One-pot synthesis of 1-(benzothiazolylamino)aryl methyl-2-naphthols and 3-benzothiazolyl 2,3-dihydroquinazolinones using a magnetically recoverable core-shell nanocomposite as catalyst

Article abstract of DOI:10.1515/znb-2021-0010

Nano-magnetite-supported sulfated polyethylene glycol (Fe3O4@PEG-SO3H) was prepared, characterized and utilized as a magnetically recoverable heterogeneous catalyst for the one-pot, three-component reaction of 2-aminobenzothiazole, aldehydes and 2-naphtho

Full text of DOI:10.1515/znb-2021-0010

Z. Naturforsch. 2021; 76(6–7)b: 385–393
Yousef Mardani, Zahed Karimi-Jaberi* and Mohammad Jaafar Soltanian Fard
One-pot synthesis of 1-(benzothiazolylamino)aryl
methyl-2-naphthols and 3-benzothiazolyl
2,3-dihydroquinazolinones using a magnetically
recoverable core–shell nanocomposite as
catalyst
https://doi.org/10.1515/znb-2021-0010
Received January 23, 2021; accepted April 29, 2021;
published online May 26, 2021
magnetic field. Some have been shown to be of advantage
in terms of easy synthesis, reusability, high catalytic ac-
tivity and excellent thermal and chemical stability in
various organic solvents and chemical processes [3, 4].
Considering these aspects, magnetic core–shell nano-
composites have attracted much attention in green
organic synthesis [5, 6]. These composite systems have
shown remarkable potential in practical applications
[7, 8]. In particular, various organic/inorganic materials
as the shell supported on magnetite (Fe3O4) nanoparticles
as the core have been synthesized and utilized as catalysts
in diverse organic transformations [9–16].
2-Aminobenzothiazoles are widely used in the
formation of a variety of fused heterocyclic compounds,
which have gained attention in medicinal and biological
chemistry [17]. Benzothiazole derivatives have shown a
wide spectrum of pharmacological applications in partic-
ular for their antiinflammatory, anticonvulsant, antitumor,
and antitubercular activities [18–20]. Furthermore, they are
also commercially important as antioxidants [21], vulca-
nization accelerators [22], and a dopant in light-emitting
organic electroluminescent devices [23].
Abstract: Nano-magnetite-supported sulfated polyethylene
glycol (Fe3O4@PEG-SO3H) was prepared, characterized
and utilized as a magnetically recoverable heterogeneous
catalyst for the one-pot, three-component reaction of
2-aminobenzothiazole, aldehydes and 2-naphthol/isatoic
anhydride resulting in efficient formation of 1-(benzo-
thiazolylamino)arylmethyl-2-naphthol or dihydroquina-
zolinones derivatives. The significant features of this
method include green conditions, operational simplicity,
minimizing production of chemical waste, shorter reac-
tion times and good to high yields. In addition, the
nanocatalyst can easily be separated from the reaction
mixture by application of a magnetic field and reused
without significant deterioration in its catalytic activity.
Keywords: heterocycles; heterogeneous catalyst; magne-
tite nanoparticles; multicomponent reaction.
Various protocols havebeen developed for the synthesis
of functionalized benzothiazoles [24, 25]. Among them,
1-(benzothiazolylamino)aryl-methyl-2-naphthols have two
biologically active parts, 2-aminobenzothiazole and amino-
alkyl naphthols (Betti Base). Aminoalkyl-2-naphthols have
provided convenient access to some useful synthetic build-
ing blocks through their amino and phenolic hydroxy
functional groups [26].
1 Introduction
Magnetic nanoparticles have attracted much attention in
biomedical fields, electronics, and catalytic processes
due to their unique features [1, 2]. Catalytic magnetic
nanoparticles have the notable advantage to be simply
separable from a reaction mixture by application of a
In the literature, 1-(benzothiazolylamino)arylmethyl-
2-naphthols have been synthesized by three-component
condensationreactionsof2-aminobenzothiazole, aldehydes
and 2-naphthol. Catalysts utilized for these syntheses
include maltose [27], heteropoly acids [28], oxalic acid [29],
Fe3O4@SiO2-ZrCl2 [12], imidazolium ionic liquids [30, 31] and
magnetic heterogeneous catalysts [32–34].
*Corresponding author: Zahed Karimi-Jaberi, Department of
Chemistry, Firoozabad Branch, Islamic Azad University, Firoozabad,
Iran, E-mail: zahed.karimi@yahoo.com. https://orcid.org/0000-
0002-9075-5911
Yousef Mardani and Mohammad Jaafar Soltanian Fard, Department of
Chemistry, Firoozabad Branch, Islamic Azad University, Firoozabad,
Iran, E-mail: mardani0096@gmail.com (Y. Mardani),
Quinazolinone derivatives are of particular value
because of their promising biological and pharmacological
mohammadjaafar_soltanian@yahoo.com (M.J. Soltanian Fard).
https://orcid.org/0000-0001-9842-3148 (M.J. Soltanian Fard)

386
Y. Mardani et al.: Synthesis of benzothiazole derivatives
activities such as anticancer, antidiuretic, anticonvulsant
and sedative behavior [35, 36]. Due to these advantages
of the quinazoline scaffold, some marketed drugs like
Quinethazone, Gefitinib, Fenquizone, Proquazone,
Febrifugine and Erlotinib are derived from this structure
[37]. A large number of synthetic approaches to dihy-
droquinazolinones has been advanced [38–42].
However, it is deemed worthwhile to explore a
convenient protocol for the synthesis of 1-(benzothiazo-
lylamino)arylmethyl-2-naphthols and 3‐benzothiazolyl
2,3-dihydroquinazolinones. As a continuation of our
interest in catalytic applications of solid acid catalysts in
organic synthesis, we herein report the three-component
reaction of 2-aminobenzothiazole, aldehydes and
2-naphthol/isatoic anhydride with a magnetite (Fe3O4)
nanocomposite coated with sulfonated polyethylene
glycol (Fe3O4@PEG-SO3H) as a magnetically recoverable
heterogeneous catalyst (Scheme 1).
2 Results and discussion
The magnetite nanoparticles were prepared by the
chemical coprecipitation of Fe2+ and Fe3+ according to a
method reported previously [12]. In the next step, the
nanoparticles were coated with polyethylene glycol
to give Fe3O4@PEG. Finally, the surface of these nano-
particles was reacted with chlorosulfonic acid using a
procedure modified with respect to the one given in
Ref. [14] (Scheme 2). This procedure led to the introduction
of SO3H as a functional group on the Fe3O4@PEG
nanoparticles in the form of Fe3O4@PEG-SO3H. As it is
indicated in Schemes 1 and 2, SO3H is bound as a sulfuric
acid mono ester ROSO2(OH) to the PEG outer shell. The
such prepared magnetic nanocomposite was character-
ized by energy-dispersive X-ray spectroscopy (EDX),
scanning electron microscopy (SEM) and vibrating sam-
ple magnetometry (VSM).
Scheme 1: Synthesis of 1-(benzothiazolylamino)arylmethyl-2-naphthols 5 and 3‐benzothiazolyl 2,3-dihydroquinazolinones 6.
Scheme 2: Preparation of the core–shell nanocomposite Fe3O4@PEG-SO3H.

Y. Mardani et al.: Synthesis of benzothiazole derivatives
387
As can be seen in Figure 1, EDX analysis of
The magnetization hysteresis of Fe3O4@PEG-SO3H
Fe3O4@PEG-SO3H proves that the nanostructure is was studied with a VSM. The result is shown in Figure 3.
composed of carbon, oxygen, sulfur and iron and gives The saturation magnetization value of Fe3O4@PEG-SO3H
some indication for the existence of a PEG-SO3H shell on (∼31.3 emu g−1) is lower than that of Fe3O4 nanoparticles
the surface of Fe3O4.
(∼59.2 emu g−1), which is in accord with the presence
The particle size and morphology of the synthesized of a diamagnetic outer shell (PEG-SO3H). Nevertheless,
Fe3O4@PEG-SO3H nanoparticles was investigated by SEM. such magnetizations are sufficient to allow the mag-
The SEM image (Figure 2) shows that the main structure of netic separation of the catalyst from the reaction
the nanocomposite has a sphere-like morphology with an mixture.
average sphere size of about 25 nm.
In order to screen the catalytic activity of the
nanocomposite, the reaction of benzaldehyde, 2-amino
benzothiazole, and 2-naphthol was studied as a model re-
action under a variety of different conditions. The results are
summarized in Table 1. They clearly indicate that the
Fe3O4@PEG-SO3H nanocatalyst allows for much shorter
reaction times and better yields as compared to the catalysis
by nano-Fe3O4 or PEG-SO3H alone or the uncatalyzed
reaction.
The amount of Fe3O4@PEG-SO3H catalyst required
has been optimized next. The maximum yield of
1-(benzothiazolylamino)phenyl methyl-2-naphthol 4a
(95%) was obtained when the reaction was performed with
10 mg of catalyst under ethanol reflux conditions with a
reaction time of 15 min (entry 5, Table 1). Further increase of
the amount of catalyst gave no pronounced enhancement
of the yield.
The effect of different protic and aprotic solvents such
as EtOH, H2O, CHCl3, DMF, CH3CN as well as solvent-free
conditions were studied next (Table 1, entries 8–12). The
results suggest that good product yields are obtained in
ethanol under reflux conditions. However, it should be
mentioned that the condensation reaction is not effective at
room temperature (entry 7).
Figure 1: EDX spectrum of Fe3O4@PEG-SO3H.
Figure 3: The magnetization curve of (a) Fe3O4 and (b)
Figure 2: SEM image of core–shell Fe3O4@PEG-SO3H.
Fe3O4@PEG-SO3H.

388
Y. Mardani et al.: Synthesis of benzothiazole derivatives
Table : Optimization of synthesis of -(benzothiazolylamino)phenyl methyl--naphthol a.
N
S
H
N
O
OH
OH
S
H
NH2
N
1
2
5a
3
Entry
Catalyst
Reaction conditions
Time (min)
Yield (%)a

None
Nano-FeO ( mg)
PEG-SOH ( mg)
EtOH, reflux
EtOH, reflux
EtOH, reflux
EtOH, reflux
EtOH, reflux
EtOH, reflux
EtOH, r.t.
HO, reflux
CHCl, reflux
DMF, reflux








Trace









FeO@PEG-SOH ( mg)
FeO@PEG-SOH ( mg)
FeO@PEG-SOH ( mg)
FeO@PEG-SOH ( mg)
FeO@PEG-SOH ( mg)
FeO@PEG-SOH ( mg)
FeO@PEG-SOH ( mg)
FeO@PEG-SOH ( mg)
FeO@PEG-SOH ( mg)

















CHCN, reflux
Solvent-free,  °C
aBenzaldehyde ( mmol), -aminobenzothiazole ( mmol), -naphthol ( mmol) and solvent ( mL).
In order to study the applicability of the three-
The resulting optimized protocol can be summarized
component reaction catalyzed by Fe3O4@PEG-SO3H as follows. The reaction can be carried out in a simple
various aromatic aldehydes were used. The resulting manner, just by mixing the three components and
products are outlined in Table 2. Different aldehydes Fe3O4@PEG-SO3H in EtOH and heating the mixture at
with electron-donating or electron-withdrawing groups reflux. The products are formed in excellent yield within
were investigated. The condensation reaction proceeds 10–15 min followed by a simple work-up. After completion
efficiently under mild conditions to give the correspond- of the reactions the catalyst is easily separated by an
ing 1-(benzothiazolylamino)aryl methyl-2-naphthols external magnet. Recyclability and durability are crucial
5a–l in excellent yield in short times (10–15 min) in the criteria in designing an efficient catalytic system from the
presence of 10 mg of Fe3O4@PEG-SO3H nanocomposite. viewpoint of green chemistry. The recovered magnetic
As can be seen, the nature of the aromatic substituents nanoparticles were washed several times with ethanol,
on the ring does not strongly effect the reaction in terms dried at 80 °C under reduced pressure for 2 h and reused in
of yields under the selected conditions. Moreover, the the next cycle. Figure 4 indicates that the catalyst could be
condensation of polycyclic aromatic aldehydes such reused with good activity even after eight consecutive
as 1-naphthaldehyde with 2-aminobenzothiazole, and cycles.
2-naphthol can also be carried out successfully and
These good results encouraged us to extend our
the corresponding 1-(benzothiazolylamino)aryl methyl- study to other organic transformations. Accordingly, we
2-naphthol 5k was obtained in high yield. The direct attempted the efficient synthesis of 3-benzothiazolyl
three-component reaction also works well with 2,3-dihydroquinazolinones. With the optimized condi-
thiophene-2-carbaldehyde as a heterocyclic aldehyde tions in hand (10 mg of Fe3O4@PEG-SO3H nanoparticles,
(Table 2, 5l). All of the products are known and were ethanol, reflux), the one-pot three-component reaction
characterized using melting point, IR and NMR spectra of 2-aminobenzothiazole, isatoic anhydride and alde-
[27–31] (see Supplementary material available online).
hydes was carried out to afford 3-benzothiazolyl 2,

Y. Mardani et al.: Synthesis of benzothiazole derivatives
389
Table : Synthesis of -(benzothiazolylamino)aryl methyl--naphthols in the presence of FeO@PEG-SOH nanocomposite.
N
S
N
S
Br
Cl
N
S
N
S
NH
OH
NH
OH
NH
OH
NH
OH
O2N
5c
5b
5d
5a
Time:  min
Yield: %
Time:  min
Yield: %
Time:  min
Yield: %
Time:  min
Yield: %
M. p.: – °C
Ref. []
M. p.: – °C
Ref. []
M. p.: – °C
Ref. []
M. p.: – °C
Ref. []
Br
N
S
O2N
N
S
Cl
N
S
N
S
NH
OH
NH
OH
NH
OH
Cl
NH
OH
Cl
5h
5e
5f
5g
Time:  min
Yield: %
Time:  min
Yield: %
Time:  min
Yield: %
Time:  min
Yield: %
M. p.: – °C
Ref. []
M. p.: – °C
Ref. []
M. p.: – °C
Ref. []
M. p.: – °C
Ref. []
N
S
H3CO
N
S
H3C
N
S
N
S
NH
OH
NH
OH
NH
OH
NH
OH
S
5i
5j
5k
5l
Time:  min
Yield: %
Time:  min
Yield: %
Time:  min
Yield: %
Time:  min
Yield: %
M. p.: – °C
Ref. []
M. p.: – °C
Ref. []
M. p.: – °C
Ref. []
M. p.: – °C
Ref. []

390
Y. Mardani et al.: Synthesis of benzothiazole derivatives
Based on a literature survey [38–42], a plausible
mechanism for the synthesis of 3‐benzothiazolyl
2,3-dihydroquinazolinones is shown in Scheme 3. The role
of the catalyst is believed that the acid groups distributed
on the surface of the Fe3O4@PEG-SO3H nanoparticles
activate the carbonyl groups of isatoic anhydride and the
aldehydes. The first step involves the condensation of the
activated isatoic anhydride 4 with 2-aminobenzothiazole 2
followed by decarboxylation to give the corresponding
2-aminobenzamide under the effect of the nanocatalyst.
Afterwards, the activated aldehyde 1 reacts with the amino
group of 2-aminobenzamide to the imine, which undergoes
cyclization and tautomerization to furnish the desired
products 6.
The utility of the current work in comparison to
previous studies for the synthesis of 1-(benzothiazoly-
lamino)phenyl methyl-2-naphthol 5a and 3-(2ʹ-benzo-
thiazolyl)-2-phenyl-2,3-dihydroquinazolin-4(1H)-one 6a
is summarized in Table 4. The data indicate that the
Fe3O4@PEG-SO3H appears to catalyze the reaction more
effectively than a number of other reported catalysts,
particularly in terms of the reaction time and the ob-
tained yields. Moreover, this synthetic protocol avoids
disadvantages of the other procedures, such as difficult
preparation of the catalyst, expensive reagents, and
tedious separation of the catalyst.
Figure 4: Reusability of catalyst for the synthesis of 5a.
3-dihydroquinazolinones (Table 3). Substrates with
various functional groups tolerated the reaction condi-
tions and resulted in good to excellent yields in rather
short reaction times.
As can be seen in Table 3, hetero-aromatic aldehydes
(such as pyridine-2-carbaldehyde, entry 10) afford the cor-
responding dihydroquinazolinones without by-products.
The reaction is compatible with aliphatic aldehydes such
as acetaldehyde and heptanal (entries 11, 12, Table 3).
Table : Synthesis of -benzothiazolyl ,-dihydroquinazolinones in the presence of FeO@PEG-SOH
Entry
R
Product
Time (min)
Yield (%)
M. p. (°C)
Ref.

CH
-ClCH
a
b
c
d
e
f
g
h
i














–
–
–
–
–
–
–
–
–
–
–
–
[]
[]
[]
[]
[]
[]
[]
[]
[]
[]
[]
[]


-CHCH
-CHOCH
-BrCH
-NOCH
-BrCH
,-ClCH
,-(CHO)CH
-Pyridyl
CH



















j
k
l
CH(CH)

Y. Mardani et al.: Synthesis of benzothiazole derivatives
391
Scheme 3: Proposed mechanism for the
synthesis of 3‐benzothiazolyl
2,3-dihydroquinazolinones.
Table : Comparison of the efficiency of FeO@PEG-SOH with other reported catalysts.
Entry
Catalyst
Reaction conditions
Product
Time (min)
Yield (%)
Ref.

FeO@SiO-ZrCl ( mg)
Solvent‐free
 °C
Solvent‐free
 °C
Solvent‐free
 °C
Solvent‐free
 °C
a


[]



Maltose ( mol.%)
a
a
a





[]
[]
[]
[(CH)SOHMIM][HSO] ( mol.%)
Rice husk ash-[pmim]HSO ( mol.%)




FeO@PEG-SOH ( mg)
[bmim]Br (. g)
Al(HPO) (. g,  mol.%)
Ethanol, reflux
Solvent‐free,  °C
Solvent‐free
 °C
Solvent‐free
 °C
a
a
a






This work
[]
[]

[n-BuPCHC(O)OH]+[FeClBr]– ( mol.%)
Ionic liquid-functionalized SBA- (. g)
FeO@PEG-SOH ( mg)
a
a
a






[]

Solvent‐free
 °C
[]

Ethanol, reflux
This work
include green conditions, operational simplicity, mini-
mizing production of chemical waste, shorter reaction
times and good to high yields. Mild reaction conditions,
the broad substrate scope, short reaction times, easy
performance and good yields make this method versatile
and showing its practical synthetic value. The excellent
catalytic performance, thermal stability and easy sepa-
ration and reusability of the catalyst make this green and
eco-friendly method a superior alternative to existing
protocols.
3 Conclusion
In conclusion, nano-magnetite-supported sulfated poly-
ethylene glycol (Fe3O4@PEG-SO3H) as a magnetically
recoverable heterogeneous catalyst has been used for the
one-pot, three-component reaction of 2-aminobenzo-
thiazole, aldehydes and 2-naphthol/isatoic anhydride
resulting in efficient formation of 1-(benzothiazolyla-
mino)arylmethyl-2-naphthol or dihydroquinazolinones
derivatives. The significant features of this method

392
Y. Mardani et al.: Synthesis of benzothiazole derivatives
the reaction was complete as monitored by TLC. After completion of
the reaction, the mixture was cooled to room temperature, diluted
with ethanol and the catalyst was separated by an external magnet.
The residue was recrystallized from aqueous ethanol to afford the
pure product 5. See Supplementary material available online for the
spectral data of compounds 5.
The recovered Fe3O4@PEG-SO3H nanoparticles were washed
several times with ethanol, dried at 80 °C under reduced pressure for
2 h and reused for the next cycle.
4 Experimental
4.1 Materials and apparatus
All starting materials and reagents were commercially available and
used without further purification. Thin-layer chromatography (TLC)
was performed on aluminum plates pre-coated with Merck silica gel.
Melting points were measured by an Electrothermal type 9100
melting point apparatus (Electrothermal Engineering Ltd, U.K.). The
infrared (IR) spectra were recorded on a Bruker Tensor 27 FTIR
spectrophotometer as KBr disks. NMR spectra were determined on
a Bruker AC 500 MHz instrument as DMSO-d6 solutions at room
temperature. The EDX measurements were performed with a SAMx
analyzer (France). SEM images were taken with a MIRA3-TESCAN
(Germany). The magnetic properties of nanoparticles were measured
with a VSM (BHV-55, Riken, Japan).
4.5 General procedure for the synthesis of 3-
(2ʹ-benzothiazolyl)-2,3-dihydroquinazolin-4(1H)-
one derivatives 6a–l
A mixture of the aldehyde (1 mmol), 2-aminobenzothiazole (1 mmol),
isatoic anhydride (1 mmol) and Fe3O4@PEG-SO3H(10 mg) in ethanol
(5 mL) was stirred under reflux for the appropriate times indicated in
Table 3. Upon completion of the reaction as monitored by TLC, the
reaction mixture was cooled to room temperature, diluted with
ethanol and the catalyst was separated from the reaction medium with
an external magnet. The crude product was recrystallized from
ethanol to provide the pure product 6. See Supplementary material
available online for the spectral data of compounds 6.
4.2 Preparation of Fe3O4 nanoparticles
Fe3O4 nanoparticles were synthesized by the coprecipitation method
as reported in Ref. [12]. Initially, a mixture of FeCl2·4H2O (2 g), FeCl3·
6H2O (5.2 g) was dissolved in 25 mL of deionized water containing
0.85 mL of HCl. Then, it was added dropwise to a solution of sodium
hydroxide (NaOH, 15 g) in 25 mL of deionized water with vigorous
stirring to make a black solid product. The resultant mixture was
heated in a water bath for 4 h at 80 °C. The black solid magnetic Fe3O4
nanoparticles were isolated using an external magnet and washed
with deionized water and ethanol three times and then dried at 80 °C
for 6 h.
5 Supporting information
Spectral data of the products 5a–l and 6a–l are given as
supplementary material available online (https://doi.org/
10.1515/znb-2021-0010).
4.3 Preparation of Fe3O4@PEG-SO3H nanocomposite
Author contributions: All the authors have accepted
responsibility for the entire content of this submitted
manuscript and approved submission.
Research funding: None declared.
Conflict of interest statement: The authors declare no
conflicts of interest regarding this article.
Fe3O4 nanoparticles (1 g) were dispersed in 100 mL of deionized wa-
ter in an ultrasonic bath for 20 min. Then polyethylene glycol
(PEG400, 1 g) was added, and the mixture was stirred overnight at
room temperature. The obtained Fe3O4@PEG nanoparticles were
isolated as a dark solid using an external magnet, washed several
times with deionized water and ethanol and dried at 80 °C in an oven.
The Fe3O4@PEG nanoparticles were sulfated using chlor-
osulfonic acid (ClSO3H) [14]. Fe3O4@PEG (1 g) was added to a flask
equipped with a dropping funnel containing the chlorosulfonic
acid (0.5 mL). The mixture was dispersed in dry CH2Cl2 (50 mL) in an
ultrasonic bath for 20 min. Subsequently, chlorosulfonic acid (0.5 mL)
was added dropwise over a period of 30 min at room temperature.
Upon completion of the addition, the mixture was stirred for 6 h at
room temperature. The resulting nanocomposite was separated from
the suspension by an external magnet, washed several times with
CH2Cl2 and diethyl ether and then dried to afford Fe3O4@PEG-SO3H
(Scheme 2).
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Supplementary Material: The online version of this article offers
supplementary material (https://doi.org/10.1515/znb-2021-0010).