Mn(pbdo)2Cl2/MCM-41 as a green catalyst in multi-component syntheses of some heterocycles

Article abstract of DOI:10.1007/s11164-015-2191-2

Mn(pbdo)₂Cl₂/MCM-41 as a solid acid catalyst was used as an efficient, green, reusable catalyst for an improved and rapid one-pot multi-component reaction in the synthesis of bis-(4-hydroxycoumarin), bis(indolyl)methane, and 4H-benzo

Full text of DOI:10.1007/s11164-015-2191-2

Res Chem Intermed
DOI 10.1007/s11164-015-2191-2
Mn(pbdo) Cl /MCM-41 as a green catalyst in multi-
2
2
component syntheses of some heterocycles
1
1
Majid M. Heravi
•
Mansoureh Daraie
Received: 8 May 2015 / Accepted: 24 July 2015
Ó Springer Science+Business Media Dordrecht 2015
Abstract Mn(pbdo) Cl /MCM-41 as a solid acid catalyst was used as an efficient, green,
2
2
reusable catalyst for an improved and rapid one-pot multi-component reaction in the syn-
thesis of bis-(4-hydroxycoumarin), bis(indolyl)methane, and 4H-benzo[b]pyran derivatives.
Graphical Abstract
&
Majid M. Heravi
mmh1331@yahoo.com
1
Department of Chemistry, School of Science, Alzahra University, Vanak, Tehran, Iran
123

M. M. Heravi, M. Daraie
Keywords Mn(pbdo) Cl /MCM-41 Á Multi-component reactions Á Solid acid
2
2
catalysts Á Bis-(4-hydroxycoumarin) derivatives Á Bis(indolyl)methanes Á
4
H-benzo[b]pyrans
Introduction
Multi-component reactions (MCRs) have emerged as an important tool for building
diverse and complex organic molecules through carbon–carbon and carbon–hetero
atom bond formations taking place in a tandem manner [1]. In recent years in
particular, MCRs have captured the attention and interest of synthetic organic
chemists, and a number of one-pot three- and four-component reactions have been
developed and introduced [2]. As a matter of fact, MCRs can go beyond four-
component reactions [3]. Interestingly, multi-component reactions today have been
expanded to the synthesis of peptides [4] and asymmetric synthesis [5]. The use of
small heterocycles [6] and the synthesis of common heterocyclic compounds [7] in
MCRs are other recent developments. Undoubtedly, the combination of MCRs and
biology should be considered as the state of the art among organic chemists and
biologists [8].
In the past decade, heterogeneous catalysis has been widely used in industrial
chemical transformations because of its mild reaction conditions, easy separation
from the reaction mixture by filtration, and good thermal stability. The replacement
of homogeneous with heterogeneous catalysts could represent a more environmen-
tally friendly substitute in acid-catalyzed organic reactions [9].
Since 1992, when MCM-41 (Mobil Composition of Matter No. 41) was
discovered by Mobil Corporation laboratory scientists [10], silica-based materials
have been employed as efficient catalysts and catalyst supports in various
reactions [11–15]. MCM-41 possesses several unique properties, including high
surface area, uniform and tunable pore sizes, excellent physicochemical stability,
and modifiable surfaces. However, its direct use as a catalyst is difficult due to a
lack of sufficient acidity. Therefore, many research groups have worked on
introducing various kinds of metals, metal ions, and metal complexes into MCM-
4
1 to improve its catalytic activity [16–21]. Functionalization of MCM-41 with
transition metals, especially by manganese (Mn), leads to effective catalysts for a
variety of organic reactions [22, 23].
Manganese complexes have been intensively studied as catalysts for epoxida-
tion reactions [24]. In recent years, researchers have investigated the immobi-
lization of Mn complexes onto silica mesoporous materials. The preparation of
Mn-MCM-41 using a molecular organic chemical vapor deposition (MOCVD)
method was reported by Caps and Tsang [25]. Surface-grafted manganese–oxo
species on the walls of MCM-41 channels were obtained by Burch et al. [26], and
a template ion-exchange (TIE) method used in another study for the synthesis of
Mn-MCM-41 [27].
As a part of our ongoing program to develop new synthetic transformations using
inexpensive and eco-friendly materials as catalysts [28–33], and given our interest
in MCRs, we examined the possibility of using Mn(pbdo) Cl /MCM-41 in several
2
2
1
23

2 2
Mn(pbdo) Cl /MCM-41 as a green catalyst in multi-component…
multi-component one-pot reactions, including the synthesis of bis-(4-hydroxy-
coumarin), bis(indolyl)methane, and 4H-benzo[b]pyran derivatives.
We previously reported the synthesis and catalytic activity of the Mn(II)
0
0
complex with a 2,2 -bipyridine and 1,1 -dioxide ligand within nanoreactors of
MCM-41 [34].
Catalytic reactions
Synthesis of bis-(4-hydroxycoumarin) derivatives
Coumarin derivatives exhibit a wide range of activities [35–38]. Studies have
recently revealed novel biological activity with remarkable potential in therapeutic
applications apart from their traditional employment [39–42]. However, the drugs of
this group exhibit some side effects, including the warfarin-related purple toes
syndrome. 4-Hydroxycoumarin derivatives are also of interest because of their
anticoagulant [43], spasmolytic [44], and rodenticidal [45] properties. Through the
0
synthesis of different 3,3 -arylidene-bis-4-hydroxycoumarins, it is possible to obtain
compounds with biological activity similar to that of warfarin but with lower
0
toxicity and fewer side effects. Synthesis of 3,3 -arylidene-bis-4-hydroxycoumarins
from the condensation of benzaldehyde derivatives with 4-hydroxycoumarin has
been reported in the literature [46] (Scheme 1).
To optimize the catalytic system, the synthesis of 3,3 -phenylmethylene-bis-(4-
0
hydroxycoumarin) from the condensation of 4-hydroxycoumarin and benzaldehyde
was used as a model reaction. We examined a variety of catalysts, solvents, and
temperatures. Mn(bpyo) Cl /MCM-41 was found to be the best catalyst among
2
2
tested catalysts, which included basic alumina, DABCO, H [NaP W O110], and
1
4
5
30
sulfamic acid, in the model reaction (Table 1).
Scheme 1 Synthesis of bis-(4-hydroxycoumarine) derivatives
123

M. M. Heravi, M. Daraie
Table 1 Optimization of reaction conditions in the model reaction in reflux conditions
a
Entry
Catalyst
Solvent
Time (min)
Yield (%)
1
2
3
4
5
6
7
a
Basic alumina
DABCO
H
2
H
2
H
2
H
2
H
2
H
2
H
2
O
O
O
O
O
O
O
85
90
70
80
65
70
30
70
70
80
85
89
70
96
H
5 30 110
14[NaP W O ]
Sulfamic acid
MCM-41
Mn(bpyo)
2
2
Cl
2
2
Mn(bpyo)
Cl
/MCM-41
Yields are related to isolated pure products
The best results are obtained in H O in the presence of Mn(bpyo) Cl /MCM-41
2
2
2
(
0.04 g) under reflux conditions.
Using these optimized reaction conditions, we explored the scope and efficiency
of this aqueous approach for the synthesis of a wide variety of substituted bis-(4-
hydroxycoumarin) methanes, and the results obtained are summarized in Table 2.
All reactions afforded the desired products in high yields and accommodated a wide
range of aromatic aldehydes bearing both electron-donating and electron-with-
drawing substituents. In all cases, the pure product was isolated by simple filtration
and recrystallization in absolute ethanol.
It is worth noting that the catalyst is recyclable and can be reused without
significant loss of activity. The catalyst was recycled and reused twice in the model
reaction, and the results obtained are summarized in Table 3.
Synthesis of bis(indolyl)methanes
Indole fragments are important intermediates and exhibit various physiological and
pharmaceutical properties [48]. Bis(indolyl)methanes are members of an important
class of heterocyclic compounds that show a broad spectrum of biological activities
[
49, 50]. These compounds have demonstrated pharmaceutical potencies including
0
Table 2 Synthesis of 3,3 -phenylmethylene-bis-(4-hydroxy-2H-1-benzopyran-2-one) derivatives
a
Entry
Aromatic aldehyde
Time (min)
Yield (%)
m.p. (°C)
Found
Rep. [47]
1
2
3
4
5
6
7
a
C
6
H
5
35
30
30
35
40
30
42
96
98
98
95
94
96
94
232
242
269
236
245
253
200
228–30
240–2
265–7
232–4
242–4
252–4
197–8
3-NO
4-Me–C
4-NO –C
4-MeO–C
4-Cl–C
2,4-di-MeO–C
2
–C
6
H
4
6
H
4
2
6
H
4
6 4
H
6 4
H
6 4
H
Isolated yield
1
23

2 2
Mn(pbdo) Cl /MCM-41 as a green catalyst in multi-component…
Table 3 Reusability of catalyst
in the model reaction (35 min)
a
Entry
Number of uses
Yield (%)
1
2
3
Fresh
96
95
91
1
2
a
Isolated yield
anti-HIV, antiviral, antimicrobial, and antihyperglycemic properties, and are known
as cytotoxic active compounds against human tumor cells [51]. Importantly,
bis(indolyl)methanes are known to promote estrogen metabolism [52–54].
A simple and direct method for the synthesis of bis(indolyl)methanes is the
reaction of indole with aldehydes (Scheme 2).
Our initial studies were focused on the optimization of the reaction conditions
for the synthesis of bis(indolyl)methanes. 4-Nitrobenzaldehyde and indole were
chosen as model substrates. The reaction in the presence of 0.04 g Mn(bpyo)2-
Cl /MCM-41 in refluxing water afforded the corresponding product at an 87 %
2
yield. With the optimized reaction conditions in hand, we next studied the
reaction of a series of aldehydes with indole derivatives. The results are shown
in Table 4.
Synthesis of 4H-benzo[b]pyrans
4
H-benzo[b]pyrans represent an important class of compounds, appearing as the
main components of many naturally occurring products [59]. They have diverse
pharmacological properties, including anticoagulant, anticancer, spasmolytic,
diuretic, and anti-anaphylactic activity [60]. 4H-Pyrans also constitute the structural
unit of a series of natural products [61] (Scheme 3).
To optimize the catalytic system, the condensation of benzaldehyde, dimedone
and malononitrile under reflux conditions (Table 5) was used as a model reaction. A
variety of solvents and catalysts were examined in the model reaction, and the best
results were obtained using by Mn(bpyo) Cl /MCM-41 in refluxing water (Table 5).
2
2
Scheme 2 Synthesis of bis(indolyl)methanes
123

M. M. Heravi, M. Daraie
Table 4 Synthesis of bis(indolyl)methane derivatives
a
Entry
Aldehyde
Time (min)
Yield (%)
m.p. (°C)
Found
Rep.
1
2
3
4
5
6
7
a
C
6
H
5
25
30
25
35
35
30
25
91
90
89
87
86
88
92
123
125–127 [55]
77–81 [56]
–
3-NO
4-Me–C
4-NO –C
4-MeO–C
4-Cl–C
–CH=CHCHO
2
–C
6
H
4
260–262
95–97
244–246
264–266
192
6
H
4
2
6
H
4
220–222 [57]
265–266 [55]
191–193 [55]
94–96 [58]
6 4
H
6 4
H
C
6
H
4
96–98
Isolated yield
Scheme 3 Synthesis of 4H-benzo[b]pyranes
Table 5 Optimization of
Entry
a
Catalyst
Solvent
Yield (%)
reaction conditions in the
condensation of benzaldehyde,
1
Mn(bpyo)
2
2
Cl
2
2
/MCM-41
/MCM-41
CH CN
3
85
60
78
96
90
82
85
dimedone and malononitrile
under reflux conditions for
2
3
4
5
6
7
Mn(bpyo)
Cl
CH COOEt
3
20 min
Mn(bpyo) Cl /MCM-41
DCM
2
2
2
2
2
2
Mn(bpyo)
Mn(bpyo)
MCM-41
HMTA
Cl
Cl
/MCM-41
/MCM-41
2
H O
2 5
C H OH
H
2
O
O
H
2
a
Isolated yield
The optimized conditions were used to construct a variety of 4H-benzo[b]pyran
derivatives. This method was found to be effective with a variety of substituted
aromatic aldehydes independently of the nature of the substituents in the aromatic
rings (Table 6).
1
23

Mn(pbdo)
2
2
Cl /MCM-41 as a green catalyst in multi-component…
Table 6 Synthesis of pyran derivatives using aromatic aldehydes
a
Entry
Aromatic aldehyde
Time (min)
Yield (%)
m.p.
Found
Rep.
1
2
3
4
5
6
7
8
9
C
6
H
5
20
18
25
20
30
25
28
32
30
25
96
92
90
91
90
90
92
91
96
92
227–230
209–211
212–214
177–179
202–204
207–209
184–186
205–207
197–200
226–228
227–229 [62]
208–210 [62]
208–210 [64]
177–178 [63]
199–201 [63]
207–209 [64]
186–188 [62]
208–210 [62]
201–203 [62]
224–226 [63]
3-NO
4-Me–C
4-NO –C
4-OMe–C
4-Cl–C
2,4-DiCl–C
4-OH–C
4-Br–C
3-Cl–C
2
–C
6
H
4
4
6
H
4
2
6
H
6
H
4
6 4
H
6
H
4
6 4
H
6 4
H
1
0
6 4
H
a
Isolated yield
General procedure
General procedure for the synthesis of bis-(4-hydroxycoumarin) derivatives (3a–g)
A solution of an aromatic aldehyde (1 mmol), 4-hydroxycoumarin (2 mmol), and
Mn(bpyo) Cl /MCM-41 (0.04 g) in H O (5 mL) was stirred under heating
2
2
2
conditions for an appropriate time. After completion of the reaction, which was
monitored by thin-layer chromatography (TLC), the mixture was cooled to room
temperature. The resulting solid product was then removed by filtration, washed
with water to separate the catalyst, and recrystallized from absolute ethanol to give
the pure product.
General procedure for the synthesis of bis(indolyl)methanes (5a–g)
A mixture of an appropriate aromatic aldehyde (1 mmol), indole derivative
2 mmol), and Mn(bpyo) Cl /MCM-41 (0.04 g) in H O (5 mL) was heated under
2 2 2
(
reflux conditions. The progress of the reaction was monitored by TLC. Upon
completion of the reaction, the mixture was cooled to room temperature. The
resulting solid product was then removed by filtration and pure product was
obtained by recrystallization from the solvent.
General procedure for the synthesis of 4H-benzo[b]pyran derivatives (8a–j)
A solution of an aromatic aldehyde (1 mmol), dimedone (1 mmol), malononitrile
(
1 mmol) and Mn(bpyo) Cl /MCM-41 (0.04 g) in H O (5 mL) was stirred under
2 2 2
heating conditions for an appropriate time. After completion of the reaction, which
was monitored by TLC, the mixture was filtered off and the filtrate was washed with
water and dissolved in boiling ethanol. The catalyst was filtered off and the mixture
123

M. M. Heravi, M. Daraie
was cooled to room temperature. The resulting solid product was then removed by
filtration and washed with ethanol.
Selected spectroscopic data
0
(
3,3 -Phenylmethylene-bis-(4-hydroxycoumarin) (3a) IR (KBr) tmax = 3067,
-
1
1
2889, 1659, 1608, 758 cm ; H-NMR (CDCl , 500 MHz) t = 6.15 (s, 1H,
CH), 7.26–7.46 (m, 9H, ArH), 7.66–7.69 (t, 2H, J = 7.6, ArH), 8.05–8.11 (d, 2H,
3
H
J = 27.8, ArH), 11.33 (s, 1H, OH), 11.56 (s, 1H, OH) ppm.
3
,3-(3-Nitrophenylmethylene)bis-(4-hydroxycoumarin) (3b) IR (KBr) tmax =
-1 1
3
069, 1654, 1613, 1528, 1311,761 cm ; H-NMR (CDCl , 500 MHz) d = 6.17
3
H
(
s, 1H, CH), 7.44–7.49 (m, 4H, ArH), 7.54–7.57 (t, 1H, J = 7.99, ArH), 7.61–7.63
m, 1H, ArH), 7.69-7.71 (t, 2H, J = 7.4), 8.11–8.20 (m, 4H, ArH), 11.41 (s,1H,
(
OH), 11.61 (s,1H, OH) ppm.
3
,3-(4-Methoxyphenylmethylene)bis-(4-hydroxycoumarin) (3e) IR (KBr) tmax =
-1 1
3
379, 3068, 1670, 1606, 1259, 1050, 767 cm ; H-NMR (CDCl , 500 MHz)
3
t = 3.84 (s, 3H, CH ), 6.09 (s,1H, CH), 6.89–6.91 (d, 2H, J = 8.69, ArH),
H
3
7
.16–7.18 (d, 2H, J = 8.51, ArH), 7.44–7.46 (d, 2H, J = 8.24, ArH), 7.65–7.68 (m,
2H, ArH), 8.05–8.10 (d, 2H, J = 26.93, ArH), 11.32 (s, 1H, OH), 11.54 (s, 1H, OH)
ppm.
0
0
1
H,1H -3,3 -(4-Nitro-phenylmethanediyl)-bisindole (5d) m.p. = 244–246 °C; IR
-1
(
1
KBr) mMax = 3454, 3420, 3100, 3050, 2925, 2850, 1593, 1454, 1339, 1037 cm
H-NMR (CDCl , 500 MHz): d = 6.03 (s,1H, CH), 6.85–6.90 (m, 4H, Ar–H),
;
3
H
7.02–7.08 (m, 2H, Ar–H), 7.27–7.3 (d, 2H, J = 9.6, Ar–H), 7.35–7.38 (d, 2H,
J = 9.6, Ar–H), 7.59–7.63 (d, 2H, J = 10.5), 8.13–8.17 (d, 2H, J = 10.9), 10.93 (s,
2
H, 2NH) ppm.
0
0
1
H,1H -3,3 -(4-Methoxy-phenylmethanediyl)-bisindole (5f) m.p. = 264–266 °C;
= 3444, 3403, 3100, 3052, 2924, 2842, 1544, 1454, 1337,
IR (KBr) m
Max
1
-
1
1037 cm ; H-NMR (CDCl , 300 MHz): d = 3.50 (s,3H, CH ), 5.85 (s,1H,
CH), 6.67–6.85 (m,2H, Ar–H), 6.99–7.04 (m, 2H, Ar–H), 7.15–-7.20 (t, 2H,
3
H
3
J = 9.6, Ar–H), 7.25–7.28 (3, 2H, J = 9.6, Ar–H), 7.36–7.42 (m, 4H, J = 10.5),
.92 (s, 2H, J = 10.9) ppm.
7
2
-amino-3-cyano-4-phenyl-7,7-dimethyl-5-oxo-4H-5,6,7,8-tetrahydrobenzo[b]pyran
1
(
8a) m.p. = 227–230 °C; IR (KBr) mMax = 3395, 3212, 2960, 2199, 1680. H
NMR (400 MHz, DMSO-d6) d: 0.96 (s, 3H, Me), 1.05 (s, 3H, Me), 2.11 (d,
J = 16.1 Hz, 1H, CH ),2.26 (d, J = 16.1 Hz, 1H, CH ), 2.53 (s, 2H, CH ),4.18 (s,
2
2
2
1H, CH),7.02 (s, 2H, NH ), 7.14–7.21 (m,3H, H–Ar) 7.29 (t, J = 7.5 Hz, 2H, H–Ar)
2
ppm [65].
2
-amino-3-cyano-4–(3-nitro-phenyl)-7,7-dimethyl-5-oxo-4H-5,6,7,8-tetrahydrobenzo
[
b]pyran (8b) m.p. = 209–211 °C; IR (KBr) mMax = 3438, 3328, 2961, 1686,
1
1
t, J = 7.1 Hz, Me), 2.21 (1H, d, J = 16.0 Hz, H-6), 2.28 (1H, d, J = 16.0 Hz, H-6),
525. H NMR (300 MHz, CDCl3), d: 1.03 (3H, s, Me), 1.16 (3H, s, Me), 1.19 (3H,
1
23

2 2
Mn(pbdo) Cl /MCM-41 as a green catalyst in multi-component…
2
.51 (2H, m, CH ), 4.07 (2H, m, OCH ), 4.85 (1H, s, H-4), 6.28 (2H, br, NH ) 7.40
2 2 2
(1H, t, J = 7.9 Hz, H–Ar), 7.68 (1H, d, J = 7.90 Hz, H–Ar), 8.0 (1H, d,
J = 7.90 Hz, H–Ar) ppm [66].
Conclusion
In summary, we report here a high-yielding, simple, convenient, straightforward,
and practical one-pot procedure for the synthesis of bis-(4-hydroxycoumarin),
bis(indolyl)methane and 4H-benzo[b]pyran derivatives. The conditions are mild,
and a wide range of functional groups can be tolerated. The use of Mn(bpyo) Cl /
2
2
MCM-41 as a catalyst affords advantages that include simplicity of operation, easy
work-up, and high product yields.
Acknowledgments We gratefully acknowledge partial financial support from the Alzahra University
Research Council.
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