FULL PAPER
Palladium(II) Immobilized Onto the Glucose Functionalized
Magnetic Nanoparticle as a New and Efficient Catalyst for
the One‐pot Synthesis of Benzoxazoles
Firouz Matloubi Moghaddam | Vahid Saberi | Sepideh Kalhor | Nazila Veisi
Laboratory of Organic Synthesis and
Natural Products, Department of
Chemistry, Sharif University of
Technology, Tehran, Iran
Correspondence
Firouz Matloubi Moghaddam, Laboratory
of Organic Synthesis and Natural
Products, Department of Chemistry, Sharif
University of Technology, Azadi Street, PO
Box 111559516, Tehran, Iran
Email: matloubi@sharif.edu
Funding information
Sharif University of Technology (SUT)
Palladium(II) have been immobilized into the nano magnetic Fe
3
O
4
which was
functionalized with glucose in order to achieve a one‐pot synthesis of 2‐
substituted benzoxazole derivatives with high yields in the diverse range of
organic solvents. The nano catalyst is highly dispersive in polar solvents and
can be easily recovered and reused for 6 runs without significant loss of its
activity. Finally, the catalyst was fully characterized by FT‐IR, TGA, CHN,
SEM, EDX and atomic absorption spectroscopy.
KEYWORDS
benzoxazole, dispersive magnetic nanoparticle, glucose, palladium
1 | INTRODUCTION
2‐Arylbenzoxazoles are important class of heterocyclic
compounds which have been widely used in pharmaceuti-
cal industry and medicinal chemistry.
[1]
so far, broad range
of application of these structures such as HIV‐reverse tran-
scriptase inhibitors
[2]
, anticancer drugs
[3]
, cathepsin S
inhibitors,
[4]
5‐HT
3
receptor partial agonists,
[5]
DNA topo-
isomerase inhibitors,
[6]
peroxisomes proliferator‐activated
receptor γ (PPAR‐γ) antagonists,
[7]
and estrogen receptor‐β
agonists have been studied.
[8]
In addition, they have also
application in the treatment of stroke, depression, immune
diseases, and cerebral ischemia.
[9]
Moreover, most of the benzoxazole containing com-
pounds exhibit biological profile. These compounds can
interact with target protein because of their structural
properties. It is demonstrated that O and N atoms of
benzoxazole which are able to form hydrogen‐bond can
affect the acceptors and the aromatic ring of benzoxazole
derivatives which have this potential to generate both π‐π
stacking and π‐cation interactions with the host molecule
might be essential for bioactivity of these structures.
[10]
The benzoxazole scaffold are also present in a
number of natural products such as salvianen and
pseudosalvianen.
[11,12]
According to the points discussed above, many
researches focusing on the biological activity of
benzoxazole derivatives against cancer cell lines such as
MCF‐7 and HepG2 essentially.
[13]
Benzoxazoles motifs
have potential use in the synthesis of dyes because of
their fluorescent nature
[14]
and also it is indicated that
the benzoxazole based compounds have effective use
in the synthesis of various photochromic materials
[15]
,
mesogenic polymers
[16]
and liquid crystals
[17,18]
Due to the importance of 2‐substituted benzoxazole
derivatives, many studies have been focused on the syn-
thesis and transformations of trans‐2‐[β‐(2‐Furyl)vinyl]
benzoxazole.
[19]
In order to synthesize benzoxazole derivatives in the
past years, different methods have been developed, such
as cyclization of 2‐aminophenols with aldehydes and
carboxylic acids.
[20]
Noticeably, the catalytic construction of this frame-
work has become an ideal platform to develop and
testify new catalysts including homogeneous catalysts such
as ruthenium/iridium complexes, Pd(OAc)
2
, RuCl
3
, Ortho‐
iodoxybenzoicacid (IBX), 4‐methoxy‐TEMPO (2,2,6,6‐
tetramethyl‐piperidyl‐1‐oxy), FeCl
3
, CuCl
2
, and NaCN.
[21]
On the other hand, most of the reactions catalyzed by
homogeneous catalysts suffer from contamination of
Received: 16 October 2017 Revised: 28 November 2017 Accepted: 28 November 2017
DOI: 10.1002/aoc.4240
Appl Organometal Chem. 2018;e4240.
https://doi.org/10.1002/aoc.4240
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