Bis[2-(4-pyridyl)ethyl](2-cyanoethyl)phosphine Oxide: Synthesis and Reactions with 1,4-Dihalobutanes

Article abstract of DOI:10.1134/S1070363219020117

Bis[2-(4-pyridyl)ethyl]phosphine reacts with acrylonitrile under mild conditions to form bis[2-(4- pyridyl)ethyl](2-cyanoethyl)phosphine which is readily oxidized in air to the corresponding bis[2-(4-pyridyl)- ethyl](2-cyanoethyl)phosphine oxide. The latter compound reacts with 1,4-dihalobutanes according the scheme of polyquaternization with practically quantitative formation of high-molecular cationic compounds (ionenes) bearing phosphine oxide groups and pyridinium cycles in the main chain. The thus obtained ionenes enter the intermolecular interaction with anionic polyelectrolytes (polyacrylic acid, heparin). They were also found to exhibit antibacterial activity.

Full text of DOI:10.1134/S1070363219020117

ISSN 1070-3632, Russian Journal of General Chemistry, 2019, Vol. 89, No. 2, pp. 236–241. © Pleiades Publishing, Ltd., 2019.
Russian Text © S.I. Verkhoturova, V.L. Mikhailenko, S.N. Arbuzova, O.F. Vyatchina, V.N. Kizhnyaev, 2019, published in Zhurnal Obshchei Khimii, 2019,
Vol. 89, No. 2, pp. 237–243.
Bis[2-(4-pyridyl)ethyl](2-cyanoethyl)phosphine Oxide:
Synthesis and Reactions with 1,4-Dihalobutanes
a
b
a
S. I. Verkhoturova *, V. L. Mikhailenko , S. N. Arbuzova ,
b
b
O. F. Vyatchina , and V. N. Kizhnyaev
a
Favorsky Institute of Chemistry, Siberian Branch, Rusian Academy of Sciences,
ul. Favorskogo 1, Irkutsk, 664033 Russia
*
e-mail: verkhoturova@irioch.irk.ru
b
Irkutsk State University, Irkutsk, Russia
Received August 2, 2018; revised August 2, 2018; accepted August 10, 2018
Abstract—Bis[2-(4-pyridyl)ethyl]phosphine reacts with acrylonitrile under mild conditions to form bis[2-(4-
pyridyl)ethyl](2-cyanoethyl)phosphine which is readily oxidized in air to the corresponding bis[2-(4-pyridyl)-
ethyl](2-cyanoethyl)phosphine oxide. The latter compound reacts with 1,4-dihalobutanes according the
scheme of polyquaternization with practically quantitative formation of high-molecular cationic compounds
(
ionenes) bearing phosphine oxide groups and pyridinium cycles in the main chain. The thus obtained ionenes
enter the intermolecular interaction with anionic polyelectrolytes (polyacrylic acid, heparin). They were also
found to exhibit antibacterial activity.
Keywords: pyridylphosphine oxides, bis[2-(4-pyridyl)ethyl](2-cyanoethyl)phosphine oxide, acrylonitrile, bis[2-
(
4-pyridyl)ethyl]phosphine, ionenes, polyquaternization
DOI: 10.1134/S1070363219020117
Pyridylphosphine oxides and their reduced pre-
cursors, pyridylphosphines, are now widely investigated
as effective ligands in metal complexes used for
various purposes [1–7], as building blocks in organo
element synthesis [8–11], and as intermediates in the
synthesis of medicinal compounds [12–17]. Another
promising area is the directed synthesis of functionally
substituted pyridylposphine oxides containing other
pharmacophoric groups. As one example, it could be
expected that incorporation of the cyanoethyl fragment
into the molecule of pyridylphosphine oxides would
lead to the formation of new physiologically active
compounds, specically, showing antitumor [18], anti-
phlogistic [19], or antibacterial activity [20].
Bispyridines and bispyridylphosphine oxides are also
successfully used in the syntheses of ionens [21–23].
These latter substances are heterochain polymers with
positively charged quaternary nitrogen atoms which
found wide practical use, specifically, in the synthesis
of medicinal agents [21, 24–26].
from red phosphorus, 4-vinylpyridine, and acrylonitrile,
and to study the reaction of this polyfunctional tertiary
phosphine oxide with 1,4-dihaloalkanes in order to obtain
new pharmaceutically active nitrogen- and phosphorus-
containing ionenes.
As the basis, for the synthesis of the target [2-(4-
pyridyl)ethyl](2-cyanoethyl)phosphine oxide 3 we
used the reaction of nucleophilic addition of bis[2-(4-
pyridyl)ethyl]phosphine 1 to acrylonitrile in the
system: acetonitrile, 50% aqueous solution of NaOH
(
Scheme 1). The reaction proceeds at 47–50°С for 7 h
and leads, in the first stage, to the formation of bis[2-(4-
pyridyl)ethyl](2-cyanoethyl)phosphine 2 which is
readily oxidized in air to give the corresponding
phosphine oxide 3. The practical yield of this latter
compound, after purification by flash-chromatography
on Al O , was 57%.
2
3
The course of the reaction was monitored with the
3
1
use of Р NMR spectroscopy to the disappearance of
the signal of bis[2-(4-pyridyl)ethyl]phosphine
The aim of the present investigation was to find a
convenient approach to the synthesis of bis[2-(4-
pyridyl)-ethyl](2-cyanoethyl)phosphine oxide starting
1
(–70 ppm) and development of the signal of bis[2-(4-
pyridyl)ethyl](2-cyanoethyl)phosphine 2 (–26 ppm).
2
36

BIS[2-(4-PYRIDYL)ETHYL](2-CYANOETHYL)PHOSPHINE OXIDE
237
Scheme 1.
N
N
N
NaOH, H O−MeCN (Ar)
2
P H +
P
o
4
7−50 C, 7 h
CN
CN
N
1
2
N
N
CN
O (air)
2
P
O
3
The starting bis[2-(4-pyridyl)ethyl]phosphine 1 was
prepared by the Trofimov–Gusarova reaction [27, 28]
from red phosphorus and 4-vinylpyridine [29–31]
The ionenes 4а, 4b are slightly colored powders,
soluble in water. The structure of 4а, 4b was proved
with the use of Н, Р NMR spectroscopy, and their
1
31
(Scheme 2). The thus obtained bis[2-(4-pyridyl)ethyl](2-
composition was confirmed by the elemental analysis.
cyanoethyl)phosphine oxide 3 was used then for the prepa-
ration of new nitrogen- and phosphorus-containing ionenes.
Aqueous solutions of the ionenes 4а, 4b have
specific electric conductivities within the interval of
–
3
(
1–3)×10
S/сm and show the effect of
It was experimentally shown that bis(pyridyl)phos-
phine oxide 3 readily reacts with 1,4-dibromo- or 1,4-
diiodobutane (60°С, 24–48 h, ethanol, reagents molar
ratio 1 : 1) to give ionenes (linear high-molecular
substances of cationic origin) 4a, 4b with nearly
quantitative yield (Scheme 3).
polyelectrolytic swelling (increasing reduced viscosity
with dilution) which can be eliminated by the addition
of low-molecular salts.
By the correlation between the measured under the
similar conditions reduced viscosities of the obtained
Scheme 2.
N
N
N
KOH(H O)
2
Pn
PH /H2
P H
3
toluene
KOH−DMSO (H O)
2
1
Scheme 3.
(
CH ) CN
2 2
3
+ X(CH ) X
N
(CH )
P
(CH
2
)
2
N
(CH )
2 4
2
4
2 2
−
−
X
X
O
n
4
а, 4b
X = Br (4а, 88%), I (4b, 99%).
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 89 No. 2 2019

2
38
VERKHOTUROVA et al.
(
а)
(b)
z
z
Fig. 1. Turbodimetric titration curves: (a) Titration of of sodium polyacrylate solution with solutions of ionenes 4а (1) and 4b (2);
b) Titration of heparin solution with solutions of ionenes 4а (3) and 4b (4).
(
ionenes [0.11 dL/g (4а), 0.22 dL/g (4b)] and pyridine-
containing ionenes with known molecular weights
described in the literature [32] it became possible to
estimate tentatively the molecular weights of the
polycations obtained in the present work [9500 (4а),
tures of sodium polyacrylate and ionenes 4а (Fig. 2,
curve 1) and 4b (Fig. 2, curve 2) at рН 9.5, or mixtures
of heparin and ionene 4а (Fig. 2, curve 3) and 4b
(Fig. 2, curve 4) at рН 5.0 were titrated with 2 М
solution of NaCl at the component ratio z = 0.33 (Fig. 2).
1
5000 (4b)].
Addition of even small amounts of NaCl to the
system results in marked development of turbidity
which can be attributed to the destruction of non-
stoichiometric polyelectrolyte complexes and the
formation of stoichiometric polyelectrolyte complexes
as sediments. It should be noted that solutions of non-
stoichiometric polyelectrlyte complexes with heparin
show a slightly higher resistance to the increase in the
ionic strength of the solution (Fig. 2, curves 3, 4). The
result is anticipated considering that in heparin-based
polyelectrlyte complexes both carboxylate and sul-
fonate anions are participating in the formation of ionic
bonds, while with polyacrylic acid only carboxylate
anions are taking part. Further increase in the con-
centration of NaCl in the system results in dissolution
of the precipitated stoichiometric polyelectrolyte
complex. For all the studied systems, there is observed
the area of the components ratio z where no
sedimentation of insoluble complexes is taking place
Ionenes 4а, 4b enter the interpolymer interaction
with polyanions of synthetic (polyacrylic acid) or
natural (heparin) origin to form water-insoluble
polyelectrolyte complexes, as it was demonstrated by
the results of turbodimetric titration. Aqueous solution
of sodium polyacrylate was titrated with aqueous
solutions of ionenes 4а (Fig. 1, curve 1) and 4b (Fig. 1,
curve 2) at рН 9.5; aqueous solution of heparin was
titrated with aqueous solutions of ionenes 4а (Fig. 1,
curve 3) and 4b (Fig. 1, curve 4) at рН 5.0 (Fig. 1).
The ratio z = [ionene] : [sodium polyacrylate or
heparin] shows the ratio of a given ionene and poly-
anion as converted to the content of positevely charged
–
(
in ionene) or negatively charged (–COO in sodium
–
3
–
polyacrylate, –SO and –COO in heparin) groups.
Resistance of the formed complexes to the action of
low-molecular electrolytes was studied by the method
of turbodimetric titration: aqueous solutions of mix-
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 89 No. 2 2019

BIS[2-(4-PYRIDYL)ETHYL](2-CYANOETHYL)PHOSPHINE OXIDE
а) (b)
239
(
[NaCl], M
[NaCl], M
Fig. 2. Turbodimetric titration curves: (a) Titration of aqueous solutions of mixtures of sodium polyacrylate and ionenes 4а (1) and
b (2); (b) Titration of mixtures of heparin with ionenes 4а (3) and 4b (4) with 2 М solution of NaCl.
4
(
Fig. 1), and it is only at z ≥ 0.35–0.5 when the
and 161.98 MHz, respectively) instruments with
1
13
formation of the insoluble stoichiometric polyelec-
trolyte complex as a precipitate is observed. With
polycation present in excess in the reaction mixture, in
all the systems the formed stoichiometric poly-
electrolyte complex dissolves nearly completely to
form the water-soluble non-stoichiometric polyelec-
trolyte complex.
HMDS ( Н, C) as an internal standard and 85%
3
1
H PO ( P) as an external standard. IR spectra were
3
4
recorded on a Varian 3100 FT-IR spectrometer in KBr
tablets. Electric conductivity measurements of aqueous
solutions of the ionenes were made with the use of an
ОK-302 Radelkis conductometer. Viscosities of the
studied ionenes were determined in 0.4 М aqueous
solution of KBr with an Ubellohde viscosimeter at 20°С.
Molecular weights of the ionenes were estimated
basing on the intrinsic viscotities of their solutions in
water-salt systems. Antibacterial activities of the
ionenes were determined from the rate of suppression
of bacteria growth, Escherichia coli АТСС 35218 and
Staphylococcus aureus АТСС 29213 lines were used
as test cultures [33].
It was also shown that the above-described ionenes
а, 4b exhibit a distinct antibacterial activity toward
4
the test strain cultures of Escherichia coli and Staphylo-
coccus aureus at concentrations of 0.01–0.1% [33].
To conclude, it was found that bis[2-(4-pyridyl)-
ethyl](2-cyanoethyl)phosphine oxide which can be
easily prepared starting from the available bis[2-(4-
pyridyl)ethyl]phosphine and acrylonitrile reacts with
The starting bis[2-(4-pyridyl)ethyl]phosphine 1 was
prepared from red phosphorus and 4-vinylpyridine
according to the procedure [29]. 1,4-Dibromobutane
and 1,4-diiodobutane (Merck) were used as quaterniza-
tion agents.
1
,4-dibromo- and 1,4-diiodobutanes under mild condi-
tions to give in high yields polycations (ionenes),
bearing phosphine oxide groups and charged pyri-
dinium cycles in the main chain. The obtained ionenes
are capable of binding in aqueous media heparin as
insoluble complexes which can be used in medical
practice for the regulation of blood coagulability.
Bis[2-(4-pyridyl)ethyl](2-cyanoethyl)phosphine
oxide (3). To a mixture of 1.32 g (5.4 mmol) of bis[2-
(
4-pyridyl)ethyl]phosphine dissolved in 3 mL of aceto-
EXPERIMENTAL
31
nitrile and 0.64 g of a 50% aqueous solution of NaОН
(8 mmol) blown through with argon and cooled to 10°С,
a solution of 0.57 g (10.7 mmol) of acrylonitrile in
1
13
Н, C, and Р NMR spectra were obtained on a
Bruker DPX 400 and Bruker AV-400 (400.13, 101.61,
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 89 No. 2 2019

2
40
VERKHOTUROVA et al.
2
1
mL of acetonitrile was added over a period of
5 min. The reaction mixture was heated (47–50°С)
Ionene 4b. Yield 0.37 g (99%), light yellow
–
1
powder. IR spectrum, ν, cm : 1166 (P=O), 1516, 1592
3
1
1
for 3 h and then analyzed with use of the Р NMR
method. In the spectrum signals of the starting bis[2-(4-
pyridyl)ethyl]phosphine 1 (–70 ppm), bis[2-(4-pyridyl)-
eyhyl](2-cyanoethyl)phosphine 2 (–26 ppm), and bis[2-
and 1639 (Py), 2240 (СN). Н NMR spectrum, δ, ppm
(D O): 2.02 m (4Н, NСН СН СН ), 2.46 m (6Н,
2
2
2
2
СН Р), 2.80 m (2Н, СН СN), 3.23 m (4Н, СН Py),
2
2
2
3
,5
4.65 m (4Н, NСН СН СН СН ), 7.95 d (4Н, Н , Py,
JHH = 5.7 Hz), 8.69 d (4Н, Н , Py, J = 5.7 Hz). Р
2
2
2
2
2,6
3
3
31
(
(
4-pyridyl)ethyl](2-cyanoethyl)phosphine oxide
47 ppm) in the ratio 2 : 1 : 0.1 were present. To the
3
HH
NMR spectrum (D O): δ 54.5 ppm. Found, %: C
2
Р
reaction mixture heated to 40°С 0.64 g of 50% of
aqueous solution of NaОН and 0.42 g (8 mmol) of
acrylonitrile in 1 mL of acetonitrile were added for
40.89; H 4.97; N 6.98; P 4.41. C H I N OP.
Calculated, %: C 40.47; H 4.53; N 6.74; P 4.97.
21 28 2 3
Turbodimetric titration. For the investigation of
interpolymer interaction of ionenes 4а, 4b with
synthetic and natural polymeric anions we used
commercial heparin (Spofa, Czech Republic, acid
groups content 30%, acid number 81.3 mg/g) and
unfractionated specimen of polyacrylic acid (М =
1
0 min. The obtained mixture was then heated (47–50°С)
for more 4 h, and then passed through Al O (2 cm)
2
3
with acetonitrile as an eluent. The obtained yellow oily
substance was purified by column chromatography on
Al O (d = 3.5 cm, h = 5 cm) with chloroform as an
2
3
eluent. Yield 0.96 g (57%), white powder, mp 129–
170000, estimated by viscosimetry in dioxane at 30°С).
–
1
1
30°С. IR spectrum, ν, cm : 1158 (Р=О), 1499, 1559
Formation of interpolymer complexes was studied by
turbodimetric titration with the use of a KFK-2
photocolorimeter. Concentrations of sodium poly-
acrylate, heparin, and ionenes 0.01 base-mol/L; D is an
optical density, relative units.
1
and 1601 (Py), 2239 (C≡N). H NMR spectrum, δ,
ppm (CDCl ): 2.12 m (6Н, СН Р), 2.74 m (2Н,
3
2
3
,5
СН СN), 2.95 m (4Н, СН Py), 7.14 d (4Н, Н , Py,
2
2
3
2,6
3
13
JHH = 5.1 Hz), 8.55 d (4Н, Н , Py, J = 5.1 Hz). C
HH
NMR spectrum, δ , ppm (CDCl ): 10.4 d (СН CN,
С
3
2
2
1
JСP = 3.2 Hz), 24.3 d (СН СН CN, J = 62.3 Hz),
2
2
СP
FUNDING
2
2
7.0 d (СН Py, J = 2.8 Hz), 29.5 d (PyСН СН ,
2 СP 2 2
1
3
J
= 64.3 Hz), 118.6 d (СN, J = 10.8 Hz), 123.4
СP
C , Py), 149.0 d (С , J = 13.6 Hz), 150.3 (С ). Р
СP
,5
This study was performed with the use of the
equipment of the Baikal Analytic Center for Joint Use of
the Siberian Branch of Russian Academy of Sciences.
3
4
3
2,6 31
(
CP
NMR specrum (CDCl ): δ 44.2 ppm. Found, %: С
3
Р
6
4.92; Н 6.20; N 13.18; Р 9.61. С H N OP. Cal-
17 20 3
culated, %: C 65.16; Н 6.43; N 13.41; Р 9.89.
CONFLICT OF INTEREST
No conflict of interest was declared by the authors.
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RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 89 No. 2 2019

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RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 89 No. 2 2019