Introduction of a new bi-SO3H ionic liquid based on 2,2′-bipyridine as a novel catalyst for the synthesis of various xanthene derivatives

Article abstract of DOI:10.1039/c4ra12361a

In this study, 1,1′-disulfo-[2,2′-bipyridine]-1,1′-diium chloride, [BiPy](SO₃H)₂Cl₂ as a new ionic liquid, is prepared, characterized and used as an efficient catalyst for the promotion of the synthesis of various symmetri

Full text of DOI:10.1039/c4ra12361a

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Introduction of a new bi-SO H ionic liquid based on
3
0
2
,2 -bipyridine as a novel catalyst for the synthesis
Cite this: RSC Adv., 2014, 4, 63526
of various xanthene derivatives
Farhad Shirini,* Masoumeh Abedini, Mohaddeseh Seddighi, Omid Goli Jolodar,
Mohadeseh Safarpoor, Nikoo Langroodi and Solmaz Zamani
0
0
0
3 2 2
In this study, 1,1 -disulfo-[2,2 -bipyridine]-1,1 -diium chloride, [BiPy](SO H) Cl as a new ionic liquid, is
prepared, characterized and used as an efficient catalyst for the promotion of the synthesis of various
symmetric and asymmetric xanthene derivatives under solvent free conditions. All products were formed
in excellent yields over short reaction times. Easy preparation of the catalyst, simple and easy work-up,
mild reaction conditions, low cost, excellent yields and short reaction times are some of the advantages
of this work.
Received 14th October 2014
Accepted 5th November 2014
DOI: 10.1039/c4ra12361a
www.rsc.org/advances
To improve these reactions several methodologies were
reported in the literature. Although these procedures provide
Introduction
9
–25
Ionic liquids (ILs) are compounds with unique properties an improvement, most of them suffer from disadvantages such
such as non-ammability, no miscibility with non-polar as long reaction times, harsh reaction conditions, need to
solvents, negligible vapor, reasonable thermal and chemical excess amounts of the reagent, use of organic solvents and use
stability and the ability to be used many times without of toxic reagents. Additionally, only some of them are useful for
considerable decrease in their activity. Because of these the synthesis of all of the above mentioned xanthenes. There-
important characteristics, the use of ILs in organic reactions fore, it is important to nd more efficient catalysts and methods
is under the considerable attention of many organic chem- for the synthesis of these types of compounds.
ists. These compounds have found three major applications
in chemistry as eco-friendly solvents, catalysts and reagents.
In recent years, preparation and use of ionic liquids in
organic transformations became an important part of our
1
26–29
Among these types of compounds, acidic ionic liquids are the ongoing research program.
most important ones which have been successfully used in
Herein and in continuation of these studies we wish to
2
0
0
different types of organic transformations. In the last report the preparation and characterization of 1,1 -disulfo-[2,2 -
0
decade, xanthenes and their derivatives have been the bipyridine]-1,1 -diium chloride, [BiPy](SO
H)
Cl
2
,
and its
3
2
subject of considerable levels of interest because of their applicability in the promotion of the synthesis of different types
numerous applications in biological and pharmaceutical of xanthenes derivatives. All reactions are performed under mild
research such as antitumor, anticancer, antimicrobial and conditions during relatively short reaction time in good to high yields.
3
–6
antiviral activities. In addition, these compounds can be
used in uorescent material for visualization of biomolecules
7
,8
Experimental section
and in laser technology.
On the basis of the above
mentioned applications the synthesis of xanthenes deriva- Reagents and materials
tives is of much importance. Xanthenes are in both
symmetrical and asymmetrical forms and there are two ways
to prepare them.
The reaction of aldehydes with cyclic 1,3-dicarbonyl
compounds and/or b-naphthol for the preparation of symmet-
rical xanthenes.
The reaction of aldehydes with b-naphthol and cyclic 1,3-
dicarbonyl compounds for the preparation of asymmetrical
xanthenes.
Chemicals were purchased from Fluka, Merck, and Aldrich
chemical companies. All yields refer to the isolated products.
Products were characterized by comparison of their physical
constants and also their IR and NMR spectra with authentic
samples and those reported in the literature. The purity deter-
mination of the substrate and reaction monitoring were
accompanied by TLC on silicagel polygram SILG/UV 254 plates.
Characterization
The IR spectra were recorded on a Perkin Elmer 781 Spectro-
photometer. In all the cases the H NMR spectra were recorded
Department of Chemistry, College of Sciences, University of Guilan, Rasht, Iran, 41335.
E-mail: shirini@guilan.ac.ir; Fax: +98 131 3233262; Tel: +98 131 3233262
1
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ꢀ
with Bruker Avance 400 and 500 MHz instruments. All chemical an oil-bath at 90 C for an appropriate time. Aer completion of
shis are quoted in parts per million (ppm) relative to TMS using the reaction, as monitored with TLC [EtOAc–n-hexane (2 : 8)],
1
3
deuterated solvent. The C NMR data were collected on Bru- the reaction mixture was cooled to room temperature, H O
2
kerAvance400 MHz instrument. MS studies were performed (5 mL) was added and ltered to separate the catalyst. Then the
using 5973 network mass selective detector, Agilent Technology product was recrystallized from EtOH to give the pure product.
(
HP) company (ion source: electronic (EI) 70 eV; ion source
ꢀ
temperature: 230 C; analyzer: quadrupole). Melting points were
recorded on a B u¨ chi B-545 apparatus in open capillary tubes.
Result and discussions
Preparation of [BiPy](HSO ) Cl
2
Catalyst characterization
3
2
Chlorosulfonic acid (1.75 g, 15 mmol) was added dropwise to a The infrared spectra of 2-(pyridin-2-yl) pyridine and
0
round-bottomed ask (100 mL) containing 2,2 -bipyridine [BiPy](SO
3
H)
2
Cl
2
are shown in Fig. 1. The IR spectrum of the
ꢂ1
(
1.17 g, 7.5 mmol) in dry CH Cl (50 mL), over a period of 5 min product shows a broad peak at 2690–3600 cm which can be
in an ice bath. Aer the addition was completed, the reaction related to the OH stretching of the SO
mixture was stirred for 2 h at room temperature, then stood for the two peaks observed at 1174 cm and 1281 cm correspond
2
2
2
9,30
3
H groups.
Moreover,
ꢂ1
ꢂ1
5
min, and the solvent was decanted. The residue was washed to the O–SO
2
symmetric and asymmetric stretching, respectively
ꢂ1
with dry diethylether (3 ꢁ 50 mL) and dried under vacuum to and other band at 1068 cm is assigned to N–SO
stretching. In
2
give [BiPy](HSO
3
)
2
Cl
2
as a white solid in 98% yield (Scheme 1). addition, C]N and C]C vibrations are observed at 1604 and
ꢂ1
30
1
513 cm correspondingly.
The H NMR spectrum of [BiPy](HSO
1
3
)
2
Cl
2
in addition to the
Spectroscopic data for [BiPy](SO H) Cl are as
3
2
2
other protons, shows the SO
ppm. This observation claries that [BiPy](HSO ) Cl is exactly
3 2 2
synthesized (Fig. 2).
The mass spectrum of [BiPy](SO H) Cl is shown in Fig. 3. In
this spectrum the correct molecular ion peak appears at 389.
3
H acidic hydrogen peak at 9.58
ꢀ
Mp 86 C; MS: 81, 155, 162, 191, 228, 272, 389 m/z; FT-IR (KBr,
ꢂ1
1
cm ) nmax: 3402, 1604, 1513, 1437, 1281, 1232, 1174, 877. H
NMR (400 MHz, DMSO-d6): d ¼ 7.92 (1H, ddd, J ¼ 8, J ¼ 5.2, J
1
2
3
3
2
2
¼
1.2), 8.46 (1H, td, J ¼ 8, J ¼ 1.6), 8.70 (1H, d, J ¼ 8), 8.91 (1H,
1
2
1
3
ddd, J
1
¼ 5.2, J
2
¼ 1.6, J ¼ 0.8), 9.58 (1H, OH, s) ppm; C NMR
3
+
Other ion peaks are also observed at 272 (M ꢂ SO H and Cl),
3
(
100 MHz, DMSO-d6) d ¼ 147.84, 147.02, 143.39, 127.66, 124.23
+
+
2
(
28 (M ꢂ 2SO
3
H), 191 (M ꢂ 2SO
3 3
H and Cl), 162 (2SO H), 155
ppm; elemental analysis: C, 29.52; H, 3.93; N, 6.39; O, 26.22; S,
4.65. The amount of chloride in [BiPy](SO H) Cl was deter-
mined by potentiometric titration method (titration of 50 mL
.01 M [BiPy](SO H) Cl with 0.l M AgNO , that was 1.91 mmol
+
M ꢂ 2SO
3 3
H and 2Cl) and 81 (SO H) as well.
1
3
2
2
The Hammett acidity method is an effective way to the
acidity strength of an acid in organic solvents, using UV-vis
0
3
2
2
3
31
technique. The Hammett function is dened as:
Cl per mol of catalyst.
+
/[IH ]
H
0
¼ pK(I)aq + log([I]
s
s
)
Synthesis of symmetric xanthenes derivatives: a typical
procedure
A mixture of aldehyde (1 mmol), 2-naphthol and/or diketone
(
2 mmol) and [BiPy](SO
3
H)
2
Cl
2
(10 mg) was stirred in an oil-bath
ꢀ
at 90 C under solvent-free conditions. Aer completion of the
reaction [monitored by TLC: EtOAc–n-hexane (2 : 8)], the reac-
2
tion mixture was cooled, H O (5 mL) was added and ltered to
separate the catalyst. Then the product was recrystallized from
EtOH to give the pure product.
Synthesis of asymmetric xanthenes derivatives: a typical
procedure
A mixture of 2-naphthol (1 mmol), diketone (1 mmol), aldehyde
3 2 2
(1 mmol) and [BiPy](SO H) Cl (10 mg, 2.5 mol%) was stirred in
Fig. 1 FT-IR spectra of 2-(pyridin-2-yl) pyridine (up) and [BiPy]-
(SO H) Cl (down).
Scheme 1 Preparation of [BiPy](HSO
3 2
) Cl
2
.
3
2
2
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1
Fig. 2 H NMR spectra of [BiPy](SO
3
H)
2 2
Cl .
Table
1
Calculation of Hammett acidity function (H
0
)
for
a
[BiPy](HSO ) Cl
3 2 2
+
Entry
Catalyst
A
max
[I]
s
%
[IH ]
s
%
H
0
1
2
—
2.2261
1.5984
100
71.80
0
28.2
—
1.40
[BiPy](HSO
3
)
2
Cl
2
a
4
Condition for UV-visible spectrum measurement: solvent: CCl ,
ꢂ4
ꢂ1
indicator: 4-nitroaniline (pK(I)aq ¼ 0.99), 1.44 ꢁ 10 mol L (10 mL);
ꢀ
catalyst: [BiPy](HSO
3
)
2
Cl
2
(10 mg), 25 C.
3 2 2
Fig. 3 Mass spectra of [BiPy](SO H) Cl .
Fig.
4
Absorption spectra of 4-nitroaniline (indicator) (a) and Scheme 2 Synthesis of various xanthene derivatives catalyzed by
Cl (catalyst) (b) in CCl [BiPy](SO H) Cl
[
BiPy](HSO
)
3 2
2
4
.
3
2
2
.
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Table 2 Optimization of the reaction conditions for the synthesis of be seen in Fig. 4, the maximal absorbance of the unproto-
xanthenes derivative of 4-chlorobenzaldehyde and 2-naphthol
nated form of the indicator was observed at 328 nm in CCl4.
When [BiPy](HSO ) Cl as the ionic liquid catalyst was added
3
2
2
Catalyst
(mg mol %)
Temperature
( C)
Time
(min)
Conversion
(%)
ꢂ1
ꢀ
to the indicator solution, the absorbance of the unprotonated
form of the indicator decreased, which indicated that the
Entry
+
1
2
3
4
5
5/1.25
10/2.5
10/2.5
10/2.5
20/5
90
110
90
80
90
24
25
10
30
5
70
98
98
40
70
indicator was partially in the form of [IH ]. These results that
have listed in Table 1, show the acidity strength of
[
3 2 2
BiPy](HSO ) Cl .
Catalytic activity
On the basis of the obtained information, we anticipated that
BiPy](HSO ) Cl can be used as an efficient catalyst for the
acceleration of the reactions which need the use of an acidic
catalyst to speed-up. So we were interested to investigate the
applicability of this reagent in the promotion of the synthesis of
xanthenes derivatives.
[
where the pK(I)aq is the pK
cator, [IH ] and [I]
s s
a
value of aqueous solution of indi-
are the molar concentrations of protonated
and unprotonated forms of the indicator in the solvent, respec-
3 2
2
+
+
s s
tively. According to Lambert–Beer's Law, the value of [I] /[IH ]
can be determined and calculated through UV-visible spectrum.
At rst, we focused our attention to study the synthesis of 14-
aryl-14H-dibenzo[a,j] xanthenes. For optimization of the reac-
tion conditions, the condensation of 4-chlorobenzaldehyde
For this purpose, 4-nitroaniline (pK(I)aq ¼ 0.99) as the
basic indicator and CCl as the solvent were chosen. As can
4
a
Table 3 [BiPy](SO
3
2
H) Cl
2
catalyzed the synthesis of xanthene derivatives
ꢀ
Mp ( C)
24
Entry
Product
Aldehydes
Time (min)
Yield (%)
Found
Reported
1
2
3
4
5
6
7
8
9
C
4-ClC
2-ClC
4-BrC H CHO
6 4
4-NO
3-NO
4-MeOC
2-MeOC
4-HOC
6 5
C H
4-ClC
2-ClC
4-BrC
3-BrC
4-NO
3-NO
4-MeOC
3-MeOC
2-MeOC
6
H
5
CHO
15
10
30
18
25
23
30
50
45
2
4
3
4
8
2
5
5
1
2
1
2
3
2
2
3
15
10
15
20
25
20
15
20
16
20
15
95
98
95
95
95
90
90
80
80
98
98
98
98
96
95
90
98
98
98
98
98
95
98
98
95
90
98
80
98
85
90
95
80
90
95
80
185–184
280
206–207
294–295
310–312
212
185–186
280–283
206–209
294–295
310–311
212–214
199–201
258–259
130–133
197–198
227–229
224–225
240–242 (ref. 26)
281–282
223–224
164–165
243–245
190–191
209–210
203–204
228–229
248–249
227–228
280–281
263–264
150–151
173–174
221–224
180–182
164–165
175–178
166–169
218–220
205–208
218–220
213–215
6
H
H
4
CHO
CHO
6
4
C
2 6
H
4
CHO
CHO
C
2 6
H
4
6
H
4
CHO
CHO
199–201
258–259
130–132
197–198
225–229
220–223
240–242
280–282
223–224
162–163
241–242
190–191
209–210
203–205
228–230
247–248
227–229
280–281
260–261
150–151
170–171
220–224
180–182
164–166
175–176
166–169
218–220
205–207
218–220
213–214
6 4
H
6 4
H CHO
CHO
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
6
H
H
4
CHO
CHO
6
4
6
H
H
4
CHO
CHO
6
4
C
2 6
H
4
CHO
CHO
C
2 6
H
4
6
H
4
CHO
CHO
CHO
6
H
H
4
4
6
C
6
H
5
CHO
4-ClC
2-ClC
4-BrC
3-BrC
6
H
H
4
CHO
CHO
6
4
6
H
H
4
CHO
CHO
6
4
4-NO
C
2 6
H
4
CHO
C
6
H
5
CHO
4-ClC
2-ClC
4-BrC
3-BrC
4-NO
3-NO
2-NO
4-MeOC
3-MeOC
6
H
H
4
CHO
CHO
6
4
6
H
H
4
CHO
CHO
6
4
2
C
6
6
6
H
H
H
4
4
4
CHO
CHO
CHO
2
C
C
2
6
H
4
CHO
CHO
6 4
H
2-Naphthaldehyde
a
Isolated yields.
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with 2-naphthol to the corresponding product was selected as a investigations claried that under the same optimal conditions,
model reaction in different conditions in the presence of the products can be obtained in high yields in very short reac-
different amounts of [BiPy](SO H) Cl . The results are tabulated tion times (Table 3, entries 10–25).
3
2
2
in Table 1.
On the basis of these studies and aer the successful
The obtained results showed that the reaction using 10 mg of application of [BiPy](SO
the catalyst at 90 C proceeded with highest yield in shortest xanthenes, we decided to use this reagent in the synthesis of 12-
3
H)
2
Cl
2
in the preparation of symmetric
ꢀ
reaction times (Scheme 2).
aryl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-ones. The same
It should be noted that using lower or higher amounts of the reaction condition was applied for this purpose and the results
catalyst lead to the product in longer times. On the other hand showed that using this method the requested products were
by decreasing of the temperature, the reaction became slower obtained under mild conditions in excellent yields during very
(Table 2, entry 4). It is also important to note that by increasing short times (Table 3, entries 26–36).
of the temperature, the mixture became sticky which resulted in
the increasing of the reaction time (Table 2, entry 2).
Table 4 compares our results with the results reported in the
literature using some of the other ionic liquids in the synthesis
Aer optimization of the reaction conditions, we explored of xanthenes. This comparison indicates that in some cases, the
the protocol with a variety of simple readily available substrates reaction time is too long in the presence of the other catalysts
under the optimal conditions. As presented in Table 3, different (Table 4, ref. 18, 34 and 36–41). In addition, the amount of the
aromatic aldehydes were condensed with 2-naphthol under the catalyst in this work have been reduced relative to the other ILs
selected conditions with high yields in very short reaction times. and it is clear that [BiPy](HSO ) Cl is superior in terms of TOF
3
2
2
As can be seen, the strict effect of the substituents on the (turnover frequency) to the compared ionic liquids.
aromatic ring led to the addition of the reaction times (Table 3,
entries 1–9).
To check the reusability of the catalyst, the reaction of 4-
chlorobenzaldehyde and dimedone under the optimized reac-
In the next step, this ionic liquid was used as a catalyst in the tion conditions was studied again. When the reaction
condensation of dimedone or cyclohexadione with aldehydes completed, H O (3 mL) was added to separate the catalyst. The
leading to 1,8-dioxo-octahydroxanthenes (Scheme 2). Our solvent was evaporated under reduced pressure and resulting
2
Table 4 Comparison of the results obtained from the synthesis of xanthenes in the presence of [BiPy](HSO
ionic liquids
3
)
Cl
2 2
with those obtained using other
a
ꢀ
Product
Catalyst loading (mol%)
Temperature ( C)
Time (min)
Yield (%)
[
[
Dsim]Cl (10)
Et N-SO H]Cl (15)
110
120
90
110
125
100 (Water)
90
5
30
3
20
90
7
90 (ref. 32)
96 (ref. 18)
94 (ref. 26)
96 (ref. 33)
85 (ref. 34)
93 (ref. 35)
95 (this work)
3
3
DSIMHS (25)
[H-NMP][HSO
[Hmim]HSO
[MIMPS]HSO
[BiPy](HSO
4
] (10)
(12)
(25)
Cl (2.57)
4
4
a
3
)
2
2
15
[
Dsim]Cl (10)
70
55
80
80
100
80
90
4
3
96 (ref. 32)
92 (ref. 26)
91 (ref. 36)
90 (ref. 37)
87 (ref. 38)
91 (ref. 18)
98 (this work)
DSIMHS (25)
[
[
[
[
[
Hmim]TFA (100 mg)
bmim]HSO (100 mg)
] (20)
H]Cl (25)
Cl (2.57)
180
210
45
40
4
4
Et
Et
3
NH][HSO
N-SO
4
3
3
b
BiPy](HSO
3
)
2
2
[
Et
3
N-SO
3
H]Cl (25)
120
55
100
80
110
90
40
12
30
40
7
89 (ref. 39)
93 (ref. 26)
87 (ref. 40)
87 (ref. 41)
95 (ref. 32)
98 (this work)
DSIMHS (25)
Py(HSO (10)
PO (20)
Msim]BF (10)
BiPy](HSO Cl
4
)
2
[
[
[
NMP]H
2
4
4
c
3
)
2
2
(2.57)
10
a
TOF (hꢂ1): a ¼ 147.8, b ¼ 572, c ¼ 228.8.
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Table 5 Reusability of [BiPy](SO
benzaldehyde and dimedone
3
2
H) Cl
2
in the reaction of 4-chloro
9 H. R. Shaterian, M. Ghashang and A. Hassankhani, Dyes
Pigm., 2008, 76, 564.
1
0 M. Seyyedhamzeh, P. Mirzaei and A. Bazgir, Dyes Pigm., 2008,
Run
Time (min)
Yield (%)
76, 836.
1
2
3
4
4
7
10
20
98
95
92
85
11 G. C. Nandi, S. Samai, R. Kumar and M. S. Singh,
Tetrahedron, 2009, 65, 7129.
1
1
1
1
1
2 M. M. Heravi, H. Alinejhad, K. Bakhtiari and H. A. Oskooie,
Mol. Diversity, 2010, 14, 621.
3 H. A. Oskooie, L. Tahershamsi, M. M. Heravi and
B. Baghernejad, Eur. J. Chem., 2010, 7, 717.
4 S. Kokkirala, N. M. Sabbavarapu and V. D. N. Yadavalli, Eur.
J. Chem., 2011, 2, 272.
5 B. F. Mirjalili, A. Bamoniri, A. Akbari and N. Taghavinia, J.
Iran. Chem. Soc., 2011, 8, 129.
6 A. Zare, M. Mokhlesi, A. Hasaninejad and T. Hekmat-Zadeh,
Eur. J. Chem., 2012, 9, 1854.
ionic liquid was reused directly for the next run. It was found
that the catalyst could be recovered and reused at least for three
runs (Table 5).
Conclusions
1
1
7 N. G. Khaligh, Ultrason. Sonochem., 2012, 19, 736.
8 A. Zare, A. R. Moosavi-Zare, M. Merajoddin, M. A. Zolgol,
T. Hekmat-Zadeh, A. Hasaninejad, A. Khazaei,
M. Mokhlesi, V. Khakyzadeh, F. Derakhshan-Panah,
M. H. Beyzavi, E. Rostami, A. Argoon and R. Roohandeh, J.
Mol. Liq., 2012, 167, 69.
3 2 2
In conclusion, in this study we have introduced [BiPy](HSO ) Cl
as a highly powerful ionic liquid for the simple preparation of
symmetric and asymmetric xanthenes derivatives. Ease of
preparation and handling of the catalyst, high reaction rates,
simple procedure, use of lower loading of the catalyst, high yield
of the products without side reactions and solvent-free condi-
tions are some of the advantages of this method.
1
9 A. Khazaei, M. A. Zolgol, A. R. Moosavi-Zare, A. Zare,
M. Khojasteh, Z. Asgari, V. Khakyzadeh and A. Khala-
Nezhad, Catal. Commun., 2012, 20, 54.
2
2
2
2
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Acknowledgements
The authors are thankful to University of Guilan Research
Council for the partial support of this work.
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