Eco-friendly, ultrasound-assisted, and facile synthesis of one-pot multicomponent reaction of acridine-1,8(2H,5H)-diones in an aqueous solvent

Article abstract of DOI:10.1002/jccs.201800411

A one-pot, multistep synthesis of acridine-1,8(2H,5H)-diones (4a–m) was achieved by three-component reaction of dimedone (1) with an aromatic aldehyde (2a–m) and an ammonium acetate (3) using water as a green solvent without any catalyst and a simple, eas

Full text of DOI:10.1002/jccs.201800411

Received: 2 November 2018
DOI: 10.1002/jccs.201800411
Revised: 21 March 2019
Accepted: 25 March 2019
C O M M U N I C A T I O N
Eco-friendly, ultrasound-assisted, and facile synthesis of one-pot
multicomponent reaction of acridine-1,8(2H,5H)-diones in an
aqueous solvent
Pravin N. Chavan1 | Dattatraya N. Pansare2
| Rohini N. Shelke2
1Department of Chemistry, Doshi Vakil
College, Goregaon, India
2Department of Chemistry, Deogiri College,
Abstract
A one-pot, multistep synthesis of acridine-1,8(2H,5H)-diones (4a–m) was achieved
by three-component reaction of dimedone (1) with an aromatic aldehyde (2a–m)
and an ammonium acetate (3) using water as a green solvent without any catalyst
and a simple, easily handled, and ultrasonic technique as well as conventional
method.
Aurangabad, India
Correspondence
Dattatraya N. Pansare, Department of
Chemistry, Deogiri College, Station Road,
Aurangabad, 431005, Maharashtra, India.
Email: dattatraya.pansare7@gmail.com
K E Y W O R D S
ammonium acetate, aqueous solvent, aromatic aldehydes, dimedone, ultrasound irradiation
Nowadays, many time reactions are carried out using the
ultrasonic irradiation method. The ultrasonic irradiation
1 | INTRODUCTION
method has been acknowledged as an innocuous, environ-
mentally friendly, and green technique, and its application
today has been a boon in serving a new pathway for several
chemical processes. [27–32]
Herein, we report an efficient, easy to handle, and conve-
nient experimental procedure for the synthesis of
3,3,6,6-tetramethyl-9-R-3,4,6,7,9,10-hexahydroacridine-1,8
(2H,5H)-dione in an aqueous solvent through a one-pot
multicomponent reaction of aromatic aldehyde (1a–m),
dimedone (2), ammonium acetate (3), without catalyst using
ultrasonic irradiation as well as a conventional method.
Acridines are heterocyclic natural products. Acridinedione
derivatives have a wide range of biological active proper-
ties such as antimalarial and anticancer properties.[1–6] Fur-
thermore, their derivatives are also used in laser dyes.[7–9]
Use of acridine derivatives in the synthesis of proteins,
peptides, and nucleic acid also reported to show antitumor
and binding (DNA) activities.[10–13] Substituted acridines
were synthesized from aromatic aldehydes, dimedone,
and nitrogen-containing reagents such as urea,[14] ammo-
nium acetate and basic alumina catalyst,[15] ammonium
bicarbonate,[16] ammonium hydroxide,[17] hydroxyl
amine,[18] various anilines,[19] and using different catalysts
such as ceric ammonium nitrate,[20] SPNP,[21] ammonium
chloride,[22] copper sulfate pentahydrate,[23] SiO2-I,[24]
CuO,[25] dodecyl benzenesulfonic acid (phase transfer cata-
lyst)[26] in hazardous/nonhazardous solvents using micro-
wave, reflux, and traditional heating methods.
2 | RESULTS AND DISCUSSION
We report here the eco-friendly synthesis of substituted
acridinediones via one-pot Knoevenagel condensation,
Michael addition, and cyclization of aromatic aldehydes
(1a–m), dimedone (2), ammonium acetate in aqueous
medium as a green solvent under controlled ultrasonic irradi-
ation without the use of catalysts (Scheme 1).
Some of these methods have drawbacks for synthesis of
substituted acridines such as complicated handling, multistep
reaction, low yield, prolonged reaction time, expensive
reagents, which necessitated the development of newest
methodology for synthesis of substituted acridine.
First, we examined different solvents in reactions, we car-
ried out a model reaction of 2,5-dimethoxy benzaldehyde
© 2019 The Chemical Society Located in Taipei & Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
J Chin Chem Soc. 2019;1–7.
http://www.jccs.wiley-vch.de
1

2
CHAVAN ET AL.
acetonitrile, water, and dichloromethane solvents (entries
6–10) under ultrasonic irradiation at room temperature, so we
increased the temperature of the sonication bath up to 70ꢀC.
As a result, we observed yields of products (81, 83, 80, and
91%) in methanol, ethanol, acetonitrile, and water solvents
(entries 11–13 and 15) increased with time. However, in the
case of dichloromethane, yield of the product (60%) (entry
14) is low as compared to other solvents (Table 1).
SCHEME 1 General reaction of 3,3,6,6-tetramethyl-9-substitited
phenyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione
We have concentrated here in the case of acetonitrile,
under reflux conditions, low (30%) yield of the product
(entry 2) was observed, but high (80%) yield of the product
(entry 12) was observed under ultrasonication because of the
effect of ultrasonic irradiation. It was observed that all sol-
vents are favorable for synthesis of acridinedione derivatives
under ultrasonic irradiation at 70ꢀC. However, we selected
water solvent because water is a green solvent.
Finally, we have checked the reaction conditions at room
temperature in water solvent without reflux and ultrasonic
irradiation, (0%) yield of the product was observed
(Table 1).
Under the optimized set of model reaction conditions
(entry 15) in one-pot containing dimedone (1), aromatic alde-
hyde (2a–m), and ammonium acetate (3) without any catalyst
in aqueous medium under ultrasonic irradiation at 70ꢀC. The
results are reported in Table 1. We report that all aromatic
aldehydes containing acridinedione derivatives are given in
Table 2. We have observed that the electron-withdrawing
aldehydes give more time for reaction completion than
(1a), dimedone (2), ammonium acetate(3) in a solvent viz.
ethanol acetonitrile, methanol, dichloromethane, and water
at room temperature, reflux, and using an ultrasonic irradia-
tion method at different temperatures. The results are sum-
marized in Table 1. Yields of 88, 82, 70, and 79% of the
products were obtained in ethanol, methanol, dic-
hloromethane, and water solvents under reflux conditions
(entries 1, 3–5). However, in the case of acetonitrile, a very
low (30%) yield of the product (entry 2) was observed
(Table 1).
Furthermore, we have compared the reaction methods for
a conventional, eco-friendly procedure such as at room tem-
perature, reflux (110ꢀC), and under ultrasonic irradiation
(with room temperature and 70ꢀC temperature) conditions
using a choosable reaction model. Ultrasonic bath tempera-
tures were controlled by adding water in the sonication bath
time to time (Table 1).
As we have observed, low yields (35, 33, 26, 32, and
23%) of the products were obtained using methanol, ethanol,
TABLE 1 To optimize the reaction conditions for synthesis of substituted acridinediones (4a)a
Entry
1
Solvent
Method
Reflux
Reflux
Reflux
Reflux
Reflux
US
Temperature (ꢀC)
Time (hr)
03
% yield
88
30
82
70
60
33
26
35
23
32
83
80
81
76
91
0
Ethanol
110
2
Acetonitrile
Methanol
Dichloromethane
Water
110
09
3
110
03
4
110
04
5
110
04
6
Ethanol
R.T.
R.T.
R.T.
R.T.
R.T.
70ꢀC
70ꢀC
70ꢀC
70ꢀC
70ꢀC
R.T.
03
7
Acetonitrile
Methanol
Dichloromethane
Water
US
03
8
US
03
9
US
03
10
11
12
13
14
15
16
US
03
Ethanol
US
1.30
1.30
1.30
1.30
1.30
09
Acetonitrile
Methanol
Dichloromethane
Water
US
US
US
US
Water
—
Abbreviations: R.T., room temperature; US: ultrasonication.
aReaction conditions: The reaction was carried out by the addition of 2,5-dimethoxybenzaldehyde (1 mmol), dimedone (2 mmol), ammonium acetate (1 mmol), and
each solvent 8 mL).

CHAVAN ET AL.
3
TABLE 2 Synthesis of 3,3,6,6-tetramethyl-9-R-3,4,6,7,9,10-
hexahydroacridine-1,8(2H,5H)-dione derivatives via one-pot
multicomponent reaction under ultrasonic irradiation at 70ꢀC (4a–m)a
Entry Ar
Product Time (min) Yield (%)
1.
2,5-(CH3O)2C6H3
4a
4b
4c
41
39
47
43
35
52
36
34
40
42
54
55
32
91
89
83
88
90
87
91
92
95
90
82
83
92
2.
3,4-(OH)2C6H3
4-CNC6H4
3.
4.
3-OH-4-CH3OC6H3 4d
5.
C6H5
4e
4f
6.
3-BrC6H4
4- CH3OC6H4
4-OHC6H4
4- ClC6H4
2,4-(cl)2C6H3
4-NO2C6H4
2-NO2C6H4
4-FC6H4
7.
4g
4h
4i
8.
9.
10.
11.
12.
13.
4j
4k
4l
4m
aReaction condition: The reaction was carried out by the addition of aromatic
aldehyde (1 mmole) dimedone (2 mmol), ammonium acetate (1 mmol), and
aqueous solvent 08 mL.
electron-donating aldehyde. All electrons withdrawing and
donating aromatic aldehydes worked well, leading to good to
excellent yields of products due to the ultrasonic effect.
A possible mechanism to the synthesis of acridinedione
derivatives (4a–m) is outlined in Scheme 2. These products
were formed by a multistep reaction in one-pot as discussed
below.
SCHEME 2 A possible mechanism of acridinedione derivatives
In step I, aromatic aldehyde (1a–m) was condensed with
dimedone (2) by knoevenagel condensation to form interme-
diate (5) and simultaneously another molecule of dimedone
(2) was condensed with ammonium acetate (3) to form
enaminone (6). In step II, addition of intermediate (5) and
enaminone (6) called Michael addition was carried out, and
finally cyclization of Michael addition is shown in step III,
forming substituted acridinediones (4a–m).
The reaction progress and completion was monitored by
thin layer chromatography (TLC) using the hexane and ethyl
acetate ratio of 8:2. After completion of the reaction, the
reaction mixture was allowed to cool, filtered, washed, dried,
and recrystallized by using AR grade ethanol to afford the
pure product (Figure 1).
FIGURE 1 Ultrasonication (frequency of 50 Hz and power of
250 V AC, 5.5 L and temperature 70ꢀC)
melting point was measured using SRS optimelt instru-
ments and all the synthesized compounds were character-
3 | EXPERIMENTAL
3.1 | Materials and methods
1
ized using H NMR and 13C NMR. Both NMR spectra
were obtained in CDCl3 using TMS as an internal stan-
dard (Bruker) 400 and 100 MHz Frequency. ESI-MS
analysis was obtained using an ESI-QTOF Analytical
instrument, elemental analysis was performed using an
All the chemicals were purchased from Sigma-Aldrich.
Reactant were purified before starting the reactions. The

4
CHAVAN ET AL.
Elementar vario MICRO cube analyzer instrument, and
the IR spectra were recorded on a Perkin-Elmer FT-IR
Spectrometer.
CDCl3) δ 11.91 (s, 1H, D2O exchangeable NH), 7.51 (s,
1H,Ar), 6.79 (d, 1H,Ar), 6.70 (d, 1H,Ar), 5.69 (s, 2H, 2OH),
4.82 (s, 1H, CH), 2.60 (s,4H, 2CH2), 2.11 (s, 4H 2CH2),1.04
(s, 6H, 2CH3), and 0.99 (s, 6H, 2CH3); 13C NMR
(100 MHz, CDCl3): 191.12, 151.44, 147.52, 146.21,
140.62, 127.85, 119.13, 117.95, 115.52, 113.29, 112.95,
112.21, 56.7, 55.89, 52.65, 43.15, 34.75, 33.89, and
28.68 ppm. Mass (m/z): [M + 1]+ 381.19. Element Analy-
sis: Mol. Formula C23H27NO4: C, 72.42; H, 7.13; N, 3.67;
and O, 16.78%. Founded: C, 72.49; H, 7.20; and N, 3.71.
3.2 | General procedure for synthesis of
acridine-1,8 (2H,5H)-dione derivatives
In a 50 mL round bottom flask, a mixture of aromatic alde-
hyde (1 mmol), dimedone (2 mmol), ammonium acetate
(1 mmol), and water (8 mL) was irradiated to ultra-
sonication (a frequency of 50 Hz and a power of 250 V AC,
5.5 L) at 70ꢀC temperature for nearly about 2 hr. The round
bottom flask was placed at the center of the ultrasonic bath
using a stand and the surface of the reactants in round bot-
tom flasks was placed slightly lower than the water level in
the sonication bath. The reaction progress was assessed by a
TLC plate using 20% n-hexane: ethyl acetate (8:2). After the
completion of reaction, the reaction mixture was cooled at
room temperature, filtered, and washed with 3 × 10 mL
water. The solid products were dissolved in ethyl acetate
(7 mL). The organic layer was dried over anhydrous
NaS2O4, separated, and ethyl acetate was evaporated using a
vacuum pressure pump. The solid products were then col-
lected and purified by recrystallization using pure
A.R. grade ethanol.
3.3.3 | 4-(3,3,6,6-tetramethyl-1,8-dioxo-
1,2,3,4,5,6,7,8,9,10-decahydroacridin-9-yl)
benzonitrile (4c)
Dark Yellow crystals, m.p. 270–272ꢀC. FTIR (KBr cm−1):
1
3,291, 2,989, 2,286, 1,675, and 1,608; H NMR (400 MHz,
CDCl3) δ 11.93 (s, 1H, D2O exchangeable NH), 7.81 (d,
2H,Ar), 7.66 (d, 2H,Ar), 4.86 (s, 1H, CH), 2.61 (s,4H,
2CH2), 2.13 (s, 4H 2CH2),1.05 (s, 6H, 2CH3), and 1.00 (s,
6H, 2CH3); 13C NMR (100 MHz, CDCl3): 195.11, 151.14,
150.52, 136.21, 130.52, 119.10, 112.85, 111.21, 52.7,
41.15, 33.65, 33.79, and 28.72 ppm. Mass (m/z): [M + 1]+
374.2. Element Analysis: Mol. Formula C24H26N2O2: C,
76.98; H, 7.00; N, 7.48; and O, 8.54%. Founded: C,
72.49; H, 7.20; and N, 3.71.
3.3 | Spectral data of the synthesized derivatives
of 9-R-3,3,6,6-tetramethyl-3,4,6,7,9,10-
hexahydroacridine-1,8(2H,5H)-dione
3.3.4 | 9-(3-hydroxy-4-methoxyphenyl)-
3,3,6,6-tetramethyl-3,4,6,7,9,10-
hexahydroacridine-1,8(2H,5H)-dione (4d)
3.3.1 | 9-(2,5-dimethoxyphenyl)-
3,3,6,6-tetramethyl-3,4,6,7,9,10-
hexahydroacridine-1,8(2H,5H)-dione (4a)
Yellow crystals, m.p. 300–304ꢀC. FTIR (KBr cm−1): 3,392,
3,278, 2,942, 1,682, and 1,601; 1H NMR (400 MHz,
CDCl3) δ 11.89 (s, 1H, D2O exchangeable NH), 7.03 (s,
1H,Ar), 6.89 (d, 1H,Ar), 6.71 (d, 1H,Ar), 5.73 (s, 1H, OH),
4.83 (s, 1H, CH), 2.62 (s,4H, 2CH2), 2.13 (s, 4H 2CH2),
1.12 (s, 6H, 2CH3), and 0.99 (s, 6H, 2CH3); 13C NMR
(100 MHz, CDCl3): 195.12, 151.84, 149.32, 148.32,
123.45, 115.13, 113.95, 112.95, 112.21, 57.01, 52.65,
42.15, 39.87, 35.15, 33.79, and 28.79 ppm. Mass (m/z):
[M + 1]+395.2. Element Analysis: Mol. Formula
C24H29NO4: C, 72.89; H, 7.39; N, 3.54; and O, 16.18%.
Founded: C, 72.90; H, 7.38; and N, 3.55.
Light yellow crystals, m.p. 295–297ꢀC. FTIR (KBr cm−1):
3,290, 2,950, 1,640, and 1,604; 1H NMR (400 MHz,
CDCl3) δ 11.94 (s, 1H, D2O exchangeable NH), 7.56 (s,
1H,Ar), 6.88 (d, 1H,Ar), 6.78 (d, 1H,Ar), 4.81 (s, 1H, CH),
3.91 (s, 6H, 2CH3), 2.59 (s,4H, 2CH2), 2.10 (s, 4H 2CH2)
1.03 (s, 6H, 2CH3), and 0.99 (s, 6H, 2CH3); 13C NMR
(100 MHz, CDCl3): 194.1, 152.97, 152.12, 151.41, 115.52,
113.29, 112.95, 112.21, 56.7, 55.89, 52.32, 41.75, 36.15,
34.30, and 28.45 ppm; Mass (m/z): [M + 1]+ 409.2. Ele-
ment Analysis: Mol. Formula C25H31NO4: C, 73.32, H,
7.63, N, 3.42; and O, 15.63%. Founded: C, 73.42; H, 7.69;
and N, 3.41.
3.3.5 | 3,3,6,6-tetramethyl-9-phenyl-
3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-
dione (4e)
3.3.2 | 9-(3,4-dihydroxyphenyl)-
3,3,6,6-tetramethyl-3,4,6,7,9,10-
hexahydroacridine-1,8(2H,5H)-dione (4b)
White crystals, m.p. 290–293ꢀC. FTIR (KBr cm−1):
3,299, 2,986, 1,646, and 1,610; 1H NMR (400 MHz,
White crystals, m.p 308–310ꢀC. FTIR (KBr cm−1): 3,387,
CDCl3)
δ 11.88 (s, 1H, D2O exchangeable NH),
3,289, 2,944, 1,686, and 1,606; 1H NMR (400 MHz,
7.30–7.68 (m, 5H,Ar), 4.80 (s, 1H, CH), 2.82 (s,4H,

CHAVAN ET AL.
5
2CH2), 2.25 (s, 4H 2CH2),1.16 (s, 6H, 2CH3), and 0.98
(s, 6H, 2CH3); 13C NMR (100 MHz, CDCl3): 194.12,
150.74, 143.32, 129.94, 129.24, 126.54, 112.65, 52.32,
42.35, 36.87, 33.65, and28.65 ppm. Mass (m/z):
[M + 1]+349.2. Element Analysis: Mol. Formula
C23H27NO2: C, 79.05; H, 7.79; N, 4.01; and O, 9.16%.
Founded: C, 79.1; H, 7.75; and N, 4.06.
C23H27NO3: C, 75.59; H, 7.45; N, 3.83; and O, 13.13%.
Founded: C,75.60; H, 7.47; and N, 3.83.
3.3.9 | 9-(4-chlorophenyl)-3,3,6,6-tetramethyl-
3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-
dione (4i)
White crystals, m.p. 245–249ꢀC. FTIR (KBr cm−1): 3,302,
2,951, 1,638, and 1,601;1H NMR (400 MHz, CDCl3) δ
11.88 (s, 1H, D2O exchangeable NH),7.75 (d, 2H,Ar),7.26
(d, 2H,Ar), 4.81 (d, 1H, CH), 2.61 (s,4H, 2CH2), 2.31(s, 4H
2CH2),1.12 (s, 6H,2CH3), and 0.99 (s, 6H, 2CH3); 13C
NMR (100 MHz, CDCl3):195.08, 151.00, 144.01, 132.14,
131.12, 129.57, 111.94, 52.11, 41.05, 36.41, 33.74, and
28.68.ppm. Mass (m/z): [M + 1]+383.1. Element Analysis:
Mol. Formula C23H26ClNO2: C, 71.96; H, 6.83; Cl, 9.23; N,
3.65; and O, 8.33%. Founded: C,71.98; H, 6.86;
and N, 3.70.
3.3.6 | 9-(3-bromophenyl)-3,3,6,6-tetramethyl-
3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-
dione (4f)
White crystals, m.p. 288–291ꢀC. FTIR (KBr cm−1): 3,278,
2,961, 1,660, and 1,607; 1H NMR (400 MHz, CDCl3) δ
11.94 (s, 1H, D2O exchangeable NH), 7.71 (d, 1H,Ar), 7.61
(s, 1H,Ar), 7.52–7.40 (m, 2H,Ar), 4.82 (s, 1H, CH), 2.63
(s,4H, 2CH2), 2.16 (s, 4H 2CH2),1.15 (s, 6H, 2CH3), and
0.99 (s, 6H, 2CH3); 13C NMR (100 MHz, CDCl3): 195.01,
150.62, 145.12, 136.21, 130.52, 129.41, 127.52, 124.85,
112.16, 52.35, 40.95, 33.70, 33.59, and 28.78 ppm. Mass
(m/z): [M + 1]+ 427.1. Element Analysis: Mol. Formula
C23H26BrNO2: C, 64.49; H, 6.12; Br, 18.65; N, 3.27; and O,
7.47%. Founded: C, 64.50; H, 6.18; and N,3.32.
3.3.10 | 9-(2,4-dichlorophenyl)-
3,3,6,6-tetramethyl-3,4,6,7,9,10-
hexahydroacridine-1,8(2H,5H)-dione (4j)
White crystals, m.p. 278–281ꢀC. FTIR (KBr cm−1):
3,299, 2,949, 1,641, and 1,604; 1H NMR (400 MHz,
CDCl3) δ 11.89 (s, 1H, D2O exchangeable NH), 7.03 (s,
1H,Ar), 6.89 (d, 1H,Ar), 6.71 (d, 1H,Ar), 5.73 (s, 1H,
OH), 4.83 (s, 1H, CH), 2.62 (s,4H, 2CH2), 2.13 (s, 4H
2CH2),1.09 (s, 6H, 2CH3), and 0.99 (s, 6H, 2CH3); 13C
NMR (100 MHz, CDCl3): 195.12, 151.84, 149.32,
148.32, 123.45, 115.13, 113.95,112.95, 112.21, 57.01,
52.65, 42.15, 39.87, 35.15, 33.79, and 28.79 ppm.
Mass (m/z): [M + 1]+ 395.2. Element Analysis: Mol.
Formula C23H25Cl2NO2: C, 66.03; H, 6.02; Cl, 3.35; N,
3.35; and O, 7.65%. Founded: C, 66.10; H, 605;
and N, 3.32.
3.3.7 | 9-(4-methylphenyl)-3,3,6,6-tetramethyl-
3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-
dione (4g)
Light Yellow crystals, m.p. 290–293ꢀC. FTIR (KBr cm−1):
3,301, 1,636, and 1,462; 1H NMR (400 MHz, CDCl3) δ
11.88 (s, 1H, D2O exchangeable NH), 7.58–7.61 (d, 4H,Ar),
4.84 (s, 1H, CH), 2.59 (s,4H, 2CH2), 2.26 (s, 4H 2CH2),
1.11 (s, 6H, 2CH3), and 0.99 (s, 6H, 2CH3); 13C NMR
(100 MHz, CDCl3): 195.12, 151.96, 142.58, 136.32,
132.20, 112.09, 52.31, 41.51, 33.24, 33.15, and
128.69 ppm. Mass (m/z): [M + 1]+363.2. Element Analysis:
Mol. Formula C24H29NO2: C, 79.30; H, 8.04;N, 3.85;
and O, 8.80%. Founded: C, 79.36; H, 8.10; and N,3.84.
3.3.11 | 9-(4-nitrophenyl)-3,3,6,6-tetramethyl-
3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-
dione (4k)
3.3.8 | 9-(4-hydroxyphenyl)-
3,3,6,6-tetramethyl-3,4,6,7,9,10-
hexahydroacridine-1,8(2H,5H)-dione (4h)
Colorless crystals, m.p. 298–300ꢀC. FTIR (KBr cm−1):
3,292, 2,963, 1,681, and 1,609; 1H NMR (400 MHz,
White crystals, m.p. 306–308ꢀC. FTIR (KBr cm−1): 3,290,
2,926, 1,635, and 1,437; 1H NMR (400 MHz, CDCl3) δ
11.88 (s, 1H, D2O exchangeable NH),7.75 (d, 2H,Ar),6.92
(d, 2H,Ar), 5.62 (s, 1H, OH), 4.82 (d, 1H, CH), 2.60 (s,4H,
2CH2), 2.32 (s, 4H 2CH2),1.14 (s, 6H, 2CH3), and 0.99 (s,
6H, 2CH3);13C NMR (100 MHz, CDCl3): 194.98, 160.01,
151.48, 140.21, 132.54, 116.84, 113.04, 52.10, 41.15,
39.41, 35.41, 33.74, and 28.70.ppm. Mass (m/z):
[M + 1]+365.2. Element Analysis: Mol. Formula
1
DMSO: H NMR 400 MHz, CDCl3) δ 11.76 (s, 1H, D2O
exchangeable NH), 8.15 (d, 2H,Ar), 7.36 (d, 2H,Ar), 4.98
(s, 1H, CH), 2.51 (s,4H, 2CH2), 2.23 (s, 4H 2CH2), 1.15
(s, 6H, 2CH3), and 1.01 (s, 6H, 2CH3); 13C NMR
(100 MHz, CDCl3): 190.21, 181.60, 147.52, 146.12,
127.21, 123.52, 114.10, 111.21, 50.7, 33.65, 32.79,,
30.14, and 28.54 ppm. Mass (m/z): [M + 1]+394.1. Ele-
ment Analysis: Mol. Formula C23H26N2O4: C, 70.03; H,

6
CHAVAN ET AL.
6.64; N, 7.10; and O, 16.22%. Founded: C, 70.10; H,
6.63; and N, 7.09.
41.15, 33.65, 33.79, and 28.72 ppm. Mass (m/z):
[M + 1]+367.1. Element Analysis: Mol. Formula
C23H26FNO2: C, 75.18; H, 7.13; F, 5.17; N, 3.81; and O,
8.71%. Founded: C, 75.9; H, 7.20; and N, 3.73 (Scheme 3).
3.3.12 | 9-(2-nitrophenyl)-3,3,6,6-tetramethyl-
3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-
dione (4l)
4 | CONCLUSIONS
White crystals, m.p. 289–292ꢀC. FTIR (KBr cm−1): 3,210,
2,968, 1,687, and 1,607; 1H NMR (400 MHz, CDCl3) δ
11.78 (s, 1H, D2O exchangeable NH), 8.31 (d, 2H,Ar), 7.68
(d, 2H,Ar), 4.92 (s, 1H, CH), 2.66 (s,4H, 2CH2), 2.34 (s, 4H
2CH2), 1.13 (s, 6H, 2CH3), and 1.06 (s, 6H, 2CH3); 13C
NMR (100 MHz, CDCl3): 195.21, 153.14, 150.56, 136.11,
131.52, 120.10, 112.87, 111.22, 52.7, 41.15, 33.60, 33.75,
and 28.74 ppm. Mass (m/z): [M + 1]+ 394.1. Mol. Formula
C23H26N2O4: C, 70.03; H, 6.64; N, 7.10; and O, 16.22%.
Founded: C, 70.11; H, 6.61; and N, 7.12.
We have developed an efficient, short reaction time, easily
handled ultrasonic irradiation method for synthesis of acri-
dinedione derivatives (4a–m) by one-pot multicomponent
reaction of aromatic aldehyde (1a–m), dimedone (2), ammo-
nium acetate (3) without catalysts using an aqueous solvent
as a green solvent. Thus, hazardous pollution is minimized
to achieve an environmentally friendly method.
ACKNOWLEDGMENTS
We are grateful to Department of Chemistry, DoshiVakil
Arts, G.C.U.B. Science and Commerce College, Goregaon,
Raigad for providing the necessary laboratory facility during
our research.
3.3.13 | 9-(4-flurophenyl)-3,3,6,6-tetramethyl-
3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-
dione (4m)
White Crystals, m.p. 275–277ꢀC. FTIR (KBr cm−1): 3,289,
2,964, 1,688, and 1,608; 1H NMR (400 MHz, CDCl3) δ
11.89 (s, 1H, D2O exchangeable NH), 7.22 (d, 2H,Ar), 6.78
(d, 2H,Ar), 5.10 (s, 1H, CH), 2.55 (s,4H, 2CH2), 2.22 (s, 4H
2CH2), 1.30–1.03 (s, 6H, 2CH3), and 0.99 (s, 6H, 2CH3);
13C NMR (100 MHz, CDCl3): 191.11, 187.54, 151.14,
150.52, 136.21, 130.52, 119.10, 112.85, 111.21, 52.7,
ORCID
Dattatraya N. Pansare https://orcid.org/0000-0002-0419-
3538
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How to cite this article: Chavan PN, Pansare DN,
Shelke RN. Eco-friendly, ultrasound-assisted, and
facile synthesis of one-pot multicomponent reaction
of acridine-1,8(2H,5H)-diones in an aqueous solvent.
J Chin Chem Soc. 2019;1–7. https://doi.org/10.1002/
jccs.201800411