Hybrid magnetic Irish moss/Fe3O4 as a nano-biocatalyst for synthesis of imidazopyrimidine derivatives

Article abstract of DOI:10.1039/c6ra08504k

Irish moss (IM), derived from the Chondrus crispus is a family of sulphated polysaccharide that are extracted from certain kinds of algae (red edible seaweeds). In this study, new magnetically separable, recoverable Fe₃O₄ nanoparticl

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Hybrid Magnetic Irish Moss/Fe3O4 as a Nano-Biocatalyst for
Synthesis of Imidazopyrimidine Derivatives
Behnaz Hemmati,a Sharzad Javanshira* and Zahra Dolatkhaha
Received 00th January 20xx,
Accepted 00th January 20xx
DOI: 10.1039/x0xx00000x
Irish moss (IM), derived from the Chondrus crispus is a family of sulphated polysaccharide that are extracted from certain
kinds of algae (red edible seaweeds). In this research, a new magnetically separable recoverable Fe3O4 nanoparticles were
synthesized in the presence of natural Irish moss (IM) to afford Fe3O4@IM. FT-IR analysis, scanning electron microscopy
(SEM), Transmission electron microscopy (TEM), VSM analysis, Energy-Dispersive X-ray Spectroscopy (EDX) and X-ray
diffraction (XRD) were combined for the characterization of Fe3O4@IM nanocomposite. Afterward, the first catalytic report
of Fe3O4@IM with no post-modification was achieved by studying its catalytic activity in the synthesis of imidazopyrimidine
derivatives via a three-component reaction of 2-aminobenzimidazole, aldehyde, and C-H acidic compounds under reflux in
ethanol. 1H nuclear overhauser effect (NOE) experiments has been used to ascertain the regioselectivity of addition and
condensation reactions. Based on this study, Fe3O4@IM was an efficient, magnetically separable, recyclable, and green
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catalyst
with
natural
source.
Introduction
particular interest especially those composed of natural polymers,
has become a very interesting approach in Nano catalytic protocols.
Amongst these polymers, polysaccharides of algal origin include
alginates, agar and carrageenan. 'IM' or carrageenan moss derived
from the Chondrus crispus and extracted from certain kinds of algae
(red edible seaweeds) are highly sulfated galactans. Due to their
half-ester sulfate moieties they are strongly anionic polymers. In
this respect they differ from agars and alginates. Carrying both
sulfate and OH group it can act as a bifunctional catalyst. Irish moss,
are which are built up from D-galactopyranose units only and grows
abundantly along the rocky parts of the Atlantic coast of Europe
and North America. The Irish moss is mostly composed of protein
(50%) and carbohydrates (40%). Inside Irish Moss, these
carbohydrates are mainly κ- and ι−carrageenan (Figure 1), whereas
λ-carrageenan is found in the sporophytic phase of the life cycle.2
The combination of these polysaccharides with Fe3O4 magnetic
nanoparticles (MNPs) as inorganic supports opens up the possibility
of exploiting their properties in a synergistic manner, which
constitutes an appealing approach to generate new materials for
sustainable chemistry.3 Magnetically recoverable Nano catalysts
have emerged recently as an alternative for the easy separation of
Nano sized catalysts from reaction mixtures by employing an
Green catalysis is probably one of the most important subsection of
green chemistry. The greener catalytic protocols and
environmentally benign reaction conditions which avoid the use of
volatile organic solvents, toxic reagents, hazardous or harsh
reaction conditions, as well as challenging and time consuming
wasteful separations have become more popular and increasingly
important for the chemists who try to avoid the annihilation of our
blue planet for a sustainable future.
Catalysis, providing durable, economical and efficient means for
converting raw materials into chemicals is essential to the
development of modern society. In this regard, the development of
Nano sciences, unimagined a century ago, has made the greening of
chemistry conceivable. Although Nano catalysts have several
advantages over conventional catalyst systems; however, isolation
and recovery of these tiny Nano catalysts from the reaction mixture
is not easy and the conventional methods, such as filtration are not
efficient due to the combination of Nano size and solvation
properties of the catalyst particles. This limitation hinders the
sustainability of these Nano catalytic protocols. To overcome this
problem, the use of magnetic nanoparticles has emerged as a
feasible solution; their insoluble and paramagnetic nature enables
easy and efficient separation of the catalysts from the reaction
mixture with an external magnet.1
The use of polymer-coated magnetic particles, are currently of
external magnetic field and so promote the economics of these
Nano catalytic protocols.1
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–
Fig. 1 Kappa carrageenan (R is H) and iota carrageenan (R is SO3 )
surrounding the Fe3O4 can be clearly confirmed by comparing
Multicomponent reactions (MCRs) as important organic reactions related peaks in FT-IR spectrums of Fe3O4@IM nanocomposite
are one-pot processes in which three or more components come and IM. The two spectrum exhibited the typical absorption
together to form a product containing substantial elements of all bands of IM polysaccharide: ~1230 cm-1, S-O asymmetric
the reactants.4 This strategies grant exceptional advantages over sulphate stretch; ~1010–1065 cm-1, C-O and C-OH stretching
routine reactions, owing to the convergence, operational simplicity, and 843 cm−1, α(1,3) D-galactose C-O-S stretch8 thus indicating
atom-economy, structural diversity, and shortness of their synthetic that the biopolymer chains maintained their chemical
pathway and have recently gained a new dimension in the field of characteristics when in contact with the Fe3O4. The -OH
designing methods to produce detailed libraries of biologically absorption band shifting in position from a higher in IM
active compounds and new molecular structure for potential drugs spectra to a lower wavenumber in Fe3O4@IM spectra indicated
6
with different pharmacological activities.5, Nitrogen-containing that the spatial structure of the biopolymer is changed after
heterocyclic compounds are in focus of intense investigations by stabilization on metallic oxide nanoparticles (see
researchers due to their major role in the pharmaceutical industries
and numerous applications, because of their strong physiological
properties. Among them Imidazopyrimidine are important
compounds possessing antimicrobial activity, antiviral, molluscidal
activities, antibiotic, antidiabetic, herbicidal activity, platelet anti-
aggregant antiulcer activity, DNA-gyrase inhibitors and anti-
inflammatory activities as well as anticancer efficacy; they can play
the role of antagonists of the paralyzing action of antidiabetic
activity and are important core motifs in a broad range of
biologically active compounds that are often used in
pharmaceutical and drug research, agricultural science, and dye
industry.7 Despite its attractiveness only few methods have been
reported for the one-pot synthesis of imidazopyrimidine
derivatives. However, these procedures suffer from comparatively
long reaction times and low yields. They could be synthesized via
MCRs in fewer-step and reduced processing times, cost, and waste.
The aim of this work was to develop a novel formulation of Nano
composite comprised of natural marine-derived polymer Irish Moss
and magneticly Fe3O4 nanoparticles, Fe3O4@IM, and evaluate its
catalytic activity in the synthesis of imidazopyrimidine derivatives
by
a
one-pot, multi-compound condensation of 2-
Supplementary Information). EDX analysis is used to study the
chemical composition of the catalyst.
aminobenzimidazole, aldehydes, and malononitrile or dimedone
Fig. 2 Preparation of Fe3O4@IM catalyst.
The EDX analysis of the prepared Nano catalyst revealed C, O,
S and Fe as significant elements with Fe/S ratio of 13.4 (see
supplementary information).
The XRD difractograms of IM@Fe3O4 exhibiting sharp peaks at
2θ range, 35, 43.22, 57 and 62 confirm the presence, and
crystal properties of Fe3O4. The wide peak with low intensity
of14-20, reflect the amorphous properties of Irish moss on the
under reflux conditions in ethanol.(Scheme1)
Scheme 1 Synthesis of imidazopyrimidine
Results and discussion
The synthesis and Characterisation of Fe3O4@IM
In this work, Fe3O4 was synthesized in the presence of IM
which led to the synthesis of Fe3O4@IM (Figure 2). During the
synthesis, IM acted as a stabilizer and after the synthesis,
Fe3O4 nanoparticles are functionalized by IM. Hydroxyl
enriched IM herein can act as a reaction mediator to proceed
the reaction. Functionalization of Fe3O4 can be performed by
both hydroxyl and sulfate groups. The presence of IM
Fe3O4 surface (Figure 3).
Fig. 3 X-ray diffraction pattern of Fe3O4@IM
2 | J. Name., 2012, 00, 1-3
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The magnetic hysteresis loop measurements of the Fe3O4@IM
indicate that its saturation magnetization value (33.3 emu·g−1)
is less than Fe3O4 (51.19 emu·g−1) (Figure 4). This diminution of
Ms value indicted the incorporation of IM in the surface of
Fe3O4.
structure and the SEM image shows small particles. It shows
that Fe3O4 nanoparticles are synthesized and embedded inside
the Irish moss network.
Scheme
2
The model reaction for the synthesis of
imidazopyrimidine derivatives
Optimization of reaction conditions
To evaluate the catalytic activity of Fe3O4@IM (1) for the synthesis
of imidazopyrimidine derivatives, first domino knoevenagel
condensation followed by Michael addition and heteroannulation
of 2-aminobenzimidazole (2), 4-Chlorobenzaldehyde (3b), and
malononitrile (4) (1: 1: 1 mole ratio) was considered as a model
reaction (Scheme 2). The results have been tabulated in Table 1.
Under solvent-free conditions only a trace amount of the desired
Fig.
4
VSM
analysis
of
Fe3O4@IM
and
Fe3O4
Table 1. Optimization of the model reaction for the preparation of
imidazopyrimidine.
Catalyst/
loading (g)
Time
(min)
Yield
(%)
Entry
Solvent
Condition
Fe3O4@IM
(0.02g)
Fe3O4@IM
(0.02g)
Fe3O4@IM
(0.02g)
Fe3O4@IM
(0.02g)
1
2
3
4
5
-
80°C
reflux
reflux
reflux
r.t
60
15
15
60
60
trace
78
H2O
EtOH
CHCl3
EtOH
95
35
Fe3O4@IM
(0.02g)
15
Fe3O4@IM
(0.02g)
6
EtOH
40°C
60
50
Fe3O4@IM
(0.02g)
Fig. 5 a, b and c) The TEM micrograph of Fe3O4@IM d) The
7
8
9
EtOH
EtOH
EtOH
60°C
reflux
reflux
60
120
25
75
30
85
SEM micrograph of Fe3O4@IM
-
In order to investigate the morphology of the catalyst. In order
to investigate the morphology of the catalyst, the TEM
micrographs (Figure 5a, b and c) and SEM (Figure 5d) were
used. SEM images show the morphology of Fe3O4@IM. The
morphology of the nanocomposite displayed homogeneous
Fe3O4@IM
(0.01g)
Fe3O4@IM
(0.03g)
IM
(0.02g)
Nano-Fe3O4
(0.02g)
10
11
12
EtOH
EtOH
EtOH
reflux
reflux
reflux
15
30
75
95
90
65
product (7) was obtained even at 80 °C (entry 1).
To find a suitable solvent various solvents such as H2O, EtOH and
CHCl3, were tested for the model reaction at different temperature.
The best results were obtained in ethanol under reflux conditions
(Table 1, entry 3). Consequently the reaction mixture was heated in
ethanol under reflux in the presence or absence of Fe3O4@IM to
afford
2-Amino-4-(4-chlorophenyl)-1,4-
The
dihydrobenzo[4,5]imidazole[1,2-a]pyrimidine-3-carbonitrile.
reaction did not proceed to completion in the absence of catalyst
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Table 2. The Comparison of the catalytic efficiency of Fe3O4@IM
with other catalysis.
solvent
(Reflux)
time
(min)
Yield
(%)
Entry
catalyst
ref
1
2
3
4
p-TSA
KAl(SO4)2*12H2O
Triethylamine
MgO
-/80°C
Ethanol
Ethanol
CH3CN
30
210
180
45
93
86
60
75
7
9
10
11
[This
5
Fe3O4@IM
Ethanol
15
95
work]
and only 30% of the product 7 was isolated after 2h (entry 8).
Interestingly the use of Fe3O4@IM improved yields of the desired
product 7 (entry 9). Optimization of catalyst loading was also
performed and the results show that 0.02g of Fe3O4@IM was
adequate and excessive amounts of catalyst did not increase the
yields. The results obtained from separate use of IM and Fe3O4
revealed the synergic effect of the nanoparticles and the sulfated
polysaccharide (entry 11 and 12). To demonstrate the effectiveness
of Fe3O4@IM, it has been compared with some of the previously
reported and published procedures (Table 2). The results clearly
illustrate that this protocol is indeed higher than many of the other
in terms of product yield, the reaction time and using a green
solvent. To further extend the scope of this new efficient Fe3O4@IM
catalysed protocol, we performed the reaction between 2-
aminobenzimidazole (2), a variety of aromatic aldehydes (3a-l), and
C-H acidic compounds (4, 5a and 5b) under optimized reaction
conditions which lead to a series of imidazopyrimidine (7, 8, 9) in
high -to-excellent yields. As shown in Table 3 (see Supplementary
Information), all aromatic aldehydes carrying either electron-
donating or electron-withdrawing group substituents reacted
Fig. 6 NOE spectra of 7 in DMSO-d6
presumably proceeds in two steps: initial condensation of aldehyde
3 and malononitrile (4) by standard Knoevenagel reaction takes
place to form the arylidene malononitrile intermediate (I) in the
presence of Fe3O4@IM as
a bifunctional organocatalyst. The
reaction of 2-aminobenzimidazole (2) with arylidene malononitrile
(I) may proceed by two possible mechanistic pathways depending
on whether the initial attack of the alkenenitrile is by the exocyclic
amino group (path A) or by the benzimidazole nitrogen atoms (path
B) to give the isomeric pyrimido[1,2 a]benzimidazoles (7') or (7)
(Scheme 3).
To elucidate which of the two possible products 7b or 7b’are
obtained, 1H nuclear overhauser effect (NOE) experiments were
carried out. The irradiation of Ha led to an enhancement in the
signal
of Hb. These results are in accordance with the structure 7b (Figure.
6), which mean the electrophilic attack would preferably occur on
the N atoms of the heterocyclic ring fused to the benzene ring. This
result are in accordance with the results obtained from quantum
chemical calculations performed on 2-aminobenzimidazole.12 The
reusability of Fe3O4@IM was also examined for at least 6 runs (see
supplementary information). Upon completion of each run, the
catalyst was collected by an external magnet, washed several times
with ethyl acetate and ethanol, dried and used in the next run. The
recycled catalyst could be reused several times in the subsequent
runs without a considerable loss of catalytic activity. Comparison of
FT-IR spectrum of recycled Fe3O4 @IM and fresh catalyst has
allowed us to conclude that the reaction cycles did not affect the
Scheme 3. Plausible mechanism of the Fe3O4@IM catalyzed
synthesis of 7
chemical structure of catalyst (see supporting information). The
XRD patterns of catalyst after recycling show 24% of reduction of
Sulfur. This could explain the diminished yield after 6 run.
efficiently to give excellent yields, nonetheless aldehydes carrying
withdrawing groups react in a prolonged time. The reaction
4 | J. Name., 2012, 00, 1-3
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118.58, 118.93, 120.02, 123.44, 126.87, 129.20, 132.80, 143.48,
148.23, 149.37, 151.47.
Conclusions
In summary, the hybrid magnetic materials prepared from
natural Chondrus crispus, Fe3O4@IM was found to be a highly
efficient Nano-Biocatalyst for synthesis of imidazopyrimidine
2-Amino-4-phenyl-1,4-dihydrobenzo[4,5]imidazo[1,2-
a]pyrimidine-3-carbonitrile (7k)
1
IR (KBr): 3350cm-1, 3110cm-1, 2175cm-1. H NMR (300 MHz, DMSO-
derivatives via
a
three-component reaction of 2-
d6): δ=5.20 (1H, s, CH), 6.82 (2H, s, NH2), 7.0 (1H, t, J=7.89 Hz), 7.12
(1H, t, J=7.49 Hz), 7.21-7.37(6H, m), 7.62 (1H, d, J=8.03 Hz), 8.58
(1H, s, NH). 13C NMR (75 MHz, DMSO-d6): δ =151.70, 149.06,
143.60, 142.89, 129.26, 128.63, 127.77, 125.86, 123.26, 119.79,
119.07, 116.02, 112.34, 61.98, 53.23.
aminobenzimidazole, aldehyde, and malononitrile or
dimedone. 1H nuclear overhauser effect (NOE) experiments
has been used to ascertain the regioselectivity of addition and
condensation reactions
.
This method offers several
advantages, such as omitting toxic solvents or catalyst, high
yields, short reaction time, very simple work-up, magnetically
separable, recyclable and green catalyst from a natural source.
This catalyst also showed 6-run recyclability with no significant
yield decrease. The XRD patterns of catalyst after recycling
show 24% of reduction of Sulfur (See Supplementary
Information). The Fe/S ratio after 6 run recycling is 1.6 times
higher than the fresh catalyst.
3,3-Dimethyl-12-(4-Chlorophenyl)-1,2,3,4,5,12-hexahydrobenzo
[4,5]imidazo[2,1-b]-quinazolin-1-one (8b)
IR (KBr): 3553 cm-1, 3444 cm-1, 1566 cm-1. 1H NMR (300 MHz,
DMSO-d6): δ =0.93 (3H, s, CH3), 1.07 (3H, s, CH3), 2.29-2.04 (2H, m,
CH2), 2.67- 2.51 (2H, m, CH2), 6.45 (1H, s, CH), 6.98 (1H, t, J = 7.6
Hz), 7.07 (1H, t, J = 7.6 Hz), 7.25 (1H, d, J = 8.4 Hz), 7.39-7.31 (5H,
m), 11.19 (1H, s, NH).
3,3-Dimethyl-12-(3-hydroxy-phenyl)-1,2,3,4,5,12-hexahydrobenzo
[4,5]imidazo[2,1-b]-quinazolin-1-one (8o)
Experimental
IR (KBr): 3533 cm-1, 3450 cm-1, 1564 cm-1. 1H NMR (300 MHz,
DMSO-d6): δ = 0.94 (3H, s, CH3), 1.05 (3H, s, CH3), 2.07 (1H, d,
J=16.2, CH2), 2.26 (1H, d, J=16.2, CH2), 2.88 (2H, s, CH2), 6.31 (1H, s,
CH), 6.54 (1H, d, J=7.8), 6.68 (1H, s), 6.76 (1H, d, J=7.5), 6.95-7.08
(3H, m), 7.25 (1H, d, J=7.8), 7.38 (1H, d, J=7.8), 7.94 (1H, s, OH), 9.41
(1H, s, NH).
General procedure for preparation of (Fe3O4@IM)
In a typical synthesis, 2 g of IM (ANGEL BRAND) was dissolved in 100
mL distilled water. Then, FeCl3·6H2O (5 g) and FeCl2.4H2O (2 g) were
slowly added into the mixture. The mixture was stirred strongly at
80°C to obtain a clear solution, and then aqueous ammonia was
added to the solution until the pH of 12 was obtained. The solution
was kept at 80°C under vigorous stirring for further 30 min. The
precipitate was collected with an external magnet, washed with
water and methanol several times and dried in vacuum for 6 h.
Acknowledgements
The authors wish to express their gratitude for the financial
support provided by the Research Council of Iran University of
Science and Technology (IUST), Tehran, Iran.
General Procedure for the Preparation of imidazopyrimidine
Derivatives
A mixture of 2-aminobenzimidazole (2, 1 mmol), aldehyde (3, 1
mmol), C-H acidic compounds (4, 1 mmol) and Fe3O4@IM (1, 20 mg)
was refluxed in Ethanol (3ml). Progress of the reaction was
monitored by TLC. After completion of the reaction, the catalyst
was collected by an external magnet. The reaction mixture was
then filtered and washed with ethanol. The solid residue was
recrystallized from ethanol to afford the pure product.
Notes and references
1.
V. Polshettiwar, R. Luque, A. Fihri, H. Zhu, M. Bouhrara
and J.-M. Basset, Chemical reviews, 2011, 111, 3036-3075.
C. J. Chandler, B. D. Wilts, S. Vignolini, J. Brodie, U.
Steiner, P. J. Rudall, B. J. Glover, T. Gregory and R. H.
Walker, Scientific reports, 2015, 5.
2.
2-Amino-4-(4-Chlorophenyl)-1,4-dihydrobenzo[4,5]imidazo[1,2-
a]pyrimidine-3-carbonitrile (7b)
3.
C. A. Mak, S. Ranjbar, P. Riente, C. Rodríguez-Escrich and
M. A. Pericàs, Tetrahedron, 2014, 70, 6169-6173.
M. Reactions, Ed.; Wiley-VCH: Weinheim, 2005.
L. Weber, Drug Discovery Today, 2002, 7, 143-147.
D. O’Hagan, Nat. Prod. Rep., 2000, 17, 435-446.
M. V. Reddy, J. Oh and Y. T. Jeong, Comptes Rendus
Chimie, 2014, 17, 484-489.
IR (KBr): 3427cm-1, 3326cm-1, 2187cm-1. 1H NMR (300 MHz, DMSO-
d6): δ= 5.25 (1H, s, CH), 6.89 (2H, s, NH2), 7.01 (1H, t, J = 7.5 Hz),
7.12 (1H, t, J = 7.8 Hz), 7.24 (1H, d, J = 7.8 Hz,), 7.30 (2H, d, J = 8.7
Hz), 7.43 (2H, d, J= 8.7 Hz), 7.62 (1H, d, J=7.8 Hz), 8.61 (1H, s, NH).
13C NMR (75 MHz, DMSO-d6): δ = 52.93, 60.54, 110.34, 115.25,
115.95, 119.19, 119.70, 123.20, 127.27, 129.29, 133.13, 143.63,
148.91, 151.73, 157.06.
4.
5.
6.
7.
8.
9.
J. Prado-Fernández, J. Rodrıguez-Vázquez, E. Tojo and J.
Andrade, Analytica Chimica Acta, 2003, 480, 23-37.
A. R Karimi and F. Bayat, Letters in Organic Chemistry,
2011, 8, 631-636.
2-Amino-4-(4-cyanophenyl)-1,4-dihydrobenzo[4,5]imidazo[1,2-
a]pyrimidine-3-carbonitrile (7g)
IR (KBr): 3448cm-1, 3410cm-1, 2180cm-1. H NMR (300 MHz, DMSO- 10.
d6): δ=5.36 (1H, s, CH), 6.94 (2H, s, NH2), 6.99 (1H, t, J=8.0 Hz), 7.11
(1H, t, J = 7.5 Hz), 7.23 (1H, d, J = 7.7 Hz), 7.45 (2H, d, J = 8.2 Hz),
B. Insuasty, A. Salcedo, R. Abonia, J. Quiroga, M. Nogueras
and A. Sánchez, Heterocyclic Communications, 2002, 8,
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1
7.61 (1H, d, J = 7.7 Hz), 7.83 (2H, d, J =8.2 Hz), 8.71 (1H, s, NH); 13
C
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NMR (75 MHz, DMSO-d6): δ =52.70, 60.73, 110.57, 112.50, 116.18,
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Hybrid Magnetic Irish Moss/Fe3O4 as a Nano-Biocatalyst for Synthesis of Imidazopyrimidine
Derivatives under Mild Conditions
Behnaz Hemmati, Shahrzad Javanshir, Zahra Dolatkhah
A new magnetically separable Fe3O4@IM Nano-Biocatalyst were synthesized using natural Irish moss
(IM) and its catalytic activity was studied in the synthesis of imidazopyrimidine derivatives.