.12; N
4.33; S 9.92.
3
2
3
SeCH=, J 10.0, JSeH 47.0 Hz), 6.88 d (2Н, SCH=, J
10.0 Hz), 8.30 d.d (1Н, H5, C5H4N, 3J 7.8, 3J 6.1 Hz), 8.72
d (1Н, H4, C5H4N, 3J 7.8 Hz), 9.12 d (1Н, H6, C5H4N, 3J
6.1 Hz), 9.14 m (1Н, H2, C5H4N). 13С NMR spectrum
1
(D2O), δ, ppm: 24.64 (СН2Se, JSeC 71.1 Hz), 65.27
1-(2,3-Dihydro-1,4-thiaselenin-2-yl)-3-formylpy-
ridinium bromide (3b). Reaction time 3 h. Yield
0.681 g (97%), brown powder, mp 129‒130°С. IR
spectrum, ν, cm–1: 1706 (С=О). In D2O it is present as
1-(2,3-dihydro-1,4-thiaselenin-2-yl)-3-(dihydroxyme-
thyl)pyridinium bromide. 1Н NMR spectrum (D2O), δ,
ppm: 3.22 d.d (1H, SeCH2, 2J 13.3, 3J 5.1 Hz), 3.60 d.d
(SСНN+), 65.45 (OCH2), 99.12 (OCHO), 111.93 (=СНSe,
1JSeC 113.8 Hz), 117.35 (=СНS), 127.90 (С5, C5H4N),
138.79 (C3, C5H4N), 141.46 (С2, C5H4N), 144.12 (C4,
C5H4N), 144.89 (C6, C5H4N). 15N NMR spectrum (D2O),
δ, ppm: ‒153.2. 77Se NMR spectrum (D2O), δ, ppm: 85.3.
Found, %: C 36.23; H 3.89; N 3.82. C12H14BrNO2SSe.
Calculated, %: C 36.47; H 3.57; N 3.54.
2
3
(1Н, SeСН2, J 13.3, J 2.1 Hz), 6.15 s (1Н, ОСНО),
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 53 No. 11 2017

AMOSOVA et al.
1694
1-(2,3-Dihydro-1,4-thiaselenin-2-yl)-4-(1,3-dioxo-
C9H7N), 129.5 (C4а, C9H7N), 130.99 (C6, C9H7N),
131.12 (C7, C9H7N), 138.06 (C5, C9H7N), 146.93 (C2,
C9H7N), 148.16 (C4, C9H7N), 137.65 (C8а, C9H7N).
77Se NMR spectrum, δ, ppm: 78.2. Found, %: С 41.42;
Н 3.11; N 4.02. С13H12BrNSSe. Calculated, %: С
41.84; Н 3.24; N 3.75.
lan-2-yl)pyridinium bromide (3e). Reaction time 3 h.
1
Yield 0.743 g (94%). Brown oily substance. Н NMR
spectrum (CDCl3), δ, ppm: 3.66 d.d (1Н, SeСН2, 2J 13.9,
2
3
3J 4.4 Hz), 3.71 d.d (1Н, SeСН2, J 13.9, J 2.6 Hz),
4.07‒4.11 m (2Н, ОСН2СН2О), 6.03 s (1Н, ОСНО),
6.64 s (2Н, SeCH=СНS), 7.78 s (1Н, SСНN+), 8.10 d
(2Н, Н3,5, C5H4N, 3J 6.5 Hz), 9.72 d (2Н, Н2,6, C5H4N,
3J 6.5 Hz). 13С NMR spectrum (CDCl3), δ, ppm: 25.74
(СН2Se, 1JC–Se 72.3 Hz), 64.63 (SСНN+), 65.85 (OCH2),
99.95 (OCHO), 111.16 (=СНSe), 116.68 (=СНS),
124.70 (С3,5, C5H4N), 144.19 (C2,6, C5H4N), 157.85 (C4,
ACKNOWLEDGMENTS
The study was performed under a financial support
of the Complex program of fundamental scientific
research of Siberian Branch of the Russian Academy
of Sciences (project no. 8.04) using the equipment of
Baikal analytic center of joint usage of Siberian
Department of Russian Academy of Sciences.
15
C5H4N). N NMR spectrum (CDCl3), δ, ppm: ‒153.8.
77Se NMR spectrum (CDCl3), δ, ppm: 77.9. Found, %:
С
36.33;
Н
3.58;
N
3.32. С12H14BrNO2SSe.
Calculated, %: C 36.47; H 3.57; N 3.54.
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3
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3
9.4 Hz), 8.36 d (1Н, H5, C9H7N, J 7.6 Hz), 8.60 br.d
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RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 53 No. 11 2017

UNCOMMON REACTION OF 2-BROMOMETHYL-1,3-THIASELENOLE WITH PYRIDINE
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