Synthesis and structure of β-aryl-α-nitroacrylates

Article abstract of DOI:10.1134/S1070363213090223

The method for preparation of ethyl α-nitrocinnamates by nitroacetic acid ester alkenylation with aromatic aldehydes in the presence of acetic acid and β-alanine has been modified. Structures of the prepared compounds have been proved by electronic, IR, <

Full text of DOI:10.1134/S1070363213090223

ISSN 1070-3632, Russian Journal of General Chemistry, 2013, Vol. 83, No. 9, pp. 1764–1770. © Pleiades Publishing, Ltd., 2013.
Original Russian Text © R.I. Baichurin, L.V. Baichurina, N.I. Aboskalova, V.M. Berestovitskaya, 2013, published in Zhurnal Obshchei Khimii, 2013,
Vol. 83, No. 9, pp. 1547–1554.
On the 100th anniversary of V.V. Perekalin
Synthesis and Structure of β-Aryl-α-nitroacrylates
R. I. Baichurin, L. V. Baichurina, N. I. Aboskalova, and V. M. Berestovitskaya
Herzen State Pedagogical University of Russia, Moyka emb. 48, St. Petersburg, 191186 Russia
e-mail: kohrgpu@yandex.ru
Received April 18, 2013
Abstract—The method for preparation of ethyl α-nitrocinnamates by nitroacetic acid ester alkenylation with
aromatic aldehydes in the presence of acetic acid and β-alanine has been modified. Structures of the prepared
compounds have been proved by electronic, IR, 1H, and 13C–{1H} NMR spectroscopy (including heteronuclear
correlation experiments 1H–13C HMQC and 1H–13C HMBC). In solution these compounds exist in the form of
→
←
Z-isomer; the Z E isomerization is observed in the case of the compound containing strong electron-donor
group [N(CH3)2] at benzene ring.
DOI: 10.1134/S1070363213090223
Conjugated nitroethenes are highly reactive
synthons suitable for preparation of organic com-
pounds of different classes [1, 2].
roxy-1,2-oxazin-6-one-3-carboxylates, the structure of
their isolated salts having been confirmed by X-ray
diffraction analysis [9]. The gem-alkoxycarbonylnitro-
ethenes can be prepared from nitroacetic acid ester by
using the Schiff’s bases or diacetals instead of
aldehydes [3, 10–12]. The direct alkenylation of ethyl
nitroacetate with heterocyclic aromatic aldehydes has
been achieved for the first time in a mixture of
anhydrous THF and CCl4 in the presence of an excess
of titanium tetrachloride and N-methylmorpholine
[13]. However, this method is quite expensive, and
time-taking.
Introduction of ester group at the gem-position with
respect to the nitro group expands the range of
nitroethenes synthetic applications due to the increased
electrophilicity of the double bond and possibilities of
additional transformations involving the electron-
withdrawing ester group. The α-nitroalkenecarboxy-
lates can be converted into α-amino acids through
hydrogenation and subsequent hydrolysis. These poly-
functional electron-deficient compounds are of parti-
cular interest due to the possibility of their conversion
into carbocyclic and heterocyclic systems, the
promising intermediates in drug design.
We succeeded in preparation of α-nitrocinnamic
esters I–IV via condensation of ethyl nitroacetate with
aromatic aldehydes under acid catalysis conditions:
refluxing the reagents in benzene in the presence of
acetic acid and β-alanine in a flask equipped with a
Dean–Stark trap. Similar techniques were applied
previously for the synthesis of gem-benzoylnitro-
ethenes [14, 15] and α-nitro-β-furyl(thienyl)acrylates
[16]. However, synthesis of the title compounds under
such conditions had some limitations. In particular, the
preparation of the α-nitrocynnamic acid ester
derivative V, bearing a nitro group in the para-position
of the benzene ring, was a success only when
performed according to the reported method [3]
(reaction of nitroacetic acid ester with the Schiff’s base
synthesized from 4-nitrobenzaldehyde and n-butyl-
amine).
Unlike simple β-nitrostyrenes, most of α-nitro-
cinnamic acid esters cannot be obtained via condensa-
tion of aromatic aldehydes with nitroacetic acid ester
under basic catalysis conditions. In the presence of
basic agents, the condensation results in the substituted
2,4-dinitroglutarates salts or products of their
heterocyclization – five-membered isoxazoline N-
oxides and isoxazoles [3–8]. Such reaction pathway
can be probably due to the interaction of nitroacetic
acid ester with the initially formed highly reactive
gem-substituted nitroethenes. Sensationally been
recently shown that reaction of aromatic aldehydes
with nitroacetic acid ester in alcohol in the presence of
diethylamine results in six-membered substituted 5-hyd-
1764

1765
SYNTHESIS AND STRUCTURE OF β-ARYL-α-NITROACRYLATES
R
NO2
NO2
COOCH2CH3
3
2
1
C6H6, β-Ala, AcOH, Δ or
EtOH, p-MeC6H4SO3H, 18−20oC
OCH2CH3
HA
O
I−IV
O
H
R
R
NO2
NO2
n-BuNH2
COOCH2CH3
Ac2O, 60oC
3
2
R
NBu-n
1
OCH2CH3
HA
O
V
R = H (I), OMe (II), NMe2 (III), Cl (IV), NO2 (V).
α-Nitrocinnamic acid ester III containing p-di-
methylamino substituent at the benzene ring could be
obtained as well from 4-dimethylaminobenzaldehyde
and nitroacetic ester in ethanol in the presence of p-
toluenesulfonic acid at room temperature [17].
However, we failed to synthesize compounds I, II, and
IV under those conditions. For example, reaction of 4-
methoxybenzaldehyde with nitroacetic acid ester in the
presence of p-toluenesulfonic acid gave 2-(4-methoxy-
phenyl)-1-nitroethene (the product could be isolated
after the prolonged exposure). Probably, in those cases
the desired process was accompanied by hydrolysis of
the ester group followed by decarboxylation.
ground state; thus, acceleration of the Z–E transition
could be expected as compared to the unsubstituted
analog I.
1
Indeed, in the H NMR spectrum of III in CDCl3
solution, after 2–3 days exposure the proton signals
were split into pairs thus indicating the presence of two
isomers in the solution (Table 1, Fig. 1b). The
spectrum contained the signals of olefinic protons at
7.38 ppm (Z-) and 8.01 ppm (E-); the ratio of Z- and E-
isomers was of ~1:1.1. In more polar solvents
(methanol-d4 and DMSO-d6), compound III formed a
mixture of Z- and E-isomers (in the ratio of ~1:1)
immediately after dissolution.
The melting points and spectral properties of the
prepared β-aryl-α-nitroacrylates were identical to those
reported in [3, 13, 18–23].
The similar readily occurring isomers transforma-
tions were observed in the cases of indolylnitro-
acrylates and nitroenamines [28–30].
The structures of I–V were elucidated via com-
prehensive analysis of their spectral features (1H and
13C–{1H} NMR, UV, and IR) and their comparison
with the respective data for model nitroethenes [24–
27]. The main parameter to judge about the functio-
nalized nitroethenes geometry was the chemical shift
of olefinic proton НА in 1H NMR spectra. In contrast to
the E-isomers of model nitroethenes (НА signal at 7.87–
α-Nitroacrylate V containing strong electron with-
drawing nitro group in benzene ring existed in the form
of Z-isomer in methanol-d4 solution. Upon exposure at
18–20°C, it reacted with methanol-d4, and within
7 min the AdN product was detected in the spectra.
In the 13C–{1H} NMR spectra of α-nitroacrylates I–
V, all respective carbon signals were identified (Table 2).
The signals of ester moiety methyl and methylene
carbon atoms appeared at 13.97–14.28 ppm and 62.77–
63.81 ppm, respectively. The signals of C2 with two
electron-withdrawing substituents (nitro and ester
groups) attached were registered in a downfield region
(135.53–142.69 ppm) as compared with those of C3
(119.61–138.11 ppm). The signals at 158.48–
162.96 ppm were assigned to the carbonyl carbon atom.
3
8.03 ppm, J(НАНВ) 13.5–14 Hz), the gem-alkoxy-
carbonylnitroethenes existed in the form of Z-isomer in
CDCl3 solutions; this was confirmed by upfield
position of the НА signal (7.39–7.60 ppm) (Table 1).
In the case of nitrocinnamic ester III (bearing the
dimethylamino group, an electron-donating substituent
with strong +M effect), the barrier of internal rotation
around the carbon–carbon bond was reduced due to a
significant contribution of bipolar structures to the
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1766
BAICHURIN et al.
EtO
O−
H
C
C
C
NO2
H
COOEt
NO2
NO2
H
C
C
Me+2N
C
C
COOEt
NOO−
C O
H
C
C
Me2N
Z
Me2N
E
EtO
+
Me2N
1
The H and 13C–{1H} NMR spectra signals as-
groups. The latter signal correlated with the signal of
olefinic proton HA (7.43 ppm) as well. The proton
signal at 6.88 ppm (С5Н, С9Н) revealed cross-peaks
with the signals of carbon atoms at 121.36 ppm (C4)
and 162.96 ppm (C7); the latter signal being correlated
with the protons signals at 7.36 (С6Н, С8Н) and
3.81 ppm (OCH3) as well.
signment was confirmed by heteronuclear correlation
1H–13C HMQC and H–13C HMBC experiments. In
1
particular, the H–13C HMQC spectrum (CDCl3) of II
1
contained cross-peaks of ester protons (1.32 and 4.33 ppm)
with carbon atoms (14.16 and 62.89 ppm) signals; the
cross-peak of methoxy group protons (3.81 ppm) with
carbon atom (55.59 ppm) was observed as well. The
signal of НА olefinic proton (7.43 ppm) correlated with
the signal of C3 (132.68 ppm). Finally, the cross-peaks
characteristic of the p-substituted benzene ring were
observed: protons signals at 6.88 ppm (С5Н, С9Н) and
7.36 ppm (С6Н, С8Н) correlated with the signals of
aromatic carbon atoms at 114.99 ppm (С5,9) and
132.27 ppm (С6,8), respectively.
O
CH3
CH2
1
HA
O
3
2
H
O
NO2
5
4
9
6
H
H
8
7
H
In the H–13C HМВС spectrum of II (CDCl3),
1
CH3
methyl protons of the ester group (1.32 ppm)
correlated with the carbon atoms of methylene moiety
(62.89 ppm), and methylene protons of the ester group
(4.33 ppm) correlated with the carbon atoms of the
methyl (14.16 ppm) and carbonyl (159.68 ppm)
Z-Configuration of the discussed gem-substituted
1
nitroethenes determined from H NMR spectra was
additionally confirmed by electronic and IR spectra.
For example, in the electronic spectrum of the model
Table 1. 1Н NMR spectral data for α-nitrocinnamic acids esters I–V in CDCl3 (δ, ppm)
Comp. no.
HA
CH3
OCH2
4.37 q
4.33 q
4.32 q
4.32 q
4.45 q
4.36 q
4.41 q
CH3O [(CH3)2N]
Ar
Configuration
7.53 s
7.43 s
7.39 s
7.39 s
8.00 s
7.47 s
7.60 s
1.35 t
1.32 t
1.33 t
1.33 t
1.38 t
1.35 t
1.38 t
–
7.30–7.50 m
6.88 d, 7.36 d
6.62 d, 7.30 d
6.62 d, 7.30 d
6.65 d, 7.38 d
7.33 d, 7.38 d
7.58 d, 8.27 d
Z
Z
Z
Z
E
Z
Z
I
3.81 s
[3.05 s]
[3.05 s]
[3.08 s]
–
II
III
IIIа
IV
V
–
a The spectrum was recorded in CDCl3 after 2 days exposure.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 83 No. 9 2013

1767
SYNTHESIS AND STRUCTURE OF β-ARYL-α-NITROACRYLATES
(a)
δ, ppm
(b)
δ, ppm
Fig. 1. 1Н NMR spectra of compound III in CDCl3 immediately (a) after the dissolution and (b) after 2 days exposure.
E-2-(4-methoxyphenyl)-1-nitroethene an absorption
band was observed at 355 nm (ε = 21000 l mol–1 cm–1),
characteristic of nitrostyrenes with an electron-donor
substituent at the opposite end of the conjugated
system with respect to the nitro group [24]. Introduc-
tion of the ester group led to the blue shift of the
absorption band (λmax = 319 nm, ε = 25500 l mol–1 cm–1);
that confirmed the existence of the Z-configuration of
II (Table 2).
The electronic spectrum of III recorded in ethanol
contained two absorption bands at λmax = 400 nm (ε =
9400 l mol–1 cm–1) and λmax = 450 nm (ε =
10100 l mol–1 cm–1) (Table 3). Thus, that ester of α-
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 83 No. 9 2013

1768
BAICHURIN et al.
O−
O
nitrocinnamic acid with dimethylamino group the
para-position underwent Z →← E isomerization.
H
OEt
NO2
H
OEt
Further information on the studied compounds
structure was obtained from their IR spectra (Table 3).
The IR spectra of ethyl α-nitrocinnamate I and its
analogs II–V contained the absorption bands of
carbonyl (1715–1730 cm–1) and covalently bonded
nitro group (νas = 1535–1545 cm–1 and νs = 1370–
1375 cm–1).
NO2
(Me)2+N
(Me)2N
stituents and their furyl and thienyl analogs, existing
predominantly in the Z-form [14, 26].
It should be noted that the IR spectra of the α-nitro
cinnamic esters containing para-positioned electron-
donor methoxy or dimethylamino group (II and III)
differed significantly from those of the corresponding
model E-2-(4-methoxyphenyl)-1-nitroethene and E-2-
(4-N,N-dimethylaminophenyl)-1-nitroethene: in the
latter spectra there were no characteristic vibrations of
the covalently bonded nitro group, whereas the intense
bands appeared at 1600 and 1625 cm–1 (С=С, С=N+)
as well as at 1320 and 1260–1265 cm–1 (NOO–). That
indicated high polarization of their molecules due to
effective conjugation of nitrogen or oxygen lone-
electron pair, carbon–carbon double bond, and nitro
group [25]. Z-2-(4-Methoxyphenyl)- and Z-2-(4-N,N-
dimethylaminophenyl)-1-nitro-1-ethoxycarbonylethenes
II and III were highly polarized as well, but it was the
effective conjugation with the carbonyl group that
contributed significantly to the polarization of the
molecules.
In [25], the existence of I in the Z-form was
supported by the integral intensities of the valence
vibrations absorption bands of Аs(NO2) (1.3) and
А(С=С) (0.74) and comparison with the respective
parameters of other gem-substituted β-nitrostyrenes.
The high polarization of Z-α-nitrocinnamic esters
was confirmed by the dipole moments measurement
using methyl 2-nitro-3-(4-nitrophenyl)acrylate as an
example. Comparison of its experimental dipole
moment (5.5 D) with that calculated by the vector-
additive scheme for the s-cis and s-trans conformers
indicated the predominance of s-trans conformer [31].
The X-ray diffraction data for methyl α-nitro-
cinnamate acid and its p-methoxy analogue as well as
for ethyl α-nitroacrylates containing p-nitrophenyl or
ferrocenyl substituents listed in [32–36] demonstrated
that both in the solid phase and in solution those
compounds were of Z-configuration, and the nitro
group was deduced out of the molecule plane. For
methyl α-nitroacrylates the s-trans conformation was
Similar conclusions were made in the studies of β-
acetyl-β-nitrostyrenes containing electron-donor sub-
Table 2. 13C–{1H} NMR spectral data for α-nitrocinnamic acids esters I–V in CDCl3 (δ, ppm)
Comp. no.
C3
C2
C=O
CH2
CH3
OCH3 [N(CH3)2]
–
Ar
Confuguration
133.03
140.25
159.31
63.23
14.16
128.98, 129.49,
129.84, 132.30
Z
I
132.68
132.77
138.11
131.61
130.26
138.19
135.53
136.76
140.52
142.69
159.68
160.41
162.93
159.08
158.48
62.89
62.39
62.77
63.35
63.1
14.16
14.28
13.99
14.13
14.10
55.59
[40.05]
[40.12]
–
114.99, 121.36,
132.27, 162.96
Z
Z
E
Z
Z
II
IIIа
111.87, 115.90,
132.71, 152.95
111.97, 115.95,
132.71, 153.35
127.43, 129.85,
131.03, 138.58
IV
V
–
124.52, 130.33,
135.06, 149.30
a The spectrum was registered in CDCl3 after 2 days exposure.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 83 No. 9 2013

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SYNTHESIS AND STRUCTURE OF β-ARYL-α-NITROACRYLATES
Table 3. Data of IR and electronic spectra of α-nitro-
cinnamic acids esters I–V
typical, whereas ethyl α-nitroacrylates were predo-
minantly s-cis conformers.
Electronic spectra (EtOH)а
IR spectra (CHCl3), ν, cm–1
To summarize, we proposed a suitable synthetic
method to prepare ethyl α-nitrocinnamates via con-
densation of aromatic aldehydes with the esters of
nitroacetic acids under reflux in benzene in the
presence of acetic acid and β-alanine. The procedure
significantly facilitated the synthesis of those im-
portant compounds. Their structures were confirmed
λmax, nm
ε, l mol–1 cm–1
NO2 C=O C=C
280
319
17800
25500
1540, 1370 1730 1645
1540, 1370 1725 1640,
1600
II
400
450
9400
10100
1535, 1375 1715 1595
III
IV
V
1
by Н, 13С NMR, IR, and electronic spectroscopy. It
was shown that in solutions α-nitrocinnamic acids
esters were Z-configured. α-Nitrocinnamate containing
p-dimethylaminophenyl moiety was the most inclined
to Z →← E isomerization.
288
17150
15460
1540, 1370 1730 1650,
1595
287
1545, 1370, 1735 1655
1530, 1350b
a
Absorption bands at long-wave region (λ > 270 nm) are listed.
Absorption bands of the stretching vibrations of nitro group in
the aromatic ring.
EXPERIMENTAL
b
1
1
1H, 13C–{1H}NMR, Н–13С HMQC, and Н–13С
HMBC spectra were recorded with Jeol JNM-
ECX400A spectrometer operating at 399.78 (1H) and
100.53 MHz (13C) in chloroform-d, DMSO-d6, or
methanol-d4 solution; the signals of the residual non-
deuterated solvents were used as internal standard. IR
spectra were recorded with Shimadzu IR-Prestige-21
Fourier spectrometer in chloroform (c = 40 mg ml–1).
Electronic absorption spectra were recorded with
Shimadzu UV2401PC spectrophotometer in ethanol
solution in quartz cuvettes (l = 1.01 mm) at 0.5–
0.8 mM.
acetic acid in 30 ml of anhydrous benzene was re-
fluxed for 5 h in a flask equipped with a Dean–Stark
trap. The reaction solution was then treated as
described in the procedure of I preparation. After long-
time exposure, oily substance with inclusions of
crystalline solid was placed on a porous plate to obtain
2.28 g (36%) of pale yellow crystals, mp 62–64°C
(hexane) {mp 66–67°C (hexane–petroleum ether) [13]}.
Ethyl 3-(4-N,N-dimethylaminophenyl)-2-nitro-
propenoate (III). A mixture of 3.3 g (25 mmol) of
ethyl nitroacetate, 5.96 g (40 mmol) of 4-N,N-di-
methylaminobenzaldehyde, catalytic amount of β-
alanine, and 4 ml of glacial acetic acid in 30 ml of
anhydrous benzene was refluxed for 2 h in a flask
equipped with a Dean–Stark trap. The reaction solution
was then treated as described in the procedure of I
preparation. Yield 6.3 g (95%), orange crystals, mp
88–90°C (ethanol) {mp 92–93°C (ethanol) [13]}.
Ethyl nitroacetate [37], 4-nitrobenzal-n-butylamine
[31], and ethyl 2-nitro-3-(4-nitrophenyl)propenoate V
[3] were prepared as described in the respective
references.
Ethyl 2-nitro-3-phenylpropenoate (I). A mixture
of 3.3 g (25 mmol) of ethyl nitroacetate, 4.24 g (40 mmol)
of freshly distilled benzaldehyde, catalytic amount of
β-alanine, and 4 ml of glacial acetic acid in 30 ml of
anhydrous benzene was refluxed for 5 h in a flask
equipped with a Dean–Stark trap. After cooling, the
reaction mixture was washed with saturated aqueous
sodium chloride and dried over calcinated MgSO4.
Benzene was evaporated on a rotary evaporator, and
the residue was placed into refrigerator. After treating
with ethanol, the crystalline substance was filtered off
and dried. Yield 3.43 g (62%), pale yellow crystals,
mp 63–65°C (hexane) {mp 68–69°C (methanol) [18]}.
Ethyl 3-(4-chlorophenyl)-2-nitropropenoate (IV).
A mixture of 1.44 g (11 mmol) of ethyl nitroacetate,
1.9 g (14 mmol) of p-chlorobenzaldehyde, catalytic
amount of β-alanine, and 2 ml of glacial acetic acid in
30 ml of anhydrous benzene was refluxed for 5 h in a
flask equipped with a Dean–Stark trap. The reaction
solution was then treated as described in the procedure
of I preparation. Yield 1.09 g (39%), pale yellow
crystals, mp 60–62°C (ethanol) {mp 69°C (benzene–
petroleum ether) [3]}.
Ethyl 3-(4-methoxyphenyl)-2-nitropropenoate (II).
A mixture of 3.3 g (25 mmol) of ethyl nitroacetate,
5.39 g (40 mmol) of freshly distilled anisaldehyde,
catalytic amount of β-alanine, and 4 ml of glacial
Physico-chemical studies were performed in the
Center for Collective Use in Herzen State Pedagogical
University of Russia.
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BAICHURIN et al.
18. Samarenko, V.Ya., Markova, N.R., and Paset, B.V.,
ACKNOWLEDGMENTS
J. Org. Chem. USSR, vol. 18, no. 1, p. 122.
19. Buevich, A.V., Wu, Y., Chan, T.-M., and Stamford, A.,
Tetrahedron Lett., 2008, vol. 49, no. 13, p. 2132.
20. Fioravanti, S., Pellacani, L., and Vergari, M.C., Org.
Biomol. Chem., 2012, vol. 10, no. 3, p. 524.
This work was financially supported by the
Government of St. Petersburg (diplomas PSP no.
11035, PSP no. 11036, 2011).
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