Triton-B mediated efficient synthesis of thioxoimidazolidine-4,5-diones

Article abstract of DOI:10.14233/ajchem.2020.22252

A simple, mild and efficient protocol for the synthesis of thioxoimidazolidine-4,5-diones (1-15) from substituted thiourea employing Triton-B/CS2 system has been discussed. The protocol described is an easy, efficient, nature-friendly method using cheap,

Full text of DOI:10.14233/ajchem.2020.22252

Asian Journal of Chemistry; Vol. 32, No. 1 (2020), 183-186
A
SIAN
J
OURNAL OF HEMISTRY
C
https://doi.org/10.14233/ajchem.2020.22252
Triton-B Mediated Efficient Synthesis of Thioxoimidazolidine-4,5-diones
1
1
2
3,*
RAM KISHORE , M. KAMBOJ , M. SHUKLA and DEVDUTT CHATURVEDI
1Department ofApplied Chemistry,Amity School ofApplied Sciences,Amity University Uttar Pradesh, Lucknow Campus, Lucknow-226028,
India
2Department of Chemistry, Babu Banarasi Das National Institute of Technology, Lucknow-227105, India
3Department of Chemistry, School of Physical Sciences, Mahatma Gandhi Central University, Motihari-845401, India
*Corresponding author: E-mail: devduttchaturvedi@gmail.com
Received: 10 June 2019;
Accepted: 27 September 2019;
Published online: 18 November 2019;
AJC-19694
A simple, mild and efficient protocol for the synthesis of thioxoimidazolidine-4,5-diones (1-15) from substituted thiourea employing
Triton-B/CS2 system has been discussed. The protocol described is an easy, efficient, nature-friendly method using cheap, easily available,
less toxic reagents at room temperature. The synthesis involves the reaction between substituted thiourea in toluene and oxalyl chloride at
room temperature using phase transfer catalyst Triton-B/CS2 system.
Keywords: Thioxoimidazolidine-4,5-diones, Substituted thiourea, Oxalyl chloride, Toluene, Triton-B, Carbon disulfide.
drugs for inhibitors [15] for growth of plant, curing hypogly-
cemia [16]. The versatile application of thioxoimidazolidine-
4,5-dione make them paramount and privileged compounds.
If carbonyl group of hydantoins are replaced thiocarbonyl
group, it gives rise to thiohydantoin which have extensive appli-
cations in hypolipidemic, anticarcinogenic, antituberculosis,
anti-herpes, anti-HIV anti-HSV, etc. These thiohydantoins are
found to be significant antiinfalmatory [17], antiulcer, anti-
microbial agents. Diverse studies [18-20] have described the
synthesis of various amino acids and have used them as inter-
mediates for the synthesis of heterocyclics [21,22]. A number
of schemes are described for the synthesis of 2-thioxodihydro-
1H-imidazole-4,5-dione derivatives [23-26] under solvent free
conditions [27]. In the present paper, a safe and environmental
friendly synthesis of 2-thioxoimidazolidine-4,5-dione using
benzyl trimethylammonium hydroxide (Triton-B) as a phase
transfer catalyst is discussed. We aim to overcome, the problems
associated with other methods like higher reaction tempera-
tures, longer reaction time, tedious work-up, lesser yields, etc.
INTRODUCTION
In recent years, there is a ceaseless quest for biological
moiety for treating various infections [1]. The diversified illness
occurring to the living being drives the demand for biologically
potent scaffolds to treat such variety of illness due to increasing
resistance of pathogenic bacteria towards antibiotics. So there
is great demand of new antibacterial drugs [2]. The discovery
of effective and least toxic products needs new synthetic routes
and modification of structure of prevailing molecules using
the phenomena of bioisosterism [3]. The significance of an
atom or the group is analyzed on the basis of the bioactivity of
the drug having similar antagonistic effect.
The 1H-imidazole is a five membered ring with two hetero-
atom, is an important scaffold found in many drugs used for
microbial infection [4-7], hyperthyroidism [8] and insomnia
[9]. Thioxoimidazolidine-4,5-dione are the group of hetero-
cyclic compound with 1H-imidazole moiety has a wide range
of biological and pharmacological properties [10,11]. 2,4-Imida-
zolidinones or hydantoins [3] are interesting compounds owing
to their important pharmacological properties [12].These hetero-
cyclic moieties present in the substances make them notable
bioactive substances with broad spectrum biological activities
like anti-inflammatory [13], antibacterial, antifungal [14] drugs,
EXPERIMENTAL
The reagents used in this research were procured from
Merck, India. Products were ascertained by similarity in
spectral data with the available compounds. NMR spectra were
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184 Kishore et al.
Asian J. Chem.
obtained onBrukerAdvance spectrophotometer (400.13 MHz)
with CDCl3 as solvent and tetramethylsilane as reference. The
elements in the compounds were confirmed by high resolution
mass spectroscopy (HRMS) and it agreed approximately with
the calculated mass obtained by HRMS. Structure of all products
was drawn on similarity basis of the physical data with the
reported data.
General procedure for the synthesis of compounds (1-
15) using Triton-B:At room temperature, a solution of amine
(1.0 mmol), CS2 (10 mmol) and a Triton-B (40 wt. % in H2O)
(1.5 mmol) was stirred for 30 min, followed by addition of
NH4OH solution (28% NH3 in H2O) (1.1 mmol). The solution
is again stirred at room temperature for 14 h. After stirring,
Triton-B (40 wt. % in H2O) (2.5 mmol) was added and again
stirred for 15 more minutes. Then oxalylchloride (1 mmol)
was added at room temperature. The reaction mixture was than
stirred for 2 h. The progress of reaction was monitored by
TLC. After completion, water (50 mL) was added and the
product was extracted with ethyl acetate (3 × 20 mL). The
combined organic layer was washed with brine, dried over
sodium sulfate and concentrated under reduced pressure to
afford crude product. This crude product was further purified by
silica gel column chromatography by using eluent ethyl
acetate:hexane (1:5) to afford pure product.
C9H5N2O2SCl calcd. (found) %: C, 44.92 (45.82); H, 2.09
(2.17); Cl, 14.73 (15.99); N, 11.64 (13.94); O, 13.30 (15.65);
S, 13.32 (15.92). H NMR 400 MHz (DMSO-d6): δ 13.344
1
(bs, 1H), 7.608 (d, J = 8.4 Hz, 2H), 7.379 (d, J = 8.8 Hz, 2H).
13C NMR 400 MHz (DMSO-d6): δ 129.124, 130.364, 131.274,
133.866, 155.777, 157.223, 182.290.MS (ESI): m/z (M)–
calculated for C9H5N2O2SCl: 239.98, Found (M-1)–: 239.10.
1-Methyl-2-thioxoimidazolidine-4,5-dione (5): Yellow
solid, m.p. = 225-229 ºC. Elemental analysis of C4H4N2O2S
calcd. (found) %: C, 33.33 (34.13); H, 2.80 (2.40); N, 19.43
(20.23); O, 22.20 (23.12); S, 22.24 (23.14). 1H NMR 400 MHz
(CDCl3): δ 8.949 (bs, 1H), 3.406 (s, 3H). MS (ESI): m/z (M)–
calculated for C4H4N2O2S: 144.0, Found (M-1)–: 142.89.
1-(4-Fluorophenyl)-2-thioxoimidazolidine-4,5-dione
(6): Yellow solid, m.p. = 230-235 ºC. Elemental analysis of
C9H5N2O2SF calcd. (found) %: C, 48.21 (48.81); H, 2.25 (2.75);
F, 8.47 (8.97); N, 12.49 (12.99); O, 14.27 (14.57); S, 14.30
1
(14.93). H NMR 400 MHz (DMSO-d6): δ 13.328 (bs, 1H),
7.426-7.343 (m, 4H). 13C NMR 400 MHz (DMSO-d6): δ115.916,
116.150, 128.641, 130.756, 130847, 157.319, 160.871, 163.319,
182.588. MS (ESI): m/z (M)– calculated for C9H5N2O2SF:
224.01, Found (M-1)–: 223.08.
1-Phenyl-2-thioxoimidazolidine-4,5-dione (7): Yellow
solid, m.p. = 232-236 ºC. Elemental analysis of C9H6N2O2S
calcd. (found) %: C, 52.42 (52.92); H, 2.93 (3.23); N, 13.58
(14.98); O, 15.52 (16.12); S, 15.55 (16.15). 1H NMR 400 MHz
(CDCl3): δ 9.029 (bs, 1H), 7.7.536 (d, J = 6.8 Hz, 3H), 7.330
(d, J = 6.0 Hz, 2H). 13C NMR 400 MHz (CDCl3): δ 127.939,
129.670, 130.208, 131.200, 154.641, 177.688. MS (ESI): m/z
(M)– calculated for C9H6N2O2S: 206.01, Found (M-1)–: 205.12.
1-(3-Fluorophenyl)-2-thioxoimidazolidine-4,5-dione
(8): Yellow solid, m.p. = 236-239 ºC. Elemental analysis of
C9H5N2O2SF calcd. (found) %: C, 48.21 (49.22); H, 2.25
(2.75); F, 8.47 (9.17); N, 12.49 (13.99); O, 14.27 (15.97); S,
14.30 (15.45). 1H NMR 400 MHz (DMSO-d6): δ 13.377 (bs,
1H), 7.586 (q, J = 6.8 Hz, 1H), 7.373 (t, J = 7.2 Hz, 1H),
7.230 (d, J = 8.0 Hz, 2H). MS (ESI): m/z (M)– calculated for
C9H5N2O2SF: 224.01, Found (M-1)–: 223.10.
Spectral data
1-(4-(Trifluoromethyl)benzyl)-2-thioxoimidazolidine-
4,5-dione (1): Yellow solid, m.p. = 232-234 ºC. Elemental
analysis of C11H7F3N2O2S calcd. (found) %: C, 45.84 (46.14);
H, 2.45 (2.72); F, 19.77 (20.17); N, 9.72 (10.32); O, 11.10
(12.10); S, 11.12 (12.12). 1H NMR 400 MHz (CDCl3): δ 9.296
(bs, 1H), 7.597 (d, J = 8.4 Hz, 2H), 7.525 (d, J = 8.0 Hz, 2H),
5.147 (s, 2H). 13C NMR 400 MHz (CDCl3): δ 44.475, 125.280,
125.929, 125.967, 126.004, 126.040, 129.497, 137.930,
156.141, 156.313, 177.846. MS (ESI): m/z (M)– calculated
for C11H7N2O2SF3: 288.02, Found (M-1)–: 287.10.
1-(3-Chlorobenzyl)-2-thioxoimidazolidine-4,5-dione
(2): Yellow solid, m.p. = 235-239 ºC. Elemental analysis of
C10H7N2O2SCl calcd. (found) %: C, 47.16 (48.12); H, 2.77
(3.17); Cl, 13.92 (14.82); N, 11.00 (12.07); O, 12.56 (13.46);
1-(3,5-Dichlorophenyl)-2-thioxoimidazolidine-4,5-
dione (9): Yellow solid, m.p. = 238-242 ºC. Elemental analysis
of C9H4N2O2SCl2 calcd. (found) %: C, 39.29 (40.21); H, 1.47
(2.17); Cl, 25.77 (35.17); N, 10.18 (11.78); O, 11.63 (12.33);
1
S, 12.59 (13.49). H NMR 400 MHz (DMSO-d6): δ 13.104
(bs, 1H), 7.470 (s, 1H), 7.370-7.307 (m, 3H), 4.955 (s, 2H).
13C NMR 400 MHz (DMSO-d6): δ 43.187, 126.178, 127.246,
127.348, 130.122, 133.099, 137.804 156.383, 157.488,
182.763. MS (ESI): m/z (M)– calculated for C10H7N2O2SCl:
253.99, Found (M-1)–: 253.01.
1
S, 11.66 (12.96). H NMR 400 MHz (DMSO-d6): δ 13.515
(bs, 1H), 7.824 (s, 1H), 7.463 (s, 2H). 13C NMR 400 MHz
(DMSO-d6): δ 127.642, 129.297, 134.116, 134.525, 156.428,
157.023, 181.706. MS (ESI): m/z (M)– calculated for
C9H4N2O2SCl2: 273.94, Found (M-1)–: 272.94.
1-(4-(Trifluoromethyl)phenyl)-2-thioxoimidazolidine-
4,5-dione (3): Yellow solid, m.p. = 231-234 ºC. Elemental
analysis of C10H5N2O2SF3 calcd. (found) %: C, 43.80 (44.42);
H, 1.84 (2.14); F, 20.78 (21.38); N, 10.22 (11.12); O, 11.67
(12.47); S, 11.69 (12.60). 1H NMR 400 MHz (DMSO-d6): δ
13.405 (bs, 1H), 7.936 (d, J = 8.4 Hz, 2H), 7.609 (d, J = 8.4
Hz, 2H). 13C NMR 400 MHz (DMSO-d6): δ 125.216, 126.162,
126.234, 129.313, 129.632, 136.037, 155.667, 157.143,
182.003. MS (ESI): m/z (M)– calculated for C10H5N2O2SF3:
274.0, Found (M-1)–: 272.96.
1-(4-Phenylbutyl)-2-thioxoimidazolidine-4,5-dione
(10): Yellow solid, m.p. = 223-226 ºC. Elemental analysis of
C13H14N2O2S calcd. (found) %: C, 59.52 (60.12); H, 5.38
(6.18); N, 10.68 (11.18); O, 12.20 (13.21); S, 12.22 (13.92).
1H NMR 400 MHz (DMSO-d6): δ 13.002 (bs, 1H), 7.280-
7.243 (m, 2H), 7.196-7.140 (m, 3H), 3.760 (t, J = 6.4 Hz,
2H), 2.578 (t, J = 6.8 Hz, 2H), 1.607-1.590(m, 4H). 13C NMR
400 MHz (DMSO-d6): δ 26.806, 28.022, 34.700, 40.383,
125.683, 127.246, 127.348, 128.205 128.305, 141.870,
156.215, s157.477, 182.941. MS (ESI): m/z (M)– calculated
for C13H14N2O2S: 262.08, Found (M-1)–: 261.11.
1-(3-Chlorophenyl)-2-thioxoimidazolidine-4,5-dione
(4): Yellow solid, m.p. = 233-237 ºC. Elemental analysis of

Vol. 32, No. 1 (2020)
Triton-B Mediated Efficient Synthesis of Thioxoimidazolidine-4,5-diones 185
TABLE-1
1-(4-Chlorophenyl)-2-thioxoimidazolidine-4,5-dione
(11): Yellow solid, m.p. = 233-237 ºC. Elemental analysis of
C9H5N2O2SCl calcd. (found) %: C, 44.92 (45.62); H, 2.09
(2.17); Cl, 14.73 (15.93); N, 11.64 (12.93); O, 13.30 (13.98);
Compd. No.
Substitution R1
4-CF3-C6H4-CH2
m.w.
Yield (%)
95.01
94.53
92.53
93.12
94.35
93.54
90.12
92.36
93.87
92.58
93.25
90.53
94.02
92.30
91.58
288.02
253.99
274.22
240.67
144.15
224.21
206.22
224.21
275.11
262.33
240.67
158.18
274.22
214.28
234.27
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
3-Cl-C6H4-CH2
4-CF3-C6H4
3-Cl-C6H4
CH3
4-F-C6H4
C6H5
1
S, 13.32 (14.95). H NMR 400 MHz (DMSO-d6): δ 13.344
(bs, 1H), 7.608 (d, J = 8.4 Hz, 2H), 7.379 (d, J = 8.8 Hz, 2H).
13C NMR 400 MHz (DMSO-d6): δ 129.124, 130.364, 131.274,
133.866, 155.777, 157.223, 182.290. MS (ESI): m/z (M)–
calculated for C9H5N2O2SCl: 239.98, Found (M-1)–: 239.10.
1-Ethyl-2-thioxoimidazolidine-4,5-dione (12): Yellow
solid, m.p. = 224-230 ºC. Elemental analysis of C5H5N2O2S
calcd. (found) %: C, 37.97 (38.56); H, 3.82 (3.42); N, 17.71
(18.21); O, 20.23 (21.17); S, 20.27 (21.21). 1H NMR 400 MHz
(CDCl3): δ 9.038 (bs, 1H), 4.007 (q, J = 7.2 Hz, 2H), 1.296 (t,
J = 7.2 Hz, 3H). MS (ESI): m/z (M)– calculated for C5H5N2O2S:
158.01, Found (M-1)–: 156.94.
3-F-C6H4
3,5-Cl2-C6H3
C6H5-(CH2)4-
4-Cl-C6H5
C2H5
3-CF3-C6H4
(CH3)2CH-CH2-(CH3)CH
C6H5CH2CH2
1-(3-(Trifluoromethyl)phenyl)-2-thioxoimidazolidine-
4,5-dione (13): Yellow solid, m.p. = 237-242 ºC. Elemental
analysis of C10H5N2O2SF3 calcd. (found) %: C, 43.80 (44.56);
H, 1.84 (2.18); F, 20.78 (21.98); N, 10.22 (11.52); O, 11.67
(13.97); S, 11.69 (13.99). 1H NMR 400 MHz (CDCl3): δ 9.136
(bs, 1H), 7.870 (d, J = 7.2 Hz, 1H), 7.778-7.689 (m, 2H),
7.349 (d, J = 7.6 Hz, 1H). MS (ESI): m/z (M)– calculated for
C10H5N2O2SF3: 274.0, Found (M-1)–: 273.07.
1-(4-Methylpentan-2-yl)-2-thioxoimidazolidine-4,5-
dione (14): Yellow solid, m.p. = 225-230 ºC. Elemental
analysis of C9H14N2O2S calcd. (found) %: C, 50.45 (51.55);
H, 6.59 (6.79); N, 13.07 (14.27); O, 14.93 (15.99); S, 14.96
(16.16). 1H NMR 400 MHz (CDCl3): δ 9.490 (bs, 1H), 4.927-
4.871 (m, 1H), 3.900 (s, 1H), 2.116-2.039 (m, 1H), 1.554-
1.452 (m, 1H), 1.419 (s, 3H), 0.905 (d, J = 6.4 Hz, 6H). MS
(ESI): m/z (M)– calculated for C9H14N2O2S: 214.08, Found (M-
1)–: 213.09.
low require cost less toxic reagent. Output of the product is
improved and required less time for synthesis. The benefit of
using Triton-B as phase transfer catalyst visit is recovered from
the reaction mixture by filtration [30,31].
The compounds synthesized in this series were identified
by high resolution mass spectroscopy (HRMS), 1H NMR and
13C NMR spectra. The intermediate most probably results from
addition of oxalyl chloride to substituted thiourea and subse-
quently cyclization of the intermediate took place. Further
isomerization of the intermediate gave way to the formation
of the product (Scheme-I).
O
S
Cl
Cl
R1
O
N
O
N
H
+
NH3
R1 NH2
+
C S
S
Triton -B
RT, 16hr
O
1-Phenethyl-2-thioxoimidazolidine-4,5-dione (15):
Yellow solid, m.p. = 228-232 ºC. Elemental analysis of
C11H10N2O2S calcd. (found) %: C, 56.39 (57.34); H, 4.30
(4.51); N, 11.96 (13.26); O, 13.66 (15.96); S, 13.69 (15.99).
1H NMR 400 MHz (CDCl3): δ 9.413 (bs, 1H), 7.466 (d, J =
7.2 Hz, 1H), 7.375-7.27 (m, 4H), 3.726 (m, 2H), 1963 (m,
2H). 13C NMR 400 MHz (CDCl3): δ 43.187, 53.822, 126.393,
127.793, 127.951, 128.563, 128.967, 138.108, 154.782, 159.091,
177.068. MS (ESI): m/z (M)– calculated for C11H10N2O2S:
234.05, Found (M-1)–: 233.05.
NH3
H
N
NH2
S
SH
SH
R1
S
S
R1
H
N
H
S
HN R1
-H2S
H
N
H
N
R1
H
S
Cl
RESULTS AND DISCUSSION
Cl
O
-HCl
In this communication, one-pot synthesis of 2-thioxoimi-
dazolidin-4,5-diones (1-15) have been reported using Triton-
B as phase transfer catalyst. The reaction between amine, CS2,
ammonia and oxalyl dichloride was spontaneous in the presence
of phase transfer catalyst, Triton-B was completed with excellent
yield as given in Table-1. The synthesized compounds are
found to be soluble in acetone, methanol, ethanol, ethyl acetate,
diethylether, dichlromethane, DMF, CDCl3, etc. The confirmation
of product formation was done with the aid of spectroscopic
and analytical data. A number of phase transfer catalyst is
frequently used for the synthesis [28] but Triton-B is preferable
to other phase transfer catalyst due to high yields of the product
[29]. The method is easier and require simpler work-up and
O
H
H
N
N
N
S
R1
H
O
R1
Isomerization
S
R1
N
N H
N
S
O
Cl
O
O
O
O
Scheme-I: Synthesis of 2-thioxoimidazolidin-4,5-dione catalyzed by
Triton-B
Conclusion
Synthesis of 2-thioxoimidazolidine 4,5-diones has been
reported by highly efficient method by coupling of primary
amine, ammonia and oxalyl chloride via Triton-B/CS2 system.

186 Kishore et al.
Asian J. Chem.
14. J. Dolezel, P. Hirsova, V. Opletalova, J. Dohnal, V. Marcela, J. Kunes and
J. Jampilek, Molecules, 14, 4197 (2009);
https://doi.org/10.3390/molecules14104197.
15. Y. Inamori, C. Muro, R. Tanaka,A.Adachi, K. Miyamoto and H. Tsujibo,
Chem. Pharm. Bull. (Tokyo), 40, 2854 (1992);
This Triton-B mediated synthesis is more convenient and safer
than all other reported procedures like simplicity, normal
temperature, easier and simpler work-up, better output and
low cost reagents. This synthetic route thereby offers a more
convenient approach for formation of C-S bonds essential to
numerous organic syntheses.
https://doi.org/10.1248/cpb.40.2854.
16. Y. Momose, T. Maekawa, T. Yamano, M. Kawada, H. Odaka, H. Ikeda
and T. Sohda, J. Med. Chem., 45, 1518 (2002);
https://doi.org/10.1021/jm010490l.
17. Z.D. Wang, S.O. Sheikh and Y. Zhang, Molecules, 11, 739 (2006);
https://doi.org/10.3390/11100739.
CONFLICT OF INTEREST
The authors declare that there is no conflict of interests
regarding the publication of this article.
18. B. Lira, P. de Athayde-Filho, J. Miller, A. Simas, A. de Farias-Dias and
M. Vieira, Molecules, 7, 791 (2002);
https://doi.org/10.3390/71100791.
REFERENCES
19. P.F. De Athayde-Filho, J. Miller, A.M. Simas, B.F. Lira, J.A. De Souza
Luis and J. Zuckerman-Schpector, Synthesis, 685 (2003);
https://doi.org/10.1055/s-2003-38070.
20. B.F. Lira, J. Miller, A.M. Simas, P.F. de Athayde-Filho, A. de Farias-Dias,
R.O. Silva and V.C. de Oliveira, ARKIVOC, 12 (2004);
https://doi.org/10.3998/ark.5550190.0005.603.
21. V. Pilla, C.B. deAraújo, B.F. Lira,A.M. Simas, J. Miller and P.F.Athayde-
Filho, Optics Commun., 264, 225 (2006);
https://doi.org/10.1016/j.optcom.2006.02.012.
22. C.A.C. Bosco, G.S. Maciel, N. Rakov, C.B. de Araújo, L.H. Acioli, A.M.
Simas, P.F. Athayde-Filho and J. Miller, Chem. Phys. Lett., 449, 101
(2007);
https://doi.org/10.1016/j.cplett.2007.10.037.
23. W. Dieckmann and H. Kammerer, Ber., 38, 2977 (1905);
https://doi.org/10.1002/cber.190503803102.
24. H. Eilingsfeld, M. Seefelder and H. Weidinger, Angew. Chem., 72, 836
(1960);
https://doi.org/10.1002/ange.19600722208.
25. H. Biltz and E. Topp, Ber., 46, 1387 (1913);
https://doi.org/10.1002/cber.19130460219.
26. S. Ulrich, U.S. Patent 2,463,986 (1979); Chem. Abstr., 121, 251380v
(1979).
27. Z. Hossaini, J. Chem. Res., 37, 712 (2013);
https://doi.org/10.3184/174751913X13817707622666.
28. D. Katiyar, V.K. Tiwari, R.P. Tripathi, A. Srivastava, V. Chaturvedi, R.
Srivastava and B.S. Srivastava, Bioorg. Med. Chem., 11, 4369 (2003);
https://doi.org/10.1016/S0968-0896(03)00480-2.
29. R. Kishore, M. Kamboj, M. Shukla and N. Srivastava, Asian J. Chem.,
31, 1091 (2019);
1. N. Trotsko, U. Kosikowska, A. Paneth, M. Wujec and A. Malm, Saudi
Pharm. J., 26, 568 (2018);
https://doi.org/10.1016/j.jsps.2018.01.016.
2. D. Trojanowski, P. Skut, J. Holówka and M.J. Szafran, Postepy Hig.
Med. Dosw., 68, 701 (2014);
https://doi.org/10.5604/17322693.1106890.
3. R.D. Cramer, R.D. Clark, D.E. Patterson andA.M. Ferguson, J. Med. Chem.,
39, 3060 (1996);
https://doi.org/10.1021/jm960291f.
4. J. Heeres, L.J.J. Backx, J.H. Mostmans and J. Van Cutsem, J. Med. Chem.,
22, 1003 (1979);
https://doi.org/10.1021/jm00194a023.
5. Ü. Uçucu, N.G. Karaburun and I. Isikdag, Il Farmaco, 56, 285 (2001);
https://doi.org/10.1016/S0014-827X(01)01076-X.
6. R. Xin, X.-Y.Yu, W.-P. Gao, N. Wang, J.-J.Yang, X.-S. Qu and X. Zhang,
Inorg. Chem. Commun., 35, 38 (2013);
https://doi.org/10.1016/j.inoche.2013.05.019.
7. R.N. Brogden, R.C. Heel, T.M. Speight and G.S. Avery, Drugs, 16, 387
(1978);
https://doi.org/10.2165/00003495-197816050-00002.
8. D.S.N. Cooper, Engl. J. Med., 311, 1353 (1984);
https://doi.org/10.1056/NEJM198411223112106.
9. E.F. Godefroi, P.A.J. Janssen, C.A.M. van der Eycken,A.H.M.T. van Heertum
and C.J.E. Niemegeers, J. Med. Chem., 8, 220 (1965);
https://doi.org/10.1021/jm00326a017.
10. M.C.P.A.Albuquerque, T.G. Silva, M.G.R. Pitta,A.C.A. Silva, P.G. Silva,
E. Malaguen, J.V. Santana,A.G. Wanderley, M.C.A. Lima, S.L. Galdino
and J. Barbe, Pharmazie, 60, 13 (2005).
11. M.A.M.S. El-Sharief, S.Y.Abbas, M.A. Zahran,Y.A. Mohamed,A. Ragab
and Y.A. Ammar, Z. Naturforsch. B, 71, 875 (2016);
https://doi.org/10.1515/znb-2016-0054.
12. J.H. Bateman, Hydantoin and Derivatives, In: Grayson, Martin, Eckroth,
Kirk-Othmer Encyclopedia of Chemical Technology; Wiley: NewYork,
NY, USA, vol. 12, pp. 692-711 (1980).
https://doi.org/10.14233/ajchem.2019.21830.
R. Kishore and M. Kamboj, World J. Pharm. Res., 7, 1098 (2018).
30. S. Zaidi, A.K. Chaturvedi, N. Singh and D. Chaturvedi, Curr. Chem.
Lett., 6, 143 (2017);
https://doi.org/10.5267/j.ccl.2017.7.001.
31. R. Kishore, M. Kamboj and M. Shukla, Orient. J. Chem., 34, 2878
(2018);
13. E.H.C. Menezes, A.J.S. Góes, M.B.S. Diu, S.L. Galdino, I.R. Pitta and
C. Luu-Duc, Pharmazie, 46, 457 (1992).
https://doi.org/10.13005/ojc/340627.