Synthesis, characterization and application of a novel nanorod-structured organic–inorganic hybrid material as an efficient catalyst for the preparation of aminouracil derivatives

Article abstract of DOI:10.1007/s11164-020-04104-z

Abstract: In this work, a novel nanorod-structured organic–inorganic hybrid material namely nanorod-[SiO₂-Pr-Im-SO₃H][TFA] (N-[SPIS][TFA]) has been synthesized, and characterized by FT-IR, energy-dispersive X-ray spectroscopy, field

Full text of DOI:10.1007/s11164-020-04104-z

Research on Chemical Intermediates
https://doi.org/10.1007/s11164-020-04104-z
Synthesis, characterization and application of a novel
nanorod‑structured organic–inorganic hybrid material
as an efcient catalyst for the preparation of aminouracil
derivatives
Abdolkarim Zare1 · Jaleh Atashrooz1 · Mohammad Mehdi Eskandari2
Received: 27 December 2019 / Accepted: 13 February 2020
© Springer Nature B.V. 2020
Abstract
In this work, a novel nanorod-structured organic–inorganic hybrid material namely
nanorod-[SiO2-Pr-Im-SO3H][TFA] (N-[SPIS][TFA]) has been synthesized, and
characterized by FT-IR, energy-dispersive X-ray spectroscopy, feld emission scan-
ning electron microscopy, thermal gravimetric analysis and X-ray difraction analy-
ses. Thereafter, it has been applied as an efcient, recyclable and dual-functional
catalyst to promote the following organic transformations: (1) the preparation of
(6-amino-1,3-dimethyluracil-5-yl)-(2-hydroxy-1,4-naphthoquinone-3-yl)methanes
by the one-pot multi-component reaction of 6-amino-1,3-dimethyluracil, 2-hydroxy-
1,4-naphthoquinone and arylaldehydes; and (2) the production of bis(6-amino-
1,3-dimethyluracil-5-yl)methanes via the pseudo-three-component reaction of
6-amino-1,3-dimethyluracil (2 eq.) and arylaldehydes (1 eq.).
Electronic supplementary material The online version of this article (https://doi.org/10.1007/s1116
4-020-04104-z) contains supplementary material, which is available to authorized users.
*
Abdolkarim Zare
abdolkarimzare@pnu.ac.ir; abdolkarimzare@yahoo.com
1
2
Department of Chemistry, Payame Noor University, PO Box 19395-3697, Tehran, Iran
Nanotechnology Research Center, Research Institute of Petroleum Industry (RIPI), PO
Box 1485733111, Tehran, Iran
Vol.:(0123456789)
1 3

A. Zare et al.
Graphic abstract
O
O
OH
Ar
NH2
HO
H3C
O
O
N
N-[SPIS][TFA]
EtOH, reflux
N
O
O
O
H3C
O
H3C
N
3-4 h; 79-86%
O
+
H3C
Ar
H
N
O
N
NH2
Ar
H2N
NH2
CH3
O
N
NH2
3CH
O
H3C
N
N
CH3
N-[SPIS][TFA]
EtOH, reflux
O
N
N
O
O
CH3
H3C
1 h; 94-97%
CF3COO
O
O
O
SO3H
N-[SPIS][TFA] =
N
=
N
Si
Keywords Nanorod-structured organic–inorganic hybrid material · Nanorod-[SiO2-
Pr-Im-SO3H][TFA] (N-[SPIS][TFA]) · Aminouracil derivatives
Introduction
Hybrid materials consist of two or more diferent components in which inorganic
and organic components are brought together by specifc interactions, and this sub-
ject causes the synergistic enhancement of their functional properties [1]. The inor-
ganic part can be oxides, metal clusters or particles, salts, metal ions and nonmetal-
lic elements, and the organic moiety can be various organic groups or molecules
[1]. These materials have extensive applications in diferent scientifc, pharmaceu-
tical and industrial felds [1–23]; some their uses include: (1) utilization as antitu-
mor drug [2], (2) application for in vivo dual-modal imaging-guided synergistic
1 3

Synthesis, characterization and application of a novel…
photothermal/radiation therapy [3], (3) application as potential carrier for combined
delivery of drugs [4], (4) cryogenic application [5], (5) usage as sensor and electrode
[6–9], (6) possessing resistive switching behavior for resistive random access mem-
ory devices [10] and (7) utilization for absorbance of heavy metals [11].
Recently, much attention has been attracted on the utilization of organic–inor-
ganic hybrid materials as catalysts in organic synthesis, because they have several
advantages, including easy separation from reaction mixture, having large sur-
face-to-volume ratio (nanomaterials), high activity, efciency, ability to design for
various catalytic uses by functionalization, recoverability and eco-friendly nature
[24–36].
Among the diferent inorganic compounds [24–27, 37–45], silica is usually pref-
erable to apply as inorganic moiety for synthesis of hybrid materials, because it has
some unique properties, consisting of low cost, proper thermal and chemical stabil-
ity, safety, green nature, non‐corrosiveness, simple functionalization and easy sepa-
ration from reaction medium [28–36].
A signifcant, simple, useful and practical way for synthesis of complex mole-
cules is one-pot multi-component reaction (MCR); the benefts of MCRs have been
well-mentioned in the literature [46–49].
Uracil derivatives are essential moieties of nucleic acids in living cells [50], and
play signifcant roles in our life cycle [51]. They also show various medicinal and
biological activities; e.g., antifungal [52], adenosine receptor antagonist [52], anti-
cancer [53], antiviral [54], bactericidal [55], thymidylate synthase inhibitor [56] and
acaricidal [57] properties. Among the uracil derivatives, 6-aminouracil is a common
building block of several bioactive natural products, and is a main scafold of vari-
ous biologically active heterocycles [58]. This moiety has been also utilized as a key
precursor for the preparation of diverse pharmaceutical and bioactive compounds
[59]. Moreover, the compounds bearing aminouracil and hydroxynaphthoquinone
have been used as proliferative [60], angiogenetic [60], anticoagulant [61] and anti-
bioflm [62] agents.
Two important classes of uracil derivatives are (6-amino-1,3-dimethyluracil-
5-yl)-(2-hydroxy-1,4-naphthoquinone-3-yl)methanes and bis(6-amino-1,3-dimethy-
luracil-5-yl)methanes. The frst kind has been prepared via the one-pot multi-com-
ponent reaction of 6-amino-1,3-dimethyluracil, 2-hydroxy-1,4-naphthoquinone and
arylaldehydes using a catalyst [63, 64], and the second type has been synthesized
by the pseudo-three-component reaction of 6-amino-1,3-dimethyluracil (2 eq.) and
arylaldehydes (1 eq.) in the presence of a catalyst [65–72].
In spite of high importance of (6-amino-1,3-dimethyluracil-5-yl)-(2-hydroxy-
1,4-naphthoquinone-3-yl)methanes
and
bis(6-amino-1,3-dimethyluracil-5-yl)
methanes, a few catalysts have been reported for their synthesis by the mentioned
methods, especially for (6-amino-1,3-dimethyluracil-5-yl)-(2-hydroxy-1,4-naphtho-
quinone-3-yl)methanes. Thus, introducing new catalysts for the production of the
aminouracil derivatives is highly desirable.
Considering the above issues, we have synthesized a novel nanorod-structured
organic–inorganic hybrid material namely nanorod-[SiO2-Pr-Im-SO3H][TFA]
(N-[SPIS][TFA]), and characterized it by FT-IR, energy-dispersive X-ray spec-
troscopy (EDS), feld emission scanning electron microscopy (FE-SEM), thermal
1 3

A. Zare et al.
gravimetric analysis (TGA) and X-ray difraction (XRD) analyses. Thereafter, we
have applied N-[SPIS][TFA] as a highly efcient, recyclable and dual-functional
catalyst to prepare two important classes of aminouracil derivatives, i.e., (6-amino-
1,3-dimethyluracil-5-yl)-(2-hydroxy-1,4-naphthoquinone-3-yl)methanes and bis(6-
amino-1,3-dimethyluracil-5-yl)methanes
Experimental
Materials and instruments
The used reactants and solvents were purchased from Merck or Fluka Chemical
Companies. The nanorod-silica for the production of N-[SPIS][TFA] was prepared
according to the reported method [73, 74]. Progress of the reactions was monitored
by thin-layer chromatography (TLC) using silica gel SIL G/UV 254 plates. Melting
points were measured using a Buchi B-545 apparatus in open capillary tubes. FT-IR
spectra were recorded by Shimadzu IR-60 instrument. 1H and 13C NMR spectra were
run on a Bruker Avance DPX FT-NMR spectrometer. Energy-dispersive X-ray spec-
troscopy (EDS) was carried out by SAMx-EDS (France system). The morphologies
and particles sizes of N-[SPIS][TFA] were characterized by feld emission scanning
electron microscopy, model MIRA3TESCAN-XMU. Thermal gravimetric analysis
(TGA) was performed by Bahr STA 504 instrument (Germany), at 25–600 °C, with
temperature increase rate of 10 °C min−1 in argon atmosphere. The X-ray difraction
(XRD) analysis was performed using an apparatus model X’Pert PRO MPD, PANa-
lytical, the Netherlands (Cu Kα radiation, λ=1.5408).
Production of N‑[SPIS][TFA] (Scheme 1)
A mixture of imidazole (0.34 g, 5 mmol), (3-chloropropyl)trimethoxysilane (0.99 g,
5 mmol) and toluene (15 mL) was stirred under refux conditions for 12 h; after-
ward, the solvent was evaporated under vacuum at 100 °C to give I. Intermediate
I and nanorod-silica (0.30 g, 5 mmol) were added to EtOAc (15 mL), and stirred
d)
noro
(na
Toluene
S
ilica
Si(OEt3)
N
N
NH
N
+
Cl
Si(OEt)3
Reflux,12 h
EtOAc,Reflux,18 h
_
_
(I)
HCl
EtOH
Cl
O
O
O
O
ClSO3H
CH2Cl2,0°C,3 h
CF3COOH
r.t. 60°C
12 h
SO3H
N
N
Si
N
N
O
Si
O
(II)
(III)
_
HCl
CF3COO
O
O
O
SO3H
N
N
Si
(N-[SPIS][TFA])
Scheme 1 Production of N-[SPIS][TFA]
1 3

Synthesis, characterization and application of a novel…
under refux conditions for 18 h; the resulting mixture was centrifuged, decanted,
washed by EtOAc (2×5 mL), and dried under vacuum at 80 °C to give intermedi-
ate II. Then, II was added gradually to a stirring solution of chlorosulfonic acid
(0.58 g, 5 mmol) in dry CH2Cl2 (10 mL) at 10 °C, and stirred for 3 h at room tem-
perature. The obtained mixture was centrifuged, decanted, triturated by dry CH2Cl2
(2×10 mL), and dried to aford intermediate III. Subsequently, trifuoroacetic acid
(5 mmol) was added to a stirring solution of III in dry CH2Cl2 (10 mL) at room tem-
perature, and stirred for 10 h at the same temperature, and 2 h at 60 °C; the solvent
was evaporated to give N-[SPIS][TFA].
General procedure for the synthesis of (6‑amino‑1,3‑dimethyluracil‑5‑yl)‑
(2‑hydroxy‑1,4‑naphthoquinone‑3‑yl)methanes 1a–d
6-Amino-1,3-dimethyluracil (0.155 g, 1 mmol), aldehyde (1 mmol), 2-hydroxy-
1,4-naphthoquinone (0.174 g, 1 mmol) and N-[SPIS][TFA] (0.040 g) were added to
absolute EtOH (8 mL), and the resulting mixture was stirred and refuxed. The reac-
tion progress was monitored by TLC (EtOAc/n-hexane: 1/1); after consuming the
reactants, the solvent was evaporated, EtOAc (20 mL) was added, stirred for 2 min
under refux conditions, followed by centrifugation and decanting to separate the
insoluble nanocatalyst. The EtOAc resulted from the decanting was evaporated, and
the solid residue was recrystallized from EtOH/H2O (4/1) to aford the pure product.
General procedure for the preparation of bis(6‑amino‑1,3‑dimethyluracil‑5‑yl)
methanes 2a–f
A mixture of 6-amino-1,3-dimethyluracil (0310 g, 2 mmol), aldehyde (1 mmol) and
N-[SPIS][TFA] (0.020 g) in absolute EtOH (8 mL) was stirred under refux con-
ditions. After consuming the starting materials (as observed by TLC eluted with
EtOAc/n-hexane: 1/1), the solvent was evaporated, EtOAc (20 mL) was added,
and stirred for 2 min under refux conditions; the obtained mixture was centrifuged
and decanted to separate the insoluble N-[SPIS][TFA] {the catalyst was washed
by EtOAc (2×3 mL), dried and used for next run}. The resulted EtOAc from the
decanting was evaporated, and the solid residue was purifed by recrystallization
from EtOH/H2O (4/1) to give the product.
Note: Selected spectral data and original spectrums of the synthesized aminoura-
cil derivatives have been given in supplementary material.
Results and discussion
Characterization of the nanocatalyst
Our novel nanorod-structured organic–inorganic hybrid material {nanorod-[SiO2-
Pr-Im-SO3H][TFA] (N-[SPIS][TFA])} was characterized by FT-IR, EDS, FE-SEM,
TGA and XRD analyses.
1 3

A. Zare et al.
Table 1 FT-IR data of N-[SPIS]
Peak (cm−1
)
Bond or functional group
[TFA]
466
Rocking of Si–O
802
902
Bending of OH (silanol)
Stretching of N–S
1120
1201
1455
1682
3149
2956
2400–3700
Symmetric stretching of –SO2–
Asymmetric stretching of –SO2–
Bending of aliphatic C–H
Stretching of C=N
Stretching of aromatic C–H
Symmetric stretching of aliphatic C–H
Stretching of OH group of the SO3H
and OH groups on silica surface
Fig. 1 EDX spectrum of N-[SPIS][TFA]
The FT-IR spectrum (supplementary material, Fig. S1) confrmed the presence
of the expected bonds and functional groups in the structure of N-[SPIS][TFA].
The peaks related to the bonds and functional groups of the catalyst are shown in
Table 1; the results are in accordance with the literature [31, 34].
In the structure of N-[SPIS][TFA], there are silicon, oxygen, carbon, nitrogen,
sulfur, chlorine and fuorine elements; the EDS spectrum confrmed this topic
(Fig. 1).
The FE-SEM micrographs of the nanorod silica and N-[SPIS][TFA] are shown in
Figs. 2 and 3. In both materials, the particles were observed as nanorod with difer-
ent sizes; however, the nanorods lengths have shortened in N-[SPIS][TFA].
The TG (thermal gravimetric) and DTG (diferential thermal gravimet-
ric) analyses of the organic–inorganic hybrid nanomaterial were also studied
(Fig. 4). Weight losses of N-[SPIS][TFA] were occurred during three steps: (1)
1 3

Synthesis, characterization and application of a novel…
Fig. 2 FE-SEM micrographs of the nanorod-silica
low weight loss up to 150 °C can be related to evaporation of the adsorbed sol-
vents (or water) on the silica surface, (2) weight loss at about 150–425 °C can
be due to decomposition of the organic moieties anchored to the silica surface
and (3) weight loss at about 425–600 °C can be attributed to condensation of the
silanol groups. The literature data confrmed the above interpretations [34, 75,
76].
XRD analysis of N-[SPIS][TFA] was accomplished in a domain of 2θ ≈ 7–80
degrees (Fig. 5). In the XRD spectrum, two broad peaks were observed at
2θ ≈ 9.6–13.0° and 2θ ≈ 15.0–30.0º. Furthermore, some difraction lines were
seen at 2θ ≈ 8.9°, 11.2°, 12.4°, 13.7°, 20.1°, 21.2°, 22.2°, 22.5°, 24.0°, 26.0°,
28.2°, 41.8°, 45.4°, 50.5°, 53.6°, 54.3°, 58.1°, 67.2°, 69.0°, 71.6°, 73.7° and
77.1°. The results showed that N-[SPIS][TFA] is in amorphous and also crystal-
line forms; the literature data confrmed the explanations [34, 77].
1 3

A. Zare et al.
Fig. 3 FE-SEM micrographs of N-[SPIS][TFA]
The synthesis of aminouracil derivatives using N‑[SPIS][TFA]
To investigate catalytic activity of N-[SPIS][TFA] for the synthesis of the aminou-
racil derivatives, at frst, the following model reactions were chosen: (1) the one-
pot multi-component reaction of 6-amino-1,3-dimethyluracil (1 mmol), 2-hydroxy-
1,4-naphthoquinone (1 mmol) and 4-chlorobenzaldehyde (1 mmol) for the
preparation of (6-amino-1,3-dimethyluracil-5-yl)-(2-hydroxy-1,4-naphthoquinone-
3-yl)methanes (Scheme 2), and (2) the one-pot pseudo-three-component reaction of
6-amino-1,3-dimethyluracil (2 mmol) and 4-chlorobenzaldehyde (1 mmol) for the
production of bis(6-amino-1,3-dimethyluracil-5-yl)methanes (Scheme 2). Infuence
of the catalyst amount and solvent on the model reactions were studied (8 mL of
the solvents were used); the obtained results are briefed in Table 2. As the data in
1 3

Synthesis, characterization and application of a novel…
Fig. 4 TG and DTG diagrams of N-[SPIS][TFA]
Fig. 5 XRD pattern of N-[SPIS][TFA]
Table 2 indicate, for the synthesis of (6-amino-1,3-dimethyluracil-5-yl)-(2-hydroxy-
1,4-naphthoquinone-3-yl)methanes, utilization of 0.040 g of N-[SPIS][TFA] in
refuxed EtOH aforded higher yield and shorter reaction time (Table 2, entry 2), and
for the preparation of bis(6-amino-1,3-dimethyluracil-5-yl)methanes, application of
1 3

A. Zare et al.
O
O
OH
Ar
NH2
HO
H3C
O
O
N
N-[SPIS][TFA]
EtOH, reflux
N
O
O
O
H3C
1a-d
O
H3C
O
O
N
+
H3C
Ar
H
N
N
NH2
Ar
H2N
NH2
CH3
O
N
NH2
CH3
O
H3C
O
N
N
CH3
N-[SPIS][TFA]
EtOH, reflux
N
N
O
O
CH3
H3C
2a-f
Scheme 2 Production of (6-amino-1,3-dimethyluracil-5-yl)-(2-hydroxy-1,4-naphthoquinone-3-yl)meth-
anes (1a–d) and bis(6-amino-1,3-dimethyluracil-5-yl)methanes (2a–f)
Table 2 Efect of the catalyst amount and solvent on the model reactions
Entry
Product
The catalyst
amount (g)
Solvent
Temp. (°C)
Time (h)
Yield (%)
1
2
3
4
5
6
7
8
1a
1a
1a
1a
1a
1a
1a
2b
2b
2b
2b
2b
2b
2b
0.032
0.040
0.048
0.040
0.040
0.040
0.040
0.012
0.020
0.032
0.020
0.020
0.020
0.020
EtOH
EtOH
EtOH
THF
MeCN
EtOAc
H2O
EtOH
EtOH
EtOH
THF
MeCN
EtOAc
H2O
Refux
Refux
Refux
Refux
Refux
Refux
80
Refux
Refux
Refux
Refux
Refux
Refux
80
4
4
4
7
7
7
7
2
1
1
3
3
3
3
69
86
81
57
51
79
43
84
95
95
37
72
61
76
9
10
11
12
13
14
0.020 g of the hybrid nanomaterial in refuxed EtOH gave the better results (Table 2,
entry 9).
After fnding the best reactions conditions, diferent aminouracil derivatives
were prepared by varying arylaldehydes in the reactions; the products structures,
melting points, the reaction times and yields are illustrated in Table 3. As it can
be seen in the table, arylaldehydes bearing halogen, electron-withdrawing and
1 3

Synthesis, characterization and application of a novel…
Table 3 Synthesis of (6-amino-1,3-dimethyluracil-5-yl)-(2-hydroxy-1,4-naphthoquinone-3-yl)methanes
(1a–d) and bis(6-amino-1,3-dimethyluracil-5-yl)methanes (2a–f) using N-[SPIS][TFA]
Product No.
Product
Time (h)
Yielda (%)
M.p. (°C) [Ref.]
Cl
1a
4
86
249–251
(254–255) [63]
NH2
HO
HO
HO
H3C
N
O
O
N
O
O
O
O
H3C
CH3
1b
1c
3
4
83
79
220–222
(218–220) [64]
NH2
H3C
O
O
N
N
O
H3C
OCH3
244–246
(245–247) [64]
NH2
H3C
O
O
N
N
O
H3C
1d
2a
OCH3
HO
4
1
81
96
239–241 (new)
NH2
H3C
O
O
N
N
O
O
H3C
297–299
(294–296) [67]
H2N
NH2
CH3
O
H3C
O
N
N
N
N
O
O
CH3
H3C
1 3

A. Zare et al.
Table 3 (continued)
Product No.
Product
Time (h)
1
Yielda (%)
95
M.p. (°C) [Ref.]
Cl
2b
268–270
(267–269) [67]
H2N
NH2
CH3
O
H3C
O
N
N
N
N
O
O
CH3
H3C
2c
1
1
94
96
284–286
NO2
(282–283) [65]
H2N
NH2
CH3
O
H3C
O
N
N
N
N
O
O
CH3
H3C
CH3
2d
276–278
(274–276) [65]
H2N
NH2
CH3
O
H3C
O
N
N
N
N
O
O
O
O
O
O
CH3
H3C
OCH3
2e
2f
1
1
97
94
274–276 (new)
H2N
NH2
CH3
O
H3C
O
N
N
N
N
CH3
H3C
H3CO
272–274
(270–271) [67]
OCH3
H2N
NH2
CH3
O
H3C
O
N
N
N
N
CH3
H3C
aIsolated yield
1 3

Synthesis, characterization and application of a novel…
Table 4 Results on reusability
Recycle
Time (min)
Yield (%)
of N-[SPIS][TFA] for the
production of compound 2b
Fresh catalyst
1
2
1
1.5
2
95
90
87
electron-releasing substituents aforded the corresponding products in high yields
and relatively short reaction times. According to the results, we could claim that
N-[SPIS][TFA] was a highly efcient catalyst to promote the synthesis of the
aminouracil derivatives.
Recyclability of N-[SPIS][TFA] was tested for the synthesis of bis(6-amino-
1,3-dimethyluracil-5-yl)methane 2b. Some reactions were performed for the
preparation of this compound, the reactions mixtures were combined, and the
catalyst was recycled according to the procedure mentioned in the experimental
section; the results are given in Table 4. The catalyst was reusable for two times
without signifcant decrement in the yields; nevertheless, the reaction times were
enhanced during reusing.
O
O
O
H
F3C
O
O
O
OH
O
O
N-[SPIS][TFA]
N-[SPIS][TFA]
Ar
Ar
H
O
Step 1
Ar
H
O
S
O
H
O
O
H
O
S
H
O
O
O
O
O
O
CF3COO
O
Ar
Ar
N-[SPIS][TFA]
H
_
H2O
O
Step 2
O
CH3
N
H
F3C
O
HN
O
O
O
Ar
O
H2N
OH
N
CH3
CH3
O
O
N
Ar
Tautomerization
O
Step 3
H
N
O
O
O
O
CH3
S
O
O
Scheme 3 Mechanism for the synthesis of (6-amino-1,3-dimethyluracil-5-yl)-(2-hydroxy-1,4-naphtho-
quinone-3-yl)methanes
1 3

A. Zare et al.
Scheme 4 Proposed mechanism for the production of bis(6-amino-1,3-dimethyluracil-5-yl)methanes
Based on dual-functionality of the catalyst {possessing acidic (SO3H) and
weak basic (trifuoroacetate) sites} and the literature [63, 65, 67], logical mecha-
nisms were proposed for the synthesis of the aminouracil derivatives (Schemes 3
and 4). The catalyst tasks are obviously shown in the mechanisms, the tasks
include: (1) activating the electrophiles by the acidic moiety (SO3H) to accept
nucleophilic attacks (Scheme 3: steps 1 and 3; Scheme 4: steps 1ʹ and 3ʹ), (2)
assistance to remove H2O molecule (Scheme 3: step 2; Scheme 4: step 2ʹ), (3)
activation of nucleophiles by the basic moiety (trifuoroacetate) (Scheme 3: steps
1 and 3; Scheme 4: steps 1ʹ and 3ʹ), and (4) accelerating the tautomerization steps.
Dual-functionality of catalysts bearing SO3H as acidic moiety and anions like tri-
fuoroacetate, mesylate and hydrogen sulfate as weak basic moiety has been dis-
cussed in the literature [78, 79].
1 3

Synthesis, characterization and application of a novel…
Conclusions
Briefy, we have prepared and characterized a novel nanorod-structured
organic–inorganic hybrid material; it can use as catalyst to promote organic trans-
formations which need acidic catalyst. Herein, we have successfully applied the
nanorod material as catalyst for the synthesis of aminouracil derivatives; the
advantages of the presented catalytic processes consist of high performance, rela-
tively short reactions times, high yields, no need to column chromatography for
purifcation of the products, relatively mild conditions, utilization of few amounts
of the catalyst and reusability of the catalyst.
Acknowledgements We thank Research Council of Payame Noor University for the support of this work.
References
1. V.P. Ananikov, Nanomaterials 9, 1197 (2019)
2. L. Fu, H. Gao, M. Yan, S. Li, X. Li, Z. Dai, S. Liu, Small 11, 2938 (2015)
3. J. Wang, X. Tan, X. Pang, L. Liu, F. Tan, N. Li, A.C.S. Appl, Mater. Interfaces 8, 24331 (2016)
4. B.B. Caravieri, N.A.M. de Jesus, L.K. de Oliveira, M.D. Araujo, G.P. Andrade, E.F. Molina, A.C.S.
Appl, Bio Mater. 2, 1875 (2019)
5. Y. He, Q. Chen, S. Yang, C. Lu, M. Feng, Y. Jiang, G. Cao, J. Zhang, C. Liu, Compos. Part A Appl.
Sci. Manuf. 108, 12 (2018)
6. N. Lashgari, A. Badiei, G. Mohammadi Ziarani, Nanochem. Res. 1, 127 (2016)
7. J. Chen, Q. Yu, X. Cui, M. Dong, J. Zhang, C. Wang, J. Fan, Y. Zhu, Z. Guo, J. Mater. Chem. C 7,
11710 (2019)
8. C. Lou, T. Jing, J. Tian, Y. Zheng, J. Zhang, M. Dong, C. Wang, C. Hou, J. Fan, Z. Guo, J. Mater.
Res. 34, 2964 (2019)
9. Q. Wang, Y. Zhao, Q. Yang, D. Du, H. Yang, Y. Lin, Biosens. Bioelectron. 141, 111431 (2019)
10. E.J. Yoo, M. Lyu, J.-H. Yun, C.J. Kang, Y.J. Choi, L. Wang, Adv. Mater. 27, 6170 (2015)
11. A. Kayan, Adv. Compos. Hybrid Mater. 2, 34 (2019)
12. Y. He, Q. Chen, H. Liu, L. Zhang, D. Wu, C. Lu, W.O. Yang, D. Jiang, M. Wu, J. Zhang, Y. Li, J.
Fan, C. Liu, Z. Guo, Macromol. Mater. Eng. 304, 1900166 (2019)
13. Y. He, D. Wu, M. Zhou, H. Liu, L. Zhang, Q. Chen, B. Yao, D. Yao, D. Jiang, C. Liu, Z. Guo, Appl.
Surf. Sci. 506, 144946 (2020)
14. Y. Zheng, X. Wang, G. Wu, Polym. Adv. Technol. 31, 527 (2020)
15. Y. Zheng, L. Chen, X. Wang, G. Wu, Polymers 12, 45 (2020)
16. J. Hu, J. Lin, Y. Zhang, Z. Lin, Z. Qiao, Z. Liu, W. Yang, X. Liu, M. Dong, Z. Guo, J. Mater. Chem.
A 7, 26039 (2019)
17. J. Lin, X.Y. Chen, C.Y. Chen, J.T. Hu, C.L. Zhou, X.F. Cai, W. Wang, C. Zheng, P. Zhang, J. Cheng,
Z.H. Guo, H. Liu, A.C.S. Appl, Mater. Interfaces 10, 6124 (2018)
18. Y. Zhang, Y. An, L. Wu, H. Chen, Z. Li, H. Dou, V. Murugadoss, J. Fan, X. Zhang, X. Mai, Z. Guo,
J. Mater. Chem. A. 7, 19668 (2019)
19. H. Gu, X. Xu, J. Cai, S. Wei, H. Wei, H. Liu, D.P. Young, Q. Shao, S. Wu, T. Dingi, Z. Guo, Chem.
Commun. 55, 10068 (2019)
20. G. Zhu, X. Cui, Y. Zhang, Sh Chen, M. Dong, H. Liu, Q. Shao, T. Dinge, S. Wuf, Z. Guo, Polymer
172, 415 (2019)
21. Q. Chen, Q. Yin, A. Dong, Y. Gao, Y. Qian, D. Wang, M. Dong, Q. Shao, H. Liu, B.-H. Han, T.
Ding, Z. Guo, N. Wang, Polymer 169, 255 (2019)
22. H. Wei, H. Wang, Y. Xia, D. Cui, Y. Shi, M. Dong, C. Liu, T. Ding, J. Zhang, Y. Ma, N. Wang, Z.
Wang, Y. Sun, R. Wei, Z. Guo, J. Mater. Chem. C 6, 12446 (2018)
23. J.-N. Chen, S.-P. Zhao, W.-H. Hu, J. Zhang, M.-Y. Dong, H. Liu, Z. Huang, Y.-Q. Liu, Z. Wang, Z.
Guo, Sci. Adv. Mater. 11, 1340 (2019)
24. A.P. Shah, A.S. Sharma, S. Jain, N.G. Shimpi, New J. Chem. 42, 8724 (2018)
1 3

A. Zare et al.
25. F. Kalantari, A. Ramazani, M.R. Poor Heravi, Curr. Org. Chem. 23, 136 (2019)
26. N. Safajoo, B.B.F. Mirjalili, A. Bamoniri, RSC Adv. 9, 1278 (2019)
27. A. Maleki, F. Hassanzadeh-Afruzi, Z. Varzi, M.S. Esmaeili, Mater. Sci. Eng., C 109, 110502 (2020)
28. R. Kordnezhadian, M. Shekouhy, A. Khalaf-Nezhad, New J. Chem. 43, 18559 (2019)
29. M. Gholamhosseini-Nazari, S. Esmati, K.D. Safa, A. Khataee, R. Teimuri-Mofrad, Res. Chem.
Intermed. 45, 1841 (2019)
30. H. Sharghi, M. Aberi, P. Shiri, Appl. Organomet. Chem. 33, e4974 (2019)
31. A. Zare, M. Merajoddin, A.R. Moosavi-Zare, M. Zarei, M.H. Beyzavi, M.A. Zolfgol, Res. Chem.
Intermed. 42, 2365 (2016)
32. A. Zare, A. Kohzadian, Z. Abshirini, S.S. Sajadikhah, J. Phipps, M. Benamarad, M.H. Beyzavi,
New J. Chem. 43, 2247 (2019)
33. M. Kazemi, M. Ghobadi, A. Mirzaie, Nanotechnol. Rev. 7, 43 (2018)
34. A. Zare, M. Sadeghi-Takallo, M. Karami, A. Kohzadian, Res. Chem. Intermed. 45, 2999 (2019)
35. A. Kohzadian, A. Zare, Silicon (2019). https://doi.org/10.1007/s12633-019-00235-0.
36. G. Xu, C. Jia, Z. Shi, R. Liang, C. Wu, H. Liu, C. Yan, J. Fan, H. Hou, T. Ding, Z. Guo, Sci. Adv.
Mater. 12, 304 (2020)
37. Y. Guo, K. Ruan, X. Yang, T. Ma, J. Kong, N. Wu, J. Zhang, J. Gu, Z. Guo, J. Mater. Chem. C 7,
7035 (2019)
38. X.-L. Luo, F. Pei, W. Wang, H.-M. Qian, K.-K. Miao, Z. Pan, Y.-S. Chen, G.-D. Feng, Micropor.
Mesopor. Mater. 262, 148 (2018)
39. Y.G. Tong, Z.H. Cai, S.X. Bai, Y.L. Hu, M.Y. Hua, W. Xie, Y.C. Ye, Y. Li, Ceram. Int. 44, 16577
(2018)
40. Y. Tong, P. Qi, X. Liang, Y. Chen, Y. Hu, Z. Hu, Materials 11, 1250 (2018)
41. L. Sun, Q. Shao, Y. Zhang, H. Jiang, S. Ge, S. Lou, J. Lin, J. Zhang, S. Wu, M. Dong, Z. Guo, J.
Colloid Interface Sci. 565, 142 (2020)
42. J. Zhang, W. Zhang, L. Wei, L. Pu, J. Liu, H. Liu, Y. Li, J. Fan, T. Ding, Z. Guo, Macromol. Mater.
Eng. 304, 1900374 (2019)
43. D. Jiang, Y. Wang, B. Li, C. Sun, Z. Wu, H. Yan, L. Xing, S. Qi, Y. Li, H. Liu, W. Xie, X. Wang, T.
Ding, Z. Guo, Macromol. Mater. Eng. 304, 1900074 (2019)
44. L. Ma, Y. Zhu, P. Feng, G. Song, Y. Huang, H. Liu, J. Zhang, J. Fan, H. Hou, Z. Guo, Compos. Part
B Eng. 176, 107078 (2019)
45. Gu Hongbo, Xu Xiaojiang, Mengyao Dong, Peitao Xie, Qian Shao, Runhua Fan, Chuntai Liu, Wu
Shide, Renbo Wei, Zhanhu Guo, Carbon 147, 550 (2019)
46. J. Krishnan, A. Jose, B.S. Sasidhar, E. Suresh, R.S. Menon, V. Nair, Org. Chem. Front. 5, 1202
(2018)
47. R. Kordnezhadian, M. Shekouhy, S. Karimian, A. Khalaf-Nezhad, J. Catal. 380, 91 (2019)
48. A. Kohzadian, A. Zare, Res. Chem. Intermed. 45, 5473 (2019)
49. V. Palermo, A.A. Sosa, T.S. Rivera, L.R. Pizzio, G.P. Romanelli, Org. Prep. Proced. Int. 51, 443
(2019)
50. R.H. Garrett, D.M. Grisham, Principles of Biochemistry with a Human Focus (Brooks/Cole Thom-
son Learning, United States, 1997)
51. J.D. Noia, M.S. Neuberger, Nature 419, 43 (2002)
52. A. Drabczynska, C.E. Muller, A. Schiedel, B. Schumacher, J.K. Wojciechowska, A. Fruzinski, W.
Zobnina, O. Yuzlenko, K. Kiec-Kononowicz, Bioorg. Med. Chem. 15, 6956 (2007)
53. J.A. Valderrama, P. Colonelli, D. Vásquez, M.F. González, J.A. Rodríguez, C. Theoduloz, Bioorg.
Med. Chem. 16, 10172 (2008)
54. V. Nair, G. Chi, Q. Shu, J. Julander, D.F. Smee, Bioorg. Med. Chem. Lett. 19, 1425 (2009)
55. A. Pałasz, D. Cież, Eur. J. Med. Chem. 97, 582 (2015)
56. G. Lu, X. Li, K. Mohamed O, D. Wang, F. Meng, Eur. J. Med. Chem. 171, 282 (2019)
57. K. Yagi, K. Akimoto, N. Mimori, T. Miyake, M. Kudo, K. Arai, S. Ishii, Pest Manag. Sci. 56, 65
(2000)
58. E. Lunt, C.G. Newton, in Comprehensive Heterocyclic Chemistry, vol. 3, ed. by A.R. Katritzky,
C.W. Rees (Pergamon, Oxford, 1984)
59. G. Mohammadi Ziarani, N. Hosseini Nasab, N. Lashgari, RSC Adv. 6, 38827 (2016)
60. R.A. Al-Qawasmeh, Y. Lee, M.Y. Cao, X. Gu, A. Vassilakos, J.A. Wright, A. Young, Bioorg. Med.
Chem. Lett. 14, 347 (2004)
61. J.-C. Jung, Y.J. Jung, O.S. Park, Molecules 14, 4790 (2009)
1 3

Synthesis, characterization and application of a novel…
62. N.R. Emmadi, K. Atmakur, C. Bingi, N.R. Godumagadda, C.G. Kumar, J.B. Nanubolu, Bioorg.
Med. Chem. Lett. 24, 485 (2014)
63. R. Bharti, T. Parvin, RSC Adv. 5, 66833 (2015)
64. P. Kumari, R. Bharti, T. Parvin, Mol. Divers. 23, 205 (2019)
65. G. Brahmachari, B. Banerjee, RSC Adv. 5, 39263 (2015)
66. J. Azizian, M.R. Mohammadizadeh, F. Teimouri, A.A. Mohammadi, A.R. Karimi, Synth. Commun.
36, 3631 (2006)
67. A. Zare, A. Ghobadpoor, T. Safdari, Res. Chem. Intermed. 46, 1319 (2020)
68. A.R. Karimi, Z. Dalirnasab, M. Karimi, F. Bagherian, Synthesis 45, 3300 (2013)
69. B. Banerjee, G. Brahmachari, Curr. Organocatal. 3, 125 (2016)
70. R. Bansal, R.S. Kumar, G. Kumar, S. Thota, S. Thamotharan, V. Parthasarathi, A. Linden, J. Hetero-
cyclic Chem. 45, 1789 (2008)
71. D. Shi, J. Shi, S. Rong, Chin. J. Chem. 28, 791 (2010)
72. L. Wu, X. Jing, M. Lin, C. Yan, J. Yang, H. Zhu, Synth. Commun. 42, 849 (2012)
73. F. Kamali, M.M. Eskandari, A. Rashidi, M. Baghalha, M. Hassanisadi, T. Hamzehlouyan, J. Haz-
ard. Mater. 364, 218 (2019)
74. A. Sayari, B.-H. Han, Y. Yang, J. Am. Chem. Soc. 126, 14348 (2004)
75. A. Biabani-Ravandi, M. Rezaei, Chem. Eng. J. 184, 141 (2012)
76. M. Nikoorazm, A. Ghorbani-Choghamarani, M. Khanmoradi, Appl. Organomet. Chem. 30, 705
(2016)
77. R.E. Morsi, R.S. Mohamed, R. Soc, Open Sci. 5, 172021 (2018)
78. N. Irannejad-Gheshlaghchaei, A. Zare, S.S. Sajadikhah, A. Banaei, Res. Chem. Intermed. 44, 6253
(2018)
79. Z. Kordrostami, A. Zare, M. Karami, Z. Naturforsch. 74b, 641 (2019)
Publisher’s Note Springer Nature remains neutral with regard to jurisdictional claims in published
maps and institutional afliations.
1 3