Nitropyridines: VI.* Synthesis of 2-aryl(hetaryl)- and 2,3-polymethylene-5-nitropyridines

Article abstract of DOI:10.1134/S1070428009070112

Previously unknown 2-aryl-, 2-hetaryl-, and 2-cyclopropyl-5-nitropyridines and 2,3-polymethylene-5-nitropyridines were synthesized by reactions of 1-methyl-3,5-dinitropyridin-2(1H)-one with various cyclic and acyclic ketones in the presence of ammonia.

Full text of DOI:10.1134/S1070428009070112

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2009, Vol. 45, No. 7, pp. 1045–1049. © Pleiades Publishing, Ltd., 2009.
Original Russian Text © G.P. Sagitullina, A.K. Garkushenko, Yu.O. Vinokurova, V.A. Nyrkova, E.G. Atavin, R.S. Sagitullin, 2009, published in Zhurnal
Organicheskoi Khimii, 2009, Vol. 45, No. 7, pp. 1058–1061.
Nitropyridines: VI.* Synthesis of 2-Aryl(hetaryl)-
and 2,3-Polymethylene-5-nitropyridines
G. P. Sagitullina, A. K. Garkushenko, Yu. O. Vinokurova, V. A. Nyrkova,
E. G. Atavin, and R. S. Sagitullin
Dostoevskii Omsk State University, pr. Mira 55a, Omsk, 644077 Russia
e-mail: Sagitullina@orgchem.univer.omsk.su
Received July 16, 2008
Abstract—Previously unknown 2-aryl-, 2-hetaryl-, and 2-cyclopropyl-5-nitropyridines and 2,3-polymethylene-
5-nitropyridines were synthesized by reactions of 1-methyl-3,5-dinitropyridin-2(1H)-one with various cyclic
and acyclic ketones in the presence of ammonia.
DOI: 10.1134/S1070428009070112
We previously proposed a new synthetic approach
to metacyclophanes based on recyclization of quater-
nary 3-nitro-5,6,7,8,9,10,11,12,13,14-decahydrocyclo-
dodeca[b]pyridinium salt [2]. Further extension of this
novel procedure required nitropyridines IIIa–IIIf
having cycloalkane rings of different sizes. While
searching for convenient methods for the preparation
of 2,3-polymethylene-5-nitropyridines, we found
a simple procedure [3] for the synthesis of substituted
3-nitropyridines by reaction of 1-methyl-3,5-dinitro-
pyridin-2(1H)-one (I) with various ketones in the pres-
ence of ammonia. 1-Methyl-3,5-dinitropyridin-2(1H)-
one (I) was considered by the authors to be a latent
form of nitromalonaldehyde. The reaction of com-
pound I with cyclohexanone gave 83% of 3-nitro-
5,6,7,8-tetrahydroquinoline (IIIa) [3] (Scheme 1).
sponding nitropyridines IIIb–IIIf. The yield of IIIb–
IIIf decreased from 65 to 45% as the size of the cyclo-
alkane ring in the initial ketone increased. This proce-
dure for the synthesis of polymethylene-bridged nitro-
pyridines may be regarded as very convenient [4],
taking into account accessibility of dinitropyridinone I
and cyclic ketones and experimental simplicity.
3,5-Dinitropyridin-2(1H)-one (I) reacted with cy-
clopropyl methyl ketone (IVa) [5] in the presence of
ammonia to give 2-cyclopropyl-5-nitropyridine (Va) in
85% yield. Presumably, this reaction provides the sim-
plest way of introducing a cyclopropyl substituent into
the pyridine ring; the resulting structure attracts inter-
est from the viewpoint of its synthetic potential [6–8].
In the reaction of compound I with 3-hydroxyimino-
butan-2-one, the yield of 2-acetyl-5-nitropyridine
oxime (Vb) was as poor as 19%, whereas only traces
of 2-acetyl-5-nitropyridine (Vc) were formed from di-
nitropyridinone I and biacetyl.
We extended the series of cyclic ketones for the
above reaction by including those containing 8- to
12-membered rings with a view to obtain the corre-
Scheme 1.
O (IIa–IIf)
( )n
NH3, MeOH
RC(O)Me (IVa–IVh)
NH3, MeOH
NO2
O2N
NO2
O
O2N
( )n
N
N
Me
I
N
R
Va–Vh
IIIa–IIIf
II, III, n = 1 (a), 3 (b), 4 (c), 5 (d), 6 (e), 7 (f); IV, V, R = i-Pr (a), HON=C(Me) (b), Ac (c), 3-MeOC6H4 (d), 2-naphthyl (e),
5-methylfuran-2-yl (f), 1H-pyrrol-2-yl (g), 1H-indol-3-yl (h).
* For communication V, see [1].
1045

SAGITULLINA et al.
1046
Scheme 2.
O2N
O2N
OH
OH
OR
O2N
AlCl3, C2H4Cl2
Ac2O or BzCl
N
N
+
N
Cl
OH
OH
OR
VI
VII
VIIIa, VIIIb
O2N
AlCl3, C2H4Cl2
NO2
+
N
H
N
Vh
N
Cl
HN
VI
R = Ac (a), PhC(O) (b).
The described reaction may be used to synthesize
2-aryl-substituted 5-nitropyridines, in particular com-
pounds Vd and Ve from 3-methoxyacetophenone and
1-(2-naphthyl)ethanone, respectively. In the reactions
of I with heterocyclic ketones (2-acetyl-5-methylfuran,
2-acetyl-1H-pyrrole, and 3-acetyl-1H-indole), only
2-(5-methylfuran-2-yl)-5-nitropyridine (Vf) was ob-
tained in a satisfactory yield, which is consistent with
low reactivity of the acetyl group in 2-acetylpyrrole
and 3-acetylindole.
at 200.13 MHz using tetramethylsilane as internal
reference. The mass spectra of compounds IIIc, Vh,
VIIIa, and VIIIb were obtained on an Agilent 5973N
mass spectrometer (electron impact, 70 eV; vaporizer
temperature 230–250°C). The mass spectra of the other
compounds were recorded on a Finnigan MAT-8200
high-resolution mass spectrometer (electron impact,
70 eV; vaporizer temperature 270–300°C). The molec-
ular weights and elemental compositions of com-
pounds Va, Vd, and Vg were determined from the
high-resolution mass spectra. The elemental composi-
tions of the other compounds were determined using
a Perkin–Elmer analyzer. The progress of reactions and
the purity of products were monitored by thin-layer
chromatography on Silufol UV-254 plates (spots were
visualized under UV light).
An alternative method for the synthesis of difficult-
ly accessible 2-aryl- and 2-hetaryl-3(5)-nitropyridines
is based on hetarylation of the corresponding aromatic
and heteroaromatic compounds with 2-chloro-5-nitro-
pyridine (VI) in the presence of aluminum chloride as
catalyst [9] (Scheme 2).
1-Methyl-3,5-dinitropyridin-2(1H)-one (I) was
synthesized according to the procedures described in
[12, 13]. Cyclooctanone (IIb), cyclononanone (IIc),
cyclododecanone (IIf), 2-acetylnaphthalene (IVe),
3-methoxyacetophenone (IVd), and 2-acetyl-1H-pyr-
role (IVg) were commercial products (Fluka) and were
used without additional purification. Cyclodecanone
(IId) and cycloundecanone (IIe) were synthesized as
described in [14]. Cyclopropyl methyl ketone (IVa)
was prepared in two steps from γ-butyrolactone, fol-
lowing the procedure reported in [15]. 2-Acetyl-5-
methylfuran (IVf) [16, 17], 3-acetyl-1H-indole (IVh)
[18], 3-hydroxyiminobutan-2-one (IVb) [19], and
2-chloro-5-nitropyridine (VI) [20] were prepared by
known methods.
The reaction of indole with 2-chloro-5-nitropyri-
dine in the presence of an equimolar amount of AlCl3
gave 3-(5-nitropyridin-2-yl)-1H-indole (Vh) in 20%
yield. The corresponding 2-aryl-5-nitropyridine VII
was formed in 65% yield in analogous reaction of VI
with resorcinol. Acylation of both hydroxy groups in
VII with acetyl or benzoyl chloride resulted in the
formation of diesters VIIIa and VIIIb (Scheme 2).
Nitropyridines V and VIII are key intermediate
products in the synthesis of metacyclophanes with dif-
ferent lengths of the carbon chain, as well as of indoles
[2, 10, 11]. Their structure was determined on the basis
of analytical and spectral data.
EXPERIMENTAL
Nitropyridines IIIb–IIIf (general procedure).
A mixture of 0.395 g (2 mmol) of 3,5-dinitropyridin-
2(1H)-one (I) and 4 mmol of cyclic ketone IIb–IIf in
40 ml of methanol saturated with ammonia was heated
The IR spectra were recorded on a Specord 75IR
spectrometer from solutions in CDCl3. The H NMR
spectra were measured on a Bruker AC-200 instrument
1
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 45 No. 7 2009

NITROPYRIDINES: VI.
1047
for 3 h at 70°C in a flask equipped with a reflux con-
denser. The solvent was distilled off under reduced
pressure, and the oily residue was purified by column
chromatography on silica gel (100–160 μm) using ben-
zene as eluent.
43 (16.36), 41 (27.94), 39 (13.15), 29 (14.82), 28
(20.28), 27 (11.26). Found, %: C 67.75; H 7.95;
N 10.64. C14H20N2O2. Calculated, %: C 67.71; H 8.12;
N 11.28.
3-Nitro-5,6,7,8,9,10,11,12,13,14-decahydrocyclo-
dodeca[b]pyridine (IIIf). Yield 45%, mp 83–84°C
(from ethanol) [2].
3-Nitro-5,6,7,8,9,10-hexahydrocycloocta[b]pyri-
dine (IIIb). Yield 65%, colorless crystals, mp 45–46°C
(from hexane) [21].
Nitropyridines Va–Vh (general procedure).
A mixture of 0.395 g (2 mmol) of dinitropyridinone I
and 4 mmol of ketone IVa–IVh in 40 ml of methanol
saturated with ammonia was heated for 3 h at 100°C in
a sealed ampule. The ampule was cooled and opened,
the solvent was distilled off under reduced pressure,
and the oily residue was purified by column chroma-
tography on silica gel (100–160 μm) using benzene as
eluent.
3-Nitro-6,7,8,9,10,11-hexahydro-5H-cyclonona-
[b]pyridine (IIIc). Yield 64%, mp 14–15°C. IR spec-
1
trum, ν, cm–1: 1541, 1324 (NO2). H NMR spectrum
(CDCl3), δ, ppm: 1.24–1.48 m (6H, 7-H, 8-H, 9-H),
1.79–1.97 m (4H, 6-H, 10-H), 2.91 t (2H, 11-H, J =
6.11 Hz), 3.08 t (2H, 5-H, J = 6.35 Hz), 8.19 d (1H,
4-H, J = 2.69 Hz), 9.21 d (1H, 2-H, J = 2.44 Hz). Mass
spectrum, m/z (Irel, %): 220 (15.97) [M]+·, 205 (19.78),
192 (19.51), 191 (15.36), 179 (20.80), 178 (16.94),
177 (100), 165 (13.54), 164 (13.83), 163 (14.05), 152
(23.23), 131 (13.30), 77 (11.00). Found, %: C 65.53;
H 7.34; N 12.68. C12H16N2O2. Calculated, %: C 65.43;
H 7.32; N 12.72.
2-Cyclopropyl-5-nitropyridine (Va). Yield 85%,
mp 63–64°C (from hexane). IR spectrum, ν, cm–1:
1
1554, 1324 (NO2). H NMR spectrum (CDCl3), δ,
ppm: 2.09–2.23 m (1H, CH), 1.13–1.26 m (4H, CH2),
7.33 d (1H, 3-H, 3J = 8.55 Hz), 8.31 d.d (1H, 4-H, 3J =
4
4
3-Nitro-5,6,7,8,9,10,11,12-octahydrocyclodeca[b]-
pyridine (IIId). Yield 54%, mp 77–78°C (from aque-
ous ethanol). IR spectrum, ν, cm–1: 1541, 1338 (NO2).
1H NMR spectrum (CDCl3), δ, ppm: 1.01–1.23 m (4H,
8-H, 9-H), 1.49–1.57 m (4H, 7-H, 10-H), 1.82–2.10 m
(4H, 6-H, 11-H), 2.98 t (2H, 12-H, J = 6.59 Hz), 3.11 t
(2H, 5-H, J = 6.59 Hz), 8.25 d (1H, 4-H, J = 2.68 Hz),
9.24 d (1H, 2-H, J = 2.44 Hz). Mass spectrum, m/z
(Irel, %): 234 (17.20) [M]+·, 219 (16.60), 205 (16.51),
192 (14.54), 191 (100), 179 (11.04), 178 (15.52), 177
(42.47), 165 (16.93), 152 (54.05), 145 (13.04), 131
(13.38), 117 (11.23), 91 (10.44), 77 (17.65), 65 (11.58),
55 (11.21), 41 (23.47), 39 (14.99). Found, %: C 66.92;
H 7.88; N 11.87. C13H18N2O2. Calculated, %: C 66.64;
H 7.74; N 11.96.
8.65, J = 2.44 Hz), 9.25 d (1H, 6-H, J = 2.18 Hz).
Mass spectrum, m/z (Irel, %): 164 (29.59) [M]+·, 163
(100), 118 (16.48), 117 (47.84), 91 (20.83), 65 (17.41),
39 (12.62). Found: m/z 164.0583 [M]+·. C8H8N2O2.
Calculated: M 164.0586.
1-(5-Nitropyridin-2-yl)ethanone oxime (Vb).
Yield 19%, mp 161–162°C (from benzene) [22].
1-(5-Nitropyridin-2-yl)ethanone (Vc). Yield 2%,
mp 88–89°C (from cyclohexane) [22].
2-(3-Methoxyphenyl)-5-nitropyridine (Vd). Yield
93%, light yellow crystals, mp 105–106°C (from etha-
nol). IR spectrum, ν, cm–1: 1541, 1324 (NO2), 1190
1
(OCH3). H NMR spectrum (CDCl3), δ, ppm: 3.91 s
3
(3H, OCH3), 7.07 d (1H, 4′-H, J = 7.81 Hz), 7.38–
7.48 t (1H, 5′-H, 3J = 7.81, 8.04 Hz), 7.60–7.68 m (2H,
3-Nitro-6,7,8,9,10,11,12,13-octahydro-5H-cyclo-
undeca[b]pyridine (IIIe). Yield 51%, mp 68–69°C
(from aqueous ethanol). IR spectrum, ν, cm–1: 1541,
2′-H, 6′-H), 7.89 d (1H, 3-H, 3J = 8.80 Hz), 8.51 d.d (1H,
3
4
4
4-H, J = 8.80, J = 2.68 Hz), 9.45 d (1H, 6-H, J =
2.20 Hz). Mass spectrum, m/z (Irel, %): 231 (14.97),
230 (100) [M]+·, 229 (78.71), 201 (13.78), 200 (29.27),
183 (15.55), 157 (14.75), 155 (10.15), 154 (22.35),
142 (10.84), 141 (10.40), 128 (10.72), 127 (20.42), 114
(16.53), 92 (15.97), 77 (22.71), 64 (11.53), 63 (10.61).
Found: m/z 230.0692 [M]+·. C12H10N2O3. Calculated:
M 230.0691.
1
1324 (NO2). H NMR spectrum (CDCl3), δ, ppm:
1.09–1.48 m (10H, 7-H, 8-H, 9-H, 10-H, 11-H), 1.75–
1.92 m (2H, 6-H), 1.93–2.07 m (2H, 12-H), 2.91 t
(2H, 13-H, J = 6.35 Hz), 3.02 t (2H, 5-H, J = 6.35 Hz),
8.25 d (1H, 4-H, J = 2.44 Hz), 9.21 d (1H, 2-H, J =
2.44 Hz). Mass spectrum, m/z (Irel, %): 248 (26.09)
[M]+·, 233 (13.97), 207 (17.35), 206 (12.38), 205
(82.46), 192 (18.88), 191 (100), 179 (20.21), 178
(13.62), 177 (25.10), 165 (30.20), 163 (13.68), 152
(70.65), 145 (11.41), 133 (10.45), 131 (12.26), 117
(11.40), 106 (10.39), 77 (16.11), 65 (11.19), 55 (13.96),
2-(2-Naphthyl)-5-nitropyridine (Ve). Yield 73%,
mp 171–172°C (from propan-2-ol). IR spectrum, ν,
1
cm–1: 1554, 1338 (NO2). H NMR spectrum (CDCl3),
δ, ppm: 7.50–7.61 m (2H, 6′-H, 7′-H), 7.85–8.04 m
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 45 No. 7 2009

SAGITULLINA et al.
1048
3
(4H, 3′-H, 4′-H, 5′-H, 8′-H), 8.15 d.d (1H, 3-H, J =
was synthesized from compound VI and resorcinol
according to the procedure described in [9]. A mixture
of 0.464 g (2 mmol) of compound VII and 3.5 ml of
acetic anhydride was heated under stirring to 60°C,
a catalytic amount of concentrated sulfuric acid was
added, and the mixture was stirred for 2 h at that tem-
perature. The mixture was then poured onto ice, and
the precipitate was filtered off. Yield 70%, mp 142–
143°C (from ethanol). IR spectrum, ν, cm–1: 1748
(C=O); 1511, 1349 (NO2). 1H NMR spectrum (CDCl3),
δ, ppm: 2.23 s (3H, 1-COOCH3), 2.33 s (3H,
4
3
4
8.79, J = 1.71 Hz), 8.51 d.d (1H, 4-H, J = 9.23, J =
4
2.44 Hz), 8.58 s (1H, 1′-H), 9.51 d (1H, 6-H, J =
2.45 Hz). Mass spectrum, m/z (Irel, %): 251 (16.30),
250 (100) [M]+·, 204 (22.76), 177 (34.24), 176 (17.07),
127 (29.06), 88 (13.84). Found, %: C 71.77; H 3.64;
N 10.37. C15H10N2O2. Calculated, %: C 71.99; H 4.03;
N 11.19.
2-(5-Methylfuran-2-yl)-5-nitropyridine (Vf).
Yield 68%, light yellow crystals, mp 130–131°C (from
ethanol). IR spectrum, ν, cm–1: 1527, 1324 (NO2).
1H NMR spectrum (CDCl3), δ, ppm: 2.45 s (3H, CH3),
6.23 d (1H, 4′-H, 3J = 2.69 Hz), 7.20 d (1H, 3′-H, 3J =
3.42 Hz), 7.73 d (1H, 3-H, 3J = 8.80 Hz), 8.44 d.d (1H,
4
3-COOCH3), 7.07 d (1H, 2-H, J = 2.20 Hz), 8.18 d.d
3
4
(1H, 6-H, J = 8.67, J = 2.20 Hz), 7.75– 7.85 m (2H,
5-H, 3′-H), 8.53 d.d (1H, 4′-H, 3J = 8.78, 4J = 2.68 Hz),
4
9.49 d (1H, 6′-H, J = 2.42 Hz). Mass spectrum, m/z
3
4
4
4-H, J = 8.90, J = 2.44 Hz), 9.36 d (1H, 6-H, J =
2.44 Hz). Mass spectrum, m/z (Irel, %): 205 (11.36),
204 (100) [M]+·, 158 (10.86), 131 (52.72), 119 (10.74),
103 (11.17), 77 (14.91), 53 (10.05), 43 (24.90), 28
(10.88). Found, %: C 58.84; H 3.63; N 13.01.
C10H8N2O3. Calculated, %: C 58.82; H 3.95; N 13.72.
(Irel, %): 316 (0.22) [M]+·, 274 (24.65), 233 (12.44),
232 (100), 186 (12.53). Found, %: C 56.91; H 3.72;
N 8.72. C15H12N2O6. Calculated, %: C 56.96; H 3.82;
N 8.86.
4-(5-Nitropyridin-2-yl)benzene-1,3-diyl dibenzo-
ate (VIIIb). Benzoyl, chloride, 0.7 ml (4 mmol), was
added dropwise under stirring over a period of 30 min
to a solution of 0.464 g (2 mmol) of compound VII in
4.5 ml of anhydrous pyridine, cooled to 0°C. The mix-
ture was stirred for 3 days and poured onto ice, and the
precipitate was filtered off and washed with ice water.
Yield 70%, mp 173–174°C (from toluene). IR spec-
trum, ν, cm–1: 1747 (C=O); 1507, 1347 (NO2). 1H NMR
spectrum (CDCl3), δ, ppm: 7.31–7.72 m (8H, m-H,
p-H, 2-H, 6-H), 7.84 d (1H, 3′-H, 3J = 8.78 Hz), 7.98 d
(1H, 5-H, 3J = 8.48 Hz), 8.12–8.15 m (2H, o-H), 8.17–
5-Nitro-2-(1H-pyrrol-2-yl)pyridine (Vg). Reac-
tion temperature 90°C. Yield 27%, orange crystals,
mp 198°C (decomp., from ethanol). IR spectrum, ν,
cm–1: 3027 (NH); 1581, 1338 (NO2). H NMR spec-
1
trum (DMSO-d6), δ, ppm: 6.27–6.29 m (1H, 4′-H),
3
7.08–7.10 m (2H, 3′-H, 5′-H), 7.89 d (1H, 3-H, J =
3
9.03 Hz), 8.48 d (1H, 4-H, J = 8.79 Hz), 9.25 s
(1H, 6-H), 11.95 br.s (1H, NH). Mass spectrum, m/z
(Irel, %): 190 (10.38), 189 (100) [M]+·, 143 (24.27), 117
(11.66), 116 (66.64), 89 (17.36), 39 (11.93). Found:
m/z 189.0537 [M]+·. C9H7N3O2. Calculated: M 189.0538.
3
4
8.25 m (2H, o-H), 8.42 d.d (1H, 4′-H, J = 8.78, J =
4
3-(5-Nitropyridin-2-yl)-1H-indole (Vh). a. Fol-
lowing the general procedure, compound Vh was
obtained in 23% yield as dark orange crystals with
mp 173–174°C (from ethanol) [23, 24].
2.44 Hz), 9.40 d (1H, 6′-H, J = 2.44 Hz). Mass spec-
trum, m/z (Irel, %): 440 (0.74) [M]+·, 105 (100), 77
(21.13). Found, %: C 68.47; H 3.71; N 6.25.
C25H16N2O6. Calculated, %: C 68.18; H 3.66; N 6.36.
b. A mixture of 0.5 g (3.15 mmol) of 2-chloro-5-
nitropyridine (VI) and 0.417 g (3.15 mmol) of AlCl3 in
25 ml of anhydrous dichloroethane was stirred for
30 min at room temperature and cooled to 0°C, 0.369 g
(3.15 mmol) of indole was added, and the mixture was
stirred for 1 h at 0°C, heated for 24 h at 80°C, poured
onto ice, and extracted with dichloroethane. The
extract was washed with water, dried over anhydrous
magnesium sulfate, and evaporated, and the residue
was purified by column chromatography on silica gel
(100–160 μm) using benzene–ethyl acetate (9:1) as
eluent. Yield 20%, dark orange crystals, mp 173–
174°C (from ethanol) [23, 24].
This study was performed under financial support
by the Russian Foundation for Basic Research (project
no. 07-03-00783).
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