Study of the methylation reaction of 2,4-dinitroimidazole and potassium 2,4,5-trinitroimidazol-1-ide with dimethyl sulfate

Article abstract of DOI:10.1007/s10593-020-02767-5

[Figure not available: see fulltext.] The methylation of 2,4-dinitroimidazole and potassium salt of 2,4,5-trinitroimidazole with dimethyl sulfate was reinvestigated. When the reaction system contained a weak base, the reaction products were 1-methyl-2,4-dinitroimidazole and 1-methyl-2,4,5-trinitroimidazole, respectively. However, in the absence of a base in the reaction system, the products contained oxidation byproducts 1-methylimidazolidine-2,4,5-trione, 1,3-dimethylimidazolidine-2,4,5-trione and recovered starting materials. All products were characterized using FT-IR, NMR, and elemental analysis. The structure of 1-methylimidazolidine-2,4,5-trione and 1,3-dimethylimidazolidine-2,4,5-trione were further confirmed by single crystal X-ray diffraction.

Full text of DOI:10.1007/s10593-020-02767-5

DOI 10.1007/s10593-020-02767-5
Chemistry of Heterocyclic Compounds 2020, 56(8), 1010–1014
Study of the methylation reaction of 2,4-dinitroimidazole
and potassium 2,4,5-trinitroimidazol-1-ide with dimethyl sulfate
1
2
1
1
1
Peng-Bao Lian , Yuan Yuan , Jian Chen , Li-Zhen Chen , Jian-Long Wang *
1
School of Chemical Engineering and Technology, North University of China,
3
College Road, Taiyuan 030051, China; е-mail: wangjianlong@nuc.edu.cn
2
Henan Yuguan Safety Development Co., Ltd.,
East Section of Weisi Road Jianye Square, Zhengzhou 450000, China;
e-mail: 513824158@qq.com
Published in Khimiya Geterotsiklicheskikh Soedinenii,
020, 56(8), 1010–1014
Submitted November 26, 2019
Accepted after revision April 22, 2020
2
The methylation of 2,4-dinitroimidazole and potassium salt of 2,4,5-trinitroimidazole with dimethyl sulfate was reinvestigated. When the
reaction system contained a weak base, the reaction products were 1-methyl-2,4-dinitroimidazole and 1-methyl-2,4,5-trinitroimidazole,
respectively. However, in the absence of a base in the reaction system, the products contained oxidation byproducts 1-methyl-
imidazolidine-2,4,5-trione, 1,3-dimethylimidazolidine-2,4,5-trione and recovered starting materials. All products were characterized
using FT-IR, NMR, and elemental analysis. The structure of 1-methylimidazolidine-2,4,5-trione and 1,3-dimethylimidazolidine-2,4,5-
trione were further confirmed by single crystal X-ray diffraction.
Keywords: 1,3-dimethylimidazolidine-2,4,5-trione, 2,4-dinitroimidazole, 1-methyl-2,4-dinitroimidazole, 1-methylimidazolidine-2,4,5-
trione, 1-methyl-2,4,5-trinitroimidazole, potassium 2,4,5-trinitroimidazol-1-ide, methylation reaction.
1
0
or DMS11 afforded
In the past few decades, polynitroimidazoles and their
derivatives have been widely used as antitumor, anti-
reaction of compound 4 with CH
2
N
2
compound 2 as product (Scheme 2), the yields were 36–
65% and 71–87%, respectively.
From these data it is clear that the highest yields of
compounds 1 and 2 were obtained using DMS as
methylation agent. Since the reaction conditions used as
well as the yields differ in the published works, we decided
1–4
bacterial, antifungal, antiviral drugs.
In recent years,
polynitroimidazoles have attracted increased interest as
energetic materials, especially high-energy insensitive
5
–13
energetic materials.
1-Methyl-2,4-dinitroimidazole (1)
and 1-methyl-2,4,5-trinitroimidazole (2) are two important
nitroimidazole compounds, which can be prepared from
Scheme 1
2
,4-dinitroimidazole (3) and potassium 2,4,5-trinitro-
imidazol-1-ide (4), respectively, by reaction with
methylation reagents (such as MeI, CH , dimethyl
Meanwhile,
compound 1 is also an important precursor for the prepa-
2
N
2
1
0–14
sulfate (DMS), Schemes 1 and 2).
1
0b,c
ration of compound 2.
The methylation reaction of compound 3 with MeI,
1
2
1
2a,14
10c,13,14b
CH
pound 1 (Scheme 1). The yields of compound 1 were 23–
7%, 27–64%, and 69–76%, respectively. The methylation
2
N
2
,
or DMS
was used to synthesize com-
6
0
009-3122/20/56(8)-1010©2020 Springer Science+Business Media, LLC
1010

Chemistry of Heterocyclic Compounds 2020, 56(8), 1010–1014
Scheme 2
20:1, a significant amount of starting material 3 was
recovered after heating the reaction mixture for 2.5 h (entry
). The methylation reaction of compound 3 with DMS
without any solvent was also examined (Table 1, entries 6–
0), and the products consisted of unreacted starting
5
1
material 3 (44–73%), compounds 5 (5–7%) and 6 (7–25%),
but the methylation product 1 was not isolated. Similarly,
as the amount of DMS increased, the yield of compounds 5
and 6 was also increased. Under the same reaction
conditions, the product composition did not change with
increasing reaction time (Table 1, entries 4, 5, 9, 10).
Our next step was carrying out the reaction in DMF or
DMSO or with addition of a weak base to avoid possible
acidic conditions in the reaction medium. In this case, the
only reaction product was N-methyl derivative 1 (Table 1,
entries 11–17).
Furthermore, the methylation reaction of compound 4
with DMS was also investigated (Scheme 5). The results
were analogous to those obtained with compound 3. The
data for the methylation reaction of compound 4 with DMS
are summarized in Table 2.
The structure of compounds 5 and 6 was finally
confirmed by a single crystal X-ray study. The single
to determine the optimal methylation conditions for com-
pounds 3 and 4 in DMS in this study.
In our initial experiment, we conducted methylation of
compound 3 with a minimal excess of DMS in 1,4-dioxane
1
2a
according to Sudarsanam, however, it was surprising that
the mixture of reaction products contained the desired
compound 1 in only 5% yield, along with 1-methyl-
imidazolidine-2,4,5-trione
(5)
(3%),
1,3-dimethyl-
imidazolidine-2,4,5-trione (6) (3%), and much of unreacted
starting material (compound 3 (79%), Scheme 3, Table 1,
entry 1). The possible mechanism for the transformation of
15
compound 3 into compound 5 is shown in Scheme 4.
Furthermore, as the amount of DMS increased, the yield of
compound 1 was further increased up to 12% (entries 2–5),
but even if the molar ratio of DMS to compound 3 was
Scheme 3
Table 1. Summary of the data for the methylation of 2,4-dinitroimidazole (3) with DMS*
Yield**, %
DMS, ml
Entry
Solvent, ml
Base (amount)
Temperature, °C
Time, h
(
mol)
1
5
3
79
70
63
51
51
73
64
55
44
44
0
5
3
3
5
6
6
5
6
7
7
7
0
0
0
0
0
0
0
6
3
1
2
3
4
5
6
7
8
9
1.0 (0.01)
1.9 (0.02)
9.5 (0.10)
1,4-Dioxane, 30
1,4-Dioxane, 30
1,4-Dioxane, 30
–
–
–
–
–
–
–
–
–
–
–
98
98
0.5
0.5
0.5
0.5
2.5
2.0
2.0
2.0
2.0
4.0
2.0
2.0
2.0
1.5
1.0
2.0
2.0
8
4
98
10
12
12
0
7
19.0 (0.20) 1,4-Dioxane, 30
19.0 (0.20) 1,4-Dioxane, 30
98
9
98
9
1.0 (0.01)
1.9 (0.02)
9.5 (0.10)
19.0 (0.20)
19.0 (0.20)
1.9 (0.02)
1.9 (0.02)
1.9 (0.02)
1.9 (0.02)
1.9 (0.02)
1.9 (0.02)
1.9 (0.02)
–
100
100
100
100
100
80
7
–
0
10
19
25
25
0
–
–
0
0
1
0
1
–
0
1
DMF, 10
DMF, 10
DMSO, 10
62
62
55
66
68
68
64
1
1
1
1
1
1
2
3
4
5
6
7
K
2
CO
3
(2.76 g)
80
0
0
–
80
0
0
H
2
O, 20
–
NaOH (0.80 g)
Et N (30 ml)
25–28% aq NH (1.5 ml)
CO (2.76 g)
70
0
0
3
83
0
0
EtOH, 30
3
75
0
0
1,4-Dioxane, 30
K
2
3
95
0
0
*
*
The amount of starting compound 3 is 10.0 mmol in all cases.
* Yield of the isolated product.
1
011

Chemistry of Heterocyclic Compounds 2020, 56(8), 1010–1014
Scheme 4
Scheme 5
O
O
Me
NH
N
DMS
2
(11 23%) +
+
+
+ 4 (34 71%)
O
O
O
O
O N
2
O N
1,4-dioxane
98°C, 0.5 2.5 h
N
N
recovered
2
N
DMS
N
Me
(0 9%)
Me
5
6 (5 13%)
O N
2
NO2
Base, (solvent) O N
NO2
N
2
N
K
4
+
7
0 95°C, 1 2 h
DMS
neat
00°C, 2 4 h
Me
2
5
8 66%
5 (6 14%) + 6 (7 32%)
4 (27 66%)
recovered
1
Table 2. Summary of the data for the methylation of potassium 2,4,5-trinitroimidazol-1-ide (4) with DMS
Yield**, %
Entry DMS, ml (mol)
Solvent, ml
Base (amount)
Temperature, °C
Time, h
2
4
71
58
42
34
34
66
53
40
27
27
0
5
4
6
5
1
2
3
4
5
6
7
8
9
1.0 (0.01)
1.9 (0.02)
9.5 (0.10)
19.0 (0.20)
19.0 (0.20)
1.0 (0.01)
1.9 (0.02)
9.5 (0.10)
19.0 (0.20)
19.0 (0.20)
1.9 (0.02)
1.9 (0.02)
1.9 (0.02)
1.9 (0.02)
1.9 (0.02)
1.9 (0.02)
1.9 (0.02)
1,4-Dioxane, 30
–
–
–
–
–
–
–
–
–
–
–
98
98
0.5
0.5
0.5
0.5
2.5
2.0
2.0
2.0
2.0
4.0
2.0
2.0
2.0
1.5
1.0
2.0
2.0
11
16
21
23
23
0
1,4-Dioxane, 30
8
10
11
13
13
7
1,4-Dioxane, 30
98
8
1,4-Dioxane, 30
98
9
1,4-Dioxane, 30
98
0
–
100
100
100
100
100
80
6
–
0
9
11
25
32
32
0
–
–
0
12
14
14
0
0
1
0
–
0
1
1
2
3
4
5
6
7
DMF, 10
DMF, 10
DMSO, 10
58
60
58
63
64
66
60
1
1
1
1
1
1
K
2
CO
3
(2.76 g)
80
0
0
0
–
80
0
0
0
H
2
O, 20
–
NaOH (0.80 g)
Et N (30 ml)
25–28% aq NH (1.5 ml)
CO (2.76 g)
70
0
0
0
3
83
0
0
0
EtOH, 30
3
75
0
0
0
1,4-Dioxane, 30
K
2
3
95
0
0
0
*
*
The amount of starting compound 4 is 10.0 mmol in all cases.
* Yield of the isolated product.
1
012

Chemistry of Heterocyclic Compounds 2020, 56(8), 1010–1014
and 29.8 or 39.5 ppm for H and 13C nuclei, respectively).
Elemental analyses were taken on an Elementar Vario EL
elemental analyzer. Melting points were collected using a
Buchi Melting Point M-565 apparatus and are uncorrected.
Dimethyl sulfate (98.5%), DMF (99.5%), DMSO
1
(
99.0%), 1,4-dioxane (99.0%,
aqueous NH , Et N (99.0%), EtOH (99.7%), NaOH
96.0%), K CO (99.0%), KCl (99.5%), Et O (99.5%), and
CH Cl
H
2
O 0.1%), 25–28%
3
3
(
2
3
2
2
2
(99.5%) were provided by Xi Long Science
Company. Reagent grade (Type 3, 300–400 mesh) silica
gel was used, which was purchased from Qingdao Haiyang
17
Chemical Co., Ltd. 2,4-Dinitroimidazole (3) and potassium
10a
2
,4,5-trinitroimidazol-1-ide (4) were prepared according
to the published procedure by the North University of China.
Caution! Polynitroimidazoles are considered dangerous and
proper precaution should be taken in their handling and storage!
Methylation reaction of 2,4-dinitroimidazole (3) or
potassium 2,4,5-trinitroimidazol-1-ide (4) (General
method). 2,4-Dinitroimidazole (3) (1.58 g, 10.0 mmol) or
potassium 2,4,5-trinitroimidazol-1-ide (4) (2.41 g, 10.0 mmol)
was added to the appropriate solvent with stirring. After the
addition was complete, the mixture was stirred for
additional 15 min. DMS (19 ml, 0.2 mol) was then added
dropwise carefully at room temperature. Finally, if needed,
the requisite amount of a base was added. After completion
of the addition, the mixture was heated gradually to the
required temperature, stirred for 0.5–4 h, cooled to room
Figure 1. Molecular structure of 1,3-dimethylimidazolidine-
,4,5-trione (6) according to X-ray diffraction analysis.
2
crystal data and structure image of compound 5 are shown
in Tables 1S–5S and Figure 1S (Supplementary infor-
mation file), respectively, which are identical to that
1
6
reported in our previous article.
Compound 6 crystallizes in the orthorhombic crystal
system with space group Pna2 , and each elementary cell
1
has twelve molecules. The main crystallographic data are
listed in Table 6S (Supplementary information file). As
shown in Figure 1, the asymmetric unit of compound 6
consists of three molecules, and each of the imidazolidine
rings is almost planar with the dihedral angles 0.904, 1.362,
and 2.037°, respectively (Table 7S, Supplementary infor-
mation file). The keto groups and the carbon atoms of the
methyl groups are almost coplanar with the imidazolidine
ring; for the respective torsion angles (see Table 8S,
Supplementary information file). However, hydrogen
atoms of the methyl groups are rotated out of the plane.
In summary, we have studied the methylation reactions
of 2,4-dinitroimidazole with DMS in 1,4-dioxane, which
produced 1-methyl-2,4-dinitroimidazole in low yield along
with 1-methylimidazolidine-2,4,5-trione and 1,3-dimethyl-
imidazolidine-2,4,5-trione as oxidation byproducts, as well
as unreacted starting material. When 2,4-dinitroimidazole
reacted with DMS without solvent, no methylation took
place, and only the oxidation byproducts were formed. The
reaction of 2,4-dinitroimidazole with DMS in DMF,
DMSO, low concentration sodium hydroxide solution or
weak base allowed to obtain 1-methyl-2,4-dinitroimidazole
in moderate to good yield without side products. Similar
results were observed for the methylation of potassium
temperature, and poured into distilled H
mixture was extracted with CH Cl or Et
the case of potassium 2,4,5-trinitroimidazol-1-ide (4),
saturated K CO and KCl solutions were subsequently
added to the combined Et O extracts to obtain a yellow
2
O (50 ml). The
2
2
2
O (5×30 ml). In
2
3
2
precipitate of the starting material 4, which was filtered off
and dried. The combined organic extracts were evaporated
under reduced pressure. All compounds were purified by
column chromatography on silica gel (petroleum ether –
EtOAc, 5:1).
1-Methyl-2,4-dinitroimidazole (1). Yellow powder,
1
2a
–1
mp 141–143°C (mp 144–146°C ). IR spectrum, ν, cm :
1327 (NO
3128 (=C–H), 3152 (=C–H). (IR spectrum, ν, cm : 1138
(C–N), 1325 (NO ), 1461 (–CH ), 1498 (C=C), 1515
(C=C), 1556 (NO ), 2899 (–CH ), 3152 (=C–H). ) H NMR
spectrum (Me CO-d ), δ, ppm: 4.28 (3H, s, CH ); 8.52 (1H,
s, CH). 13C NMR spectrum (Me
CO-d ), δ, ppm: 39.0;
126.9; 143.0; 143.6. Found, %: C 27.89; H 2.35; N 32.57.
. Calculated, %: C 27.92; H 2.34; N 32.56.
1-Methyl-2,4,5-trinitroimidazole (2). Yellow powder,
2
), 1372 (N–CH
3
), 1502 (C=C), 1554 (NO
2
),
–
1
2
3
12b 1
2
3
2
6
3
2
6
2
,4,5-trinitroimidazol-1-ide with DMS. The structure of
C
4
H
4
N
4
O
4
products of these reactions indicate that 2,4-dinitro-
16
–1
1
-methylimidazole and 1-methyl-2,4,5-trinitroimidazole
mp 81–82°C (mp 81–82°C ). IR spectrum, ν, cm : 1329
(NO ), 1361 (N–CH ), 1503 (C=C), 1549 (NO ), 2899
(–CH ). (IR spectrum, ν, cm : 1329 (NO ), 1361 (N–CH ),
503 (C=C), 1549 (NO ), 2899 (–CH ). ) H NMR
spectrum (Me CO-d ), δ, ppm: 4.37 (3H, s, CH
spectrum (Me CO-d ), δ, ppm: 24.5; 154.7; 158.8; 159.0.
are susceptible to nucleophilic substitution to form methyl-
imidazolidine-2,4,5-triones.
2
3
2
–
1
3
2
3
16
1
1
2
3
Experimental
13
2
6
3
). C NMR
IR spectra were recorded on a Bruker Model Vertex 80
2
6
1
13
FTS spectrometer in KBr pellets. H and C NMR spectra
were recorded on a Bruker Model Avance spectrometer
Found, %: C 22.29; H 1.44; N 32.17. C
Calculated, %: C 22.13; H 1.39; N 32.26.
4
H
3
N
5
6
O .
(
400 and 100 MHz, respectively) in Me
2
CO-d
6
or DMSO-d
6
.
2,4-Dinitroimidazole (3). Recovered from reaction
Chemical shift values (δ) are reported in ppm relative to
Me CO-d or DMSO-d as internal standard (2.05 or 2.50,
mixture, pale-yellow powder, mp 264–266°C (mp 265–
1
7
2
6
6
274°C ).
1
013

Chemistry of Heterocyclic Compounds 2020, 56(8), 1010–1014
5. (a) Hou, K.; Ma, C.; Liu, Z. New J. Chem. 2013, 37, 2837.
Potassium 2,4,5-trinitroimidazol-1-ide (4). Recovered
from reaction mixture, yellow powder, mp 236–238°C
(
b) Katritzky, A. R.; Yang, H.; Zhang, D.; Kirichenko, K.;
10a
Smiglak, M.; Holbrey, J. D.; Reichert, W. M.; Rogers, R. D.
New J. Chem. 2006, 30, 349. (c) Lian, P.-B.; Guo, X.-J.;
Wang, J.-L.; Chen, L.-Z.; Shen, F.-F. Chem. Heterocycl.
Compd. 2018, 54, 1045. [Khim. Geterotsikl. Soedin. 2018, 54,
(
mp 234°C ).
-Methylimidazolidine-2,4,5-trione (5). Yield 0.07 g
1
1
6
(
6%), white powder, mp 146–148°C (mp 146–148°C ).
–
1
IR spectrum, ν, cm : 1330 (C–NH), 1455 (–CH
3
), 1719
), 3228
N–H). (IR spectrum, ν, cm : 1330 (C–NH), 1455 (–CH ),
719 (C=O), 1741 (C=O), 1795 (C=O), 2815 (–CH ), 3228
), δ, ppm: 3.06
); 10.77 (1H, br. s, NH). C NMR spectrum
), δ, ppm: 24.5; 154.8; 158.8; 159.1. Found, %:
1
045.]
(
(
1
(
(
(
C=O), 1741 (C=O), 1795 (C=O), 2815 (–CH
3
6
.
(a) Su, X.; Cheng, X.; Meng, C.; Yuan, X. J. Hazard. Mater.
2009, 161, 551. (b) Su, X.; Cheng, X.; Ge, S. J. Mol. Struct.:
THEOCHEM 2009, 895, 44. (c) Jadhav, P. M.; Sarangapani, R.;
Ghule, V. D.; Prasanth, H.; Pandey, R. K. J. Mol. Model.
–
1
3
3
16
1
N–H). ) H NMR spectrum (Me
3H, s, CH
Me CO-d
2
CO-d
6
1
3
2
013, 19, 3027.
3
7
.
.
Badgujar, D. M.; Talawar, M. B.; Asthana, S. N.; Mahulikar, P. P.
J. Hazard. Mater. 2008, 151, 289.
2
6
C 37.42; H 3.19; N 21.95. C
C 37.51; H 3.15; N 21.87.
4
H
4
N
2
O . Calculated, %:
3
8
Jadhav, H. S.; Talawar, M. B.; Sivabalan, R.; Dhavale, D. D.;
Asthana, S. N.; Krishnamurthy, V. N. J. Hazard. Mater. 2007,
1
,3-Dimethylimidazolidine-2,4,5-trione (6). Yield
1
43, 192.
18
0
.13 g (9%), white powder, mp 152–154°C (mp 154°C ).
9. (a) Diao, Y.; Wang, J.-L.; Wang, W.-Y.; Yu, Z.-H.; Liu, L.-L.
Chin. J. Explos. Propellants 2012, (2), 40 [In Chinese].
(b) Wang, X.-J.; Cao, D.-L.; Li, Y.-X.; Song, L.; Wang, J.-L.
Chin. J. Explos. Propellants 2009, (3), 16 [In Chinese].
–
1
IR spectrum, ν, cm : 1279 (O=C–N–), 1390 (N–CH
3
),
1
2
(
465 (N–CH
930 (–CH ), 2958 (–CH ). (IR spectrum, ν, cm : 1710
18 1
3
), 1706 (C=O), 1731 (C=O), 1768 (C=O),
–
1
3
3
10. (a) Novikov, S. S.; Khmel'nitskii, L. I.; Lebedev, O. V.;
Sevast'yanova, V. V.; Epishina, L. V. Chem. Heterocycl.
Compd. 1970, 6, 465. [Khim. Geterotsikl. Soedin. 1970, 6,
C=O), 1735 (C=O), 1770 (C=O), 2980 (CH). ) H NMR
13
spectrum (DMSO-d
spectrum (DMSO-d
6
), δ, ppm: 2.98 (6H, s, CH
3
). C NMR
6
), δ, ppm: 24.3; 154.8; 157.8.
5
03.] (b) Novikov, S. S.; Khmel'nitskii, L. I.; Lebedev, O. V.;
Found, %: C 42.29; H 4.25; N 19.69. C
Calculated, %: C 42.26; H 4.26; N 19.71.
5
H
6
N
2
O .
3
Epishina, L. V.; Sevost'yanova, V. V. Chem. Heterocycl.
Compd. 1970, 6, 614. [Khim. Geterotsikl. Soedin. 1970,
664.] (c) Cho, J. R.; Kim, K. J.; Cho, S. G.; Kim, J. K.
J. Heterocycl. Chem. 2002, 39, 141. (d) Wang, W.; Yang, W.;
Ji, Y.-P.; Ding, F. Chin. J. Explos. Propellants 2008(6), 32
X-ray structural investigation of 1-methylimidazo-
lidine-2,4,5-trione (5) and 1,3-dimethylimidazolidine-
2
2
,4,5-trione (6). Single crystals of 1-methylimidazolidine-
[
In Chinese].
1. (a) Ravi, P.; Tewari, S. P. Propellants Explos. Pyrotech. 2012,
7, 544. (b) Duddu, R.; Zhang, M.-X.; Damavarapu, R.;
,4,5-trione and 1,3-dimethylimidazolidine-2,4,5-trione
1
were obtained in CH
2
Cl solution by solvent evaporation at
2
3
ambient temperature. X-ray diffraction data were collected
on a Bruker D8 Venture Photon 100 CMOS detector
equipped with a graphite monochromator, MoKα radiation
Gelber, N. Synthesis 2011, 17, 2859. (c) Damavarapu, R.;
Surapaneni, C. R.; Gelber, N.; Duddu, R. G.; Zhang, M. X.;
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Ran, J.-P.; Wei, T.-Y. Fine Chem. Intermed. 2009, (3), 65
[In Chinese].
(
λ 0.07107 nm). The structures were solved by the direct
19
methods (SHELXL-97 software) and refined by the full-
2
matrix-block least-squares method on F with anisotropic
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thermal parameters for all non-hydrogen atoms (OLEX2
software).20 The hydrogen atoms were added according to
the theoretical models. Crystallographic data for 1-methyl-
imidazolidine-2,4,5-trione (5) and 1,3-dimethylimidazo-
lidine-2,4,5-trione (6) have been deposited at the
Cambridge Crystallographic Data Center (deposits CCDC
[
In Chinese]. (c) Yang, W.; Ji, Y.-P.; Wang, W.; Wang, Y.-L.;
Liu, W.-X.; Liu, Y.-J. Fine Chem. Intermed. 2008, (5), 30
In Chinese].
[
1
1
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5. Poje, M.; Sokolić-Maravić, L. Tetrahedron 1986, 42, 747.
6. Lian, P.-B.; Chen, J.; Chen, L.-Z.; Zhao, C.-Y.; Wang, J.-L.;
Shen, F.-F. Chem Heterocycl. Compd. 2020, 56, 55. [Khim.
Geterotsikl. Soedin. 2020, 56, 55.]
17. (a) Bulusu, S.; Damavarapu, R.; Autera, J. R.; Behrens, R., Jr.;
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18. Khattab, A. F.; Kappe, T. J. Chem. Res. 2006, 609.
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Crystallogr. 2008, A64, 112.
20. Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.;
Puschmann, H. J. Appl. Crystallogr. 2009, 42, 339.
1
966870 and 1966866, respectively).
Supplementary information file containing 1H and
C NMR spectra of all synthesized compounds and X-ray
1
3
data of compounds 5, 6 is available at the journal website at
http://link.springer.com/journal/10593.
1
1
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