An Efficient Synthesis of 1,3-Diphenyl-3-phenylamino-propan-1-one and its Derivatives by Mannich Reaction in the Presence of Doped Porous Carbon by Nitrogen and Sulfur (NS-PCS) as Catalyst

Article abstract of DOI:10.1002/jccs.201700095

Synthesis of β-amino carbonyl compounds by Mannich reaction involves the creation of various bonds in a single action and is attracting great attention as one of the most powerful synthetic tools for the expansion of molecular convolution and versatility. Carbon spheres (CSs) combine the advantages of carbon materials with spherical colloids, which gives them several inimitable features as catalysts. In this work, the reaction between acetophenone, aromatic aldehydes, and aromatic amines has been efficiently catalyzed by porous carbon spheres which were doped by nitrogen and sulfur (NS-PCS) at ambient temperature to give diverse β-amino carbonyl compounds in nearly high yields.

Full text of DOI:10.1002/jccs.201700095

JOURNAL OF THE CHINESE
CHEMICAL SOCIETY
Article
An Efficient Synthesis of 1,3-Diphenyl-3-phenylamino-propan-1-one and its Derivatives
by Mannich Reaction in the Presence of Doped Porous Carbon by Nitrogen and Sulfur
(NS-PCS) as Catalyst
b
a
Aida Mansoori,a Hossein Eshghi
and Jalil Lari
*
aDepartment of Chemistry, Payame Noor University of Mashhad, 91735-433, Iran
bDepartment of Chemistry, Faculty of sciences, Ferdowsi University of Mashhad, 91775-1436, Iran
(Received: March 18, 2017; Accepted: December 4, 2017; DOI: 10.1002/jccs.201700095)
Synthesis of β-amino carbonyl compounds by Mannich reaction involves the creation of various
bonds in a single action and is attracting great attention as one of the most powerful synthetic
tools for the expansion of molecular convolution and versatility. Carbon spheres (CSs) combine
the advantages of carbon materials with spherical colloids, which gives them several inimitable fea-
tures as catalysts. In this work, the reaction between acetophenone, aromatic aldehydes, and aro-
matic amines has been efficiently catalyzed by porous carbon spheres which were doped by
nitrogen and sulfur (NS-PCS) at ambient temperature to give diverse β-amino carbonyl com-
pounds in nearly high yields.
Keywords: β-Amino carbonyl compounds; Mannich reaction; Porous carbon-doped catalysts.
INTRODUCTION
The Mannich reaction is one of the most signifi-
has many serious disadvantages such as complex work-
up, purification procedures, and unwanted side prod-
ucts. In order to solve these problems, there have been
many modifications reported in the literature to prepare
viable products. To overcome the drawbacks of the
classical method, from the economical and environmen-
tal points of view, and to attain a wide range of struc-
tural diversity, one of the desirable routes is to use a
one-pot three-component strategy. Recently, several
reported Mannich reactions of aromatic ketones, alde-
hydes, and amines have been catalyzed by Salen Zn
cant reactions in organic synthesis, providing β-amino
ketones1,2 (Mannich bases) starting from ketone, form-
aldehyde, and secondary amines. Because of the preva-
lence of Mannich bases in biologically active
compounds and also their utility as intermediates for
the synthesis of β-lactams and β-amino acids, this kind
of reaction has attracted much attention among organic
chemists. Various derivatives of phenylpropanolamine
(the reduced form of the Mannich product) are reported
in the literature with different biological activities. Oxy-
fedrine and alifedrine derived from phenylpropanol-
amine (l-norephedrine) using the Mannich reaction are
known for their decongestant, cardiovascular, and anti-
anginal activities.3 Although the Mannich reaction is a
useful method for the preparation of β-amino carbonyl
compounds and plays a substantial role in medicinal
chemistry, the application of the Mannich reaction
products had been limited by several problems in the
classical Mannich reaction. As we know, the reaction is
initiated by two equilibrate components (formation of
imine and tautomerization of enol) and accordingly
needs intense reaction conditions and, consequently, it
complex,1 Fe3+-montmorillonite,4 nano-Mn (HSO4)2,
5
NbCl5,6 and proline7, among others. However, most of
these methods have drawbacks such as the use of a cor-
rosive reagent, high cost, the need for a large amount
of catalyst, long reaction time, detrimental reaction
media (e.g., fluorinated solvent and etc.), and low
yields. Carbon catalysts are a form of catalysts that use
heterogeneous carbon materials for the synthesis of
chemical (organic or inorganic) substrates. Because of
their unique structure and functional behaviors, such as
large specific area, low specific density, large controlla-
ble inner pore volume, and fine mechanical strength,8
these kinds of materials have been in the spotlight. The
*Corresponding author. Email: heshghi@um.ac.ir
J. Chin. Chem. Soc. 2017
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Article
Mansoori et al.
discovery of nanostructured carbon such as carbon
nanotubes,9 fullerenes,10 and graphene11 has made a
revolution in many scientific fields. These exquisite
materials therefore present great benefits for electro-
chemical sensing,12 water purification,13 catalysis,14,15
and energy storage/conversion (supercapacitors,8 lith-
ium16 and sodium17 batteries). Therefore, we turned
our attention to the nano-catalytic ability of the carbon
spheres. Different heteroatom-doped carbon spheres,
such as those with boron,18 nitrogen,17,19,20 sulfur,15 are
versatile catalysts for organic synthesis. Here we report
the investigations of the effects of the catalyst on the
direct three-component Mannich reaction. In view of
the possibility of using doped porous carbon spheres
with nitrogen and sulfur (NS-PCSs) as an environmen-
tally benign catalyst, the syntheses of 1, 3-diphenyl-3-
phenylamino-propan-1-one and its derivatives are pre-
sented (Scheme 1).
Scheme 2. Synthesis of 2,3-diphenyl-2-azabicyclo
[2.2.2]octan-5-one.
with various protic and aprotic solvents (entry 1–6,
Table 1). Ethanol and methanol were found to be the
best solvents for conducting this reaction. In order to
comply with environmental directives, ethanol was
selected. We found that temperature did not have a sig-
nificant effect on the operation of the reaction (entry
7–10, Table 1)
To better understand the generality of the proce-
dure in different amines and aldehydes, we screened
multi-functioned aldehydes such as chlorobenzalde-
hyde (entry 7,8,13, Table 2), 4-methyl benzaldehyde
(entry 6 and 10, Table 2), and 4-bromo benzaldehyde
(entry 11 and 12, Table 2) to make this reaction per-
fect. On the other hand, electron-donating and
electron-withdrawing groups on aniline such as chloro,
methyl, nitro, and methoxy gave the corresponding
products in good to excellent yields (entry 2–7 and
9–12, Table 2). 4-Boromo aniline failed in this reac-
tion because of reduced solubility of its corresponding
imines due to molecular weight increase. Although, in
most cases, the aldehyde derivatives did not give
products with acceptable yield, almost all the amines
underwent smooth reactions to produce their deriva-
tives in good to excellent yields at room temperature
(Table 2).
RESULTS AND DISCUSSION
The new doped porous carbon spheres with nitro-
gen and sulfur (NS-PCS) were prepared according to
our previously reported procedure and were character-
ized by FT-IR, X-ray diffraction (XRD), Raman spec-
troscopy, transmission electron microscopy (TEM),
thermogravimetric analysis (TGA), and elemental anal-
ysis.21 The TEM images of catalyst, shown in Figure 1,
clearly shows that the NS-PCS particles are spherical
and the average particles size is 200–500 μm. First we
focused our attention on optimizing the reaction condi-
tions. With the intention of appraising the catalytic effi-
ciency of NS-PCSs, the effect of the catalyst was
studied under various conditions. We also observed that
8 mg of the NS-PCS could catalyze the Mannich reac-
tion efficiently. Further increasing the amount of the
catalyst did not lead to any significant improvement in
the yields (entry 14, Table 1). After determining the
amount of catalyst, we further screened the reaction
Fig. 1. TEM images of (a) an individual and
(b) aggregated carbon spheres.
Scheme 1. Synthesis of 1,3-diphenyl-3-phenylamino-
propan-1-one.
2
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J. Chin. Chem. Soc. 2017

JOURNAL OF THE CHINESE
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Doped-porous Carbon Sphere as Organocatalyst
Table 1. Optimization of reaction conditions for 3 mmol of reactants
Entry
Catalyst (mg)
Solvent
Temp. (ꢀC)
Time (h)
Yield (%) a
1
2
3
4
5
6
7
8
10
10
10
10
10
10
10
10
10
10
1
2
4
8
10
15
20
25
8
Acetonitrile
Ethanol
Water
RT
RT
RT
RT
RT
RT
40
50
60
75
RT
RT
RT
RT
RT
RT
RT
RT
RT
RT
RT
RT
RT
12
6.5
24
24
24
6.5
6.5
6.5
6.5
6.5
24
75
89
45
68
—
91
89
89
90
90
—
—
56
89
89
89
90
91
87
85
80
78
74
THF
Toluene
Methanol
Ethanol
Ethanol
Ethanol
Ethanol
Ethanol
Ethanol
Ethanol
Ethanol
Ethanol
Ethanol
Ethanol
Ethanol
Ethanol
Ethanol
Ethanol
Ethanol
Ethanol
9
10
11
12
13
14b
15
16
17
18
19c
20d
21e
22f
23g
24
10
6.5
6.5
6.5
6.5
6.5
6.5
6.5
6.5
6.5
6.5
8
8
8
8
a Isolated yield.
b Optimum condition for general procedure and reusability experiments.
c-g Reusability of catalyst in new runs 2–6.
1
For example, in the HNMR spectrum of 3-((3-
iodophenyl)amino)-3-(4-isopropylphenyl)-1-phenylpro-
pan-1-one (Entry17, Table 2), we can see two dd peaks
of diastereotopic hydrogens at 3.39–3.56. The line
belonging to the amine hydrogen appears as a broad
peak at 4.63 ppm. A triple peak belonging to the
hydrogen bonded to chiral center is observed at
4.98 ppm. In the IR spectra, the peak in the region of
3379 cm−1 belongs to the amine NH.
reaction under similar reaction conditions for five
cycles. After every reaction cycle, the catalyst was sepa-
rated by filtration, washing with water, and drying in
the oven for 15 min at 110 ꢀC before reusing. The
results are reported in Table 1, which confirm the good
recyclability of our catalyst after up to 5 runs.
To show the higher efficiency of NS-PCS in com-
parison with other reported catalysts, we have summa-
rized several results for the Mannich reaction of
aniline and benzaldehyde with acetophenone in
Table 3.
To study the regeneration and reusability of the
catalyst, it was recovered from the reaction mixture by
filtration and washed with water followed by drying at
110ꢀC for 15 min. Then catalyst was used for the model
In addition, we examined the reaction with
another ketone, namely cyclohexenone, under
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Article
Mansoori et al.
Table 2. NS-PCS-catalyzed Mannich reaction between aldehyde, ketone and aminea
Mp (ꢀC)
ꢀ
Entry
R
R
Yield (%)b
Time (h)
Found
168–169
Reported
1
2
3
4
5
6
7
8
H
H
H
H
H
89
96
87
91
86
84
87
85
93
87
95
95
88
91
91
96
96
6.5
6
169–17022
167–16822
—
161–16623
130–13224
163–16523
—
95–9725
183–1847
160–16123
—
4-CH3
3-CH3
4-Cl
3-Cl
3-Cl
3-Cl
H
4-NO2
4-Cl
4-CH3
4-Cl
H
168–170
138–139
159–160
130–131
161–163
142–143
134–135
182–184
160–161
68 (imine)
71(imine)
116–118
151–152
123–124
138–139
127–128
6.5
6.5
6.5
6.5
6.5
8
6.5
6.5
24
24
8.5
8
H
4-CH3
2-Cl
2-Cl
H
9
10
11
12
13
14
15
16
17
4-CH3
4-Br
4-Br
4-Cl
4-OMe
H
—
115–11726
149–15127
—
H
4-I
H
3-I
6.5
6
6
4-Pri
4-Pri
—
—
a All products were characterized by IR and 1H NMR spectra and their melting points were compared with literature.
b Isolated yields.
Mannich reaction condition. We tried many differ-
ent conditions to reach the suitable product 1, 3-
diphenyl-3-phenylamino-propan-1-one. However, we
could not obtain the intended product according to
the ring closure, so we did not continue the project
(Scheme 2).
Table 3. Comparison of efficiency of NS-PCS catalyst with some other catalysts reported in the literature for the reaction
between benzaldehyde, aniline, and acetophenone
Entry
Catalyst
Solvent
Temp. (ꢀC)
Time (h)
Yield (%)
1
2
3
4
5
7
8
9
NbCl5
CAN
Cp2TiCl2 + POAP
Ph2IOTf
HNMPCl/ZnCl2/SBA-15
Cu-nanoparticles
CeCl3Á7H2O
SSA
HClO4–SiO2
Sulfamic acid
NS-PCS
EtOH
PEG 400
—
RT
45
25–50
RT
12
9
6
24
5–8
8
10
12
12
5
956
987
9728
8629
9530
9331
9526
9232
9533
9534
89
—
EtOH
MeOH
EtOH
EtOH
EtOH
EtOH
EtOH
60
RT, N2 atmosphere
RT
RT
RT
RT
RT
10
11
12
6.5
4
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J. Chin. Chem. Soc. 2017

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Doped-porous Carbon Sphere as Organocatalyst
EXPERIMENTAL
General
J1 = 9 Hz, J2 = 3 Hz, 1H), 5.00 (dd, J1 = 9 Hz,
J2 = 6 Hz, 1H), 4.69 (s, 1H), 3.54(dd, J1 = 15 Hz,
J2 = 6 Hz, 1H), 3.45(dd, J1 = 15 Hz, J2 = 6 Hz, 1H);
13C NMR (100 MHz, CDCl3) δ 198.08, 148.23, 142.30,
136.59, 133.56, 130.58, 128.94, 128.76, 128.22, 127.56,
126.69, 126.28, 122.62, 112.81, 95.02, 77.25, 54.55,
46.09; LCMS (m/z): 428.0.
All chemicals were purchased from Merck or
Fluka Chemical Companies. The products were identi-
fied by comparison of their melting points (mp) and
spectral data in the literature. The progress of each cata-
lyzed reaction was monitored by TLC using sheets. The
1H NMR (300 MHz) and were run on a BRUKER
300 MHz AVANCE III FT-NMR spectrometer (δ in
ppm). Melting points were recorded on a Bamstead
Electrotermal-9200 in open capillary tubes. NS-PCS was
prepared according to our previously reported procedure
[3-(4-Isopropyl phenyl)-1- phenyl-3-(phenylamino) propa-
n-1-one]
Entry 16: white solid, mp: 138–139; IR (KBr
cm−1): 3353, 1651, 749, 621; 1H NMR (300 MHz,
chloroform-d) δ 7.97 (d, J = 3 Hz, 1H), 7.57 (t,
J = 9 Hz, 1H), 7.48 (t, J = 6 Hz, 2H), 7.22 (d,
J = 6 Hz, 2H), 7.14 (t, J = 6 Hz, 2H), 6.71 (t,
J = 6 Hz, 1H), 6.63 (d, J = 9 Hz, 2H), 5.05 (t,
J = 6 Hz, 1H), 4.56 (s, 1H), 3.56 (dd, J1 = 15 Hz,
J2 = 6 Hz, 1H), 3.51 (dd, J1 = 15 Hz, J2 = 6 Hz, 1H),
2.92 (m, 1H), 1.26 (m, 6H); 13C NMR (100 MHz,
CDCl3) δ 198.45, 147.92, 147.11, 140.26, 136.77,
133.37, 129.13, 128.68, 128.24, 126.88, 126.28, 117.67,
113.77, 77.49, 77.06, 76.64, 54.48, 46.31, 33.75, 24.01,
23.98; MS (m/z): 342.2.
General procedure for the synthesis of 1,3-diphenyl-3-ph-
enylamino-propan-1-one
A mixture of acetophenone (3 mmol, 0.35 mL), aro-
matic aldehydes (3 mmol), aromatic amines (3 mmol), and
the catalyst (8 mg) was stirred in EtOH (6 mL) at room
temperature. When the reaction was completed as indi-
cated by TLC, the catalyst was filtered off and the reaction
mixture was placed at ambient temperature to evaporate
EtOH. The product was purified via recrystallization from
hot ethanol to give the relevant compounds, which were
identified by 1HNMR (see supporting information).
3-((3-Iodophenyl)amino)-3-(4-isopropylphenyl)-1-phenylp-
ropan-1-one
SPECTRAL DATA OF NEW PRODUCTS
[3-(2-Chlorophenyl)-3-((3-chlorophenyl) amino)-1-phenyl-
propan-1-one]
Entry17: light brown solid, mp: 127–128ꢀC; IR
(KBr cm−1): 3379, 1643, 751, 624; 1H NMR (300 MHz,
chloroform-d) δ 7.6 (t, J = 6 Hz, 1H), 7.48 (t,
J = 6 Hz, 2H), 7.36 (d, J = 6 Hz, 2H), 7.02 (t,
J = 6 Hz, 2H), 6.97 (t, J = 9 Hz, 1H), 6.54 (dd,
J1 = 9 Hz, J2 = 3 Hz, 1H), 4.98 (t, J = 6 Hz, 1H), 4.63
(s, 1H), 3.50 (dd, J1 = 15 Hz, J2 = 3 Hz, 1H), 3.44 (dd,
J1 = 15 Hz, J2 = 3 Hz, 1H), 2.89 (m, 1H), 1.26 (d,
J = 6 Hz, 6H); 13C NMR (100 MHz, CDCl3) δ 198.24,
148.32, 148.14, 139.57, 136.65, 133.49, 130.60, 128.72,
128.22, 126.96, 126.56, 126.18, 122.54, 112.73, 95.05,
77.47, 77.25, 77.05, 76.63, 54.22, 46.07, 33.75, 23.99,
23.96; MS (m/z): 469.0.
Entry 7: White solid, mp: 142–143ꢀC, IR (KBr
1
cm−1): 3413, 1616, 756, 621; H NMR (300 MHz, chlo-
roform) δ 7.99 (d, J = 6 Hz, 2H), 7.62 (tt, J1 = 9 Hz,
J2 = 3 Hz, 1H), 7.60–7.34 (m, 4H), 7.00 (t, J = 9 Hz,
1H), 6.64 (d, J = 10.0 Hz, 1H), 6.51 (t, J = 3 Hz, 1H),
6.36 (dd, J1 = 9 Hz, J2 = 3 Hz, 1H), 5.31 (m, 1H), 5.05
(d, J = 6 Hz, 1H), 3.62 (dd, J1 = 15 Hz, J2 = 6 Hz,
1H), 3.35 (dd, J1 = 15 Hz, J2 = 9 Hz, 1H); 13C NMR
(100 MHz, CDCl3) δ 198.41, 147.66, 138.89, 136.40,
133.69, 129.97, 128.94, 128.78, 127.56, 126.69, 113.18,
77.02, 51.89, 43.47; MS (m/z): 369.2.
[3-((4-Iodophenyl) amino)-1,3-diphenylpropan-1-one]
Entry 15: Brown solid, mp: 123–124ꢀC, IR (KBr
cm−1): 3410, 1624,730, 678; 1H NMR (300 MHz,
chloroform-d) δ 7.96 (d, J = 3 Hz, 2H), 7.63 (t,
J = 9 Hz, 1H), 7.46 (dd, J1 = 9 Hz, J2 = 6 Hz, 4H),
7.37 (t, J = 9 Hz, 2H), 7.30 (t, J = 3 Hz, 1H), 7.01
(t, J = 6 Hz, 2H), 6.82 (t, J = 6 Hz, 2H), 6.52(dd,
CONCLUSION
We have described the synthesis of β-amino car-
bonyl compounds via the direct three-component Man-
nich reaction catalyzed by NS-PCSs. This efficient
protocol has many benefits compared to those reported
in the literature: moderate and relatively highly efficient
catalyst activity, ease of handling and cost efficiency of
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Supporting information
Additional supporting information is available in
the online version of this article.
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