Alum (KAl(SO4)2·12H2O) catalyzed multicomponent transformation: Simple, efficient, and green route to synthesis of functionalized spiro[chromeno[2,3-d]pyrimidine-5,3′-indoline]-tetraones in ionic liquid media

Article abstract of DOI:10.1002/cjoc.201280014

The combination of isatin, barbituric acid, and cyclohexane-1,3-dione derivatives in the presence of alum (KAl(SO₄)₂· 12H₂O) as a catalyst for 15 min was found to be a suitable and efficient method for the synthesis of spi

Full text of DOI:10.1002/cjoc.201280014

FULL PAPER
DOI: 10.1002/cjoc.201280014
Alum (KAl(SO4)2•12H2O) Catalyzed Multicomponent Transformation:
Simple, Efficient, and Green Route to Synthesis of Functional-
ized Spiro[chromeno[2,3-d]pyrimidine-5,3'-indoline]-tetraones
in Ionic Liquid Media
Mirhosseini Moghaddam, Mojtabaa
Bazgir, Ayoobb
Mohammad Mehdi, Akhondic
Ghahremanzadeh, Ramin*,a
aNanobiotechnology Research Center, Avicenna Research Institute, ACECR, Tehran, Iran
bDepartment of Chemistry, Shahid Beheshti University, Tehran, Iran
cReproductive Research Center, Avicenna Research Institute, ACECR, Tehran, Iran
The combination of isatin, barbituric acid, and cyclohexane-1,3-dione derivatives in the presence of alum
(KAl(SO4)2•12H2O) as a catalyst for 15 min was found to be a suitable and efficient method for the synthesis of
spiro[chromeno[2,3-d]pyrimidine-5,3'-indoline]-tetraones.
Keywords isatin, spirooxindoles, dimedone, barbituric acid, ionic liquids
Introduction
and spirocyclic ethers are elegant targets in organic
synthesis because of their significant biological activi-
ties.[20,21] The spirooxindole system is the core structure
of many pharmacological agents and natural alkaloids.
For example, cytostatic alkaloids as spirotryprostatins A,
and B have been shown to modulate the function of
muscarinic serotonin receptors (Figure 1).[22-26] On the
basis of biological studies, the existence of two or more
different heterocyclic moieties in a single molecule of-
ten enhances the biocidal activity remarkably.[27-34]
Heterocycles form by far the largest of classical di-
visions of organic chemistry and are of immense im-
portance biologically and industrially. The majority of
pharmaceuticals and biologically active agrochemicals
is heterocyclic while countless additives and modifiers
used in industrial applications ranging from cosmetics,
reprography, information storage and plastics are het-
erocyclic in nature.[1] Spirocyclic systems containing
one carbon atom common to two rings are structurally
interesting.[2] The asymmetric characteristic of the
molecule due to the chiral spiro carbon is one of the
important criteria of the biological activities. The
presence of the sterically constrained spiro structure in
various natural products also adds to the interest in the
investigations of spiro compounds.[3] Spiro compounds
represent an important class of naturally occurring
substances characteristic by their highly pronounced
biological properties.[4,5] Similarly, Functionalized spiro
cycloalkyloxindoles are found in a variety of natural
products and bioactive molecules.[6,7] Consequently,
many synthetic methodologies have been developed for
constructing these spirocycles, most of which were
based on cycloaddition or condensation reactions.[8-16]
Compounds with an indole moiety exhibit antibacterial
and antifungal activities. Furthermore, it has been re-
ported that spiroindoline derivatives have highly en-
hanced biological activity.[17-19] Oxindoles derivatized at
C3 as spirocarbocycles, spiroheterocycles, spirolactones,
N
N
O
H
O
H
H
O
N
O
N
O
O
N
MeO
N
H
H
Figure 1 Spirooxindole-containing compounds.
Ionic liquids (ILs) have received vast research inter-
ests in recent years. They exhibited unique properties
such as high ionic conductivity, wide electrochemical
window, non-volatility, high thermal stability, non-
flammability and miscibility with organic compounds,
especially with the heterocyclic compounds as hydro-
philicity, hydrophobicity, Lewis acidity, viscosity and
density can be altered by the fine-tuning of parameters
such as the choice of organic cation, inorganic anion
*
E-mail: r.ghahremanzadeh@yahoo.com
Received May 22, 2011; accepted November 22, 2011.
Chin. J. Chem. 2012, 30, 709—714
© 2012 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
709

Mirhosseini Moghaddam et al.
FULL PAPER
and the length of alkyl chain attached to the organic
cation (Figure 2).[35-39] Because of these useful proper-
ties, ILs have been applied in several areas, including
catalysis, electrochemistry, separation science for ex-
traction of heavy metal ions, as solvents for green
chemistry and materials for optoelectronic applica-
tions.[40-44]
(s, 3H, CH3), 2.07—2.15 (m, 2H, CH2), 2.57—2.65 (m,
2H, CH2), 3.14 (s, 3H, NCH3), 6.85—6.90 (m, 2H,
HAr), 7.07 (d, J＝7.5 Hz, 1H, HAr), 7. 21 (d, J＝7.8 Hz,
1H, HAr), 11.01 (s, 1H, NH), 12.27 (brs, 1H, NH).
1'-Ethyl-8,8-dimethyl-8,9-dihydrospiro[chromeno-
[2,3-d]pyrimidine-5,3'-indoline]-2,2',4,6(1H,3H,7H)-
tetraone (4c)
Colorless crystals, yield 92%; m.p. 253—255 ℃ dec.
1H NMR (300 MHz, DMSO-d6) δ: 0.95 (s, 3H, CH3),
1.05 (s, 3H, CH3), 1.24 (t, J＝7.2 Hz, 3H, CH3),
2.11—2.22 (2H, CH2), 2.54—2.67 (m, 2H, CH2),
3.64—3.68 (m, 2H, NCH2), 6.84—6.94 (m, 2H, HAr),
7.05 (d, 1H, HAr), 7.22 (t, 1H, HAr), 11.02 (s, 1H, NH),
12.20 (brs, 1H, NH).
+
-
+
-
N
N
PF6
N
(
)
N
BF4
n
[Bmim]BF4
n = 1= [Bmim]PF6
n = 3 = [Hmim]PF6
n = 5 = [Octmim]PF6
Figure 2 Chemical structure of the ionic liquids.
1'-Benzoyl-8,8-dimethyl-8,9-dihydrospiro[chro-
meno[2,3-d]pyrimidine-5,3'-indoline]-2,2',4,6(1H,
3H,7H)-tetraone (4d)
Room temperature ionic liquids are increasingly
finding a range of laboratory, developmental and tech-
nical applications, for example, as media for organic
and inorganic chemical synthesis, materials productions,
and electrochemical devices.[36] In continuation of our
investigations into the synthesis of novel heterocyclic
compounds in the green media,[45-53] herein, we wish to
report an efficient and green protocol for the
three-component synthesis of some spirochromene de-
rivatives in excellent yields at short reaction time.
Colorless crystals, yield 92%; m.p. 258—259 ℃ dec.
1H NMR (300 MHz, DMSO-d6) δ: 0.96 (s, 3H, CH3),
1.03 (s, 3H, CH3), 2.03—2.21 (m, 2H, CH2), 2.57—2.74
(m, 2H, CH2), 4.81—4.90 (m, 2H, NCH2), 6.53 (d, J＝
7.6 Hz, 1H, HAr), 6.83—6.89 (m, 1H, HAr),
7.06—7.12 (m, 2H, HAr), 7.31—7.35 (m, 3H, HAr),
7.61—7.64 (m, 2H, HAr), 11.11 (s, 1H, NH), 12.4 (brs,
1H, NH).
5'-Bromo-8,8-dimethyl-8,9-dihydrospiro[chromeno-
[2,3-d]pyrimidine-5,3'-indoline]-2,2',4,6(1H,3H,7H)-
tetraone (4e)
Experimental
1
Melting points were measured on an Elecrtothermal
Colorless crystals (yield 95%); m.p.＞300 ℃; H
1
9100 apparatus. H NMR spectra were recorded on a
NMR (300 MHz, DMSO-d6) δ: 1.01 (s, 3H, CH3), 1.04
(s, 3H, CH3), 2.11—2.20 (m, 2H, CH2), 2.62 (brs, 2H,
CH2), 6.69 (d, J＝8.2 Hz, 1H, HAr), 7.20—7.25 (m, 2H,
HAr), 10.53 (s, 1H, NH), 11.08 (s, 1H, NH), 12.22 (brs,
1H, NH).
BRUKER DRX-300 AVANCE spectrometer at 300.13
MHz, respectively. The starting materials and TLC pa-
pers were prepared from Merck and Aldrich.
Typical procedure for preparation of 8,8-dimethyl-
8,9-dihydrospiro[chromeno[2,3-d]pyrimidine-5,3'-
indoline]-2,2',4,6(1H,3H,7H)-tetraone (4a)
8,8-Dimethyl-5'-nitro-8,9-dihydrospiro[chromeno-
[2,3-d]pyrimidine-5,3'-indoline]-2,2',4,6(1H,3H,7H)-
tetraone (4f)
A mixture of dimedone (0.14 g, 1 mmol), isatine
(0.15 g, 1 mmol), barbituric acid (0.13 g, 1 mmol) and
Alum (0.05 g 10 mol%) in [Bmim]PF6 (0.5 mL) was
stirred for 15 min at 100 ℃ (the progress of the reaction
was monitored by TLC). After completion, the reaction
mixture was washed with water (10 mL×2) and the
solid residue was crystallized from ethanol to give 4a as
1
Colorless crystals (yield 98%); m.p. 292 ℃ dec. H
NMR (300 MHz, DMSO-d6) δ: 1.00 (s, 3H, CH3), 1.05
(s, 3H, CH3), 2.18 (brs, 2H, CH2), 2.62 (brs, 2H, CH2),
6.90 (d, J＝8.1 Hz, 1H, HAr), 8.07 (s, 1H, HAr),
8.06—8.10 (m, 1H, HAr), 11.14 (s, 1H, NH), 11.17 (s,
1H, NH), 12.30 (brs, 1H, NH).
1
white powder (98%), m.p.＞300 ℃; H NMR (300
8,9-Dihydrospiro[chromeno[2,3-d]pyrimidine-5,3'-
indoline]-2,2',4,6(1H,3H,7H)-tetraone (4o)
MHz, DMSO-d6) δ: 0.98 (s, 3H, CH3), 1.05 (s, 3H,
CH3), 2.08, 2.10 (m, 2H, CH2), 2.57—2.65 (m, 2H,
CH2), 6.72 (d, J＝7.7 Hz, 1H, HAr), 6.79 (t, J＝7.9 Hz,
1H, HAr), 6.95 (d, J＝7.8 Hz, 1H, HAr), 6.10 (t, J＝7.4
Hz, 1H, HAr), 10.38 (s, 1H, NH), 11.00 (s, 1H, NH),
12.21 (brs, 1H, NH).
1
Colorless crystals, yield 90%, m.p.＞300 ℃; H
NMR (300 MHz, DMSO-d6) δ: 1.92 (brs, 2H, CH2),
2.21 (brs, 2H, CH2), 2.72 (brs, 2H, CH2), 6.68—6.76 (m,
2H, HAr), 6.95—7.08 (m, 2H, HAr), 10.34 (s, 1H, NH),
11.02 (s, 1H, NH), 12.21 (s, 1H, NH).
1',8,8-Trimethyl-8,9-dihydrospiro[chromeno[2,3-d]-
pyrimidine-5,3'-indoline]-2,2',4,6(1H,3H,7H)-
tetraone (4b)
1'-Methyl-8,9-dihydrospiro[chromeno[2,3-d]pyrimi-
dine-5,3'-indoline]-2,2',4,6(1H,3H,7H)-tetraone (4p)
1
1
Colorless crystals, yield 89%, m.p.＞300 ℃; H
Colorless crystals (yield 95%); m.p.＞300 ℃; H
NMR (300 MHz, DMSO-d6) δ: 1.92 (m, 2H, CH2),
NMR (300 MHz, DMSO-d6) δ: 0.98 (s, 3H, CH3), 1.00
710
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© 2012 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Chin. J. Chem. 2012, 30, 709—714

Alum (KAl(SO4)2•12H2O) Catalyzed Multicomponent Transformation
2.12—2.29 (m, 2H, CH2), 2.72 (brs, 2H, CH2), 3.14 (s,
3H, NCH3), 6.86—6.91 (m, 2H, HAr), 7.07 (d, J＝7.8
Hz, 1H, HAr), 7.17 (t, J＝8.1 Hz, 1H, HAr), 11.05 (s,
1H, NH), 12.06 (brs, 1H, NH).
led to lower yields (50%—60%) after 60 min reaction
time. At first we examined this reaction in the ultrasonic
irradiation in EtOH and THF as solvent and presence of
various Bronsted and Lewis acids at 60 ℃. It was ob-
served that the reaction did not occur in this condition
with any catalyst. The various examined conditions are
summarized in Table 1.
5'-Bromo-8,9-dihydrospiro[chromeno[2,3-d]pyrimi-
dine-5,3'-indoline]-2,2',4,6(1H,3H,7H)-tetraone (4q)
Colorless crystals, yield 90%, m.p. 242—245 ℃ dec.
1H NMR (300 MHz, DMSO-d6) δ: 1.90 (brs, 2H, CH2),
2.25 (brs, 2H, CH2), 2.67 (brs, 2H, CH2), 6.66 (brs, 1H,
HAr), 7.23 (brs, 2H, HAr), 10.49 (s, 1H, NH), 11.07 (s,
1H, NH), 12.22 (s, 1H, NH).
Table 1 Model reaction, conditions and yielda
Entry Condition
Cat.
Time/h Yield/%
1
2
3
4
5
6
Ethanol (U.S. Irradiation) Alum
Ethanol (U.S. Irradiation) p-TSA
Ethanol (U.S. Irradiation) SSA
Ethanol (U.S. Irradiation) SnCl4
Ethanol (U.S. Irradiation) CAN
4
4
4
4
4
4
0
0
0
0
0
0
5'-Nitro-8,9-dihydrospiro[chromeno[2,3-d]pyrimi-
dine-5,3'-indoline]-2,2',4,6(1H,3H,7H)-tetraone (4r)
Colorless crystals, yield 92%; m.p. 280—281 ℃ dec.
1H NMR (300 MHz, DMSO-d6) δ: 1.93 (brs, 2H, CH2),
2.26 (2H, brs, CH2), 2.70 (brs, 2H, CH2), 6.90 (d, 1H,
Hz, HAr), 8.07 (s, 1H, HAr), 8.11 (d, J＝8.8 Hz, 1H,
HAr), 11.13 (s, 1H, NH), 11.17 (s, 1H, NH), 12.34 (brs,
1H, 3NH).
THF (U.S. Irradiation)
Alum
7
THF (U.S. Irradiation)
THF (U.S. Irradiation)
THF (U.S. Irradiation)
THF (U.S. Irradiation)
p-TSA
SSA
SnCl4
4
4
4
4
0
0
0
0
8
9
10
CAN
a Barbituric acid (1 mmol), 5,5-dimethylcyclohexane-1,3-dione (1
Results and Discussion
mmol), isatin (1 mmol) and catalyst (10% mol).
In the course of our research and evaluation of dif-
ferent catalysts and various conditions, and in order to
evaluate the efficiency of this methodology, dimedone
1a, isatin 2a, and barbituric acid 3a were further sub-
jected to reaction using 10 mol% of a diverse type of
Lewis and Bronsted acids such as Alum [Hydrated po-
tassium aluminium sulfate (KAl(SO4)2•12H2O)], SSA (sil-
ica sulfuric acid), SnCl4, p-TSA (para-toluenesulfunic
acid), and CAN (ceric ammonium nitrate) under identical
conditions (Figure 3). We also evaluated the amount of
catalyst required for this transformation. It was found
that using 10 mol% Alum as an inexpensive and avail-
able catalyst in ionic liquid is sufficient to push the re-
action forward. More amount of the catalyst did not in-
crease the yield. We have found that use of amount 10
mol% Alum has a unique capability and best promoter
to enhance the reaction rate in [Bmim]PF6 medium.
However, use of amount 10 mol% of SSA and p-TSA
Then we examined this reaction under the solvent
free condition and in presence of various Bronsted and
Lewis acids at different temperatures. The best results
with Alum as a catalyst were seen in the case of solvent
free condition. The results are summarized in Table 2.
Table 2 Model reaction, conditions, and yielda
Entry
Condition
Cat.
Time/h Temp./℃ Yield/%
1
2
3
4
5
6
7
8
Solvent free
Solvent free
Solvent free
Solvent free
Solvent free
Solvent free
Solvent free
Solvent free
CAN
p-TSA
SSA
2
2
2
2
2
2
2
2
100
100
100
100
60
＜50
60
62
SnCl4
Alum
Alum
Alum
Alum
＜50
＜50
55
80
100
65
120
68
a Barbituric acid (1 mmol), 5,5-dimethylcyclohexane-1,3-dione (1
O
O
mmol), isatin (1 mmol) and catalyst (10% mol).
NH
HN
+
+
O
N
O
O
O
O
After that we examined this reaction in the ionic liq-
uid media and presence of various Bronsted and Lewis
acids at different temperatures. It was observed that the
best results were seen with Alum as a catalyst and
[Bmim]PF6 as media at 100 ℃. The results are summa-
rized in Table 3.
H
3a
1a
2a
HN
O
Various conditions
O
O
NH
As shown in Table 4 it was found that this procedure
works with a wide variety of substrates. Eight types of
substituted isatins, two types of 1,3-cyclohexanediones
and three types of barbituric acids were used in this re-
action for the library validation (Figure 4). Corre-
spondingly, 9-dihydrospiro[chromeno[2,3-d]pyrimi-
O
N
O
H
4a
Figure 3 Synthesis of spiro[chromeno[2,3-d]pyrimidine-
5,3'-indoline]-tetraone.
Chin. J. Chem. 2012, 30, 709—714
© 2012 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
www.cjc.wiley-vch.de
711

Mirhosseini Moghaddam et al.
FULL PAPER
Table 3 Model reaction, conditions and yielda
Entry Condition Cat. Time/min Temp./℃ Yield/%
[BMIM] Br CAN
Table 4 Synthesis of spiro[chromeno[2,3-d]pyrimidine-5,3'-
indoline]-tetraone derivativesa
Product 4 X
Y
O
O
O
O
O
O
O
O
O
O
O
S
R1
Me
Me
Me
Me
Me
Me
Me
Me
Me
Me
Me
Me
Me
Me
H
R2
H
R3 Yieldb/%
1
120
100
100
100
100
100
100
100
100
60
＜50
65
60
68
70
55
85
92
70
93
98
98
a
b
c
H
H
H
H
H
H
H
H
H
98
2
[BMIM] Br p-TSA 60
H
Me
Et
Bz
H
95
3
[BMIM] Br SnCl4 60
H
92
4
[BMIM] Br SSA
[BMIM] Br Alum
[BMIM] Cl Alum
[BMIM] BF4 Alum
[BMIM] Trif Alum
[BMIM] PF6 Alum
[BMIM] PF6 Alum
[BMIM] PF6 Alum
[BMIM] PF6 Alum
60
60
60
30
60
30
15
15
15
d
e
H
92
5
Br
NO2
Br
Me
H
95
6
f
H
98 (98, 96, 96)c
7
g
h
i
Me
H
94
94
8
9
H
Me 88
Me 88
Me 90
10
11
12
80
j
H
Me
H
100
k
l
NO2
H
120
a Barbituric acid (1 mmol), 5,5-dimethylcyclohexane-1,3-dione (1
mmol), isatin (1 mmol) and catalyst (10% mol).
Me
H
H
H
H
H
H
H
H
92
91
94
90
89
90
92
m
n
o
p
q
r
Br
NO2
H
S
S
H
O
O
O
O
O
O
O
S
H
dine-5,3'-indoline]-2,2',4,6(1H,3H,7H)-tetraones 4 were
synthesized by the one-pot, three-component conden-
sation of cyclohexane-1,3-diones 1, isatins 2 and barbi-
turic acids 3 in excellent yields in ionic liquid media in
the presence of Alum as a catalyst for 15 min. Work-up
gave products 4a—4x in 88% to 98% yields. The results
are summarized in Table 4. All the products 4a—4x are
known compounds and were characterized by compari-
son of their 1H NMR spectra and TLC with our previous
synthetic products.[54]
H
H
Me
H
Br
NO2
H
H
H
H
s
H
Me
H
Me 88
Me 89
Me 89
t
Br
NO2
H
H
u
v
w
x
H
H
H
H
H
H
H
88
92
90
Br
S
H
H
NO2
S
H
H
a Barbituric acids (1 mmol), cyclohexane-1,3-diones (1 mmol),
isatins (1 mmol), ionic liquid (0.1 mL) and alum (10% mol).
b Isolated yield. c Isolated yield after recycling of catalyst.
Y
R1
O
R1
R3
O
R3
O
X
N
N
+
O
O
+
O
N
R2
of catalyst is possible for three successive times without
significant loss of activity (Table 4, Entry 4f). The cata-
lyst can be removed from the aqueous phase by remov-
ing the water under vacuum then washing with EtOH
and drying at r.t.
We have not established an exact mechanism for the
formation of products 4, however, a reasonable possibil-
ity is shown in Figure 5.
1a, 1b
3a - 3c
2a - 2h
R2
N
X
O
O
O
R3
[Bmim]PF6
Alum, 100 oC, 15 min
N
R1
O
N
R3
Y
R1
4a - 4x
Conclusions
Figure 4 Synthesis of spiro[chromeno[2,3-d]pyrimidine-5,3'-
In conclusion, we have reported an environmentally
friendly three-component, efficient, clean and simple
method for the synthesis of some new spirooxindole
derivatives using readily available starting materials.
This is the first report on the synthesis of spiro[chro-
meno[2,3-d]pyrimidine-5,3'-indoline]-tetraones in an
ionic liquid and these new reaction conditions open an
important alternative to the use of volatile organic sol-
vents. Prominent among the advantages of this new
method are short reaction times, operational simplicity,
use of IL media, high yields, easy work-up procedures,
indoline]-tetraone derivatives.
This procedure is a convenient and simple method
for the preparation of extensive chemical library for
spirooxindole derivatives by accessible starting materi-
als to find widespread application in the ground of com-
binatorial chemistry, and drug innovation.
We also checked the reusability of the catalyst by
recovering the alum and using it for new runs and found
that the catalyst could be reused several times without
any decrease in the product yield. Apparently, recycling
712
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© 2012 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Chin. J. Chem. 2012, 30, 709—714

Alum (KAl(SO4)2•12H2O) Catalyzed Multicomponent Transformation
X
OH
OH
R1
H+
N
R2
H+
R1
R1
O
R1
O
R3
Y
O
N
O
R3
1
O
N
O
O
R2
O
X
-H2O
O
N
4
N
OH
Y
R2
R3
R3
O
2
O
N
N
X
X
R1
R1
O
3
OH
1
H+
H+
N
O
R2
R3
O
O
N
N
R3
Y
Figure 5 Proposed mechanism of the reaction.
[16] Feldman, K. S.; Karatjas, A. G. Org. Lett. 2006, 8, 4137.
[17] Da-Silva, J. F. M.; Garden, S. J.; Pinto, A. C. J. Braz. Chem. Soc. 2001,
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and using of Alum as a nontoxic, easy available, recy-
clable and inexpensive catalyst. Moreover, the advan-
tage of such media is that often smaller amounts of the
ILs can be used compared with organic solvents in reac-
tion; in addition, the reaction media can be recycled for
several times.
[18] Joshi, K. C.; Jain, R.; Sharma, K. J. Indian Chem. Soc. 1988, 115, 202.
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