One-pot multi component synthesis of xanthenediones and acridinediones at room temperature

Article abstract of DOI:10.14233/ajchem.2013.13260

A facile and efficient protocol for the synthesis of xanthenedione and acridinrdione derivatives has been developed via the one-pot condensation reaction between dimedone and aldehydes (for the synthesis of xanthenediones) and dimedone, aldehydes and prim

Full text of DOI:10.14233/ajchem.2013.13260

Asian Journal of Chemistry; Vol. 25, No. 4 (2013), 1981-1984
http://dx.doi.org/10.14233/ajchem.2013.13260
One-Pot Multi Component Synthesis of Xanthenediones and Acridinediones at Room Temperature
1,*
1
1
HAMID REZA SAFAEI , ABOLFAZL ESHGHI MOVAHHED , MANSOOREH DAVOODI ,
1,2
3
3
MOHSEN SHEKOUHY , VAHID RAHMANIAN and MARYAM SAFAEI
1Department of Applied Chemistry, Faculty of Science, Shiraz Branch, Islamic Azad University, P.O. Box 71993-5, Shiraz, Iran
2Young Researchers Club, Shiraz Branch, Islamic Azad University, Shiraz, Iran
3Department of Industrial Polymer Engineering, Shiraz Branch, Islamic Azad University, Shiraz, Iran
*Corresponding author: Fax : +98 711 6412488; Tel: +98 711 6402715; E-mail: hrs@iaushiraz.net; hrsafaei@yahoo.com
(Received: 15 December 2011;
Accepted: 10 October 2012)
AJC-12262
A facile and efficient protocol for the synthesis of xanthenedione and acridinrdione derivatives has been developed via the one-pot
condensation reaction between dimedone and aldehydes (for the synthesis of xanthenediones) and dimedone, aldehydes and primary
amines (for the synthesis of acridinediones) in presence of the formic acid as solvent at room temperature. All the products were obtained
in good to excellent yields and all reactions were completed in short times.
Key Words: Xanthenedione, Acridinediones, Formic acid, Multi component reactions.
In recent years, 1,4-dihydropyridines and their derivatives have
attracted strong interest for the treatment of cardiovascular
diseases, such as angina pectoris8 and hypertension9.Acridine
derivatives have been used to synthesize labeled conjugates
with medicinals, peptides, proteins and nucleic acids10-12 that
exhibit antitumor and DNA-binding properties. There are
several reports in the literature for the synthesis of xanthene-
diones and acridinediones include InCl3·4H2O in ionic liquid13,
solid-state condensation by grinding at room temperature14,
diammonium hydrogen phosphate15, p-dodecylbenzene-
sulfonic acid in water16, Fe3+-montmorilonite17, NaHSO4-SiO2
or silica chloride18, amberlyst-1519, silica sulfuric acid20,
tetrabutyl ammonium hydrogen sulphate21, trimethyl-
silylchloride22, 1-butyl-3-methylimidazolium hydrogen
sulphate23, montmorillonite K-10-supported24 and covalently
anchored sulfonic acid on silica gel25. Each of these methods
have their own advantages but also some of them often suffer
from one or more disadvantages such as prolonged reaction
time, tedious work-up processes, low yield25, expensive
reagents26 and hazardous organic solvents25. Moreover most
of these reported methods were applied at reflux temperature.
It is well known that for many chemical processes, a major
adverse effect to environment is the consumption of energy
for heating and cooling. So design of methods for the synthesis
of organic compounds at room temperature is a useful strategy
to overcome this problem.
INTRODUCTION
Multi component reactions (MCRs) provide unmatched
opportunities for the expeditious increase of complexity and
diversity in synthetic outcomes. The strategy offers signifi-
cant advantages over classical stepwise approaches, allowing
the formation of several bonds and the construction of complex
molecular architectures from simple precursors in a single
synthetic operation without the need for isolation of interme-
diates1. One-pot multi component synthesis of xanthenediones
and acridinediones are two important examples of the appli-
cation of multi component reactions for the synthesis of
biologically active compounds.
Xanthene-based compounds are important because of
their use in medicine as they possess antimicrobial activities2.
These compounds have also been investigated for agricultural
bactericidal activity2a, photo dynamic therapy, antiinflamma-
tory effects3 and antiviral activity4. In particular, octahydro-
xanthene constitutes a structural unit in several natural products5
and they are valuable synthons because of the inherent reac-
tivity of the in built pyran ring6. A number of xanthene-based
compounds are also available from natural sources. Santalin
pigments are popularly known, have been isolated from a
number of plant species7. The wide-ranging biological activities
associated with xanthenes, both naturally occurring and synthetic,
ensure that the synthesis of these compounds remains a topic
of current interest. Moreover, acridinediones and their deriva-
tives are poly functionalized 1,4-dihydropyridine derivatives.
Considering the above facts herein we report a convenient
and efficient method for one-pot multi component synthesis

1982 Safaei et al.
Asian J. Chem.
O
O
R1
O
O
R1
O
Formic acid
Formic acid
R1 CHO
Room temperature
Room temperature
R2 NH2
(3)
O
O
N
R2
(1)
(2)
5a-k
4a-n
Scheme-I: One-pot multi component synthesis of xanthenediones and acridinediones at room temperature
of xanthenedione and acridinedione derivatives at room
temperature (Scheme-I).
Hz), 8.37 (dd, 1H, J1 = 4.7 Hz, J2 = 1.5 Hz), 8.46 (d, 1H, J =
1.9 Hz); 13C NMR (CDCl3, 125 MHz) δ: 27.8, 29.6, 32.6, 41.2,
51.0, 115.1, 123.4, 136.9, 140.0, 148.1 149.9, 163.3, 196.8.
9-(4-Chlorophenyl)-3,4,6,7-tetrahydro-3,3,6,6-
tetramethyl-10-p-tolylacridine-1,8-(2H,5H,9H,10H)-dione
EXPERIMENTAL
All chemicals were purchased from Merck or Fluka
Chemical Companies. All synthesized compounds are known
and were identified by comparison of their melting points and
1H NMR data with those in the authentic samples. The 1H NMR
1
(5d): H NMR (CDCl3, 500 MHz) δ: 0.83 (s, 6H), 0.99 (s,
6H), 1.88 (d, 2H, J = 17.5 Hz), 2.08-2.14 (m, 4H), 2.21 (d,
2H, J = 16.2 Hz), 2.55 (s, 3H), 5.25 (s, 1H), 7.12 (d, 2H, J =
8.0 Hz), 7.23 (d, 2H, J = 8.0 Hz), 7.36-7.42 (m, 4H); 13C NMR
(CDCl3, 125 MHz) δ: 21.6, 27.1, 30.1, 32.9, 32.9, 42.1, 50.6,
114.7, 128.5, 129.2, 129.7, 130.0, 131.6, 136.6, 140.2, 145.3,
150.6, 196.1.
13
(500 MHz) and C NMR (125 MHz) were run on a Bruker
Avance DPX-250, FT-NMR spectrometer. Melting points were
recorded on a Stuart ScientificApparatus SMP3 (UK) in open
capillary tubes.
3-(1,2,3,4,5,6,7,8-Octahydro-3,3,6,6-tetramethyl-9-(3-
nitrophenyl)-1,8-dioxo-acridin-10(9H)-yl)benzonitrile (5h):
1H NMR (CDCl3, 500 MHz) δ: 0.85 (s, 6H), 1.00 (s, 6H), 1.82
(d, 2H, J = 17.5 Hz), 2.14 (d, 2H, J = 17.5 Hz), 2.18 (d, 2H,
J = 16.4 Hz), 2.28 (d, 2H, J = 16.4 Hz), 5.37 (s, 1H), 7.45 (t,
1H, J = 7.8 Hz), 7.63-7.68 (m, 2H), 7.84 (t, 1H, J = 7.8 Hz),
7.91-7.95 (m, 2H), 8.01 (dd, 1H, J1 = 8.0 Hz, J2 = 1.4 Hz),
8.21 (s, 1H); 13C NMR (CDCl3, 125 MHz) δ: 27.1, 30.1, 33.1,
33.2, 42.5, 50.6, 114.9, 117.5, 121.7, 122.6, 129.7, 133.2,
135.2, 140.7, 148.2, 148.8, 149.0, 196.01.
General procedure for the synthesis of xanthenedione
and/or acridinedione derivatives: In a typical example,
dimedone (2 mmol) and aromatic aldehyde (1 mmol) were
added [in the case of the synthesis of acridinedione primary
amine (1 mmol) was also added] in a 25 mL round-bottomed
flask contained formic acid (1 mL) and the resulting mixture
was stirred magnetically at room temperature. The completion
of the reaction was followed by TLC using n-hexane/ethyl
acetate 3:1 as an eluent. After completion, water (10 mL) was
added and insoluble products were separated by simple filtration
and recrystallized from ethanol for more purification.
3,4,6,7-Tetrahydro-3,3,6,6-tetramethyl-9-phenyl-2H-
3,4,6,7-Tetrahydro-3,3,6,6-tetramethyl-9-(4-(methylthio)-
phenyl)-10-p-tolyl-acridine-1,8-(2H,5H,9H,10H)-dione
1
(5k): H NMR (CDCl3, 500 MHz) δ: 0.88 (s, 6H), 0.99 (s,
1
xanthene-1,8-(5H,9H)-dione (4a): H NMR (CDCl3, 500
6H), 1.85 (d, 2H, J = 17.5 Hz), 2.12 (d, 2H, J = 17.5 Hz), 2.17
(d, 2H, J = 16.5 Hz), 2.25 (d, 2H, J = 16.5 Hz), 2.44 (s, 3H),
2.55 (s, 3H), 5.25 (s, 1H), 7.10 (d, 2H, J = 7.5 Hz), 7.19 (d,
MHz) δ: 1.02 (s, 6H), 1.14 (s, 6H), 2.18 (d, 2H, J = 16.0 Hz),
2.25 (d, 2H, J = 16.0 Hz), 2.51 (s, 4H), 4.77 (s, 1H), 7.12 (t,
1H, J = 7.0 Hz), 7.25 (t, 2H, J = 7.5 Hz), 7.31 (d, 2H, J = 7.6
Hz). 13C NMR (CDCl3, 125 MHz), δ: 27.6, 29.5, 32.2, 32.6,
41.3, 51.1, 116.0, 126.7, 128.5, 128.8, 144.5, 162.7, 196.6.
3,4,6,7-Tetrahydro-3,3,6,6-tetramethyl-9-(4-chloro-
13
2H, J = 8.0 Hz), 7.36-7.40 (m, 4H); C NMR (CDCl3, 125
MHz) δ: 16.3, 21.6, 27.2, 30.1, 32.7, 32.9, 42.1, 50.6, 114.7,
127.3, 128.8, 135.4, 136.8, 139.9, 144.0, 150.8, 196.2.
1
phenyl)-2H-xanthene-1,8-(5H,9H)-dione (4b): H NMR
(CDCl3, 500 MHz) δ: 1.02 (s, 6H), 1.15 (s, 6H), 2.21 (d, 2H,
J = 16.3 Hz), 2.29 (d, 2H, J = 16.3 Hz), 2.51 (s, 4H), 4.77 (s,
RESULTS AND DISCUSSION
At first the one-pot condensation reaction between
dimedone (1) (2 mmol) and benzaldehyde (2a) (1 mmol) was
selected as a model reaction (Scheme-II). In order to find the
best reaction conditions, we examined the model reaction in
the presence of various organic acids at room temperature and
the obtained results are summarized in Table-1.
13
1H), 7.21 (d, 2H, J = 8.5 Hz), 7.26 (d, 2H, J = 8.5 Hz). C
NMR (CDCl3, 125 MHz) δ: 27.7, 29.7, 31.7, 32.6, 41.2, 51.2,
115.6, 128.6, 130.1, 132.5, 143.0, 162.8, 196.7.
3,4,6,7-Tetrahydro-3,3,6,6-tetramethyl-9-p-tolyl-2H-
1
xanthene-1,8-(5H,9H)-dione (4f): H NMR (CDCl3, 500
MHz) δ: 0.97 (s, 6H), 1.07 (s, 6H), 2.14 (d, 2H, J = 16.3 Hz),
2.22-2.24 (m, 5H), 2.45 (s, 4H), 4.72 (s, 1H), 7.02 (d, 2H, J =
8.0 Hz), 7.17 (d, 2H, J = 8.0 Hz). 13C NMR (CDCl3, 125 MHz)
δ: 21.3, 27.9, 29.7, 31.8, 32.7, 41.3, 51.2, 116.2, 128.6, 129.2,
136.1, 141.6, 162.4, 196.7.
CHO
O
O
O
Organic acid (1 mL)
Room Temperature
+
O
3,4,6,7-Tetrahydro-3,3,6,6-tetramethyl-9-(pyridin-3-
yl)-2H-xanthene-1,8(5H,9H)-dione (4m): 1H NMR (CDCl3,
500 MHz) δ: 1.02 (s, 6H), 1.12 (s, 6H), 2.17 (d, 2H, J = 16.3
Hz), 2.26 (d, 2H, J = 16.3 Hz), 2.51 (s, 4H), 4.77 (s, 1H),
7.16-7.18 (m, 1H), 7.72-7.75 (dt, 1H, J1 = 7.8 Hz, J2 = 1.9
O
(1)
(2a)
(4a)
Scheme-II: One-pot condensation reaction between dimedone (1) (2 mmol)
and benzaldehyde (2a) (1 mmol) in the presence of some
organic acids at room temperature

Vol. 25, No. 4 (2013)
One-Pot Multi Component Synthesis of Xanthenediones and Acridinediones 1983
one-pot multi component condensation reaction between
TABLE-1
ONE-POT CONDENSATION REACTION BETWEEN DIMEDONE
(2 mmol) AND BENZALDEHYDE (1 mmol) IN THE PRESENCE
OF SOME ORGANIC ACIDS (1 mL) AT ROOM TEMPERATURE
dimedone (1), aromatic aldehydes (2) and primary amines (3)
were investigated in presence of the formic acid at room
temperature and obtained results are summarized in Table-3.
As it is clear from Table-3, here also the aromatic aldehydes
containing both electron-donating and electron-withdrawing
groups afforded the products in high yields. Moreover it is
obviously showed that various aniline derivatives reacted
smoothly under the reaction conditions.
Entry
Catalyst
Time (h)
Yield (%)a
1
Formic acid
Acetic acid
2
5
8
8
8
90
75
69
60
55
2
3
Propanoic acid
Butanoic acid
Pantanoic acid
4
5
aIsolated yield.
The experimental procedure is remarkably simple. After
the completion of the reaction, water was added to the reaction
mixture and the insoluble crude products were isolated by
simple filtration and recrystalized from ethanol for more
purification. To the best of our knowledge, this is the first report
on the synthesis of acridinedione derivatives at room tempe-
rature and all of the last reported procedures were applied under
reflux conditions.
As it is clear from Table-1, the best results were obtained
in the presence of formic acid at room temperature. These
observations demonstrate that there are a direct relationship
between the acid strength of the applied organic acid and the
rate of the one-pot condensation reaction between dimedone
and benzaldehyde.As it is clear fromTable-1, as the acid strength
decreased, the reaction time was increased and the yield was
decreased obviously.
In another study we examined the one-pot three component
condensation reaction between dimedone (1) (1 mmol), benza-
ldehyde (2a) (1 mmol) and aniline (3a) (1 mmol) in the presence
of formic acid at room temperature to afford compound (6)
and unfortunately only a mixture of unknown products were
obtained even after a long time (24 h) (Scheme-III).
In the next step, a broad range of structurally diverse
aldehydes were condensed with dimedone to furnish the
corresponding products in high yield and the obtained results
are presented in Table-2. We investigated further the electronic
effect of different substituents present on the aldehyde
component. As it is shown in Table-2, electron withdrawing
substituents in aromatic ring of aryl-alkyl ketones accelerated
the reaction rate (entries 10, 11, 12) whereas electron releasing
substituents reduced the reaction rate (entries 7, 8, 9) but
nature of substituents is not affected the yield of the reaction.
So a wide range of aldehydes having both electron-donating
and electron withdrawing groups were equally facile for the
reaction, resulting in the formation of xanthenedione deriva-
tives in very good yields. An important feature of this method
is that the heterocyclic functionality present in the molecule
remains unaffected. This fact was amply demonstrated by the
reaction of pyridine-3-caboxaldehyde with dimedone, which
gave 9-(pyridine-3-yl)-1,8-dioxo-octahydroxanthene (4m) in
excellent yield.
O
CHO
O
NH2
Formic acid (1 mL)
Room Temperature
+
+
O
N
H
(1)
(2a)
(3a)
(6)
Scheme-III: Oone-pot three component condensation reaction between
dimedone (1) (1 mmol), benzaldehyde (2a) (1 mmol) and
aniline (3a) (1 mmol) in the presence of formic acid (1 mL) at
room temperature
In order to assess the capability of the present method
with respect to the reported methods for the preparation of
titled compounds, the synthesis of compound 5a was compared
with the reported methods (Table-4). As it is clear from Table-4,
the present method is more efficient.
In the next step, we decided to apply other method for the
synthesis of acridinedione derivatives. For this purpose, the
TABLE-2
ONE-POT MULTI COMPONENT SYNTHESIS OF XANTHENEDIONE
DERIVATIVES IN THE PRESENCE OF FORMIC ACID AT ROOM TEMPERATURE
m.p. (ºC)
Reported [Ref.]
Entry
R1
Compound
Time (h)
Yield (%)a
Founded
201-202
231-232
186-187
227-228
240-242
213-216
243-245
250-252
224-226
220-221
172-174
250-252
185-187
173-175
1
C6H5
2.0
2.0
2.0
3.0
2.5
3.0
5.0
6.0
5.0
1.0
1.0
1.0
3.0
4.0
90
91
91
90
93
90
89
85
90
92
91
93
92
90
203-20426
230-23226
184-18626
225-22726
240-24126
215-21726
242-24426
249-25117
225-22617
222-22326
170-17226
252-25426
184-18626
174-17626
4a
4b
4c
4d
4e
4f
2
4-Cl-C6H4
3-Cl-C6H4
2-Cl-C6H4
4-Br-C6H4
4-CH3-C6H4
4-CH3O-C6H4
4-OH-C6H4
3-OH-C6H4
4-NO2-C6H4
3-NO2-C6H4
2-NO2-C6H4
3-pyridine
C6H5-C2H2
3
4
5
6
7
4g
4h
4i
8
9
10
4j
11
4k
4l
12
13
4m
4n
14
aIsolated yields.

1984 Safaei et al.
Asian J. Chem.
TABLE-3
ONE-POT MULTI COMPONENT SYNTHESIS OF XANTHENEDIONE
DERIVATIVES IN THE PRESENCE OF FORMIC ACID AT ROOM TEMPERATURE
m.p. (ºC)
Entry
R1
R2
Compound
Time (h)
Yield (%)a
Founded
255-257
296-298
283-285
273-275
266-268
>300
Reported [Ref.]
254-25627
297-29928
284-28528
273-27526
267-26926
> 30026
289-29126
26-26826
> 30026
1
C6H5
C6H5
3
3
91
90
91
90
92
92
91
90
90
92
91
5a
5b
5c
5d
5e
5f
2
4-CH3-C6H4
3-NO2-C6H4
4-Cl-C6H4
4-CH3-C6H4
4-CH3-C6H4
4-CH3-C6H4
3-OH-C6H4
3-OH-C6H4
4-CH3-C6H4
3-CN-C6H4
3-CN-C6H4
4-CH3-C6H4
4-CH3-C6H4
3
2
4
3
5
4-Cl-C6H4
2
6
4-NO2-C6H4
3-NO2-C6H4
3-NO2-C6H4
3-OH-C6H4
3-CN-C6H4
4-CH3S-C6H4
2
7
2
288-290
267-269
>300
5g
5h
5i
8
3.5
4
9
10
3
256-258
237-138
256-25726
23926
5j
11
aIsolated yields.
3
5k
4. J.M. Jamison, K. Krabill, A. Hatwalkar, E. Jamison and C. Tsai, Cell
Biol. Int. Rep., 14, 1075 (1990).
TABLE-4
COMPARATIVE THE SYNTHESIS OF COMPOUND 5a USING
THE REPORTED METHODS VERSUS THE PRESENT METHOD
5. S. Hatakeyama, N. Ochi, H. Numata and S. Takano, Chem. Commun.,
17, 202 (1998).
Time
(min)
Yield
(%)
Entry
1
Reagents and conditions
Ref.
28
6. Y.M. Shchekotikhin and T.G. Nikolaeva, Chem. Heterocycl. Compd.,
1, 32 (2006).
Proline (10 mol %), EtOH/H2O
5:1, reflux
360
79
7. J. Kinjo, H. Uemura, T. Nohara, M. Yamashita, N. Marubayashi and K.
Yoshihira, Tetrahedron Lett., 36, 5599 (1995).
2
Amberlyst-15 (200 mg),
CH3CN, reflux
300
81
18
8. E. Antman, J. Muller, S. Goldberg, R. Macalpin, M. Ruben-fire, B.
Tabatznik, C. Liang, F. Heupler, S. Achuff, N. Reichek, E. Geltman,
N.Z. Kerin, R.K. Neff and E. Raunwald, N. Engl. J. Med., 302, 1269
(1980).
3
4
[Hmim]TFA (0.1 g), 80 ºC
Silica-bonded S-sulphunic acid
(30 mg), EtOH, reflux
Formic acid (1 mL), room
temperature
270
120
86
94
29
26
9. (a) M. Guazzi, M. Olivari, A. Polese, C. Fiorentini, F. Margrini and P.
Moruzzi, Clin. Pharmacol. Ther., 22, 528 (1977); (b) R.S. Hornung,
B.A. Gould, R.I. Jones, T.N. Sonecha and E.B. Raferty, Am. J. Cardiol.,
51, 1323 (1983).
5
30
95
This
work
aIsolated yield.
10. E. Delfourne, C. Roubin and J. Bastide, J. Org. Chem., 65, 5476 (2000).
11. J. Antonini, P. Polucci, A. Magnano and S. Martelli, J. Med. Chem.,
44, 3329 (2001).
Conclusion
We have developed an efficient method for the synthesis
of xanthenedione and acridinedione derivatives in high yields
in the presence of formic acid at room temperature. The mild
reaction conditions and simplicity of the procedure offers
improvements over many existing methods.
12. M.G. Ferlin, C. Marzano, G. Chiarelotto, F. Baccichetti and F. Bordin,
Eur. J. Med. Chem., 827 (2000).
13. X. Fan, X. Hu, X. Zhang and J. Wang, Can. J. Chem., 83, 16 (2005).
14. T.S. Jin, J.-S. Zhang, A.-Q. Wang and T.-S. Li, Synth. Commun., 35,
2339 (2005).
15. F. Darviche, S. Balalaie, F. Chadegani and P. Salehi, Synth. Commun.,
37, 1059 (2007).
16. T.S. Jin, J.S. Zhang, J.C. Xiao, A.Q. Wang and T.S. Li, Synlett, 866
(2004).
ACKNOWLEDGEMENTS
The authors are thankful to the Research Council of
Islamic Azad University, Shiraz branch for the financial
support of this work.
17. G. Song, B. Wang, H. Luo and L.Yang, Catal. Commun., 8, 673 (2007).
18. B. Das, P. Thirupathi, I. Mahender, K.R. Reddy, B. Ravikanth and L.
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