Heterocyclization of 5-(Arylmethylidene)pyrimidine-2,4,6(1H,3H,5H)-triones with Arenecarbaldehyde Oximes in the Presence of N-Bromosuccinimide and Triethylamine

Article abstract of DOI:10.1134/S1070428019070108

5-(Arylmethylidene)pyrimidine-2,4,6(1H,3H,5H)-triones reacted with substituted benzaldehyde oximes in the presence of N-bromosuccinimide and triethylamine to give 1,4-diaryl-2-oxa-3,7,9-triazaspiro-[4.5]dec-3-ene-6,8,10-triones and 3,4-diaryl-1,2,5-oxadia

Full text of DOI:10.1134/S1070428019070108

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2019, Vol. 55, No. 7, pp. 978–982. © Pleiades Publishing, Ltd., 2019.
Russian Text © The Author(s), 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 7, pp. 1079–1083.
Heterocyclization of 5-(Arylmethylidene)pyrimidine-
2,4,6(1H,3H,5H)-triones with Arenecarbaldehyde Oximes
in the Presence of N-Bromosuccinimide and Triethylamine
A. G. Tyrkova* and E. A. Yurtaevab**
a Astrakhan State University, Astrakhan, Russia
*e-mail: tyrkov@rambler.ru
b Pyatigorsk Medical and Pharmaceutical Institute (Branch), Volgograd State Medical University, Pyatigorsk, Russia
**e-mail: huitre_88@mail.ru
Received January 9, 2019; revised March 10, 2019; accepted March 15, 2019
Abstract—5-(Arylmethylidene)pyrimidine-2,4,6(1H,3H,5H)-triones reacted with substituted benzaldehyde
oximes in the presence of N-bromosuccinimide and triethylamine to give 1,4-diaryl-2-oxa-3,7,9-triazaspiro-
[4.5]dec-3-ene-6,8,10-triones and 3,4-diaryl-1,2,5-oxadiazole N-oxides.
Keywords: 5-(arylmethylidene)pyrimidine-2,4,6(1H,3H,5H)-triones, arenecarbaldehyde oximes, 1,3-dipolar
cycloaddition, N-bromosuccinimide, triethylamine, 1,4-diaryl-2-oxa-3,7,9-triazaspiro[4.5]dec-3-ene-6,8,10-tri-
ones, 3,4-diaryl-1,2,5-oxadiazole N-oxides.
DOI: 10.1134/S1070428019070108
Published data on chemical transformations of
benzonitrile oxides generated by dehydrohalogenation
of benzohydroximoyl chlorides with triethylamine are
limited to 1,3-dipolar cycloadditions to conjugated or
unconjugated nitroethenes, which lead to the formation
of 3,5-substituted dihydroisoxazoles [1, 2]. Reactions
of nitrile oxides with trinitroacetonitrile and ethyl
chloro(cyano)nitroacetate afforded 5-nitromethyl-
1,2,4-oxadiazole derivatives [3–5]. Heterocyclizations
of 5-(arylmethylidene)pyrimidine-2,4,6(1H,3H,5H)-
triones with nitrile oxides generated in situ from aro-
matic aldehyde oximes by the action of N-bromo-
succinimide (NBS) and triethylamine were not studied
previously.
dimerization of intermediate nitrile oxides, 3,4-diaryl-
1,2,5-oxadiazole N-oxides 4a–4c in 52–55% yield
(Scheme 1).
Presumably, oximes 2a–2c react with NBS and tri-
ethylamine to produce nitrile oxides A, and 1,3-dipolar
cycloaddition of the latter to dipolarophiles 1a–1d
gives 1,4-diaryl-2-oxa-3,7,9-triazaspiro[4.5]dec-3-ene-
6,8,10-triones 3a–3l. The possibility of generation of
nitrile oxides by the action of NBS on aromatic alde-
hyde oximes in the presence of triethylamine was
demonstrated previously [6]. The low yields of 3a–3l
and the formation of nitrile oxide dimerization prod-
ucts 4a–4c may be rationalized by the low reactivity of
barbituric acids 1a–1d in comparison to trinitroaceto-
nitrile or ethyl chloro(cyano)nitroacetate. Presumably,
nitrile oxides undergo dimerization independently of
the presence of 1a–1d in the reaction mixture.
In continuation of our studies of the synthetic
potential of reactions of nitrile oxides with various
dipolarophiles, in this work we examined reactions of
substituted benzonitrile oxides with 5-(arylmethyli-
dene)barbituric acids 1a–1d. The reactions of 1a–1d
with oximes 2a–2c were carried out in the presence of
NBS and triethylamine in DMF at 0–5°C. As a result,
we isolated a series of previously unknown 1,4-diaryl-
2-oxa-3,7,9-triazaspiro[4.5]dec-3-ene-6,8,10-triones
3a–3l in 35–38% yield. In addition, from the reaction
mixtures we isolated products of spontaneous
Compounds 3a–3l are stable colorless or colored
high-melting solids soluble in ethanol. The structure of
1
3a–3l was determined on the basis of their IR, H and
13C NMR, and mass spectra and elemental analyses.
The IR spectra of 3a–3l showed no C=C stretching
band at 1625 cm–1, which was typical of initial py-
rimidine-2,4,6-triones 1a–1d [7]. The 1H and 13C NMR
spectral parameters of 3a–3l were consistent with the
978

HETEROCYCLIZATION OF 5-(ARYLMETHYLIDENE)PYRIMIDINE-2,4,6(1H,3H,5H)-TRIONES
979
Scheme 1.
Ar2
O
O
N
Ar2
Ar2
NBS, Et3N
0 to 20°C
O
HN
Ar1
HN
Ar2
+
1a–1d
+
Ar2
N
O
+
NOH
Ar1
N
N
O
N
H
O
O
N
H
O
O
O
1a–1d
2a–2c
A
3a–3l
4a–4c
1, Ar1 = Ph (a), 4-MeOC6H4 (b), 4-Me2NC6H4 (c), 4-MeC6H4 (d); 2, Ar2 = Ph (a), 4-MeOC6H4 (b), 4-Me2NC6H4 (c); 3, Ar1 = Ar2 =
Ph (a), Ar1 = Ph, Ar2 = 4-MeOC6H4 (b), 4-Me2NC6H4 (c); Ar1 = 4-MeOC6H4, Ar2 = Ph (d), 4-MeOC6H4 (e), 4-Me2NC6H4 (f);
Ar1 = 4-Me2NC6H4, Ar2 = Ph (g), 4-MeOC6H4 (h), 4-Me2NC6H4 (i); Ar1 = 4-MeC6H4, Ar2 = Ph (j), 4-MeOC6H4 (k), 4-Me2NC6H4 (l);
4, Ar2 = Ph (a), 4-MeOC6H4 (b), 4-Me2NC6H4 (c).
proposed structure and with the spectra of model
compounds of the dihydroisoxazole series [8]. For
instance, in the 1H NMR spectra of 3a–3l we observed
a signal at δ 5.30–5.38 ppm due to proton in the
isoxazole ring, which was absent in the spectra of
initial compounds. The 13C NMR spectra displayed
a new signal at δC 164.2–164.8 ppm due to the C=N
carbon atom in the same ring. The molecular ion and
[M – H]+ ion peaks in the mass spectra of 3a–3l had
low intensity, but ion peaks corresponding to dis-
sociative ionization via retro-1,3-dipolar cycloaddition
at the C–O and C–C bonds of the isoxazole ring were
distinguished. Apart from the above noted ions, there
was a set of ion peaks to which several formulas could
be assigned; therefore, more detailed interpretation of
the mass spectra was difficult.
progress of reactions and the purity of the isolated
compounds were monitored by ascending thin-layer
chromatography on Silufol UV-254 plates using
acetone–hexane (2:3) as eluent; spots were visualized
by treatment with iodine vapor [11]. The elemental
compositions were determined using a Euro Vector
EA-3000 automated CHNS analyzer. The melting (de-
composition) points were measured with an OptiMelt
melting point apparatus.
5-(Arylmethylidene)pyrimidine-2,4,6-(1H,3H,5H)-
triones 1a–1d [12], aromatic aldehyde oximes 2a–2c
[13], and NBS [14] were synthesized according to
previously described procedures; triethylamine of
chemically pure grade was commercial product
(Aldrich).
1,4-Diaryl-2-oxa-3,7,9-triazaspiro[4.5]dec-3-ene-
6,8,10-triones 3a–3l (general procedure). A mixture of
6 mmol of N-bromosuccinimide and 6 mmol of
aldehyde oxime 2a–2c in 30 mL of anhydrous DMF
was vigorously stirred for 30 min at 0°C, a solution of
6.5 mmol of triethylamine in 5 mL of DMF was added,
and 5 mmol of compound 1a–1d was then added under
vigorous stirring. The mixture was stirred for 30 min at
0–5°C and kept for 24 h at 20–25°C, and the precip-
itate was filtered off and washed with 10 mL of DMF.
The solvent was evaporated under reduced pressure,
and the residue was subjected to chromatography in
a glass column charged with activated silica (100–
400 μm). Compounds 3a–3l were eluted with ethanol,
compounds 4a and 4b, with benzene, and compound
4c, with chloroform.
Thus, the reaction of 5-(arylmethylidene)pyrimi-
dine-2,4,6(1H,3H,5H)-triones 1a–1d with substituted
benzaldehyde oximes 2a–2c in the presence of NBS
and triethylamine provides the possibility of incor-
porating a dihydroisoxazole ring into the base part of
molecule 1a–1d in a one-pot fashion. The obtained
compounds are interesting as potential biologically
active substances, in particular as antibacterial agents
or imidazoline receptor agonists [9, 10].
EXPERIMENTAL
The IR spectra in the range 4000–400 cm–1 were
recorded on an InfraLUM FT-02 spectrometer from
1
samples pelletized with KBr. The H and 13C NMR
spectra were recorded on a Bruker Avence II 300 SF
instrument at 500 and 125 MHz, respectively, using
DMSO-d6 as solvent and hexamethyldisiloxane as
internal standard. The mass spectra (electron impact,
70 eV) were obtained on a Finnigan SSQ-7000 mass
spectrometer with direct sample admission into the
ion source; vaporization temperature 500–550°C. The
1,4-Diphenyl-2-oxa-3,7,9-triazaspiro[4.5]dec-3-
ene-6,8,10-trione (3a). Yield 0.586 g (35%), colorless
crystals, mp 235–239°C (decomp.). IR spectrum, ν,
1
cm–1: 3355 (NH), 1770, 1750 (C=O). H NMR spec-
trum, δ, ppm: 5.38 s (1H, CH), 7.35–7.58 m (10H,
H
arom), 11.42 br.s (1H, NH), 11.47 br.s (1H, NH).
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 55 No. 7 2019

TYRKOV, YURTAEVA
980
13C NMR spectrum, δC, ppm: 62.3 (C5), 69.5 (C1),
128.1–142.5 (Carom), 152.2 (C6), 161.3 (C10), 162.5
(C8), 164.7 (C4). Mass spectrum, m/z (Irel, %): 335 (10)
[M]+·, 334 (4) [M – 1]+, 216 (100), 119 (20.4). Found,
%: C 64.32; H 3.76; N 12.36. C18H13N3O4. Calculated,
%: C 64.47; H 3.91; N 12.53. M 335.31.
(3H, CH3O), 5.37 s (1H, CH), 6.90–7.52 m (8H,
arom), 11.43 br.s (1H, NH), 11.46 br.s (1H, NH).
H
13C NMR spectrum, δC, ppm: 55.3 (CH3O), 55.5
(CH3O), 61.6 (C5), 61.8 (C1), 113.8–158.3 (Carom),
161.4 (C6), 161.8 (C10), 162.3 (C8), 164.1 (C4). Mass
spectrum, m/z (Irel, %): 395 (8) [M]+·, 394 (5) [M – 1]+,
246 (100), 149 (26.5). Found, %: C 60.58; H 4.17;
N 10.48. C20H17N3O6. Calculated, %: C 60.76; H 4.33;
N 10.63. M 395.37.
4-(4-Methoxyphenyl)-1-phenyl-2-oxa-3,7,9-tri-
azaspiro[4.5]dec-3-ene-6,8,10-trione (3b). Yield
0.676 g (37%), pale yellow crystals, mp 245–248°C
(decomp.). IR spectrum, ν, cm–1: 3355 (NH), 1770,
4-(4-Dimethylaminophenyl)-1-(4-methoxy-
phenyl)-2-oxa-3,7,9-triazaspiro[4.5]dec-3-ene-
6,8,10-trione (3f). Yield 0.755 g (37%), pale yellow
crystals, mp 305–309°C (decomp.). IR spectrum, ν,
1
1750 (C=O). H NMR spectrum, δ, ppm: 3.82 s (3H,
CH3O), 5.37 s (1H, CH), 6.90–7.52 m (9H, Harom),
11.43 br.s (1H, NH), 11.48 br.s (1H, NH). 13C NMR
spectrum, δC, ppm: 55.6 (CH3O), 62.4 (C5), 68.4 (C1),
114.4–158.5 (Carom), 161.5 (C6), 161.9 (C10), 162.7
(C8), 164.2 (C4). Mass spectrum, m/z (Irel, %): 365 (8)
[M]+·, 364 (5) [M – 1]+, 216 (100), 149 (25.2). Found,
%: C 62.31; H 3.97; N 11.32. C19H15N3O5. Calculated,
%: C 62.46; H 4.14; N 11.50. M 365.34.
1
cm–1: 3355 (NH), 1770, 1750 (C=O). H NMR spec-
trum, δ, ppm: 2.42 s (6H, CH3N), 3.80 s (3H, CH3O),
5.34 s (1H, CH), 6.95–7.55 m (8H, Harom), 11.42 br.s
(1H, NH), 11.48 br.s (1H, NH). 13C NMR spectrum,
δC, ppm: 40.5 (CH3N), 55.4 (CH3O), 62.6 (C5), 68.1
(C1), 112.8–155.2 (Carom), 161.5 (C6), 161.8 (C10),
162.8 (C8), 164.5 (C4). Mass spectrum, m/z (Irel, %):
408 (10) [M]+·, 407 (5), [M – 1]+, 246 (100), 162
(25.3). Found, %: C 61.60; H 4.77; N 13.54.
C21H20N4O5. Calculated, %: C 61.76; H 4.94; N 13.72.
M 408.41.
4-(4-Dimethylaminophenyl)-1-phenyl-2-oxa-
3,7,9-triazaspiro[4.5]dec-3-ene-6,8,10-trione (3c).
Yield 0.719 g (38%), red crystals, mp 310–314°C
(decomp.). IR spectrum, ν, cm–1: 3355 (NH), 1770,
1
1750 (C=O). H NMR spectrum, δ, ppm: 2.43 s (6H,
1-(4-Dimethylaminophenyl)-4-phenyl-2-oxa-
3,7,9-triazaspiro[4.5]dec-3-ene-6,8,10-trione (3g).
Yield 0.663 g (35%), pink crystals, mp 280–285°C
(decomp.). IR spectrum, ν, cm–1: 3355 (NH), 1770,
CH3N), 5.37 s (1H, CH), 6.95–7.55 m (9H, Harom),
11.43 br.s (1H, NH), 11.48 br.s (1H, NH). 13C NMR
spectrum, δC, ppm: 40.7 (CH3N), 62.5 (C5), 68.3 (C1),
112.6–154.4 (Carom), 161.4 (C6), 161.6 (C10), 162.5
(C8), 164.6 (C4). Mass spectrum, m/z (Irel, %): 378 (9)
[M]+·, 377 (6) [M – 1]+, 216 (100), 162 (26.5). Found,
%: C 63.32; H 4.67; N 14.62. C20H18N4O4. Calculated,
%: C 63.48; H 4.79; N 14.81. M 378.38.
1
1750 (C=O). H NMR spectrum, δ, ppm: 2.41 s (6H,
CH3N), 5.37 s (1H, CH), 6.95–7.58 m (9H, Harom),
11.42 br.s (1H, NH), 11.48 br.s (1H, NH). 13C NMR
spectrum, δC, ppm: 40.7 (CH3N), 62.7 (C5), 68.3 (C1),
112.5–154.7 (Carom), 161.5 (C6), 161.7 (C10), 162.6
(C8), 164.6 (C4). Mass spectrum, m/z (Irel, %): 378 (12)
[M]+·, 377 (8), [M – 1]+, 259 (100), 119 (20.5). Found,
%: C 63.32; H 4.61; N 14.62. C20H18N4O4. Calculated,
%: C 63.48; H 4.79; N 14.81. M 378.13.
1-(4-Methoxyphenyl)-4-phenyl-2-oxa-3,7,9-tri-
azaspiro[4.5]dec-3-ene-6,8,10-trione (3d). Yield
0.657 g (36%), pale yellow crystals, mp 215–219°C
(decomp.). IR spectrum, ν, cm–1: 3355 (NH), 1770,
1
1750 (C=O). H NMR spectrum, δ, ppm: 3.81 s (3H,
1-(4-Dimethylaminophenyl)-4-(4-methoxy-
phenyl)-2-oxa-3,7,9-triazaspiro[4.5]dec-3-ene-
6,8,10-trione (3h). Yield 0.779 g (38%), pink crystals,
mp 320–325°C (decomp.). IR spectrum, ν, cm–1: 3355
CH3O), 5.36s (1H, CH), 6.90–7.55 m (9H, Harom),
11.43 br.s (1H, NH), 11.48 br.s (1H, NH). 13C NMR
spectrum, δC, ppm: 55.8 (CH3O), 61.7 (C5), 68.2 (C1),
114.5–160.2 (Carom), 161.3 (C6), 161.7 (C10), 162.2
(C8), 164.5 (C4). Mass spectrum, m/z (Irel, %): 365 (11)
[M]+·, 364 (6) [M – 1]+, 246 (100), 119 (20.6). Found,
%: C 62.28; H 3.96; N 11.33. C19H15N3O5. Calculated,
%: C 62.46; H 4.14; N 11.50. M 365.34.
1
(NH), 1770, 1750 (C=O). H NMR spectrum, δ, ppm:
2.40 s (6H, CH3N), 3.80 s (3H, CH3O), 5.30 s (1H,
CH), 6.90–7.54 m (8H, Harom), 11.42 br.s (1H, NH),
11.48 br.s (1H, NH). 13C NMR spectrum, δC, ppm:
40.4 (CH3N), 55.3 (CH3O), 62.5 (C5), 68.1 (C1),
112.7–155.4 (Carom), 161.4 (C6), 161.7 (C10), 162.8
(C8), 164.5 (C4). Mass spectrum, m/z (Irel, %): 408 (10)
[M]+·, 407 (5), [M – 1]+, 259 (100), 149 (25.2). Found,
%: C 61.58; H 4.81; N 13.54. C21H20N4O5. Calculated,
%: C 61.76; H 4.94; N 13.72. M 408.41.
1,4-Bis(4-methoxyphenyl)-2-oxa-3,7,9-triaza-
spiro[4.5]dec-3-ene-6,8,10-trione (3e). Yield 0.751 g
(38%), pale yellow crystals, mp 282–286°C (decomp.).
IR spectrum, ν, cm–1: 3355 (NH), 1770, 1750 (C=O).
1H NMR spectrum, δ, ppm: 3.80 s (3H, CH3O), 3.81 s
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 55 No. 7 2019

HETEROCYCLIZATION OF 5-(ARYLMETHYLIDENE)PYRIMIDINE-2,4,6(1H,3H,5H)-TRIONES
981
161.4 (C6), 161.6 (C10), 162.7 (C8), 164.6 (C4). Mass
spectrum, m/z (Irel, %): 392 (12) [M]+·, 391 (10),
[M – 1]+, 230 (100), 162 (22.4). Found, %: C 64.09;
H 4.95; N 14.11. C21H20N4O4. Calculated, %: C 64.28;
H 5.14; N 14.28. M 392.41.
1,4-Bis(4-dimethylaminophenyl)-2-oxa-3,7,9-tri-
azaspiro[4.5]dec-3-ene-6,8,10-trione (3i). Yield
0.782 g (37%), red crystals, mp 272–277°C (decomp.).
IR spectrum, ν, cm–1: 3355 (NH), 1770, 1750 (C=O).
1H NMR spectrum, δ, ppm: 2.40 s (6H, CH3N), 2.41 s
(6H, CH3N), 5.33 s (1H, CH), 6.95–7.62 m (8H,
Harom), 11.43 br.s (1H, NH), 11.48 br.s (1H, NH).
13C NMR spectrum, δC, ppm: 40.5 and 40.6 (CH3N),
62.3 (C5), 68.2 (C1), 112.9–154.5 (Carom), 161.3 (C10),
161.4 (C6), 162.5 (C8), 164.5 (C4). Mass spectrum, m/z
(Irel, %): 421 (11) [M]+·, 420 (6), [M – 1]+, 259 (100),
162 (24.5). Found, %: C 62.52; H 5.34; N 16.47.
C22H23N5O4. Calculated, %: C 62.70; H 5.50; N 16.62.
M 421.45.
3,4-Diphenyl-1,2,5-oxadiazole N-oxide (4a). Yield
0.747 g (52%), colorless crystals, mp 114°C [15].
3,4-Bis(4-methoxyphenyl)-1,2,5-oxadiazole
N-oxide (4b). Yield 0.969 g (54%), colorless crystals,
mp 113°C [15].
3,4-Bis(4-dimethylaminophenyl)-1,2,5-oxadi-
azole N-oxide (4c). Yield 1.065 g (55%), colorless
crystals, mp 123°C [15].
1-(4-Methylphenyl)-4-phenyl-2-oxa-3,7,9-triaza-
spiro[4.5]dec-3-ene-6,8,10-trione (3j). Yield 0.663 g
(38%), colorless crystals, mp 255–260°C (decomp.).
IR spectrum, ν, cm–1: 3355 (NH), 1770, 1750 (C=O).
1H NMR spectrum, δ, ppm: 2.32 s (3H, CH3), 5.35 s
(1H, CH), 7.05–7.55 m (9H, Harom), 11.42 br.s (1H,
NH), 11.48 br.s (1H, NH). 13C NMR spectrum, δC,
ppm: 21.6 (CH3), 62.4 (C5), 68.6 (C1), 125.6–137.3
(Carom), 161.4 (C6), 161.7 (C10), 162.5 (C8), 164.8 (C4).
Mass spectrum, m/z (Irel, %): 349 (10) [M]+·, 348 (5),
[M – 1]+, 230 (100), 119 (18.5). Found, %: C 65.14;
H 4.17; N 11.85. C19H15N3O4. Calculated, %: C 65.32;
H 4.33; N 12.03. M 349.34.
FUNDING
This study was performed under financial support
by the Ministry of Science and Higher Education of
the Russian Federation (project no. 4.9288.2017BCh).
CONFLICT OF INTERESTS
The authors declare the absence of conflict of
interests.
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55.4 (CH3O), 62.4 (C5), 68.2 (C1), 112.6–155.3 (Carom),
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(3l). Yield 0.725 g (37%), colorless crystals, mp 301–
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