Vanadium-Catalyzed Condensation of Ethyl Cyanoacetate with Ketones

Article abstract of DOI:10.1134/S1070363218030052

Vanadium compounds and complexes activated by pyridine or morpholine catalyze condensation of ethyl cyanoacetate with ketones and aldehydes leading to alkylidenecyanoacetates in 75–100% yield.

Full text of DOI:10.1134/S1070363218030052

ISSN 1070-3632, Russian Journal of General Chemistry, 2018, Vol. 88, No. 3, pp. 403–409. © Pleiades Publishing, Ltd., 2018.
Original Russian Text © R.I. Khusnutdinov, N.А. Shchadneva, Yu.Yu. Mayakova, 2018, published in Zhurnal Obshchei Khimii, 2018, Vol. 88, No. 3,
pp. 375–381.
Vanadium-Catalyzed Condensation of Ethyl Cyanoacetate
with Ketones
R. I. Khusnutdinov*, N. А. Shchadneva, and Yu. Yu. Mayakova
Institute of Petrochemistry and Catalysis of Russian Academy of Sciences,
pr. Oktyabrya 141, Ufa, 450075 Russia
*
e-mail: inklab4@gmail.com
Received October 5, 2017
Abstract—Vanadium compounds and complexes activated by pyridine or morpholine catalyze condensation of
ethyl cyanoacetate with ketones and aldehydes leading to alkylidenecyanoacetates in 75–100% yield.
Keywords: ethyl cyanoacetate, aldehydes, ketones, vanadium complexes, pyridine, morpholine
DOI: 10.1134/S1070363218030052
The Knoevenagel reaction, which is one of the most
important reactions for the design of a new carbon–
carbon bond, is widely used in organic synthesis [1, 2].
The Knoevenagel condensation products of ketones
and aldehydes with active methylene group
compounds are key intermediates for preparation of
various compounds [3–7].
catalysts of condensation of ketones and aldehydes
with malononitrile leading to the formation of
alkylidene- and cycloalkylidenemalononitriles in 75–
99% yields (140°С, 5 h) [11]. Later on, it was shown
that compounds and complexes of vanadium V O ,
2
4
V O , VCl , VCl , VO(acac) activated with pyridine
2
5
3
4
2
or morpholine also effectively catalyze these reactions.
The best results were obtained with VO(acac) , V O ,
2
2
4
Classical Knoevenagel reaction is catalyzed by
bases, in particular, by secondary and tertiary amines,
pyridine and their salts taken in stoichiometric
amounts. The bases deprotonate active methylene
group to produce an anion, which attacks the carbonyl
group of the aldehyde or ketone with the formation of
α,β-conjugated enone and elimination of water
molecule [8]. It was shown that ionic liquids [9] and
heterogeneous systems could be used as effective
catalysts for the Knoevenagel reaction: zirconium
phosphate, gallium alumophosphates, silica gels doped
with amines, zeolites doped with alkali metal
carbonates [10]. As СН-acids in the Knoevenagel
reaction most often malononitrile and ethyl cyano-
acetate are used. Although a large number of studies
corresponds to the reaction of the latter with alde-
hydes, there are only few reports on similar reactions
with ketones, apparently due to lower activity of the
latter. The goal of the present work is to elaborate an
efficient catalyst for condensation of ethyl
cyanoacetate with ketones and aldehydes.
VCl . VCl turned out to be ineffective in this reaction,
3
4
while in the presence of V O the condensation of
2
5
ethyl cyanoacetate with carbonyl compounds proceeds
with low selectivity. The role of the transition metal is
to activate the carbonyl group of an aldehyde or ketone
due to coordination, and the СН group of ethyl
2
cyanoacetate due to chelate coordination to CN and
CO Et groups. Morpholine and pyridine abstract
2
proton from the СН group of ethyl cyanoacetate. The
2
reaction can be performed without solvent, but the
reactions with solid ketones and aldehydes should be
preferably carried out in methylene chloride with the
molar ratio of the catalyst and reagents [V] : [pyridine/
morpholine] : [ketone] : [ethyl cyanoacetate] = 3 : 1–
3
: 100 : 120. The reaction can be successfully carried
out in chloroform, carbon tetrachloride, and water.
Principal features of the reaction have been studied
by the example of the reaction of cyclopentanone 1
with ethyl cyanoacetate (Scheme 1). Most active and
selective among the tested catalysts VCl , V O ,
3
2
4
Earlier we have shown that systems Мо(СО) –Ру
VO(acac) was VO(acac) activated with morpholine
6
2 2
and Мо(СО) –morpholine (pyridine) are efficient
[VO(acac) ] : [morpholine] = 1 : 1 (see the table). The
2
6
4
03

4
04
KHUSNUTDINOV et al.
Effect of the nature and concentration of the catalyst and reaction conditions on the features of the reaction of cyclopentanone
1
with ethyl cyanoacetate
Catalyst
Ligand (L)
[V] : [L] : [1] : [ethyl cyanoacetate]
0 : 20 : 100 : 100
0 : 20 : 100 : 100
3 : 0 : 100 : 100
3 : 3 : 100 : 100
3 : 3 : 100 : 100
3 : 3 : 100 : 100
1 : 0 : 100 : 100
1 : 0 : 100 : 100
3 : 0 : 100 : 100
3 : 3 : 100 : 100
3 : 3 : 100 : 100
3 : 3 : 100 : 100
3 : 3 : 100 : 100
1 : 0 : 100 : 100
3 : 0 : 100 : 100
3 : 0 : 100 : 100
3 : 1 : 100 : 100
3 : 2 : 100 : 100
3 : 3 : 100 : 100
3 : 3 : 100 : 100
3 : 4 : 100 : 100
3 : 1 : 100 : 100
3 : 2 : 100 : 100
3 : 3 : 100 : 100
3 : 4 : 100 : 100
3 : 3 : 100 : 100
3 : 3 : 100 : 100
Т, °С
40
40
40
40
40
40
20
40
40
20
40
20
40
20
20
40
40
40
20
40
40
40
40
40
40
40
40
Time, h
Yield of 1а, %
–
–
Pyridine
Morpholine
–
1
12
16
10
28
32
44
15
23
29
46
62
49
67
24
45
62
67
73
75
87
81
69
88
98
90
71
65
1
VСl
3
3
3
3
1
VСl
VСl
VСl
Pyridine
Morpholine
Morpholine
–
1
1
2
V
V
V
V
V
V
V
2
2
2
2
2
2
2
O
4
4
4
4
4
4
4
2
O
O
O
O
O
O
–
2
–
1
Pyridine
Pyridine
Morpholine
Morpholine
–
1
1
1
1
VO(acac)
VO(acac)
VO(acac)
VO(acac)
VO(acac)
VO(acac)
VO(acac)
VO(acac)
VO(acac)
VO(acac)
VO(acac)
VO(acac)
VO(acac)
VO(acac)
2
2
2
2
2
2
2
2
2
2
2
2
2
2
1
–
1
–
1
Pyridine
Pyridine
Pyridine
Pyridine
Pyridine
Morpholine
Morpholine
Morpholine
Morpholine
Morpholine
Morpholine
1
1
1
1
1
1
1
1
1
0.5
0.25
system VO(acac) –pyridine was less active apparently
As is seen from the table, optimal reaction condi-
2
due to a lower basicity of pyridine than morpholine
tions and the ratio of the reagents are as follows: 40°С,
(
the рK of the corresponding conjugated acids are
1 h, [VO(acac) ] : [morpholine] : [ketone] : [ethyl
а
2
5
.23 and 8.33).
cyanoacetate] = 3 : 3 : 100 : 100. In the absence of
Scheme 1.
O
CN
CN
[V]L
CO Et
+
2
_
_
2
0 40°C, 1 2 h
CO Et
2
1
1a
[
V] = VO(acac) , L = morpholine.
2
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 88 No. 3 2018

VANADIUM-CATALYZED CONDENSATION OF ETHYL CYANOACETATE
405
Scheme 2.
O
CN
CN
3
mol % [V]L
0_40°C, 1 h
CO Et
+
2
2
(
CH2)n
(CH )
2 n
CO Et
2
1a−4a
n = 1 (1), 2 (2), 4 (3), 8 (4).
Scheme 3.
CN
O
+
CN
3 mol % [V]L
CO Et
2
4
0°C, 5 h, CH Cl
2 2
CO Et
2
5
5a (98%)
VO(acac) : morpholine = 1 : 1.
2
vanadium compounds morpholine and pyridine in
concentration of 20 mol % catalyze the condensation
of ethyl cyanoacetate with ketones, in particular, with
cyclopentanone 1, but they show low activity and the
yield of the condensation product under these condi-
tions does not exceed 12–16%. Besides, morpholine
and pyridine do not catalyze condensation of ethyl
cyanoacetate with aldehydes.
Aliphatic ketones readily enter the reaction of
condensation with ethyl cyanoacetate in the system
VO(acac) –morpholine. Unlike cyclic ketones, acetone
2
6, heptanone-2 7, and decanone-2 8 react with ethyl
cyanoacetate in quantitative yield irrespective of the
length of the alkyl radical (Scheme 4). While for cyclic
ketones the use of V O as a catalyst decreases the
2
5
selectivity of the reaction, no such effect was observed
for acyclic ketones. The reaction of ketones 7 and 8 with
ethyl cyanoacetate leads to the Z-isomers 7а and 8а.
In the system [V]–morpholine, where [V] = VO(acac)2,
V O , VCl other cyclic ketones, like cyclohexanone 2,
2
4
3
cyclooctanone 3 and cyclododecanone 4 also easily
enter the condensation with ethyl cyanoacetate
Methyl cyclopropyl ketone 9 due to its high
reactivity caused by the ability of the cyclopropane
ring to stabilize the positive charge on the carbonyl
carbon atom reacts with ethyl cyanoacetate even at 20°С
in 4 h with the formation of ethyl 2-cyano-3-cyclo-
propyl-2-butenoate 9а in a high yield (Scheme 5). At
40°С, ketone 9 is polymerized.
(Scheme 2). VO(acac)2 readily dissolves in the
reaction mixture, while V O and VCl are transferred
2
4
3
to the solution in the course of the reaction. The
reaction proceeds slowly at 20°С, but when heated to
4
0°С full conversion of ketones 2–4 is reached already
in 1 h. With increasing size of the ring in the molecule
of the ketone, the yield of the condensation product
decreases, in particular, for cyclooctanone 3 the yield
of ethyl 2-cyclooctanylideneacetate 3а is 75%, and for
cyclododecanone 4 the yield of ethyl 2-cyanocyclo-
dodecanylideneacetate 4а is 30%.
In the presence of catalytic system VO(acac) –Ру
1 : 1) ethyl cyanoacetate very actively reacts with
2
(
aliphatic (butanal, heptanal, octanal) and aromatic
aldehydes (benzaldehyde, anisaldehyde, vaniline,
naphthaldehyde). However, in the case of aliphatic
aldehydes the product of the reaction is polymer,
which is formed from both reagents. In the absence of
the catalyst no reaction occurs with aliphatic al-
dehydes. Blank experiments in the absence of ethyl
cyanoacetate showed that in the presence of vanadium
complexes aldehydes 11, 12 enter the reaction of aldol-
crotonic condensation (20°С, 4 h) with the formation
of the corresponding products (Scheme 6), which were
isolated and identified by their spectral characteristics
and comparison with the literature data [21].
Adamantanone-2 5 in spite of a large size of the
molecule reacts with ethyl cyanoacetate to give 2-ada-
mantanylidene ethyl cyanoacetate 5а in a quantitative
yield (Scheme 3). Functionalization of adamantanone-
2
is of great interest because it is one of the most
available synthons for the preparation of potentially
biologically active derivatives of adamantane. Since
adamantanone-2 is a crystalline compound, its reaction
was carried out in methylene chloride.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 88 No. 3 2018

4
06
KHUSNUTDINOV et al.
Scheme 4.
O
NC
CO Et
2
6
O
6
a (98%)
CO Et
NC
2
CN
3mol % [V]L
0°C, 3 h
7
8
4
CO Et
2
O
7
a (97%)
CO Et
NC
2
8
a (98%)
[V] : L = 1 : 1, L = pyridine, morpholine; [V] = VO(acac)2.
Scheme 5.
O
CH3
CN
3 mol % [V]L (1 : 1)
0°C, 4 h
CN
CH3
+
2
CO Et
CO Et
2
2
9
9a (98%)
[
V] = VO(acac) , L = Py, morpholine.
2
Scheme 6.
3 mol % VO(acac)2_Py
CN
RCHO +
0_12
Polymer
_
2
0°C, 2 3 min
CO Et
1
2
R
O
3
mol % VO(acac)2_Py
0°C, 1 h
R
RCHO
2
_
1
0b 12b
R = CH (CH ) (10, 10b), CH (CH ) (11, 11b); CH (CH ) (12, 12b).
3
2 2
3
2 5
3
2 6
In contrast to aliphatic aldehydes, aromatic al-
Therefore, the systems [V]–pyridine and [V]–
dehydes (benzaldehyde 13, naphthaldehyde 14,
vaniline 15) actively react with ethyl cyanoacetate in
the presence of the catalytic system VO(acac)2–
pyridine(morpholine) (Scheme 7). Catalytic systems
based on V O , V O , VCl , VCl are inactive in this
morpholine are active catalysts for the Knoevenagel
condensation of ethyl cyanoacetate with ketones and
aldehydes.
EXPERIMENTAL
2
4
2
5
3
4
reaction. Preliminary activation of the catalyst by
The reactions were monitored and the purity of the
products was checked by GC on a chromatograph
Chrom-5 with flame ionization detector, columns 1.2
and 3 m, diameter 3 mm; stationary phase silicone SE-
30 (5%) on Chromaton-N-HMDS (0.125-0.160 mm),
refluxing the solution of VO(acac) and the ligand in
2
methylene chloride for 30-45 min with subsequent
addition of ethyl cyanoacetate and the aldehyde
decreases the reaction time to 5–60 min.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 88 No. 3 2018

VANADIUM-CATALYZED CONDENSATION OF ETHYL CYANOACETATE
407
Scheme 7.
CHO
CN
1
3
CO Et
2
2
0°C, 5 min
CHO
13a (98%)
CN
CO Et
2
CN
VO(acac) _L (1 :1 )
2
14
20°C, 15 min
CO Et
2
CHO
14a (98%)
OMe
CN
OH
1
CO Et
2
5
4
0°C, 1 h
OMe
CHO
OH
15a (98%)
CN
OMe
CO Et
2
1
6
2
0°C, 15 min
OMe
16a (98%)
L = pyridine, morpholine.
temperature programming from 50 to 280°С (8 deg/min),
gas-carrier helium (50 mL/min). IR spectra were taken
on a Bruker-Vertex 70V instrument in the range 550–
chloride (chemically pure) were distilled or crystal-
lized before use. Catalysts V O , V O , VCl , VCl ,
2
4
2
5
3
4
VO(acac) (Aсros) were dried in a vacuum dessicator
2
–
1
3
600 cm from KBr pellets or from suspensions in
before use. All reactions were carried out in a flask
equipped with a condenser and a thermometer, with
stirring, or in a glass ampule of 10 mL volume placed
in a stainless still pressur microreactor of 17 mL
capacity with constant stirring and controlled heating.
1
3
mineral oil. С NMR spectra were registered on a
Bruker Avance-400 spectrometer (100.62 MHz) in
CDCl , chemical shifts are given relative to TMS.
3
Mass spectra were measured on a Shimadzu GCMS-
QP2010Plus chromatomass spectrometer (capillary
column SPB-5 30 m×0.25 mm, gas-carrier helium,
temperature programming from 40 to 300°С with the
rate 8 deg/min, temperature of injector 280°С, tempera-
ture of ion source 200°С, ionization energy 70 eV).
Elemental composition of the samples was determined
on elemental analyzer Karlo Erba, model 1106.
General procedure for the reaction of ketones
and aldehydes with ethyl cyanoacetate in the
presence of vanadium catalysts. а. Glass reactor of
3
0 mL capacity equipped with thermometer was
charged with 0.1–0.3 mmol of vanadium catalyst, 0.1–
0
1
.3 mmol of the ligand (morpholine or pyridine),
0 mmol of ketone or aldehyde, 10 mmol of ethyl
Commercially available aldehydes, ketones, ethyl
cyanoacetate, pyridine, morpholine (Aсros), methylene
cyanoacetate, 2 mL of methylene chloride (for solid
ketones or aldehydes). The reaction mixture was stirred
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 88 No. 3 2018

4
08
KHUSNUTDINOV et al.
7
on a magnetic stirrer with condenser at 20–40°С for 1–
h. After completion of the reaction the reactor was
δ, ppm: 13.70 (СООСН СН ), 13.91 (С ), 20.98
2 3
6
5
5
[(СН )=С(СN)СООСН СН ], 22.45 (С ), 29.78 (С ),
35.28 (С ), 61.88 [=С(СN)СООСН СН ], 104.72 (C ),
2 3
115.87 (CN), 163.01 (C ), 177.79 [=С(СN)СОО·
СН СН ]. Found, %: C 67.66; H 8.80; N 7.20.
C H NО . Calculated, %: C 67.66; H, 8.78; N 7.17.
М 195.26.
Z)-Ethyl-2-cyano-3-methyl-2-tridecenoate (8a).
Yield 97%, bp 165°С (10 mmHg) {146–148°С (0.25
3 2 3
4
2
cooled, the reaction mass was filtered through a layer
of silica gel, the solvent was removed, the residue
distilled in a vacuum or crystallized from ethanol. The
yields are given for the isolated products. The structure
of products 1а–9a, 13а–16а was established by
spectral methods, by comparing to the authentic
samples and literature data.
3
2
3
1
1
17
2
(
1
3
Ethyl-2-cyanocyclopentanylidene acetate (1а).
Yield 99%, mp 47–47.5°С (47–48°С [13]). Spectral
characteristics coincide with those in the literature [14].
mmHg) [19]}. С NMR spectrum, δ, ppm: 13.91
13
12
(СООСН СН ), 14.04 (С ), 20.96 (СН ), 22.62 (С ),
2
5
3
3
7
8
9
25.24 (С ), 27.74 (С ), 28.24 (С ), 29.13 (С ), 29.26
1
0
6
11
4
(
С ), 29.36 (С ), 31.82 (С ), 35.54 (С ), (СОО·
СН СН ), 61.86 [=С(СN)СООСН СН ], 104.57 (C ),
15.80 (CN), 162.90 (C ), 177.69 [=С(СN)СОО·
СН СН ]. Found, %: C 73.19; H 11.25; N 4.78.
Ethyl-2-cyanocyclohexanylidene acetate (2а).
Yield 95%, bp 138–139°С (6 mmHg) {148°С
2
2
3
2
3
3
1
(
10 mmHg) [15]}. Spectral characteristics coincide
2
3
with those in the literature [14].
C H NО . Calculated, %: C 73.17; H, 11.26; N 4.74.
1
7
29
2
Ethyl-2-cyanocyclooctanylidene acetate (3a).
М 279.41.
Ethyl-2-cyano-3-cyclopropyl-2-butenoate (9a).
Yield 75%, bp 145°С (5 mmHg) {160°С (12 mmHg)
1
3
[
16]}. С NMR spectrum, δ, ppm: 13.63 (СОО·
1
3
4
5
3
5
2
Yield 98%, mp 66–69°С. С NMR spectrum, δ, ppm:
СН СН ), 26.55 (С , C ), 26.93 (С , C ), 27.30 (С ),
2
3
4
2'
3'
7
8
3.58 (С ), 5.97 (С ), С( ), 13.94 (СООСН
2
СН
3
),
2
1
(
7
7
9.51 (С ), 30.70 (C ), 61.14 [=С(СN)СООСН СН ],
2 3
1'
1
7.81 (С ), 61.35 (СООСН СН ), 103.00 [=С(СN)·
2
3
02.13 [=С(СN)СООСН СН ], 114.98 (CN), 170.73
2
3
1
СООСН СН ], 116.44 (CN), 162.10 (СООСН
2 3
2
СН
3
),
С ), 178.51 [=С(СN)СООСН СН ]. Found, %: C
2 3
1
6
6
78.43 [C(CH )=С(СN)СООСН СН ]. Found, %: C
3 2 3
2.30; H 9.35; N 5.60. C H NО . Calculated, %: C
13 19 2
2.25; H, 9.30; N 5.62. М 221.29.
7.02; H 7.31; N 7.88. C H NО . Calculated, %: C
1
0
13
2
7.02; H, 7.31; N 7.82. М 179.216.
Ethyl-2-cyanocyclododecanylidene acetate (4a).
1
3
(E)-Ethyl-2-cyano-3-phenyl-2-propenoate (13a).
Yield 75%, bp 180°С (10 mmHg). С NMR spectrum,
3
11
Yield 97%, mp 50–52°С (48–49°С [20]). Spectral
characteristics coincide with those in the literature
[20].
δ, ppm: 13.63 (СООСН СН ), 26.95 (С , C ), 27.52
2
3
9
5
2
7
8
4
10
(
(
[
1
9
9
С , C ), 27.74 (С , C , C ), 28.40 (С , C ), 27.81
2
12
C ), 31.21 (C ) 61.14 [=С(СN)СООСН СН ], 102.13
2 3
1
=С(СN)СООСН СН ], 114.98 (CN), 171.38 (C ),
Ethyl-2-cyano-3-(1-naphthyl)-2-propenoate (14a).
Yield 97%, mp 80–81°С (79.5–80°С [21]). Spectral
characteristics coincide with those in the literature
[22].
2
3
78.51 [=С(СN)СООСН СН ]. Found, %: C 73.63; H
2 3
.85; N 5.01. C H NО . Calculated, %: C 73.61; H,
1
7
27
2
.81; N 5.05. М 277.40.
-Adamantylidene ethylcyanoacetate (5a). Yield
8%, mp 72–74°С (79–80°С [17]). Spectral characte-
2
(E)-Ethyl-2-cyano-3-(4-hydroxy-3-methoxyphenyl)-
2-propenoate (15a). Yield 97%, mp 130–132°С.
Spectral characteristics coincide with those in the
literature [20].
9
ristics coincide with those in the literature [17].
Ethyl-2-cyano-3-methyl-2-butenoate (6a). Yield
9
8%, bp 125°С (10 mmHg) {119–120°С (18 mmHg)
(E)-Ethyl-2-cyano-3-(4-methoxyphenyl)-2-pro-
penoate (16a). Yield 97%, mp 79–82°С (78–81°С
[23]). Spectral characteristics coincide with those in
the literature [20].
1
3
[18]}. С NMR spectrum, δ, ppm: 13.63 (СОО·
1
4
СН СН ), 20.75 (С ), 21.15 (С ), 61.14 [=С(СN)СОО·
СН СН ], 106.15 (C ), 115.32 (CN), 163.19 (C ),
2
3
2
3
2
3
1
7
7
78.84 [=С(СN)СООСН СН ]. Found, %: C 62.71; H
2 3
ACKNOWLEDGMENTS
.25; N 9.20. C H NО . Calculated, %: C 62.73; H,
8
11
2
.24; N 9.14; М 153.12.
Structural experiments were performed with the use
of equipment of the Regional Center for Joint Use
“Agidel.”
(
Z)-Ethyl-2-cyano-3-methyl-2-heptanoate (7a).
1
3
Yield 97%, bp 155°С (10 mmHg). С NMR spectrum,
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VANADIUM-CATALYZED CONDENSATION OF ETHYL CYANOACETATE
409
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