Ultrasound assisted multicomponent reactions: A green method for the synthesis of N-substituted 1,8-dioxo-decahydroacridines using β-cyclodextrin as a supramolecular reusable catalyst in water

Article abstract of DOI:10.1016/S1872-2067(15)61005-1

We demonstrate a superficial method for the synthesis of N-substituted 1,8-dioxo-decahydroacridines using β-cyclodextrin as a supramolecular, biodegradable, and reusable catalyst in aqueous medium. The reaction product is in excellent yield with moderate

Full text of DOI:10.1016/S1872-2067(15)61005-1

Chinese Journal of Catalysis 37 (2016) 146–152
a v a i l a b l e a t w w w . s c i e n c e d i r e c t . c o m
j o u r n a l h o m e p a g e : w w w . e l s e v i e r . c o m / l o c a t e / c h n j c
Article
Ultrasound assisted multicomponent reactions: A green method for
the synthesis of N‐substituted 1,8‐dioxo‐decahydroacridines using
β‐cyclodextrin as a supramolecular reusable catalyst in water
Asha V. Chate, Umesh B. Rathod, Jagdish S. Kshirsagar, Pradip A. Gaikwad, Kishor D. Mane,
Pravin S. Mahajan, Mukesh D. Nikam, Charansingh H. Gill *
Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad 431004, India
A R T I C L E I N F O
A B S T R A C T
Article history:
We demonstrate a superficial method for the synthesis of N‐substituted 1,8‐dioxo‐decahydroacri‐
dines using β‐cyclodextrin as a supramolecular, biodegradable, and reusable catalyst in aqueous
medium. The reaction product is in excellent yield with moderate to excellent selectivity. The
mechanistic transformation presumably proceeds via a one‐pot, multicomponent cyclization of
dimedone in the presence of aromatic aldehydes and aromatic amines/INH, undergoing a tandem
Michael addition reaction. The proposed approach in this study provides a highly efficient and en‐
vironmentally benign route to N‐substituted 1,8‐dioxo‐decahydroacridines.
Received 19 September 2015
Accepted 25 October 2015
Published 5 January 2016
Keywords:
Tandem reaction
N‐Substituted
1,8‐dioxo‐decahydroacridines
β‐Cyclodextrin
© 2016, Dalian Institute of Chemical Physics, Chinese Academy of Sciences.
Published by Elsevier B.V. All rights reserved.
Supramolecular catalysis
Water
1. Introduction
nificant attention for the reason that, CDs [1,2] are a family of
cyclic oligomers, composed of 1‐4 linked β‐D‐glucose units.
Recently, the development of new processes that minimize
pollution in the chemical industry has received considerable
attention because of growing environmental concerns. In this
regard, supramolecular catalysis using efficient heterogeneous
catalysts have been used in various organic transformations.
The ability of supramolecular catalysis to enhance catalytic
activity provides an alternative to replace expensive catalysts
with lesser quantities of inexpensive heterogeneous catalysts.
Additionally, waste effluent is reduced or even absent, increas‐
ing the commercial viability. Catenanes, rotaxanes, crown
ether, cyclodextrin (CD), and calixarenes are examples of
emerging green and sustainable supports in heterogeneous
catalysis.
Such family members include the industrially produced α‐CD
(six glucose units), β‐CD (seven units), and γ‐CD (eight units) as
well as several other oligosaccharides having increased glucose
units. CDs are crystalline, homogeneous, non‐hygroscopic mol‐
ecules possessing a hollow truncated cone shape with all the
secondary hydroxyl groups [O2)‐H and O3)‐H] crowning the
outer edge, while all the primary hydroxyl groups [O6)‐H] re‐
side within the inner perimeter. The CD exterior, containing
numerous hydroxyl groups, possesses hydrophilic characteris‐
tics, while the cavity—containing two rings of methine pro‐
tons—is relatively hydrophobic.
Enormous interest in CDs lies in their unique structural to‐
pography, which enables them to form inclusion complexes
with a wide variety of hydrophobic guest molecules [3]. The
Among these supramolecular catalysts, CD has drawn sig‐
* Corresponding author. Tel: +91‐240‐2403311; Fax: +01‐240‐2400491; E‐mail: chgill16@gmail.com
DOI: 10.1016/S1872‐2067(15)61005‐1 | http://www.sciencedirect.com/science/journal/18722067 | Chin. J. Catal., Vol. 37, No. 1, January 2016

Asha V. Chate et al. / Chinese Journal of Catalysis 37 (2016) 146–152
147
host‐guest complexation exerts a profound effect on the physi‐
cochemical properties of the guest, such as solubility, stability
and taste modification by masking unpleasant flavors and
odors etc. Among various CDs, β‐CD is an attractive confor‐
mation as a catalyst in regard to both an economical and envi‐
ronmental point of view. The most accessible β‐CD is a cyclic
oligosaccharide composed of seven α‐1,4‐linked glucopyra‐
nosyl units. Several members of β‐CD are used industrially in
pharmaceutical and associated applications [4]. The ability to
use the hydrophobic cavity of β‐CD to encapsulate bioactive
molecules in water has drawn tremendous interest from the
pharmaceutical industry because encapsulation improves the
stability and bioavailability of drug molecules [5], apart from
being non‐toxic, metabolically safe [6], and readily recoverable
and reusable.
Many biologically important molecular scaffolds can easily
be synthesized from readily available starting materials with
the help of multi‐component reactions (MCRs) [7–10]. MCRs
combine at least three simple building blocks in situ, and pro‐
vide a diverse route to complexity in a limited number of reac‐
tion steps. MCRs constitute an especially attractive synthetic
strategy since they provide easy and rapid access to a large
library of organic compounds with diverse substitution pat‐
terns.
The MCR of dimedone, aldehydes and aniline has produced
numerous research studies since its discovery. The resulting
acridine and acridine‐1,8‐dione derivatives are interesting het‐
erocyclic compounds that have generated numerous publica‐
tions in organic, pharmaceutical and medicinal chemistry fields
because of their potential biological activities and presence in a
variety of significant natural products and synthetic dye‐stuffs.
Such characteristics exhibit diverse pharmacological activities
in areas relating to anti‐malaria [11], anti‐tumor [12], an‐
ti‐cancer [13], fungicidal [14], cytotoxic [15], an‐
ti‐multidrug‐resistant [16], antimicrobial [17], and are widely
prescribed as calcium β‐blockers [18,19]. Additionally,
1,8‐dioxo‐decahydroacridines were created to act as laser dyes
[20,21] and used as photoinitiators [22].
The significance of such heterocycles in chemical and bio‐
logical applications has been well established, and as a result,
the ready and efficient synthesis of these molecules has at‐
tracted considerable attention from the synthetic organic
community with numerous reports detailing methods for the
synthesis of acridine and acridine‐1,8‐dione derivatives. Meth‐
od development has included the use of dimedone, aldehydes
and various nitrogen sources, such as urea [23], hydroxylamine
[24], ammonium acetate on basic alumina [25], ammonium
bicarbonate [26], ammonium hydroxide and various appropri‐
ate amines or ammonium acetate [27]. Additional methods
have included conventional heating of organic solvents in the
presence of Amberlyst‐15 [28], benzyltriethyl ammonium chlo‐
ride (TEBAC) [29], the use of microwave irradiation [30,31],
[MIMPS]3PW12O40 and [TEAPS]3PW12O40 [38]. However, these
methodologies suffer from one or more shortcomings, such as
low yield, prolonged reaction time, use of toxic organic solvents
and employ costly and hazardous catalysts as well as cumber‐
some work‐up procedures. Therefore, introducing clean pro‐
cesses and utilizing eco‐friendly catalysts, which can be easily
recycled at the end of the reaction, have received increasing
attention.
Conversely, in comparison with conventional thermal heat‐
ing, ultrasound irradiation has some important advantages:
improved yields with enhanced product yield and selectivity,
substantial decreases of reaction time, lower costs and easier
handling and processing. At the same time, in many cases, reac‐
tions under ultrasound irradiation are considered to be envi‐
ronmentally friendly as they require only a limited quantity of
solvent and are more energy efficient [39]. Additionally, ultra‐
sonic irradiation provides minimal side reactions [40].
The demand for an environmentally benign procedure uti‐
lizing a heterogeneous and reusable catalyst led our investiga‐
tions to develop a safe alternative method for the synthesis of
acridine‐1,8‐dione derivatives. Bearing the above points in
mind, we believe this to be the first ever report on a sonically
enhanced one‐pot multicomponent reaction in aqueous media
using the environmentally benign β‐CD as a supramolecular
catalyst.
2. Experimental
2.1. General
All chemicals were purchased and used by further
purification. Melting points were determined on a open
capillary tube and are uncorrected. Progress of the reaction
was monitored by thin layer chromatography (TLC) on Merck’s
silica plates. 1H NMR spectra were recorded on Bruker Avance
100 MHz instruments using TMS as internal standard. 13C NMR
spectra were recorded on Bruker AvII‐400 MHz instruments.
Elemental analysis was recorded on elemental analyzers Eu‐
ro‐E 3000.
2.2. Reactions
All the reactions were carried out in Bandelin Sonorex (with
a frequency of 35 kHz and a nominal power 200 W) ultrasonic
bath (Built‐in heating, 30–80 C there‐mostatically adjustable).
The reaction vessel placed inside the ultrasonic bath containing
water.
General procedure for the synthesis of N‐substituted
decanhydroacridine‐1,8‐diones 4a–4k. The mixture of
5,5‐dimethylcyclohexane‐1,3‐dione 1a (1.98 g, 2 mmol), alde‐
hyde 2a (700 mg, 1 mmol) and aniline 3a (650 mg, 1 mmol)
were added in β‐cyclodextrin (10 mol%) solution containing
water (20 mL). The resulting mixture was stirred under ultra‐
sonication at 80 C. After completion of the reaction (monitored
by TLC), reaction mixture was extracted with ethyl acetate. The
organic layer was washed with water, saturated brine solution
and dried over anhydrous sodium sulphate. The combined
and
9,10‐diarylacridine‐1,8‐diones have also been prepared using
p‐dodecylbenzenesulfonic acid (DBSA) [34], Zn(OAc)
using
ionic
liquids
[32,33].
Furthermore,
2·2H2O,
ammonium chloride or L‐proline [35], proline [36], CAN [37]
and the sulfonated organic heteropoly acid salts,

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Asha V. Chate et al. / Chinese Journal of Catalysis 37 (2016) 146–152
organic layer was evaporated under reduced pressure and thus
obtained crude product was further purified by crystallization
from hot ethanol. The aqueous layer was then cooled to 0 C to
recover β‐CD reappeared as white solid. Thus the obtained
solid mass then filtered and washed with water to recover
β‐CD. The recovered β‐CD was reused for 3–4 consecutive runs
in this reaction without any significant loss in yield and activity.
The product was confirmed by melting point, 1H NMR, 13C NMR,
elemental analysis and the results obtained are summarized in
(Table 3).
General procedure for the synthesis of N‐substituted
decanhydroacridine‐1,8‐diones 4l–4t. The mixture of
5,5‐dimethylcyclohexane‐1,3‐dione 1a (1.31 g, 2 mmol), alde‐
hyde 2a (500 mg, 1 mmol) and isoniazid 3a (640 mg, 1 mmol)
were added in β‐cyclodextrin (10 mol%) solution containing
water (20 mL). The resulting mixture was stirred under ultra‐
sonication at 80 C. After completion of the reaction (monitored
by TLC), reaction mixture was extracted with ethyl acetate. The
organic layer was washed with water, saturated brine solution
and dried over anhydrous sodium sulphate. The combined
organic layer was evaporated under reduced pressure and thus
obtained crude product was further purified by crystallization
from hot ethanol. The aqueous layer was then cooled to 0 C to
recover β‐CD reappeared as white solid. Thus the obtained
solid mass then filtered and washed with water to recover
β‐CD. The recovered β‐CD was reused for 3‐4 consecutive runs
in this reaction without any significant loss in yield and activity.
The product was confirmed by melting point, 1H NMR, 13C NMR,
elemental analysis and the results obtained are summarized in
Table 3.
Fig. 1. Schematic of the β‐CD structure.
Reaction condition matrices—with respect to solvent and
catalyst—are typically governed on their environmental impact
and today’s environmental concerns push industrial and aca‐
demic processes away from solvents to environmentally benign
water. The chemical and physical properties of water enhance
selectivity and reactivity in reactions, which cannot be matched
using organic solvents [41–44]. However, dissolving many or‐
ganic compounds in water is difficult and for this reason, the
majority of reactions cannot proceed easily in aqueous media
[45]. One way to improve the solubility of substrates in water is
the incorporation of water‐soluble macrocycles as inverse
phase transfer catalysts. CDs, which encapsulate organic com‐
pounds in aqueous media have been found to enhance the rate
of water mediated reactions because of hydrophobic effects.
β‐CD is a cyclic oligosaccharide possessing a hydrophobic cavi‐
ty and several hydroxyl groups in two distinct regions (Fig. 1)
[46,47]. These structural characteristics allow substrates to
bind selectively through non‐covalent interactions. Being solu‐
ble in water, non‐toxic, and readily available, β‐CD is often used
as an additive for various chemical reactions in water [48–57].
In this study, a model reaction was conducted by reacting
dimedone (1), benzaldehyde (2a) and aniline (3a) in water at
room temperature in the absence of β‐CD to obtain the corre‐
sponding N‐substituted acridine‐1,8‐dione, albeit at lower
yields (25%) and longer reaction times. The poor solubility of
dimedone and aniline in water at elevated temperature result‐
ed in the formation of undesired products. When the same re‐
action was performed in the presence of β‐CD, at room tem‐
perature, the product was obtained in moderate yield (41%).
However, the controlled experiment using β‐CD as a supramo‐
lecular catalyst at 60–80 °C resulted in an excellent product
yield (94%) at 10 mol% of β‐CD within 62 min without column
3. Results and discussion
3.1. Synthesis
In this study, we describe for the first time, a sustainable
one‐pot synthesis of N‐substituted 1,8‐dioxo‐decahydroacri‐
dines 4a–4t (Scheme 1) under ultrasonication at 80 °C in
aqueous conditions using β‐CD as a reusable supramolecular
catalyst.
OH
Hydrophilic medium
R1
H2O
O
O
HO
O
O
O
OH
HO
OH H2O
O
OH
N
H2O
HO
HO
O
O
R2
CHO
R1
OH
O
O
2
4a–4k
4a-4k
-CD/H2O
)))))), 80 oC
O
HO
O
OH
R1
HO
OH
H2O
NH2
O
NHNH2
O
O
O
H2O
OR
HO
R2
OH
N
N
HO
HN
O
O
O
OH
OH O
O
HO
H2O
H2O
N
HO
O
4l-4t
4l–4t
OH
Hydrophobic cavity
β-
cyclodextrin
Scheme 1. Synthesis of N‐substituted 1,8‐dioxo‐decahydroacridines.

Asha V. Chate et al. / Chinese Journal of Catalysis 37 (2016) 146–152
149
Table 2
Synthesis of N‐substituted decahydroacridine‐1,8‐diones in the pres‐
ence of β‐CD in water under ultrasonication at 80 °C.
O
O
O
CHO
NH2

-CD/H2O
)))))), 80 oC
2
N
Time Isolated M.P. (°C)
(min) yield (%) [37,38,58]
R1
R2/INH
O
Entry Product
1
2a
3a
1
2
3
4
5
6
7
8
4a
4b
4c
4d
4e
4f
4g
4h
4i
–H
p‐Br
p‐Cl
p‐OMe
p‐OH
–H
–H
–H
–H
–H
p‐F
p‐OMe 77
p‐OMe 80
–H
62
74
70
68
70
93.57
87.35
80.12
82.04
81.02
72.36
93.45
91.55
85.27
89.11
88.09
88.77
90.18
94.56
85.12
88.23
86.58
88.30
90.12
56.35
254–257
>300
4a
242–244
219–223
263–265
216–218
252–255
278–280
280–284
110–113
278–280
148–150
96–98
99–102
252–254
109–111
92–94
85–87
153–155
280–282
Scheme 2. Standard model reaction.
chromatographic purification (Scheme 2).
p‐Cl
This result indicates that the catalyst plays a critical role in
the reaction. Method development in this study, shows the
merit of CD, as for the first time, various CDs, such as α‐CD,
β‐CD and γ‐CD were examined for their efficiency as supramo‐
lecular catalysis. The results are tabulated in Table 1.
Of these CDs (Table 1), β‐CD was found to be the superior
mediator and gave moderate to excellent yield of the desired
substituted 1,8‐dioxo‐decahydroacridines. As β‐CD is inexpen‐
sive and readily available, when compared with α‐CD and γ‐CD,
β‐CD was selected as the catalyst to perform the reaction.
Furthermore, we studied the three‐component condensa‐
tion of dimedone (2 mmol), benzaldehyde (1 mmol) and aniline
(1 mmol) to optimize the reaction conditions with respect to
temperature, time, catalyst/substrate molar ratio and catalyst
reusability.
m‐NO2
p‐OMe
p‐F
2‐Furan
–H
81
9
p‐Me 79
p‐F
–H
10
11
12
13
14
15
16
17
18
19
20
4j
4k
4l
61
70
65
62
68
63
62
65
62
61
90
INH
INH
INH
INH
INH
INH
INH
INH
4m
4n
4o
4p
4q
4r
4s
4t
p‐Cl
p‐OMe
m‐OMe
p‐F
p‐NO2
p‐Me
m‐Me
Propionaldehyde INH
Reaction conditions: dimedone 2 mmol, benzaldehyde 1 mmol, aniline
1 mmol, β‐CD 10 mol%, water, ultrasonication, 80 °C, 62 min.
1,3‐cyclohexanediones. To assess the general applicability of
this method under the given optimized reaction conditions, a
wide range of divergent aldehydes and anilines possessing
varying substituents, in the presence of two equivalents of
1,3‐cyclohexanediones, were allowed to undergo this
three‐component condensation. The nature of the functional
group on the aldehyde/aniline aromatic rings exerted a slight
influence on the reaction time. –Cl, –F, –Me, –OMe and –NO2
were found to be compatible under the optimized reaction
conditions. Heteroaromatic aldehydes, such as 2‐furan‐2‐
carbaldehyde was equally amenable to these conditions (Table
2, entry 11). An attempt to synthesize 1,8‐dioxo‐decahydroac‐
ridine by reacting the aliphatic aldehyde, propionaldehyde, was
not successful as the product yield was very low even after
prolonged reaction time (Table 2, entry 20). On the basis of the
above results, we suggest that the internal hydrophobic cavity
of β‐CD forms an inclusion complex with the aldehyde and
dimedone more effectively and enhances the rate of reaction
resulting in an increase in the product yield and a decrease in
Temperature has an important role on product yield. At
lower temperatures product formation is observed at trace
concentrations and required longer reaction times. Increasing
the temperature from room temperature to 80 °C resulted in
increased yields along with decreasing reaction times. All pro‐
ceeding reactions were performed at the elevated temperature
of 80 °C (Table 2). The fixed catalyst loading was evaluated in
the model reaction (Table 2, entry 1) at 80 °C in water. The
optimum result was obtained at 10 mol% of β‐CD affording
94% yield within 62 min under sonication in water and the use
of excess catalyst had no impact on either the rate of reaction
or on product yield.
The effect of solvent on the yield of 1,8‐dioxo‐decahydroac‐
ridines is given in Table 3. The reaction among dimedone, ben‐
zaldehyde and aniline was chosen as a model reaction for in‐
vestigating the effect of solvent. Among all the solvents, water
was found to play an effective role in this transformation af‐
fording the highest yields (Table 3, entry 6). Therefore, water
was selected as the optimum solvent for this transformation.
Another reason for this is that water is a green solvent.
After obtaining the optimized reaction conditions, thereafter
the investigation studied the reaction between a series of aro‐
matic aldehydes and aromatic amines or isoniazide with
Table 3
Optimization of solvent for the synthesis of N‐substituted 1,8‐dioxo‐
decahydroacridines.
α‐Cyclodextrin
Time Yield*
β‐Cyclodextrin
Time Yield*
γ‐Cyclodextrin
Time Yield*
En‐
try
Solvent
Table 1
(h)
7.2
8
(%)
38
41
48
40
35
45
(min)
78
(%)
86
89
78
67
71
94
(h)
5.3
4.5
4.0
5.0
5.5
5.0
(%)
78
72
68
55
60
75
Optimization of reaction conditions for the synthesis of N‐substituted
1,8‐dioxo‐decahydroacridines using various CD catalysts.
1
2
3
4
5
6
Ethanol
Aq. ethanol
CH3CN
DMF
THF
Water
75
9
8
78
Catalyst
α‐CD
β‐CD
Time (h)
10–12
1
Isolated yield (%)
40–50
72
8.2
8.8
74
80–94
62
γ‐CD
6–8
60–70
Reaction conditions: dimedone 2 mmol, benzaldehyde 1 mmol, aniline
1 mmol, β‐cyclodextrin 10 mol%, 80 °C. *Isolated yield.
Reaction conditions: dimedone 2 mmol, benzaldehyde 1 mmol, aniline
1 mmol.

150
Asha V. Chate et al. / Chinese Journal of Catalysis 37 (2016) 146–152
reaction time. The ultrasound irradiation technique was also
established to be compatible with all listed substrates (Table
2). Representative results are summarized in Table 2. Product
formation was confirmed by 1H NMR, 13C NMR, elemental anal‐
ysis and melting point data.
3.2. Catalyst recycling
The main advantages of β‐CD as a catalyst were observing
clean reactions without any side product formation, the ability
to reuse the catalyst, and efficient recovery. Reusability was
studied by three cycles, comparing back with the fresh catalyst
in the synthesis of 1,8‐dioxo‐decahydroacridines. Each cycle
showed that the catalyst was almost quantitatively recovered
and after the second and third catalyst cycle product yield was
89% and 92% of the fresh cycle yield, respectively (Fig. 2).
3.3. Reaction mechanism
β‐CD has a rigid conical molecular structure with a hydro‐
phobic interior and a hydrophilic exterior. The internal hydro‐
phobic cavity is the key structural feature of the β‐CDs. It pro‐
vides the ability to complex and holds a wide variety of inclu‐
sion molecules. To account for the very efficient catalysis by
β‐CD of this tandem reaction, wherein supramolecular cata‐
lyzed reactions are involved, it is proposed that β‐CD with its
seven free primary –OH groups synergistically behave as an
efficient host and supramolecular β‐CD catalyst (Fig. 1). In
aqueous solutions, hydrophobic bonding in β‐CD is accompa‐
nied by a favorable entropy change (ΔS) during the transfer of
the guest molecules—dimedone, aldehyde and aniline from
aqueous media to a polar media, i.e. the β‐CD cavity. Large fa‐
vorable ΔS and small unfavorable ΔH changes are observed
during the time of transfer. The favorable change in entropy to
form hydrophobic bonding is responsible for stabilization of
the host‐guest complex, i.e. complexation of CD with a polar
guest molecule (dimedone, aldehyde or aniline). No covalent
bonds are formed or broken during the complex formation and
molecules in the complex were in rapid equilibrium with free
molecules in the solution. The driving forces for the complex
formation include release of enthalpy‐rich water molecules
Scheme 3. Plausible mechanism for the synthesis of N‐substituted
1,8‐dioxo‐decahydroacridines.
from the cavity, electrostatic interactions, van der Waals inter‐
actions, hydrophobic interactions, hydrogen bonding, release of
conformational strain and charge‐transfer interactions.
A plausible mechanism is detailed in Scheme 3. In the first
step, the aldehyde binds to the β‐CD cavity. Activation of a pro‐
ton from dimedone by β‐CD catalyzes a Knoevenagel condensa‐
tion reaction with the carbonyl group to give the 2‐arylidene
dimedone. The cooperative enzyme‐like binding of these in‐
termediates ensures a tighter fit into the cavity and facilitates
further reactions, namely Michael addition of a second dim‐
edone to 2‐2‐hydroxy‐4,4‐dimethyl‐6‐oxocyclohexyl)phenyl)
methyl)‐5,5‐dimethylcyclohexane‐1,3‐dione activated by
a
dimedone proton followed by cyclization with aniline to give
the final product (Scheme 3).
Yield
Catalyst recovery
92
92
92
92
4. Conclusions
92
90
88
86
91
We have disclosed a clean and efficient procedure for the
synthesis of pharmacologically significant 1,8‐dioxo‐decahy‐
droacridine derivatives via one‐pot three‐component conden‐
sation of dimedone, benzaldehyde and aniline/INH using β‐CD
as a supramolecular catalyst in aqueous medium. This rate
enhancement is preliminary because of superior hydrophobic
binding of β‐CD to hydrophobic substituents, which in turn
enhances the reactivity of substrates. The task‐specific β‐CD
catalyst used is biodegradable, recyclable/recoverable and
purely environmentally benign. Furthermore, the catalyst is
easy to prepare and does not require any harmful sol‐
vent/chemicals. Other prominent features are: shorter reaction
90
89
88
Fresh
Run 1
Run 2
Run 3
Fig. 2. Reuse and recovery of β‐cyclodextrin and its effect on yield.

Asha V. Chate et al. / Chinese Journal of Catalysis 37 (2016) 146–152
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This work was supported by Special Assistance Programme
SAP, University Grants Commission, New Delhi, India, intended
to encourage the pursuit of excellence and teamwork in ad‐
vanced teaching and research to accelerate the realization of
international standards in specific fields, and also Sophisticated
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Chin. J. Catal., 2016, 37: 146–152 doi: 10.1016/S1872‐2067(15)61005‐1
Ultrasound assisted multicomponent reactions: A green method for the synthesis of N‐substituted
1,8‐dioxo‐decahydroacridines using β‐cyclodextrin as a supramolecular reusable catalyst in water
Asha V. Chate, Umesh B. Rathod, Jagdish S. Kshirsagar, Pradip A. Gaikwad, Kishor D. Mane, Pravin S. Mahajan, Mukesh D. Nikam,
Charansingh H. Gill*
Dr. Babasaheb Ambedkar Marathwada University, India
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N‐substituted 1,8‐dioxo‐decahydroacridine derivatives. The β‐cyclodextrin employed in the multi‐component reaction satisfies the re‐
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