Phthalimide-N-sulfonic acid, an efficient catalyst for the synthesis of various isoindoline-1,3-dione derivatives

Article abstract of DOI:10.1007/s11696-017-0223-7

An environmentally friendly method is described for the synthesis of various isoindoline-1,3-dione derivatives from the reaction of phthalic anhydride with aromatic/aliphatic amines in ethanol at 80 °C by phthalimide-N-sulfonic acid as an efficient heterogeneous acid catalyst. Some advantages include the metal-free and environmentally friendly protocol, simple operation and reusable processes, easy recovery, short reaction times, and high yields.

Full text of DOI:10.1007/s11696-017-0223-7

Chem. Pap.
DOI 10.1007/s11696-017-0223-7
ORIGINAL PAPER
Phthalimide-N-sulfonic acid, an efficient catalyst for the synthesis
of various isoindoline-1,3-dione derivatives
Davood Habibi1 Hossein Mohammadkhani Pordanjani1
•
Received: 2 February 2017 / Accepted: 3 June 2017
Ó Institute of Chemistry, Slovak Academy of Sciences 2017
Abstract An environmentally friendly method is described
for the synthesis of various isoindoline-1,3-dione derivatives
from the reaction of phthalic anhydride with aromatic/ali-
phatic amines in ethanol at 80 °C by phthalimide-N-sulfonic
acid as an efficient heterogeneous acid catalyst. Some
advantages include the metal-free and environmentally
friendly protocol, simple operation and reusable processes,
easy recovery, short reaction times, and high yields.
of the environmental and economical reasons (Gu et al.
2003).
Organocatalytic reactions were found to be an efficient
synthetic tool for creating various new carbon–carbon and
carbon–heteroatom bonds (Kiyani and Ghiasi 2015) and are
good alternative to other catalyzed processes because of their
lower costs and benignenvironmental impact (Diez-Gonzalez
et al. 2007). Other advantages of the organocatalysts are their
availability, relatively low toxicity, simple functionality, and
non-sensitivity to air and moisture. They bring a metal-free
environment to promote a wide range of chemical transfor-
mations via the various activation modes (Nyce et al. 2002;
Grasa et al. 2004, 2003; Wu et al. 2006; Reynolds and Rovis
2005; Suzuki et al. 2003; Nair et al. 2006; Tachibana et al.
2004; Ciganek 1995; Zhou et al. 2001).
Keywords Phthalic anhydride Á Amines Á Phthalimide-N-
sulfonic acid Á Isoindoline-1,3-diones Á Heterogeneous acid
catalyst
Introduction
N-Substituted cyclic imides have successfully been used
in syntheses (Bouissane et al. 2009; Easwar and Argade
2006; Mangaleswaran and Argade 2004), medicine (Janda
et al. 1990), biology (Sortino et al. 2011), and material
science (Pontrello et al. 2005) by application of different
reagents such as [Bmim]PF6 (Le et al. 2004), Ac2O/NaOAc
(Mehta et al. 1960), and others (Peterson and Eggleston
2007). There are many methods for the synthesis of cyclic
imides using acetyl chloride (Dhivare et al. 2016), acetic
acid (Pan et al. 2016), SOCl2 (Rajput and Rajput 2007),
and ZnBr2/HMDS (Reddy et al. 1997) catalysts. In addi-
tion, several methods were reported for preparation of
phthalimides, especially N-phenyl phthalimide by the use
of [Hmim]HSO4 (Dabiri et al. 2007), [bmim]PF6 (Zhou
et al. 2003), choline chloride ? ZnCl2 (Xie et al. 2009),
TFA (Shinde et al. 2011), sulphamic acid (Langade 2011),
Fe3O4@SiO2–SO3H (Thale et al. 2014), and DABCO
(Heravi et al. 2005) catalysts.
Many organic reactions such as acylation (Anderson and
Tepe 2002), isomerization (McCubbin et al. 2011), alky-
lation (Jervis et al. 2006), nitration (Aridoss and Laali
2011), and rearrangements like Beckman (Hashimoto et al.
2008) were catalyzed by acid catalysts. Therefore, acid
catalysts play important roles in organic transformations.
Most of these reactions were carried out by employing the
conventional mineral acids like HCl, HNO3, and H2SO4 or
Lewis acids such as AlCl3 and BF3, but the conventional
catalysts are replaced with the newer acid catalysts because
Electronic supplementary material The online version of this
article (doi:10.1007/s11696-017-0223-7) contains supplementary
material, which is available to authorized users.
& Davood Habibi
davood.habibi@gmail.com
1
Since cyclic imides are well known to be very important
antitumor agents such as mitonafide and amonafide,
Department of Organic Chemistry, Faculty of Chemistry,
Bu-Ali Sina University, Hamedan, Iran
123

Chem. Pap.
Sharma and coworkers synthesized two series of cyclic
imide derivatives containing two cyclic imide moiety in
their structures (one series of bis-cyclic imide derivatives
synthesized by condensation of acid anhydrides with
diamines and another series synthesized by condensation of
various diamines with diacids), and screened them for
in vitro anticancer activity against five human cancer cell
lines, i.e., breast (T47D), lung (NCl H-522), colon (HCT-
15), ovary (PA-1), and liver (Hep G2) (Kumar et al. 2016).
Guo and coworkers reported an efficient synthesis of N-
substituted phthalimides from o-phthalic acids or anhy-
drides with amines using SiO2-tpy-Nb as heterogeneous
and reusable catalyst (Wan et al. 2016). Shimizu and
coworkers reported direct synthesis of cyclic imides from
carboxylic anhydrides and amines by Nb2O5 as a water-
tolerant Lewis acid catalyst (Ali et al. 2016). Kumar and
coworkers used p-toluenesulfonic acid as catalyst for the
three steps synthesis of N-substituted cyclic imides from
the reaction of phthalic, maleic, and succinic anhydride
with various Ar-NH2 in solid phase (Kumar et al. 2014).
Langade reported an efficient one-pot synthesis of N-alkyl
and N-aryl phthalimides and succinimides using 10 mol %
sulphamic acid catalyst (Langade 2011).
Scheme 1 Phthalimide-N-sulfonic acid catalyzed synthesis of
isoindolinediones
phthalimide (3.704 g, 20 mmol) in anhydrous CH2Cl2
(15 mL), and then, chlorosulfonic acid (2.33 g, 20 mmol)
was added dropwise over a period of 20 min at 0 °C. After
completion, the reaction mixture was filtered off; the solid
residue washed with water and diethyl ether and dried
under vacuum; the yield was about 92%.
General procedure for the synthesis of isoindoline-
1,3-dione derivatives
A mixture of phthalic anhydride (0.296 g, 2 mmol), amine
(2.2 mmol), and phthalimide-N-sulfonic acid (0.091 g,
20 mol%) in ethanol (5 ml) was stirred for 3 h at 80 °C.
After completion (monitored by TLC), the insoluble cata-
lyst was separated by filtration, washed with acetone, and
dried (weight: 0.090 g, 99% recovered). The organic layer
was concentrated under reduced pressure to give the
desired product, washed with water, and recrystallized in
ethanol (each product was dissolved in a minimum amount
of hot ethanol and allowed to reach gradually to room
temperature). In addition, some products needed extra
purification step by small column chromatography using
the CH2Cl2/n-hexane solvent mixture (50:50).
For many years, synthesis of the cyclic imides, especially
isoindoline-1,3-dione and its derivatives, has been of
remarkable interest in organic and medicinal chemistry,
because these heterocyclic nuclei are in a large number of
drugs and natural products and also their broad range of
applications as analgesics, anticonvulsants, anti-inflamma-
tories, immuno-modulatory, herbicidal, insecticidal agents,
and hyperlipidemic activities (Ahuja et al. 2014; Dunn 2013;
Al-Azzawi and Al-Razzak 2013; Sharma et al. 2010).
Former methods suffer from some drawbacks such as the
use of expensive and hazardous reagents, application of non-
green reagents, low yields, long reaction times, harsh reac-
tion conditions, and tedious work-up (Braish and Fox 1992).
Herein, we would like to report the application of
phthalimide-N-sulfonic acid as a highly efficient and reu-
sable heterogeneous acid catalyst for the synthesis of var-
ious isoindoline-1,3-dione compounds (2a–l) via the
condensation reaction of phthalic anhydride with various
aliphatic and aromatic amines (1a–l) in ethanol at 80 °C
(Scheme 1).
Isoindoline-1,3-dione derivatives were characterized by
comparing their IR and 1H-NMR spectra with those of
corresponding authentic samples.
Results and discussion
In the synthesis of various isoindoline-1,3-dione deriva-
tives, the role of solvents on the reaction rate as well as the
product yield was initially investigated by screening dif-
ferent solvents (DMF, DMSO, toluene, and ethanol) in
model reaction [synthesis of 2-phenyl-isoindoline-1,3-
dione (2a) from the reaction of phthalic anhydride with
aniline in ethanol at 80 °C by phthalimide-N-sulfonic
acid]. Results showed that the reaction rate is highly effi-
cient in ethanol with excellent yield (3 h, 92%) (Table 1).
Optimization of the catalyst amount was the next step,
so different amounts of phthalimide-N-sulfonic acid (0.0,
5.0, 10.0, 15.0, 20.0, and 25 mol%) were used in the model
Experimental
General procedure for preparation
of the phthalimide-N-sulfonic acid catalyst
Phthalimide-N-sulfonic acid catalyst was prepared
according to the literature (Kiyani and Ghiasi 2015).
Briefly, a flask was charged with a solution of potassium
123

Chem. Pap.
Mechanism of the reaction
Table 1 Effect of different solvents for the synthesis of isoindoline-
1,3-diones
The plausible mechanism for the synthesis of isoindoline-
1,3-diones is shown below (Scheme 2). At first, carbonyl
groups of phthalic anhydride will be activated by phthal-
imide-N-sulfonic acid, and then, nucleophilic attack of
NH2 group of amine to this activated carbonyl groups takes
place to give the relative intermediate. By dehydration of
the intermediate and another nucleophilic attack of the NH
group, ring closing performs and the desired isoindoline-
1,3-dione obtained (Reddy et al. 1997).
Solvent
DMF
DMSO
Toluene
Ethanol
Rate %
61
4
55
4
75
4
92
3
Time (hour)
Table 2 Effect of different catalyst amount on the synthesis of
isoindoline-1,3-diones
Catalyst (mol %)
Yield %
0.0
29
5
5.0
46
5
10.0
70
5
15.0
88
4
20.0
92
3
25.0
92
3
Time (hour)
Comparison of the catalytic activities of different
catalysts
reaction to find the best condition. According to the
obtained results, in terms of both time and yield, a
20 mol% of the catalyst was found to be the most effective
(3 h, 92%), although the same result was obtained with
more loading of the catalyst (Table 2).
A number of synthetic methods have been reported for
preparation of various isoindoline-1,3-dione derivatives
(Table 4), and application of the phthalimide-N-sulfonic
acid catalyst (Entry 9) compared with those methods
reported in the literature to show its advantages.
To assess the efficiency of the applied methodology in
the synthesis of various isoindoline-1,3-diones, several
aliphatic and aromatic amines (aromatic amines with
electron releasing and electron-withdrawing substituents)
were tested with phthalic anhydride in the optimal reaction
conditions to give the corresponding products in high
yields and in short reaction times (Table 3).
Selected spectral data of the products
N-(Phenyl)isoindoline-1,3-dione (2a): IR (in cm-1): 3052,
1
1781, 1732, 1701, 1594, 1503, 1382, 1111; H NMR (d in
ppm, CDCl3) (90 MHz): 7.83–7.92 (4H, m, aromatic CH);
7.27–7.46 (5H, m, aromatic CH).
(2-Benzyl)isoindoline-1,3-dione (2b): IR (in cm-1):
Aliphatic amines showed high yields and short reaction
times in comparison with the aromatic ones (Entries 2, 6,
and 12). This observation can lead us that the aliphatic
amines have more nucleophilic power, since the resonance
of the nitrogen atom with the benzene ring reduces the
nucleophilicity of the aromatic amines.
1
3061, 2951, 1765, 1715, 1432, 1391; H NMR (d in ppm,
CDCl3) (90 MHz): 7.53–7.80 (4H, m, aromatic CH);
7.16–7.35 (5H, m, aromatic CH), 4.83 (2H, s).
(4-Methoxyphenyl)isoindoline-1,3-dione (2c): IR (in
cm-1): 2926, 2851, 1717, 1389, 1258, 1176, 1024; 1H
NMR (d in ppm, CDCl3) (90 MHz): 7.82–7.90 (4H, m,
aromatic CH); 6.97–7.37 (4H, m, aromatic CH), 3.85
(3H, s).
(p-Tolyl)isoindoline-1,3-dione (2d): IR (in cm-1): 3460,
1717, 1516; 1384; 724, 1H NMR (d in ppm, CDCl3)
(90 MHz): 7.73–8.00 (4H, m, aromatic CH), 7.13–7.31
(4H, m, aromatic CH), and 2.42 (3H, s).
In addition, we investigated the reactivity of some bulky
amines such as 2-methylaniline, 2,4-dimethylaniline, and
2,6-dimethylaniline (Entries 5, 10, and 11), and interest-
ingly, all desired products were obtained in good-to-ex-
cellent yields and times. 4-Aminomethylpyridine also gave
the good result (Entry 12).
(o-Tolyl)isoindoline-1,3-dione (2e): IR (in cm-1): 3050,
1745, 1717, 1516, 1384; 1H NMR (d in ppm, CDCl3)
(90 MHz): 7.74–8.02 (4H, m, aromatic CH), 7.25–7.39
(4H, m, aromatic CH), and 2.22 (3H, s).
Catalyst recyclability
In addition, the recyclability of the phthalimide-N-sul-
fonic acid catalyst was examined. Therefore, after com-
pletion of a model reaction [aniline (0.186 g, 2.2 mmol),
phthalic anhydride (0.296 g, 2 mmol) and phthalimide-N-
sulfonic acid catalyst (20 mol%) in ethanol at 80 °C], the
catalyst was collected and directly reused for the next
reaction runs. Consequently, we found that phthalimide-
N-sulfonic acid is a capable and reusable catalyst even
after five runs; and the catalytic activity was almost as
same as the fresh one (92, 91, 89, 88, and 86%,
respectively).
N-(3-Hydroxypropan)isoindoline-1,3-dione (2f): IR (in
cm-1): 3035, 2949, 1774, 1739; 1714, 1242; 1H NMR (d in
ppm, CDCl3) (250 MHz): 7.68–7.84 (4H, m, aromatic
CH), 4.27 (2H, J = 10 Hz, t), 3.92 (2H, J = 10 Hz, t), and
1.98 (2H, s).
N-(Pyridin-2-yl)isoindole-1,3-dione (2g): IR (in cm-1):
3055, 1715, 1586, 1467, 1384; 1H NMR (d in ppm, CDCl3)
(250 MHz): 8.66–8.67 (1H, d, J = 4 Hz, aromatic CH),
7.9–7.95 (2H, m, aromatic CH), 7.83–7.87 (1H, m,
123

Chem. Pap.
Table 3 Synthesis of various
isoindoline-1,3-diones catalyzed
by phthalimide-N-sulfonic acid
Entry
1
Amines (1a - m)
Isoindoline-1,3-diones (2a - m)
Time (h)
3
Yield (%)a
NH2
O
92
N
1a
O
2a
O
NH2
2
3
4
2
2
2
90
87
92
N
1b
O
2b
NH2
O
N
OCH3
H3CO
1c
O
2c
H2N
O
N
C
H
3
CH3
1d
O
2d
2e
H
3C
H
3C
O
5
3
88
H2N
N
1e
O
H2N
H2N
O
6
7
8
2
2
3
90
93
89
N
H 1f
O
OH 2f
O
O
N
N
1g
N
O
O
2g
H2N
l
C
N
C
l
1h
O
2h
O
H2N
I 1i
9
3
3
90
86
N
I
O
O
2i
2j
H C
3
H3C
H2N
10
N
C
H
3
C
H
3 1j
O
H
3C
H
3C
O
11
4
85
H2N
N
H
3C
O
H3C
1k
2k
2l
H2N
O
12
13
2
4
92
86
N
N
N
1l
O
O
H2N
N
1m
O
2m
All reactions were performed by mixing of phthalic anhydride (0.296 g, 2 mmol), amine (2.2 mmol), and
phthalimide-N-sulfonic acid (20 mol%) in ethanol at 80 °C
a
Isolated yield
aromatic CH), 7.75–7.79 (2H, m, aromatic CH), and
7.34–7.44 (2H, m, aromatic CH).
CDCl3) (90 MHz): 7.75–8.02 (4H, m, aromatic CH);
7.41–7.49 (4H, m, aromatic CH).
N-(4-Chlorophenyl)isoindoline-1,3-dione (2h): IR (in
1
N-(4-Iodophenyl)isoindoline-1,3-dione (2i): IR (in
1
cm-1): 3061, 1708, 1497, 1392, 718 H NMR (d in ppm,
cm-1): 3055, 1709, 1486, 1385, 1119, 719; H NMR (d in
123

Chem. Pap.
Scheme 2 Suggested
mechanism for the synthesis of
isoindoline-1,3-diones
Table 4 Comparison of the
catalytic activities of different
catalysts
Entry Catalyst
T (°C)
Time (min)
Yield % Ref.
1
2
3
4
5
6
7
8
9
[Hmim]HSO4
[Bmim]PF6
80
80
30–90
480
89
93
87
89
98
89
Dabiri et al. (2007)
Zhou et al. (2003)
Xie et al. (2009)
Choline chloride ? ZnCl2 60
60
TFA
70
20–45
Shinde et al. (2011)
Langade (2011)
Sulphamic acid
Fe3O4@SiO2–SO3H
DABCO
Not reported 5–10
80 45–90
Thale et al. (2014)
Heravi et al. (2005)
Nasr-Esfahani et al. (2012)
Our catalyst
Not reported Immediately 79
p-Ts-OH
80
80
30–120
2–4 h
65-88
92
Our catalyst
ppm, CDCl3) (90 MHz): 7.94–7.97 (2H, m, aromatic CH),
7.78–7.85 (4H, m, aromatic CH); 7.21–7.26 (2H, m, aro-
matic CH).
N-sulfonic acid in ethanol at 80 °C. The interesting fea-
tures of the proposed methodology include the high effi-
ciency, simplicity, and generality which lead to short
reaction times, high yields, a cleaner reaction profile, and
the catalyst recyclability.
N-(2,4-Dimethylphenyl)isoindoline-1,3-dione (2j): IR (in
1
cm-1): 3050, 1724, 1706, 1502, 1380; H NMR (d in ppm,
CDCl3)(90 MHz):7.73-8.01(4H, m, aromaticCH),7.12–7.18
(3H, m, aromatic CH), 2.39 (3H, s), and 2.18 (3H, s).
N-(2,6-Dimethylphenyl)isoindoline-1,3-dione (2k): IR
Acknowledgements We are thankful to the Bu-Ali Sina University,
Hamedan 6517838683 Iran, for the financial support of this work.
1
(in cm-1): 3058, 1738, 1710, 1470, 1377; H NMR (d in
ppm, CDCl3) (90 MHz): 7.75-8.03 (4H, m, aromatic CH);
References
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N-(4-Picolinylamine)isoindoline-1,3-dione (2l): IR (in
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