Eco-friendly synthesis of benzoxazepine and malonamide derivatives in aqueous media

Article abstract of DOI:10.1002/aoc.3463

A special, efficient and reusable heterogeneous catalytic system is reported for the one-pot three-component synthesis of a series of malonamide and 2,3,4,5-tetrahydrobenzo[b][1,4]oxazepine derivatives in the presence of a heterogeneous material composed of MCM-48/H₅PW₁₀V₂O₄₀ in aqueous media and at room temperature. The products were identified using physical data (melting points) by comparison with those reported in the literature. Also, the structures of the new compounds were characterized by means of infrared, ¹H NMR, ¹³C NMR and CHN analyses. Copyright

Full text of DOI:10.1002/aoc.3463

Full paper
Received: 30 November 2015
Revised: 23 January 2016
Accepted: 31 January 2016
Published online in Wiley Online Library: 17 March 2016
(wileyonlinelibrary.com) DOI 10.1002/aoc.3463
Eco-friendly synthesis of benzoxazepine and
malonamide derivatives in aqueous media
Mirzaagha Babazadeh*, Rahim Hosseinzadeh-Khanmiri and Solmaz Zakhireh
A special, efficient and reusable heterogeneous catalytic system is reported for the one-pot three-component synthesis of a series
of malonamide and 2,3,4,5-tetrahydrobenzo[b][1,4]oxazepine derivatives in the presence of a heterogeneous material composed
of MCM-48/H5PW10V2O40 in aqueous media and at room temperature. The products were identified using physical data (melting
points) by comparison with those reported in the literature. Also, the structures of the new compounds were characterized by
means of infrared, 1H NMR, 13C NMR and CHN analyses. Copyright © 2016 John Wiley & Sons, Ltd.
Additional supporting information may be found in the online version of this article at the publisher’s web site.
Keywords: MCM-48/H5PW10V2O40; malonamide; 2,3,4,5-tetrahydrobenzo[b][1,4] oxazepine; green chemistry
extractants,[15] poncoments in peptidomimetic substances,[16]
Introduction
excellent ionophores,[17] bidentate chelates and monomers in
the nylon family.[18]
Shaabani et al. have reported novel routes for the synthesis of
Heterocyclic chemistry is one of the most significant branches in
organic chemistry.[1] The increasing applications of catalyst-based
benzoxazepine and malonamide derivatives in the absence of cat-
alyst in CH2Cl2 as solvent and long reaction times using isocyanide-
based multicomponent reactions.[19] Herein, we report a highly
versatile, eco-friendly and efficient one-pot three-component het-
erogeneous protocol for the synthesis of benzoxazepine and
malonamide derivatives in the presence of a catalytic amount of
MCM-48/H5PW 10V2O40 in water as solvent at room temperature
(Scheme 1).
synthetic procedures in emerging industries have been favoured
by the continuous innovations observed over the last decade for
various catalytic processes.[2] Catalysts based on heteropolyacids
(HPAs) and related compounds, especially those comprising the
strongest Keggin-type HPAs, represent a field in which new and
promising developments are being achieved in both technology
and academia.[3] The main disadvantages of HPAs lie in their
water-solubility, low surface area, recycling and difficult recovery
which always limit their practical applications.[4]\ Heterogeneous
catalysts offer high atom efficiency, higher surface area, easy prod-
uct purification, lower coordinating sites, and simple and efficient
recovery and reusability.
Results and discussion
Low-angle powder X-ray diffraction (XRD) was used to study the
calcined mesoporous structure of MCM-48. This compound shows
an intense peak assigned to reflections at (100) and two low-
intensity peaks at (110) and (200), which correspond to a significant
degree of long-range ordering in the structure and well-ordered
hexagonal pore system. The (100) reflection of MCM-48 is still
observed after loading with H5PW10V2O40 (Fig. 1(a)). However,
modification of MCM-48 with H5PW 10V2O40 results in a loss of
crystalline order, as is evidenced by a significant decrease in diffrac-
tion intensities.
This observation confirms that the mesoporous structure of
MCM-48 remains almost unchanged upon H5PW 10V2O40 loading.
According to scanning electron microscopy (SEM) images (Figs. 1
(b) and (c)), the morphology of MCM-48 surface tends to be rougher
after immobilization of H5PW10V2O40, which confirms the success-
ful loading of the HPA on MCM-48.
MCM-48 is a class of mesoporous silica tube-like materials with
consistent-sized three-dimensional mesoporous structure. This
combination has led to them being of interest as sorbents and solid
supports in catalysis.[5]
The benzo[b][1,4]oxazepine derivatives show various forms of
bioactivity such as allergic bronchitis, treating of bronchial
asthma,[6] anxiolytic activity, antidepressive,[7] antihistaminic and
antiserotoninergic[8] effects, anticancer activity against breast can-
cer cells[9] and progesterone receptor agonists.[10] The common
methods for the syntheses of benzo[b][1,4]oxazepines involve N-
alkylation of N-methylanthranilic acid with an α-chloroacid[11] and
N-alkylation of 2-aminobenzhydrol, in the presence of ethanolic
sodium solution.[12] Also, a single-step synthesis of benzoxazepines
has been reported in which N-tosyl-1,3-aminoalcohols were treated
with bromoethylsulfonium salts, through vinyl sulfonium salt
formation, which upon intramolecular cyclization provide 1,4-
benzoxazepines.[13]
Malonamide derivatives are some of the most important goals
in synthetic chemistry because they display a number of inter-
esting properties in various fields.[14] These compounds have
some important applications such as effective liquid–liquid
*
Correspondence to: Mirzaagha Babazadeh, Department of Chemistry, Tabriz
Branch, Islamic Azad University, Tabriz, Iran. E-mail: babazadeh@iaut.ac.ir
Department of Chemistry, Tabriz Branch, Islamic Azad University, Tabriz, Iran
Appl. Organometal. Chem. 2016, 30, 514–518
Copyright © 2016 John Wiley & Sons, Ltd.

MCM-48/H5PW10V2O40+oxazepine and malonamide derivatives
A comparative study was carried out using the reaction of
one or two equivalents of 2-amino-4-methylphenol with
cyclohexylisocyanide and Meldrum’s acid as a model system
with various vanadium-substituted tungsten heteropolyacid
(HPW) catalysts, solvents and catalyst quantities.
In a pilot experiment, the catalytic activity of H5PW10V2O40 was
compared with that of other vanadium-substituted HPW catalysts
in the preparation of compounds 4a and 5a (Table 1). The results
indicate that the substitution of one and two vanadium atoms
instead of W(VI) and Mo(VI) in H3PM 12O40 leads to an enhance-
ment in the catalytic activity of HPW. Also, H5PW10V2O40 is a little
more active than H5PMo10V2O40. The catalytic activity of
H5PW10V2O40 could be due to coordination geometry of the
metaloxo complex species and the far distance of the vanadyl
oxygen double bond from the heteropolyanion. This geometry
exposes the vanadyl species at the surface of the heteropolyanion,
which might be involved in the catalytic cycle. This consideration
has to be taken into account for the assessment of the catalytic
activity of H5PW10V2O40 and the role of vanadium in the catalytic
system.[20]
Scheme 1. Synthesis of 2,3,4,5-tetrahydrobenzo[b][1,4]oxazepine and
malonamide derivatives.
The effect of solvent was also examined for the reaction men-
tioned above, and the results indicate that the solvent has an effect
on the reaction (Table 2). Performing the reaction of one or two
equivalents of 2-amino-4-methylphenol with cyclohexylisocyanide
and Meldrum’s acid in various protic and aprotic solvents reveals
that polar solvents are more efficient than nonpolar solvents, and
preferentially water as the reaction solvent (Table 2).
According to expectations, the catalytic efficiency should be in-
fluenced by the amount of catalyst. Thus, a set of experiments
was conducted using various amounts of MCM-48/H5PW 10V2O40
in the reaction of one or two equivalents of 2-amino-4-
methylphenol with cyclohexylisocyanide and Meldrum’s acid in
water as solvent at room temperature (Table 3). The optimum
Table 1. Effect of type of vanadium-substituted HPA catalyst in the
synthesis of 2,3,4,5-tetrahydrobenzo[b][1,4]oxazepine and malonamide
derivativesa
HPA
Amount
(mol%)
Time
(min)
Yield of
Yield of
4a (%)b
5a (%)b
H5PW10V2O40
H7SiW9V3O40
H5PMo10V2O40
H5SiW9Mo2VO 40
HPA/MCM-48
CuSO4
0.5
120
120
120
120
120
120
120
78
70
77
79
91
39
53
82
72
80
81
95
44
58
0.5
0.5
0.5
0.05 g
CuSO4/SiO2
aReaction conditions: 2-amino-4-methylphenol (1, 1.00 or 2.00 mmol),
cyclohexylisocyanide (2a, 1.00 mmol), Meldrum’s acid (3, 1.00
mmol) and HPA in water as solvent at room temperature.
bIsolated yields.
Figure 1. (a) Low-angle XRD patterns of calcined MCM-48 and MCM-48/
H5PW10V2O40. SEM images of (b) MCM-48 and (c) MCM-48/H5PW10V2O40
.
Appl. Organometal. Chem. 2016, 30, 514–518
Copyright © 2016 John Wiley & Sons, Ltd.
wileyonlinelibrary.com/journal/aoc

M. Babazadeh, R. Hosseinzadeh-Khanmiri and S. Zakhireh
Table 2. Influence of solvent on yield of 4a and 5aa
spectroscopy. As can be seen in Fig. 2, the structure of the recycled
catalyst does not change and a very slight decrease in the reaction
yield may be due to the covering of the surface of catalyst by impu-
rities. Therefore, MCM-48/H5PW10V2O40 can be considered as a
promising material for the adsorption of HPAs for catalytic
purposes.
Finally, a reasonable mechanism is proposed for the synthesis of
4a–h by means of the HPA H5PW10V2O40 immobilized on MCM-48
(Scheme 2). First, Meldrum’s acid 3 is protonated by MCM-48/H-
5PW10V2O40 and the intermediate 7 is formed from condensation
between molecules of 1 and 3 and releasing a molecule of acetone.
Then, intermediate 8 is obtained from the reaction of intermediate
7 with acetone undergoing a Knoevenagel condensation. On the
basis of the well-established chemistry of reactions of isocyanides,
intermediate 9 is formed by nucleophilic attack of isocyanide 2
on intermediate 8, followed by nucleophilic attack of an H2O mol-
ecule on the activated nitrilium moiety to produce compound 10.
Finally, tautomerization of compound 10 leads to the formation
of products 4a–h, as shown in Scheme 2.[21]
Entry
Solvent
Time
(min)
Yield of
Yield of
4a (%)b
5a (%)b
1
2
3
4
5
6
7
Water
120
120
120
120
120
120
120
86
93
89
38
87
85
79
91
95
89
46
92
88
81
Ethanol
Acetonitrile
Toluene
Dichloromethane
Chloroform
Tetrahydrofuran
aReaction conditions: 2-amino-4-methylphenol (1, 1.00 mmol or 2.00
mmol), cyclohexylisocyanide (2a, 1.00 mmol), Meldrum’s acid (3,
1.00 mmol) and MCM-48/H 5PW10V2O40 (0.10 g), solvent (3.00 ml),
at room temperature.
bIsolated yields.
amount of catalyst is 0.05 g resulting in 86 and 91% yields of com-
pounds 4a and 5a, respectively. Lower amounts of catalyst result in
a decrease in the efficacy of the reaction, while higher amounts lead
to complete conversion in the same reaction time.
Conclusions
The generality of the process was studied using a range of
isocyanides and 2-aminophenol derivatives for the synthesis of
4a–h and 5a–h in the presence of MCM-48/H5PW10V2O40
(Table 4).
Recovery/reuse is one of the important properties of catalysts. It
is observed that the MCM-48/H5PW10V2O40 catalytic activity stays
almost unaltered even after four recovery/reutilization cycles.
Therefore, the catalyst was recovered from the reaction between
2-amino-4-methylphenol, Meldrum’s acid and cyclohexylisocyanide
by filtration. Thereby, the stability of MCM-48/H5PW10V2O40 after
successive cycles of recovery/reuse was assessed (Table 5).
The changes in the morphology of MCM-48/H5PW10V2O40 after
use were determined using XRD and Fourier transform infrared
A highly efficient and environmentally friendly method is presented
for the synthesis of 2,3,4,5-tetrahydrobenzo[b][1,4]oxazepine and
malonamide derivatives in the presence of a catalytic amount of
MCM-48/H5PW 10V2O40 in aqueous media and at room tempera-
ture which led to excellent yields. Easy workup, low cost, short reac-
tion time, easy recyclability of the catalyst with no loss in its activity
and using mild reaction condition are some advantages of the
method presented. The experimental procedure for this reaction
is remarkably simple and requires no toxic organic solvents or inert
atmosphere.
Experimental
Preparation of H5PW10V2O40Á30H2O[22]
Table 3. Effect of amount of MCM-48/H5PW10V2O40 on reaction of 2-
amino-4-methylphenol with cyclohexylisocyanide and Meldrum’s acida
NaVO 3 (6.1 g, 50 mmol) was dissolved in 50 ml of boiling water
and mixed with Na 2HPO 4 (1.78 g, 12.5 mmol). After the resulting
solution was cooled to room temperature, concentrated sulfuric
acid (2.5 ml, 17 M, 43 mmol) was added to give a red solution. So-
dium tungstate dehydrate (Na 2WO 4Á2H 2O, 41.2 g, 125 mmol)
was dissolved in 50 ml of water and was added to the red solu-
tion with vigorous stirring, followed by the slow addition of con-
centrated sulfuric acid (21 ml, 17 M, 357 mmol).[21] Extraction of
the solution with diethyl ether (160 ml), foll\owed by evapora-
tion in air, afforded H 5PW 10V 2O 40 as a crystalline, orange-red
solid (yield, 75%).
Entry
Catalyst
amount (g)
Time
(min)
Yield of
Yield of
4a (%)b
5a (%)b
1
2
3
4
5
0.01
0.03
0.05
0.07
0.1
120
120
120
120
120
30
68
86
95
97
25
60
91
92
96
Synthesis of MCM-48 using Hydrothermal Method[23]
n-Hexadecyltrimethylammonium bromide (C 16H 33(CH 3) 3NBr,
template) was dissolved in deionized water, and sodium hydrox-
ide and tetraethoxysilane (TEOS) were added. The molar compo-
sition of the gel was 1 M TEOS/0.25 M Na 2O/0.65 M C 16H 33
(CH 3) 3NBr/62 M H 2O. The solution was stirred for about 1 h,
charged into a polypropylene bottle and then heated at 383 K
for 4 days. The product was filtered, washed with water and cal-
cined at 823 K for 8 h.
aReaction conditions: 2-amino-4-methylphenol (1, 1.00 mmol or 2.00
mmol), cyclohexylisocyanide (2a, 1.00 mmol), Meldrum’s acid (3,
1.00 mmol) and MCM-48/H 5PW10V2O40 in water as solvent at
room temperature.
bIsolated yields.
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Copyright © 2016 John Wiley & Sons, Ltd.
Appl. Organometal. Chem. 2016, 30, 514–518

MCM-48/H5PW10V2O40+oxazepine and malonamide derivatives
Table 4. Synthesis of 2,3,4,5-tetrahydrobenzo[b][1,4]oxazepine derivatives (4a–h) and malonamide derivatives (5a–h) in the presence of MCM-48/
a
H5PW10V2O40
Product
R1
R2
Time (min)
Yield (%)b
M.p. (°C)
Reported
Found
4a
4b
4c
4d
4e
4f
c-Hex
4-CH3
4-Cl
H
120
140
160
130
140
150
130
110
120
130
160
110
140
140
140
130
86
85
83
88
87
90
91
92
91
90
89
88
85
89
84
82
249–251
228–230
152–153
227–229
213–215
170–172
220–223
264–267
221–223
227–229
243–245
233–235
172–174
150–153
245–247
215–218
—
c-Hex
228–230[23a]
151–153[23a]
227–229[23a]
214–216[23a]
169–171[23a]
—
t-Bu
t-Bu
4-CH3
H
1,1,3,3-Tetramethylbutyl
c-Hex
H
4g
4h
5a
5b
5c
5d
5e
5f
2,6-Dimethylphenyl
2,6-Dimethylphenyl
c-Hex
H
4-CH3
4-CH3
4-CH3
H
—
220–222[23a]
227–229[23a]
242–244[23a]
233–235[23a]
172–174[23a]
151–153[23a]
—
1,1,3,3-Tetramethylbutyl
2,6-Dimethylphenyl
2,6-Dimethylphenyl
4-Methylphenylsulfonyl
4-Methylphenylsulfonyl
c-Hex
4-CH3
H
4-CH 3
4-Cl
4-CH3
5g
5h
t-Bu
—
aReaction conditions: 2-amino-4-methylphenol (1, 1.00 mmol or 2.00 mmol), cyclohexylisocyanide (2, 1.00 mmol), Meldrum’s acid (3, 1.00 mmol) and
MCM-48/H5PW10V2O40 in water as solvent at room temperature.
bIsolated yields.
Table 5. Reusability of the catalyst for the synthesis of 4a and 5aa
Compound Cycle
0
First
Second Third Fourth
4a
5a
Time (min)
120
86
120
84
120
82
120
81
120
79
Yield (%)b
Time (min)
Yield (%)b
120
91
120
90
120
88
120
86
120
84
aReaction conditions: 2-amino-4-methylphenol (1, 1.00 mmol or 2.00
mmol), cyclohexylisocyanide (2, 1.00 mmol), Meldrum’s acid (3,
1.00 mmol) and MCM-48/H 5PW10V2O40 in water as solvent at
room temperature.
bIsolated yields.
[24]
Preparation of MCM-48/H5PW10V2O40
MCM-48/H5PW10V2O40 was prepared by mixing dried MCM-48
(2 g) with a solution of H5PW10V2O40Á30H2O (0.50 g) in the min-
imum amount of deionized water. The resulting mixture was
stirred continuously with a magnetic stirrer for 17 h. After
removal of water, the solid powder was first dried at 100°C for
6–7 h, then dried at 150°C for 3 h.
Figure 2. (a) XRD pattern and (b) infrared spectra. A: MCM-48/
H5PW10V2O40 before reaction; B: MCM-48/H5PW10V2O40 after recycling.
General procedure for preparation of malonamide derivatives
4a–h
An intimate mixture isocyanide derivatives (1.00 mmol), Meldrum’s
acid (1.00 mmol), 2-aminophenol derivatives (1.00 mmol) and
MCM-48/H5PW10V2O40 (0.05 g) was reacted in water (3.00 ml) as
solvent at room temperature for appropriate times. After comple-
tion of reaction, as indicated by TLC (ethyl acetate–n-hexane, 1:1),
ethanol (3 ml) was added to the reaction mixture which was then
heated at 60°C. Catalyst was removed by filtration and the filtrate
solution was crystallized to give pure crystalline products 4a–h.
General procedure for preparation of 2,3,4,5-tetrahydrobenzo
[b][1,4]oxazepines 5a–h
An intimate mixture of isocyanide derivatives (1.00 mmol),
Meldrum’s acid (1.00 mmol), 2-aminophenol derivatives (2.00
mmol) and MCM-48/H 5PW 10V 2O 40 (0.05 g) was reacted in water
(3.00 ml) as solvent at room temperature for appropriate times
After completion of reaction, as indicated by TLC (ethyl
Appl. Organometal. Chem. 2016, 30, 514–518
Copyright © 2016 John Wiley & Sons, Ltd.
wileyonlinelibrary.com/journal/aoc

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Scheme 2. Possible mechanism for the preparation of products 4a–h
catalysed by MCM-48/H5PW10V2O40.
acetate–n-hexane, 1:1), ethanol (3 ml) was added to the reaction
mixture which was then heated at 60°C. Catalyst was removed by
filtration and the filtrate solution was crystallized to give pure
crystalline products 5a–h.
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Appl. Organometal. Chem. 2016, 30, 514–518