Nano-[Fe3O4@SiO2-R-NHMe2][H2PO4] as a Highly Effectual and Magnetically Recyclable Catalyst for the Preparation of bis(6-Amino-1,3-dimethyluracil-5-yl)methanes under Solvent-Free Conditions

Full text of DOI:10.1080/00304948.2021.1914487

Organic Preparations and Procedures International
The New Journal for Organic Synthesis
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Nano-[Fe3O4@SiO2-R-NHMe2][H2PO4] as a
Highly Effectual and Magnetically Recyclable
Catalyst for the Preparation of bis(6-Amino-1,3-
dimethyluracil-5-yl)methanes under Solvent-Free
Conditions
Nesa Lotfifar, Abdolkarim Zare & Ghasem Rezanejade Bardajee
To cite this article: Nesa Lotfifar, Abdolkarim Zare & Ghasem Rezanejade Bardajee (2021)
Nano-[Fe3O4@SiO2-R-NHMe2][H2PO4] as a Highly Effectual and Magnetically Recyclable
Catalyst for the Preparation of bis(6-Amino-1,3-dimethyluracil-5-yl)methanes under Solvent-
Free Conditions, Organic Preparations and Procedures International, 53:4, 379-386, DOI:
10.1080/00304948.2021.1914487
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ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL
2021, VOL. 53, NO. 4, 379–386
https://doi.org/10.1080/00304948.2021.1914487
EXPERIMENTAL PAPER
Nano-[Fe3O4@SiO2-R-NHMe2][H2PO4] as a Highly Effectual
and Magnetically Recyclable Catalyst for the Preparation
of bis(6-Amino-1,3-dimethyluracil-5-yl)methanes under
Solvent-Free Conditions
Nesa Lotfifar, Abdolkarim Zare , and Ghasem Rezanejade Bardajee
Department of Chemistry, Payame Noor University, Tehran, Iran
ARTICLE HISTORY Received 12 May 2020; Accepted 29 October 2020
Magnetic nanoparticles (MNPs) have many unique properties such as non-toxicity, suit-
able thermal and chemical stability, designability for different applications, environmen-
tal friendliness, high surface-to-volume ratios, and simple isolation by an exterior
magnet. Thus, they have been utilized in different scientific areas (medical, industrial
and chemical).1–19 Solvent-free reactions have many advantages, including facile isola-
tion of products, efficacy, enhanced reaction rates, cost effectiveness, less waste produc-
tion, less energy consumption and saving time.20–23
Compounds containing nitrogen heterocycles are of great importance;24–37 uracil and
its derivatives are a class of these compounds and are essential in human life.27–37
These compounds have numerous biological and pharmaceutical activities, including
anticancer,28 bactericidal,29 herbicidal,29 insecticidal,29 adenosine receptor antagonist,30
acaricidal,31 antiviral,32 and antifungal33 properties. Furthermore, 6-amino-1,3-dimethy-
luracil compounds constitute the fundamental cores of diverse medicines and bioactive
materials such as theophylline, theobromine, penciclovir and caffeine.34–37bis(6-Amino-
1,3-dimethyluracil-5-yl)methanes are uracil derivatives that have been synthesized
through the pseudo three-component reaction of 6-amino-1,3-dimethyluracil (2 eq.) and
aldehydes (1 eq.) in the presence of a catalyst.38–44 Considering the broad range of
pharmacological and biological activities of uracil derivatives, it is highly desirable to
introduce new catalysts to produce these compounds.
Bearing the above themes in mind, we have introduced the highly effective and mag-
netically
recyclable
catalyst
nano-[Fe3O4@SiO2-R-NHMe2][H2PO4]
(nano-
[FSRN][H2PO4]) for the production of bis(6-amino-1,3-dimethyluracil-5-yl)methanes
from 6-amino-1,3-dimethyluracil (2 eq.) and aldehydes (1 eq.) under solvent-free condi-
tions. Nano-[FSRN][H2PO4] was synthesized according to our reported method
(Scheme 1).14
In order to determine the most appropriate amount of the nano-[FSRN][H2PO4]
catalyst and the optimal reaction temperature for the preparation of bis(6-amino-1,3-
dimethyluracil-5-yl)methanes, the condensation of 6-amino-1,3-dimethyluracil (2 mmol)
and 4-chlorobenzaldehyde (1 mmol) was selected as a model reaction (Scheme 2); the
CONTACT Abdolkarim Zare
abdolkarimzare@yahoo.com
Department of Chemistry, Payame Noor University, P.O.
Box 19395-3697, Tehran, Iran
ß 2021 Taylor & Francis Group, LLC

380
N. LOTFIFAR ET AL.
Scheme 1. The preparation of nano-[FSRN][H2PO4].
Scheme 2. The model reaction for the synthesis of bis(6-amino-1,3-dimethyluracil-5-yl)methanes.
results are summarized in Table 1. Based on these results, the optimal amount of the
nanomagnetic catalyst and reaction temperature were 0.072 g and 120 ꢀC, respectively
(Table 1, entry 2). No improvement was observed upon increasing the amount of cata-
lyst or the temperature (Table 1, entries 3 and 4).
The scope of the present protocol for the production of bis(6-amino-1,3-dimethylura-
cil-5-yl)methanes was studied by performing the reaction of 6-amino-1,3-dimethyluracil
(2 mmol) and various substituted benzaldehydes (1 mmol) using 0.072 g of nano-
[FSRN][H2PO4] at 120 ꢀC in the absence of solvent; the results are presented in Table 2.
We were pleased to oberve that benzaldehydes with electron-releasing, electron-with-
drawing or halogen substituents at the ortho, meta or para positions afforded the
respective uracil-containing compounds in high yields in less than 30 minutes. Thus,
nano-[FSRN][H2PO4] is a general and highly effective catalyst for the synthesis of bis(6-
amino-1,3-dimethyluracil-5-yl)methanes.
The results in Table 3 compare the effectiveness of our protocol with other catalysts
that have been reported for the synthesis of compounds 1, 5 and 10. In all cases, our

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL
381
Table 1. Effect of the catalyst amount and temperature on the reaction of 6-amino-1,3-dimethylura-
cil (2 mmol) with 4-chlorobenzaldehyde (1 mmol).
Entry
The catalyst amount (g)
Temp. (ꢀC)
Time (min)
Yield (%)
1
2
3
4
5
0.060
0.072
0.080
0.072
0.072
120
120
120
125
115
45
20
20
20
35
93
97
97
97
91
Table 2. The preparation of bis(6-amino-1,3-dimethyluracil-5-yl)methanes using nano-[FSRN][H2PO4].
Compd. No.
Ar
Time (min)
Yielda (%)
M.p. (ꢀC) (Lit.)
1
2
3
4
5
6
7
8
C6H5
4-MeC6H4
10
10
20
30
10
15
10
20
20
20
20
96
95
83
85
92
89
95
91
94
97
88
293-295 (294-296)40
272-274 (274-276)44
200-202 (new)
4-PhCH2OC6H4
3-MeOC6H4
4-MeOC6H4
2,5-(MeO)2C6H3
2-O2NC6H4
4-O2NC6H4
2-ClC6H4
271-273 (274-276)43
276-278 (274-276)40
269-271 (272-274)43
263-265 (261-263)44
284-286 (282-283)44
261-263 (259-260)44
268-270 (267-269)40
282-284 (283-284)40
9
10
11
4-ClC6H4
2,4-Cl2C6H3
aIsolated yield.
Table 3. Comparing the reaction conditions and the results of nano-[FSRN][H2PO4] with those of
reported catalysts for the preparation of compounds 1, 5 and 10.
Time (min) of
Yield (%) of
Catalyst
Conditions
product 1/5/10
product 1/5/10
Ref.
Nano-[FSRN][H2PO4]
Solvent-free, 120 ꢀC
10/10/20
1200-1620b
720/720/–c
20/30/20
96/92/97
60-98b
–
TEBACa
H2O, 90 ꢀC
38
39
40
41
AcOH
MeOH, r.t.
74/67/–c
92/89/95
87/–c/95
[TMEDA][HSO4]d2
SSA-MNPse
Solvent-free, 120 ꢀC
EtOH, 50 ꢀC, ultrasound
irradiation
60/–c/60
Catalyst-free
Catalyst-free
EtOH, reflux
300/240/270
3/3/3
70/77/72
90/92/90
42
42
DMSO, microwave
irradiation (300 W)
EtOH, reflux
N-[SPIS][TFA]f
Ceric ammonium nitrate
60/–c/60
120/360/240
96/–c/95
89/89/92
43
44
EtOH/H2O, r.t.
aTriethylbenzylammonium chloride.
bIn this work, products 1, 5 and 10 have not been prepared; thus, the range of times and yields were given.
cIn this work, this product has not been synthesized.
dN,N,N0,N0-tetramethylethylenediaminium bisulfate.
eSulfuric acid functionalized silica-coated magnetic nanoparticles.
fNanorod-[SiO2-Pr-Im-SO3H][TFA].
catalyst was superior in terms of two or more of these factors: reaction conditions (solv-
ent-free versus utilization of organic solvents), time or yield. Moreover, there was no
need for ultrasound or microwave irradiation in our protocol.

382
N. LOTFIFAR ET AL.
Figure 1. Recyclability of nano-[FSRN][H2PO4].
Table 4. FT-IR data of the recycled nano-[FSRN][H2PO4] catalyst.
Peak (cmꢂ1
)
Bond or functional group
466
Rocking of Si–O
569
Fe–O
803
1097
~2929
2550-3720
Symmetric stretching vibrations of Si–O–Si
Asymmetric stretching vibrations of Si–O–Si
Stretching vibration of C–H
Stretching of OH groups of dihydrogen phosphate
and OH groups on silica surface
The recyclability of nano-[Fe3O4@SiO2-R-NHMe2][H2PO4] was studied for the reac-
tion of 6-amino-1,3-dimethyluracil with 2-nitrobenzaldehyde (see the Experimental sec-
tion for details of catalyst recovery). The results of this study are illustrated in Figure 1.
Nano-[Fe3O4@SiO2-R-NHMe2][H2PO4] could be reused up to 2 times without signifi-
cant loss of its activity; however, when the catalyst was recycled a third time (run 4),
the reaction time increased by 10 min, and the yield decreased by 11%. The recycled
catalyst was characterized by EDX (energy-dispersive X-ray spectroscopy), FT-IR and
XRD (X-ray diffraction) analyses. The EDX spectrum confirmed presence of all
expected elements in the structure of nano-[FSRN][H2PO4], i.e. Fe, O, Si, C, N, Cl and
P. The FT-IR data acquired from the recycled catalyst are summarized in Table 4; the
peaks related to all bonds and functional groups in the nanomaterial structure were
seen in the spectrum; these data were almost same as those of the fresh catalyst.14
According to the results of the EDX and FT-IR analyses, the catalyst structure did not
change during the recycling. In the XRD pattern of the recycled catalyst, some sharp
diffraction lines (at 2h ꢁ 10.2, 23.6, 29.5, 30.3, 35.7, 43.3, 53.7, 57.3, 62.9ꢀ) and one
broad peak (at 2h ꢁ 16.3-33.3ꢀ) were seen. The XRD data were slightly changed for the
recycled nano-[FSRN][H2PO4] in comparison with the fresh catalyst;14 this can be
related to slight modifications of the catalyst crystalline shapes or sizes during the recy-
cling. Considering the above explanations, the increase in reaction time and the
decrease in product yield can be attributed to loss of small amounts of the catalyst and
slight modifications of the catalyst’s crystalline structure and/or particle size during the
recycling process.

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL
383
In summary, we have introduced a new method for the synthesis of bis(6-amino-1,3-
dimethyluracil-5-yl)methanes with the following advantages: application of a recyclable
magnetic nanocatalyst, easy isolation of the catalyst from the reaction mixture, simple
purification of the products by recrystallization, wide scope, high yields, short reaction
times, superiority relative to the reported methods, and good compliance with green
chemistry principles.
Experimental section
All chemicals used in this study were purchased from Fluka and Merck Chemical
Companies. Nano-[FSRN][H2PO4] was synthesized according to our reported method.14
Progress of the reactions was monitored by thin layer chromatography (TLC) using sil-
ica gel SIL G/UV 254 plates. FT-IR spectra were collected on a Shimadzu IR-60 device.
1H and 13C NMR spectra were recorded on a Bruker Avance DPX FT-NMR spectrom-
eter. Mass spectra were recorded on a 5975C VL MSD spectrometer equipped with a
triple-axis detector. A Thermo Scientific 9200 instrument was utilized for measuring
melting points.
General procedure for the preparation of bis(6-amino-1,3-dimethyluracil-
5-yl)methanes
A mixture of 6-amino-1,3-dimethyluracil (2 mmol), aldehyde (1 mmol) and nano-
[FSRN][H2PO4] (0.072 g) was vigorously stirred using a glass rod at 120 ꢀC in an oil-
bath. After the reaction was complete (as observed by TLC), the mixture was cooled to
room temperature, and ethyl acetate (30 mL) was added. After stirring for 2 min at
reflux, the catalyst was isolated using an external magnet, washed with warm ethyl acet-
ate, dried, and used for the next run. The solvent was removed from the reaction mix-
ture, and the crude solid was recrystallized from ethanol/water (95/5) to afford the pure
product. Note: The reactions were performed in a test tube (open to air); the reaction
temperature was monitored using a thermometer.
Selected spectral data of the synthesized bis(6-amino-1,3-dimethyluracil-
5-yl)methanes
5,5’-(4-Methylphenylmethylene)bis(6-amino-1,3-dimethylpyrimidine-2,4(1H,3H)-
dione) (2)
1
IR (KBr disk): 1377, 1451, 1501, 1592, 1697, 2953, 3057, 3155, 3366, 3486 cmꢂ1; H
NMR (500 MHz, DMSO-d6): d 2.24 (s, 3H, CH3-Ar), 3.15 (s, 6H, 2N-CH3), 3.33 (s, 3H,
N-CH3), 3.36 (s, 3H, N-CH3), 5.55 (s, 1H, CH-Ar), 6.97-7.00 (AB system, 4H, Ar), 7.40
(br. s, 4H, 2NH2); 13C NMR (125 MHz, DMSO-d6): d 21.1, 28.6, 30.6, 35.6, 84.9, 86.3,
127.1, 128.9, 134.2, 137.0, 142.9, 151.1, 154.7, 161.9, 163.2; Mass (EI, 70 eV): m/z 412
(Mþ), 413 (Mþ þ 1).

384
N. LOTFIFAR ET AL.
5,5’-(4-Benzyloxyphenylmethylene)bis(6-amino-1,3-dimethylpyrimidine-2,4(1H,3H)-
dione) (3)
IR (KBr disk): 1380, 1453, 1503, 1588, 1665, 1694, 2956, 3083, 3149, 3392, 3564 cmꢂ1
;
1H NMR (500 MHz, DMSO-d6): d 3.15 (s, 6H, 2N-CH3), 3.33 (s, 3H, N-CH3), 3.35 (s,
3H, N-CH3), 5.04 (s, 2H, CH2-Ph), 5.54 (s, 1H, CH-Ar), 6.84 (d, J ¼ 7.6 Hz, 2H, Ar),
6.99 (d, J ¼ 7.8 Hz, 2H, Ar), 7.32 (t, J ¼ 6.9 Hz, 1H, Ph), 7.38 (t, J ¼ 6.8 Hz, 2H, Ph), 7.44
(d, J ¼ 7.0 Hz, 2H, Ph), 7.19-7.72 (br., 4H, 2NH2); 13C NMR (125 MHz, DMSO-d6): d
28.5, 28.7, 30.5, 35.2, 69.8, 84.5, 85.2, 114.6, 128.1, 128.2, 128.3,129.0, 138.0, 143.1,
149.4, 151.1, 153.4, 156.6, 160.5, 162.2; Mass (EI, 70 eV): m/z 474 (Mþ ˗ 2Me), 459 (Mþ
˗ 3Me), 447 [Mþ ˗ (2NH2 and Me)].
5,5’-(4-Chlorophenylmethylene)bis(6-amino-1,3-dimethylpyrimidine-2,4(1H,3H)-
dione) (10)
1
IR (KBr disk): 1379, 1456, 1499, 1594, 1678, 1701, 2956, 3047, 3163, 3357 cmꢂ1; H
NMR (500 MHz, DMSO-d6): d 3.15 (s, 6H, 2N-CH3), 3.33 (s, 3H, N-CH3), 3.39 (s, 3H,
N-CH3), 5.57 (s, 1H, CH-Ar), 7.12 (d, J ¼ 7.7 Hz, 2H, Ar), 7.23 (d, J ¼ 7.9 Hz, 2H, Ar),
7.39 (br., 4H, 2NH2); 13C NMR (125 MHz, DMSO-d6): d 27.4, 29.4, 34.4, 79.9, 83.1,
126.9, 127.9, 128.9, 138.2, 149.9, 153.8, 161.6, 162.3; Mass (EI, 70 eV): m/z 432 (Mþ),
433 (Mþ þ 1).
Acknowledgment
The authors acknowledge the Research Council of Payame Noor University for the support of
this work.
ORCID
Abdolkarim Zare
http://orcid.org/0000-0002-8210-3155
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