BF3-grafted Fe3O4@Sucrose nanoparticles as a highly-efficient acid catalyst for syntheses of Dihydroquinazolinones (DHQZs) and Bis 3-Indolyl Methanes (BIMs)

Article abstract of DOI:10.1002/aoc.4431

Current paper represents immobilization of sucrose on the Fe₃O₄ core and grafting of boron trifluoride (BF₃) onto the new surface. The catalytic activity of these nanoparticles was tested in syntheses of Dihydroquinazolinones (DHQZs) and Bis (3-Indolyl) Methanes (BIMs) as two fruitful pharmaceutical structures. Acidic capacity, FT-IR, XRD, VSM, TGA and SEM–EDX tests are carried out on such novel nanoparticles (NPs). Catalyst has shown more acidic capacity per one gram of NPs than sulfonated homologue which was reported previously.

Full text of DOI:10.1002/aoc.4431

Received: 18 December 2017
DOI: 10.1002/aoc.4431
Revised: 24 April 2018
Accepted: 27 April 2018
F U L L P A P E R
BF3‐grafted Fe3O4@Sucrose nanoparticles as a highly‐
efficient acid catalyst for syntheses of
Dihydroquinazolinones (DHQZs) and Bis 3‐Indolyl
Methanes (BIMs)
Iman Radfar
| Maryam Kazemi Miraki
| Leila Ghandi
| Naghmeh Esfandiary
|
Sepideh Abbasi | Meghdad Karimi
| Akbar Heydari
Chemistry Department, Tarbiat Modares
Current paper represents immobilization of sucrose on the Fe3O4 core and
grafting of boron trifluoride (BF3) onto the new surface. The catalytic activity
of these nanoparticles was tested in syntheses of Dihydroquinazolinones
(DHQZs) and Bis (3‐Indolyl) Methanes (BIMs) as two fruitful pharmaceutical
structures. Acidic capacity, FT‐IR, XRD, VSM, TGA and SEM–EDX tests are
carried out on such novel nanoparticles (NPs). Catalyst has shown more acidic
capacity per one gram of NPs than sulfonated homologue which was reported
previously.
University, PO Box 14155‐4838, Tehran,
Iran
Correspondence
Akbar Heydari, Chemistry Department,
Tarbiat Modares University, PO Box
14155‐4838, Tehran, Iran.
Email: heydar_a@modares.ac.ir
KEYWORDS
acid catalyst, bis indolyl methane, boron trifluoride, dihydroquinazolinone, sucrose
1 | INTRODUCTION
running of organic reactions.[5] The major problem with
the sulfonic‐based catalyst as a frequently‐applied acidi-
In recent years, a lot of attention has been obtained for
preparation and using of acidic catalyst for the running
of the multicomponent reactions (MCRs) which have
always included as a very common classification for
chemical processes either in lab‐scale or widely in indus-
trial extent.[1] Common acidifiers and the greatest amounts
of natural compounds belong to hydrogen‐bonding sites
were widely used as a catalyst in organic synthesis. Respect
to the widespread application of polyhydroxyles in the
world and also preceding report about their roles for coat-
ing of the magnetic core (in solid phase) by our recent
report[2] or in solution forms[3,4] we employed Sucrose
linked to magnetite NPs and interacted with BF3.Et2O
solution in continue.
fier relates to considerable dehydration and lower acid
capacity of poly‐sulfonated glucose which first time
designed by Hajjami and co‐workers.[5] The reported
catalyst reproduced and compared with our new sucrose‐
based structure to having no acidity as strong as Boron‐
trifluoride. On the other hand, huge dehydration degree
of sugar (glucose as an analogue for sucrose) meanwhile
preparation of a catalyst by the sulfonating agent is omitted
which can interrupt into our procedure and causes many
unwanted forms of sugar and its carbonaceous derived
scaffolds. The acceptable major form of sugar has to meet
our needs and represent the least amount of dehydration.
Such parallel happening could be ceased by applying BF3
instead of Cl‐SO3H as acidifiers for current approach.
It is vital to develop eco‐friendly methods to achieve a
less harmful catalyst with stronger acidity. Boron
Trifluoride (BF3) has emerged as safer acid, unlike
common acidifiers. In contrast to sulfonic acids, oxo
In recent years, a lot of attention has been obtained
for preparation and using of acidic catalyst for the
This article is dedicated to the memory of Abbas Saafi.
Appl Organometal Chem. 2018;e4431.
wileyonlinelibrary.com/journal/aoc
Copyright © 2018 John Wiley & Sons, Ltd.
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https://doi.org/10.1002/aoc.4431

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RADFAR ET AL.
trifluoroborate is concentrating on Hard‐Soft Acid–Base
(HSAB) theory. As it is depicted in Scheme 1, along
deprotonation we had local charge only on oxygen atoms
in sulfonated sugar but for BF3‐treated sugar, this nega-
part of our continuing interest in green chemistry and
heterogeneous catalyst,[2] we employed Sucrose linked
to magnetite NPs and interacted with BF3.Et2O solution
as a catalyst for two practiced MCRs (Scheme 2).
−
tive charge is distributed around whole part of RO‐BF3
as counter‐anion for released proton (H+) (Scheme 1).
Such fact can help us to foresee no complete dehydration
of sugar inferred to linking of BF3 which was a negative
overview in catalyst preparation stage. The greater free-
dom degree of a proton could lead stronger activation of
carbonyl site in both condensations by easier deproton-
ation afforded through loosened H‐X interaction (when
X is two different counterions in each acid catalysts).
Recently, 2,3‐ Dihydroquinazolin‐4(1H)‐ones stimu-
lated extensive interest for their anticonvulsant,[6]
antiparkinsonian,[7] antihypertensive,[8] antibacterial,[9]
anticancer,[10] diuretic,[11] as well as monoamine oxidase
inhibition[12] and plant growth regulation.[13] There are
numerous classical synthetic methods for synthesizing
such important compounds using various acids as cata-
lyst like MCM‐41‐Ni coordinated mesoporous,[14] GO
nanosheets,[15] Fe3O4‐GO[16] and also preliminary
endeavors; TiCl4‐Zn,[17] Sc(OTf)3,[18] NH4Cl,[19] I2/KI[20]
and solvent as an oxidant,[21] VO(acac)2‐oxidizer,[22]
heteropolyacids[23] and T3P™.[24] In deeper surveys, it
is revealed that enantioselective additives also have had
an important place for an investigation.[25] Another
usual promoter except for alteration of catalyst involves
microwave radiation to proceed condensation of
Anthranilamide and different carbonyls.[26]
2 | RESULT AND DISCUSSION
The characterization of the catalyst was carried out by
several techniques such as FT‐IR, XRD, VSM, SEM–
EDX, TGA and acidic capacity.
The major dislocated peaks appeared in 1054 cm−1
and 1596 cm−1 are correlated to diffused BF3 onto the
O‐H bonds and partial water releasing, respectively
(Figure 1). In case of the unchangeable peak of Fe‐O
bond in 578 cm−1, this sharp summit illustrated the resis-
tance of magnetic structure of Fe3O4 meanwhile undergo-
ing an acidic harsh condition.
Furthermore, in‐vitro sampling of synthesized catalyst
used for distinguishing XRD pattern of Fe3O4@Sucrose‐
OBF3H that indexed exact presence of magnetite (100%)
when compared with its first core (Fe3O4) and BF3‐free
(Fe3O4@Sucrose) structures (Figure 2).
The magnetism of new made NPs was analyzed via
Vibrating Magnetism Saturation (VSM) in range of
−10.000 to +10.000 Os. In a comparable diagram, magne-
tism saturation amount was 34 (emu.g−1
)
for
Fe3O4@Sucrose‐OBF3H with an eight units decrease than
Fe3O4@Sucrose. The main reason could be interpreted in
an outline relied on the co‐agglomeration of acidified NPs
comes from their strong hydrogen bonding. In continue,
as it is depicted in Figure 3, the M (H) hysteresis loop
for the samples was completely reversible which this
illustration proves all the nanoparticles has represented
superparamagnetic behavior.
Bis (3‐Indolyl) Methanes (BIMs) have attracted
considerable interest in recent years due to pharmacolog-
ical and biological properties.[27–29] Several different
protocols have been mentioned for the synthesis of BIMs
in the present of protic or Lewis acids.[30–40] Herein, as a
SCHEME 1 Acidity comparison of two
acid sites respect to HSAB theory

RADFAR ET AL.
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SCHEME 2 Synthesis of DHQZs and
BIMs
The average size of NPs calculated by 10 points of
image taken from SEM microscopy estimated around
50 nm (spherical shape) with the least possible agglomera-
tion (Figure 4a). The ratio of surface Boron atom to
Fluorine atom is around 3.5 that implies to succeeded
immobilization of BF3 onto the hydroxyl sites coated on
Fe3O4 without escape of fluoride anion (grasped by EDX
analysis) (Figure 4b).
The final test for these the NPs related to amount of
organic mass grafted on the primary Fe3O4. Thermal Gra-
vimetry Analysis (TGA) revealed that about 48.6% (w/w)
of catalyst is burnt between 55 °C to 520 °C and this proof
is correlated to percentage amount of organic motif in
catalyst (sugar plus BF3). Such decreased mass is
completely assumed by sugar and the linked BF3 as
organic motifs of NPs (Figure 5). As it is demonstrated
here and respect to preliminary thought around BF3
scape, there is a disadvantage revealing no heat‐stable
bond between O (from surface hydroxyls) and B
(from BF3). In contrast the easier releasing proton sites
of O‐BF3 can compensate such feeble point than sulfonic
homologue.
FIGURE 1 Dislocated peaks before (long dashed line) and after
(continued line) addition of BF3
The last specific measurement belongs to a simple
acid–base titration of novel catalyst that allocates to an
intensive factor for this catalyst. Each gram of
Fe3O4@Sucrose‐OBF3H NPs contains 3.72 mmol released
proton in an aqueous medium. As we estimated it has
more acidic capacity and also more stable scaffold against
sulfonated sugar‐based NPs which was reported by
other scientists. After preparation and identification, the
catalytic activity of the Fe3O4@Sucrose‐OBF3H NPs
was explored in the synthesis of DHQZs and BIMs
(Scheme 2).
FIGURE 2 Unaltered core crystallite of magnetite when there is
a comparison among Fe3O4, Fe3O4@Sucrose and Fe3O4@Sucrose‐
OBF3H
To confirm the merit of Fe3O4@Sucrose‐OBF3H NPs
as catalyst, we optimized the reaction condition for a
model reaction between anthranilamide, benzaldehyde
in the presence of varying amounts of the catalyst in
various solvents. According to the results represented in
Table 1, we found that the best result can be achieved
using 0.02 g of Fe3O4@Sucrose‐OBF3H NPs as the cata-
lyst at 60 °C under solvent‐free condition and these
FIGURE 3 Comparable VSM diagram of BF3‐linked NPs and
their BF3‐free homologue NPs (emu.g−1 vs. Os)

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RADFAR ET AL.
FIGURE 4 SEM images (a) and EDX
(b) of Fe3O4@Sucrose‐OBF3H NPs
FIGURE 5 TGA/DTG diagram
results are compared with some of the best‐yielded latter
reports.
Encouraged by these results, a wide range of desired
products were prepared by diverse aldehydes under the
optimized conditions. As shown in Scheme 3, using this
method, all of the various aldehydes were efficiently con-
verted to their corresponding products in good to high
yields with short reaction times.
After seeing these interesting results, we decided to
investigate the catalytic activity of the Fe3O4@Sucrose‐

RADFAR ET AL.
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TABLE 1 Optimization and Comparison for the synthesis of DHQZs (for benzaldehyde)
Entry
Cat. (amount)
Solvent (2 cc)
Temp. (°C)
Time (min)
Yield (%)
1
_
H2O
_
60
60
60
60
60
60
60
60
60
60
80
60
60
r.t
r.t
r.t
60
30
30
30
30
30
30
15
30
15
55
30
7
75
2
Fe3O4@Sucrose (20 mg)
Fe3O4@Sucrose (40 mg)
Fe3O4@Sucrose‐OBF3H (20 mg)
Fe3O4@Sucrose‐OBF3H (20 mg)
Fe3O4@Sucrose‐OBF3H (40 mg)
Fe3O4@Sucrose‐OBF3H (40 mg)
Fe3O4@Sucrose‐OBF3H (20 mg)
Fe3O4@Sucrose‐OBF3H (20 mg)
Fe3O4@Sucrose‐OBF3H (40 mg)
Gluconosolfonic acid (10 mg)
Fe3O4 (20 mg)
~80
~82
84
3
_
4
H2O
EtOH
EtOH
MeOH
_
5
87
6
90
7
85
8
97
9
_
93
10
11
12
13
14
15
16
_
97
EtOH
_
90[5]
70
Sucrose solution (1 M)
Ni‐MCM41
H2O
PEG
H2O
DCM
99
15
15
6‐48 h
96[14]
93[15]
93[25]
Graphene Oxide NSs
Sc(OTf)3 chiral product
OBF3H NPs in other the multicomponent reaction by the
synthesis of Bis (3‐Indolyl) Methanes. First of all, we opti-
mized the reaction conditions with respect to the solvent,
the amount of catalyst, temperature (Table 2) and the best
results was obtained using 0.020 g of the Fe3O4@Sucrose‐
OBF3H NPs in EtOAc at 70 °C after 2.5 h.
It is established that Bis (Indol‐3‐yl) Methanes can be
achieved from condensation between various aldehydes
and 1H‐indole (2 eq.) (except entry 17b which made of
2 eq. pyrrole) in EtOAc at 70 °C (Scheme 4) in good to
excellent yields by Fe3O4@Sucrose‐OBF3H NPs as
H‐activating catalyst.
The physical and spectral data of new and some of
known synthesized products (DHQZs and BIMs) are pro-
vided in Supplementary Material file. The proposed
mechanisms for the synthesis of DHQZs were presented
in Scheme 5. At first the carbonyl group of aldehydes
can be activated by Fe3O4@Sucrose‐OBF3H NPs via
hydrogen‐bonding. Subsequently, the desired product
was obtained by the formation of imine and a simple
condensation cyclization.
In viewpoint of mechanism, the synthesis of BIMs is
carried out through activation of the aldehyde by
Fe3O4@Sucrose‐OBF3H NPs via hydrogen‐bonding
empowered electrophilic addition in the carbon site of
indole and pyrrole (Scheme 6). The loaded BF3 strongly
revealed hidden benefits to compensate the lack of pres-
ence of acidified sulfonating agent in both reactions for
production of DHQZs or BIMs. Depended on amount of
active proton or H‐bonding sites from catalytic agents,
BIM formation could be ceased in first step (monoindolyl
intermediate) which in Table 2, the yields of observed
intermediates are represented in related parenthesis for
each entry.
The reusability of catalyst was checked to end of at
least 6 frequent runs. Synthesis of DHQZs could show
less meaningful recession about activity that stand for
lesser water releasing than whatever takes place in syn-
thesis of BIMs (Figure 6a and b).
In a compared IR spectrum diagram (Figure 7) among
three states of magnetite‐derived catalysts, it could easily
be seen the decreased intensity of not too stable new cat-
alyst after six runs. But there are still two major peaks
(~1050 and ~1600 cm−1) related to BF3 stretching modes
(referring to Figure 1) which shows a less amount of this
first component remains in the surface of the preliminary
catalyst.
The difference among three XRD spectra of the
synthesized nanoparticles are obviously depicted in
Figure 8. The seven distinct peaks in the specific
region have shown the stability of Fe3O4 cores along
organic section layer linking either in non‐reacted or
after using under two current acidic multicomponent
condensations.
To evaluate the decline of catalyst efficiency amid six
recycling process for both of MCRs, the acidic capacity
was measured. 2.80 and 2.35 mmol H+ per each gram cat-
alyst were final amounts of releasing proton (primary
number of capacity is equal to 3.72) after six runs for
DHQZs and BIMs syntheses, respectively.

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RADFAR ET AL.
SCHEME 3 Aldehyde scope of the reaction
crystalline structure of the catalyst nanoparticles. Data
were collected from 10° to 90° (2θ) with a scan speed of
0.04° s−1. The magnetic properties were measured with
a vibrating magnetometer/alternating gradient force mag-
netometer (MDCo., Iran, www.mdk‐magnetic.com).
Thermogravimetric analysis (TGA) was performed using
a thermal analyzer with a heating rate of 20 °C min−1
over the temperature range 25–900 °C under flowing
compressed nitrogen (an inert gas).
3 | EXPERIMENTAL
The quality of the solvents and starting materials are
commercially selected synthesis‐grade and purchased
from Merck company. All reagents were transferred to
the reaction vessel (Pyrex tube with a screw cap). FT‐IR
spectra were collected with a Nicolet IR100 FT‐IR in the
wavenumber range of 400–4000 (cm−1) using spectro-
scopic grade KBr. The melting points of products tested
by Barnstead Electronics 9100. Additionally, the 1H‐
NMR (500 MHz) spectra were recorded on a Bruker
Avance DPX‐500NMR spectrometer instrument that was
recorded in CHCl3 as a solvent. The morphology of the
catalyst was studied using scanning electron microscopy
(SEM; Philips XL 30 and S‐4160) with coated gold
equipped with dispersive X‐ray spectroscopy capability.
Powder X‐ray diffraction (XRD) spectra were recorded
at room temperature with a Philips X‐Pert 1710 diffrac-
tometer using Co Kα radiation (λ = 1.78897 Å) at a volt-
age of 40 kV and current of 40 mA to define the
3.1 | Synthesis of Fe3O4@Sucrose‐OBF3H
nanoparticles
Experimentally, in a typical procedure, Fe3O4 was pre-
pared through previous methods as it has been reported
from iron (II) and (III) salts sources in the strong basic
medium.[42] After transformation of hydroxyls of the
primary NPs into the activated form of Fe3O4@Sucrose
in an ice‐bath container, the magnetic residue continu-
ously used for next step. The sugar‐handed sector

RADFAR ET AL.
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TABLE 2 Optimization and Comparison for the synthesis of BIMs (IM* = monoindolyl‐Intermediate) (for benzaldehyde)
Solvent
Yield (%)
Entry
Cat. (amount)
(1 cc)
Temp. (°C)
Time (h)
(IM*%)
1
–
–
r.t
60
70
70
60
60
60
60
70
90
70
70
70
70
70
60
24
12
6
<20% (20)
80 (15)
~ 70 (5)
~ 70 (5)
~35 (40)
68 (30)
~65 (20)
~75 (15)
~80 (15)
82 (5)
2
Sucrose solution (1 M)
H2O
3
Fe3O4@Sucrose (20 mg)
EtOAc
EtOAc
H2O
4
Fe3O4@Sucrose (40 mg)
6
3
Fe3O4@Sucrose‐OBF3H (20 mg)
Fe3O4@Sucrose‐OBF3H (20 mg)
Fe3O4@Sucrose‐OBF3H (20 mg)
Fe3O4@Sucrose‐OBF3H (20 mg)
Fe3O4@Sucrose‐OBF3H (20 mg)
Fe3O4@Sucrose‐OBF3H (20 mg)
Fe3O4@Sucrose‐OBF3H (20 mg)
Fe3O4@Sucrose‐OBF3H (20 mg)
Fe3O4@Sucrose‐OBF3H (20 mg)
Fe3O4@Sucrose‐OBF3H (40 mg)
–
8
4
EtOH
MeOH
EtOAc
EtOAc
EtOAc
EtOAc
EtOAc
EtOAc
EtOAc
EtOAc
EtOAc
8
5
8
6
8
7
8
8
8
8
6
90 (5)
9
2.5
4
92 (5)
10
11
12
13
92 (5)
4
92 (5)
8
45 (50)
95[41]
Acidic tetrabutylammonium
hydrogen sulfate (TBAHS)
(Note: homogeneous catalyst)
1
14
15
[bmim]Br/MW irradiation (400 W)
(Note: homogeneous catalyst
and harsh condition)
–
150
80
8 (min)
2
95[30]
Cu‐isatin Schiff base supported
on γ‐Fe2O3 (Note: long time
and difficult condition for
synthesis of catalyst)
H2O
95 (~90)[31]
16
17
1,3‐Dibromo‐5,5 dimethylhydantoin
(DBDMH) (Note: homogeneous catalyst)
–
–
90
60
50 (min)
10 (min)
90[32]
98[33]
benzyl tributylammonium
chloride (BTBAC)Cl‐FeCl3
(N = 0.5) (Note: homogeneous
catalyst and so larger amount
than current work)
interacted with
a well‐studied Lewis acid, boron
3.2 | General procedure for the preparation
of 2,3‐ Dihydroquinazolin‐4(1H)‐ones
trifluoride solution in ether (BF3.Et2O) along 12 hr. In
more detail, after formation of magnetite nanoparticles,
1 g of Fe3O4 NPs was dispersed in 50 ml of a 1 M
sucrose solution and stirred for 30 minutes. The
brown‐black NPs of Fe3O4@Sucrose were dried at
120 °C for 2 hr. Owing to removal of excess and not
strong enough sucrose, the new‐made NPs washed five
times with ethanol using the external magnet for
decanting. Then, 1.2 g Fe3O4@Sucrose as a potent was
added to 25 ml BF3 in diethyl ether solution and stirred
for 12 hr. Final black powder washed by stirring in
diethyl ether three times to clear out extra BF3.
To a mixture of an anthranilamide (1 mmol) and benzal-
dehyde (1 mmol) was added 0.02 gr of the catalyst under
a solvent‐free condition at room temperature. The reac-
tion mixture was stirred for 15 min to afford the corre-
sponding product. After the completion of the reaction
(Progress of the reaction was continuously checked by
TLC), 5 ml EtOAc (as eluent in work‐up step) was added
to the reaction mixture. Then, the catalyst was separated
by an external magnet and final product purified by non‐
flash chromatography on the silica‐gel type plates.

8 of 10
RADFAR ET AL.
SCHEME 4 Aldehyde scope of the
reaction
SCHEME 5 The proposed mechanism for first condensation
SCHEME 6 The proposed mechanism of formation of BIMs
(DHQZs)
using current catalyst

RADFAR ET AL.
9 of 10
FIGURE 8 Comparison among three various states of sugar‐
based catalysts
3.4 | General procedure for Recycling of
Fe3O4@Sucrose‐OBF3H nanoparticles in
syntheses of DHQZs and BIMs
After each run either for DHQZ or BIM syntheses, EtOAc
was added to reaction mixture and the dispersed catalyst
was isolated by an external magnet. The remained cata-
lyst collected and two times washed with 5 ml EtOAc/
Ether (1:1; v/v) to remove residual organic reactants and
products. In following, the used catalyst applied for next
run as well it was fresh at starting performance. In each
run, the yield percentage of synthesized products were
calculated by weight measurements.
FIGURE 6 Catalyst reusability tests for syntheses of a) DHQZs
and b) BIMs
4 | CONCLUSION
The obvious advantage of such two multi‐component
approaches is an improvement in final yield of obtained
products. In the synthesis of these compounds, we
achieved to more different derivative for both of the
DHQZs and BIMs. Through a delicate viewpoint, we also
checked the amount of formed intermediate in the opti-
mization of BIMs (shown in parenthesis in yield column
of Table 2). This overview could help scientist to have a
more definite survey on stepwise syntheses.
FIGURE 7 Comparison among three various states of sugar‐
based catalysts
ACKNOWLEDGMENT
The authors gratefully acknowledge Tarbiat Modares
University for partial support of this work.
3.3 | General procedure for the
preparation of Bis (3‐Indolyl) Methanes
(BIMs)
ORCID
A mixture of benzaldehyde (1 mmol), indole (2 mmol)
0.02 gr of the catalyst. Was stirred in EtOAc at 70 °C.
After completion of the condensation reaction (within
2.5 hr) for both equivalent of indoles, the catalyst was
separated by an external magnet and solid products
purified by recrystallization in n‐hexane/ether or via
non‐flash chromatography on the silica‐gel type plates.
Iman Radfar http://orcid.org/0000-0003-4965-1982
Maryam Kazemi Miraki
http://orcid.org/0000-0003-4834-
1990
Leila Ghandi http://orcid.org/0000-0002-2663-5851
Naghmeh Esfandiary
http://orcid.org/0000-0002-8413-
9952
Meghdad Karimi http://orcid.org/0000-0001-5350-9861

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RADFAR ET AL.
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