One-pot synthesis of xanthene derivatives catalyzed by Fe(III) tetranitrophthalocyanine immobilized on activated carbon

Article abstract of DOI:10.1134/S1070363216040307

Xanthene derivatives were synthesized by a multicomponent one-pot reaction of aromatic aldehydes, β-naphthol, and 5,5-dimethylcyclohexane-1,3-dione or 1,3-cyclohexanedione upon efficient and eco-friendly catalysis of Fe(III) tetranitrophthalocyanine immob

Full text of DOI:10.1134/S1070363216040307

ISSN 1070-3632, Russian Journal of General Chemistry, 2016, Vol. 86, No. 4, pp. 934–938. © Pleiades Publishing, Ltd., 2016.
One-Pot Synthesis of Xanthene Derivatives
Catalyzed by Fe(III) Tetranitrophthalocyanine Immobilized
1
on Activated Carbon
H. Huang, Y. Yao, Q. Lin, J. Zhao, C. Hua, and X. Gou
Key Laboratory of Synthetic and Natural Functional Molecule Chemistry (Ministry of Education),
College of Chemistry and Materials Science, Northwest University, Xi’an, 710127 China
e-mail: xdny917@163.com
Received October 22, 2015
Abstract—Xanthene derivatives were synthesized by a multicomponent one-pot reaction of aromatic
aldehydes, β-naphthol, and 5,5-dimethylcyclohexane-1,3-dione or 1,3-cyclohexanedione upon efficient and
eco-friendly catalysis of Fe(III) tetranitrophthalocyanine immobilized on activated carbon in ethanol. The
method tolerated a variety of functional groups and the process was carried out under mild conditions to give
high yield of products (85–91%) in 30 min. The catalyst can be recycled without any loss in catalytic activity.
Keywords: xanthene, Fe(III) tetranitrophthalocyanine immobilized on activated carbon, multicomponent
DOI: 10.1134/S1070363216040307
INTRODUCTION
RESULTS AND DISCUSSION
The optimized reaction conditions have been
worked out for the reaction of benzaldehyde (1 mmol),
β-naphthol (1 mmol) and 5,5-dimethylcyclohexane-
Xanthene derivatives demonstrate various bio-
logical and pharmaceutical activities including anti-
inflammatory [1], anti-bacterial [2] and anti-viral
[
3, 4]. Due to their specific spectroscopic properties,
Table 1. Catalysts tested in the synthesis of 9,9-dimethyl-
the xanthene derivatives found diverse applications in
dyes industry [5], laser technology [6] and pH-
sensitive fluorescent materials [7].
1
2-phenyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one (1a)
Time,
Entry
Catalyst
–
T, °C
Yield, %
h
12.0
3.0
3.0
3.0
3.0
3.0
3.0
2.0
2.0
2.0
2.0
The earlier developed methods of synthesis of
tetrahydrobenzo[a]xanthene-11-ones by condensation
of aldehydes, β-naphthol and cyclic 1,3-dicarbonyl
compounds had been catalyzed by a wide variety of
catalysts [10–19]. Many of those methods led to
moderate yields of products upon long reaction time,
harsh conditions and involved toxic organic solvents
a
1
2
3
4
5
6
7
8
9
Reflux
Reflux
Reflux
Reflux
Reflux
Reflux
Reflux
Reflux
Reflux
Reflux
Reflux
Reflux
Reflux
Cu(II)Pc/C
11
35
34
41
40
52
21
59
53
54
56
91
Zn(II)Pc/C
Co(II)Pc/C
Ni(II)Pc/C
Mn(II)Pc/C
Fe(III)Pc/C
[20].
Here in, we report a simple, efficient and environ-
mentally friendly protocol for the synthesis of
xanthene derivatives via one-pot multicomponent con-
densation of aromatic aldehydes, β-naphthol and 5,5-
dimethylcyclohexane-1,3-dione or 1,3-cyclohexane-
dione catalyzed by Fe(III) tetranitrophthalocyanine
NO
2
–Cu(II)Pc/C
NO –Zn(II)Pc/C
2
1
0
1
2
3
NO
NO
NO
NO
2
2
2
2
–Co(II)Pc/C
1
1
1
–Ni(II)Pc/C
immobilized on activated carbon [NO –Fe(III)Pc/C]
upon refluxing in ethanol (Scheme 1).
2
–Mn(II)Pc/C 2.0
–Fe(III)Pc/C 0.5
1
a
The text was submitted by the authors in English.
Not determined.
9
34

ONE-POT SYNTHESIS OF XANTHENE DERIVATIVES
935
Scheme 1. Synthesis of xanthene derivatives.
R1
CHO
O
O
OH
O
NO −FePc/C
2
+
+
alcohol/reflux
R2
R2
R2
R1
O
R2
1
a−1o
1
2
1
2
1
2
1
2
1
2
1
a: R = H, R = CH
3
; 1b: R = 4-CH
3
, R = CH
3
; 1c: R = 4-Cl, R = CH
3
; 1d; R = 4-OH, R = CH
3
; 1e: R = 4-OCH
3
, R =
1
2
1
2
1
2
1
2
3 3 3 3 2 3 2 3
CH ; 1f: R = 3-OCH -4-OH, R = CH ; 1g: R = 2,4-di-Cl, R = CH ; 1h: R = 4-NO , R = CH ; 1i: R = 3-NO , R = CH ;
j: R = H, R = H; 1k: R = CH , R = H; 1l; R = 4-Cl, R = H; 1m; R = 4-OCH , R = H; 1n: R = 4-NO , R = H; 1o:
3 3 2
1
2
1
2
1
2
1
2
1
2
1
1
2
2
R = 4-NO , R = H.
1
,3-dione (1.2 mmol) considered as a model process.
The experimental data demonstrated that the
reaction proceeded smoothly with different aldehydes
substituted with electron-donating or electron-withd-
rawing groups giving high yields of products (Table 4).
Various phthalocyanine catalysts were tested in the
model reaction (Table 1). The desired product was not
accumulated in the absence of catalysts. Fe(III)
tetranitrophthalocyanine immobilized on activated
carbon demonstrated the highest catalytic activity
EXPERIMENTAL
(
Table 1, entry 13).
Melting points were determined by an XT-4
melting point microscope without correction. IR spectra
were recorded on a EQUINOX55 FT-IR spectrophoto-
Among various solvents tested in the reaction
THF, CHCl , actone, CH CN, toluene, DMF, MeOH,
(
3
3
and EtOH) the latter one proved to be the most
efficient (Table 2). The most favorable reaction
temperature and time of the process have been
determined experimentally (Table 2, entry 8). The
catalyst of choice, Fe(III) tetranitrophthalocyanine im-
mobilized on activated carbon, could be recycled and
used repeatedly (Table 3).
1
meter. H NMR (400 M Hz) spectra were measured on
a BRUKER pectrometer using CDCl as a solvent.
3
Mass spectra were measured on an Agilent AXIMA-
CFR-plus MALDI-TOF-Ms Spectrometer. The reac-
tion progress and purity of the products were
monitored by TLC on silica gel.
General procedure for synthesis of compounds
1a–1i. A mixture of 5,5-dimethylcyclohexane-1,3-
dione 0.168 g (1.2 mmol), β-naphthol 0.144 g (1 mmol),
aromatic aldehyde (1 mmol), two drops of con-
centrated hydrochloric acid, ethanol (10 mL), and a
catalytic amount of Fe(III) tetranitrophthalocyanine
immobilized on activated carbon (5 mol %) was loaded
Table 2. Solvents tested in the synthesis of 9,9-dimethyl-12-
phenyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one (1a)
Time,
h
Entry
Solvent
THF
T, °C
Yield, %
1
2
3
4
5
6
7
8
9
4.0
4.0
4.0
4.0
4.0
4.0
1.0
0.5
5.0
5.0
Reflux
Reflux
Reflux
Reflux
Reflux
Reflux
Reflux
Reflux
50
12
14
15
35
38
45
82
91
63
37
CHCl
Acetone
CH CN
3
Table 3. Yield of the synthesis of 1a catalyzed by the
recycled Fe(III) tetranitrophthalocyanine immobilized on
activated carbon in EtOH upon refluxing for 30 min
3
Toluene
DMF
Run no.
Yield, %
1
2
3
4
5
91
91
90
90
89
MeOH
EtOH
EtOH
EtOH
1
0
25
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 86 No. 4 2016

9
36
HUANG et al.
Table 4. Yield of xanthene derivatives in the presence of
Fe(III) tetranitrophthalocyanine immobilized on activated
carbon
7.21–7.42 m (5H, ArH), 7.73–7.77 t (2H, J = 8.8 Hz,
ArH), 8.00 d (1H, J = 8.4 Hz, ArH). ESI-MS, m/z.
Found: 369.1855. C H O . Calculated: 369.1855.
2
6
24
2
+
1
[
M + H ].
9,9-Dimethyl-12-(4-chlorophenyl)-8,9,10,12-
tetrahydrobenzo[a]xanthen-11-one (1c). Yield 91%,
Comp. no.
R
R
Yield, %
91
1
1
1
1
1
1
1
1
1
1
1
1
1
1
1
a
b
c
d
e
f
H
CH
CH
CH
CH
CH
CH
CH
CH
CH
H
3
4-CH
4-Cl
3
3
3
3
3
3
3
3
3
90
–
1
mp 179–181°C. IR spectrum, ν, cm : 3078, 2952,
1
1
91
649, 1595, 1371, 1226, 874, 752. H NMR spectrum,
δ, ppm: 0.96 s (3H, CH ), 1.12 s (3H, CH ), 2.22–2.33
4–OH
89
3
3
m (2H, CH ), 2.56 s (2H, CH ), 5.68 s (1H, CH), 7.13
2
2
4-OCH
3-OCH
3
3
88
d (2H, J = 8.4 Hz, ArH), 7.25–7.45 m (5H, ArH),
7.76–7.79 t (2H, J = 7.2 Hz, ArH), 7.90 d (1H, J =
–4-OH
86
8
.4 Hz, ArH). ESI-MS, m/z. Found: 411.1116. C H O Cl.
25 21 2
g
h
i
2,4-Cl
2
85
+
Calculated: 411.1128. [M + Na ].
,9-Dimethyl-12-(4-hydroxyphenyl)-8,9,10,12-
tetrahydrobenzo[a]xanthen-11-one (1d). Yield 89%,
mp 219–221°C. IR spectrum, ν, cm : 3365, 3060,
2
4-NO
3-NO
H
2
89
9
2
88
–
1
j
93
1
952, 1651, 1595, 1373, 1230, 819, 771. H NMR
k
l
4-CH
4-Cl
3
H
90
spectrum, δ, ppm: 0.97 s (3H, CH ), 1.11 s (3H, CH ),
3
3
H
91
2
.23–2.34 m (2H, CH ), 2.56 s (2H, CH ), 5.60 s (1H,
2 2
m
n
o
4-OCH
3
H
88
OH), 5.63 s (1H, CH), 6.60 d (2H, J = 8.8 Hz, ArH),
7
7
8
.17 d (2H, J = 8.4 Hz, ArH), 7.30–7.43 m (3H, ArH),
.74–7.79 t (2H, J = 9.2 Hz, ArH), 7.97 d (1H, J =
4-NO
3-NO
2
2
H
89
H
86
.4 Hz, ArH). ESI-MS, m/z. Found: 371.1653.
+
C H O . Calculated: 371.1647. [M + H ].
2
5
22
3
in a 50 mL round-bottomed flask. and refluxed for ca
0 min upon stirring. The catalyst was recovered by
filtration followed by washing with ethanol repeatedly
and drying. The liquid filtrate was cooled and
crystallized. The solid precipitated was filtered off,
dried and purified by recrystallization from ethanol.
9
,9-Dimethyl-12-(4-methoxyphenyl)-8,9,10,12-
3
tetrahydrobenzo[a]xanthen-11-one (1e). Yield 88%,
mp 205–206°C. IR spectrum, ν, cm : 3057, 2956,
647, 1595, 1379, 1226, 837, 748. H NMR spectrum,
δ, ppm: 0.97 s (3H, CH ), 1.11 s (3H, CH ), 2.22–2.32
–
1
1
1
3
3
m (2H, CH ), 2.56 s (2H, CH ), 3.68 s (3H, OCH ),
2
2
3
5
7
.65 s (1H, CH), 6.70 d (2H, J = 8.4 Hz, ArH), 7.23–
.45 m (5H, ArH), 7.73–7.78 t (2H, J = 9.2 Hz, ArH),
9
,9-Dimethyl-12-phenyl-8,9,10,12-tetrahydro-
benzo[a]xanthen-11-one (1a). Yield 91%, mp 148–
50°C. IR spectrum, ν, cm : 3055, 2956, 1651, 1595,
373, 1226, 746, 698. H NMR spectrum, δ, ppm: 0.96
–
1
7.98 d (1H, J = 8.4 Hz, ArH). ESI-MS, m/z. Found:
385.1826. C H O . Calculated: 385.1804. [M + H ].
1
1
+
1
2
6
24
3
s (3H, CH ), 1.12 s (3H, CH ), 2.23–2.33 m (2H, CH ),
3
3
2
9,9-Dimethyl-12-(3-methoxy-4-hydroxyphenyl)-
2
.57 s (2H, CH ), 5.70 s (1H, CH), 7.03–7.07 t (1H,
2
8,9,10,12-tetrahydrobenzo[a]xanthen-11-one (1f).
–
1
J = 7.4 Hz, ArH), 7.15–7.19 t (2H, J = 7.6 Hz, ArH),
.31–7.45 m (5H, ArH), 7.75–7.79 t (2H, J = 7.6 Hz,
Yield 86%, mp 163–165°C. IR spectrum, ν, cm :
7
3471, 3070, 2958, 1645, 1595, 1371, 1226, 877, 813,
1
ArH), 7.99 d (1H, J = 8.4 Hz, ArH). ESI-MS, m/z.
752. H NMR spectrum, δ, ppm: 0.97 s (3H, CH ),
3
Found: 377.1495. C H O . Calculated: 377.1517.
1.11 s (3H, CH ), 2.23–2.33 m (2H, CH ), 2.55 s (2H,
2
5
22
2
3
2
+
[
M + Na ].
,9-Dimethyl-12-(4-methylphenyl)-8,9,10,12-
tetrahydrobenzo[a]xanthen-11-one (1b). Yield 90%,
CH ), 3.81 s (3H, OCH ), 5.48 s (1H, OH), 5.64 s (1H,
2 3
CH), 6.63–6.68 m (2H, ArH), 7.00 s (1H, ArH), 7.30–
.43 m (3H, ArH), 7.74–7.78 t (2H, J = 9.6 Hz, ArH),
9
7
–
1
7.98 d (1H, J = 8.4 Hz, ArH). ESI-MS, m/z. Found:
mp 173–175°C. IR spectrum, ν, cm : 3043, 2951,
1
+
1
401.1757. C H O . Calculated: 401.1753. [M + H ].
2
6
24
4
649, 1597, 1371, 1228, 813, 756. H NMR spectrum,
δ, ppm: 0.97 s (3H, CH ), 1.11 s (3H, CH ), 2.19 s
9,9-Dimethyl-12-(2,4-dichlorophenyl)-8,9,10,12-
3
3
(
3H, Ar–CH ), 2.21–2.32 m (2H, CH ), 2.56 s (2H,
tetrahydrobenzo[a]xanthen-11-one (1g). Yield 85%,
mp 179–181°C. IR spectrum, ν, cm : 3070, 2954,
3
2
–
1
CH ), 5.66 s (1H, CH), 6.97 d (2H, J = 8.0 Hz, ArH),
2
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 86 No. 4 2016

ONE-POT SYNTHESIS OF XANTHENE DERIVATIVES
937
1
1
652, 1597, 1369, 1228, 846, 752. H NMR spectrum,
8.4 Hz, ArH). ESI-MS, m/z. Found: 349.1199. C H O .
23 18 2
Calculated: 349.1204. [M + Na ].
+
δ, ppm: 0.99 s (3H, CH ), 1.14 s (3H, CH ), 2.21–2.34
3
3
m (2H, CH ), 2.60 s (2H, CH ), 5.94 s (1H, CH), 7.02–
2
2
1
2-(4-Methylphenyl)-8,9,10,12-tetrahydrobenzo-
7
.05 m (1H, ArH), 7.21–7.27 m (3H, ArH), 7.29–7.39
[
a]xanthen-11-one (1k). Yield 90%. mp 201–203°C.
IR spectrum, ν, cm : 3022, 2960, 1661, 1595, 1371,
t (1H, J = 7.2 Hz, ArH), 7.46–7.50 t (1H, J = 7.4 Hz,
ArH), 7.74–7.78 t (2H, J = 7.8 Hz, ArH), 8.12 d (1H,
J = 8.4 Hz, ArH). ESI-MS, m/z. Found: 423.0920.
–
1
1
1
224, 819, 746. H NMR spectrum, δ, ppm: 1.97–2.05
m (2H, CH ), 2.20 s (3H, CH ), 2.33–2.48 m (2H,
CH ), 2.62–2.77 m (2H, CH ), 5.70 s (1H, CH), 6.98 d
+
2
3
C H O Cl [M + H ]. Calculated: 423.0919.
2
5
20
2
2
2
2
(
7
2H, J = 8.0 Hz, ArH), 7.22–7.44 m (5H, ArH), 7.74–
.78 t (2H, J = 8.0 Hz, ArH), 7.97 d (1H, J = 8.4 Hz,
ArH). ESI-MS, m/z. Found: 363.1361. C H O .
9
,9-Dimethyl-12-(4-nitrophenyl)-8,9,10,12-
tetrahydrobenzo[a]xanthen-11-one (1h). Yield 89%,
mp 177–178°C. IR spectrum, ν, cm : 3073, 2950,
654, 1597, 1375, 1226, 810, 764. H NMR spectrum,
–
1
24 20
2
+
1
Calculated: 363.1361. [M + Na ].
1
δ, ppm: 0.95 s (3H, CH ), 1.14 s (3H, CH ), 2.22–2.36
3
3
1
2-(4-Chlorophenyl)-8,9,10,12-tetrahydrobenzo[a]-
m (2H, CH ), 2.60 s (2H, CH ), 5.81 s (1H, CH), 7.35–
2
2
xanthen-11-one (1l). Yield 91%, mp 206–208°C. IR
spectrum, ν, cm : 3076, 2962, 1651, 1594, 1375,
222, 856, 718. H NMR spectrum, δ, ppm: 1.94–2.10
m (2H, CH ), 2.34–2.45 m (2H, CH ), 2.62–2.76 m
7
7
.43 m (3H, ArH), 7.52 d (2H, J = 8.8 Hz, ArH), 7.81–
.84 m (3H, ArH), 8.04 d (2H, J = 8.8 Hz, ArH). ESI-
–1
1
1
MS, m/z. Found: 422.1378. C H O N. Calculated:
2
5
21
4
+
2
2
4
22.1368. [M + Na ].
(
2H, CH ), 5.71 s (1H, CH), 7.13 d (2H, J = 8.4 Hz,
2
ArH), 7.27–7.43 m (5H, ArH), 7.77–7.80 t (2H, J =
.0 Hz, ArH), 7.88 d (1H, J = 8.4 Hz, ArH). ESI-MS,
m/z. Found: 361.1003. C H O Cl. Calculated: 361.0095.
9
,9-Dimethyl-12-(3-nitrophenyl)-8,9,10,12-
7
tetrahydrobenzo[a]xanthen-11-one (1i). Yield 88%,
mp 168–170°C. IR spectrum, ν, cm : 3073, 2953, 1657,
375, 1224, 963, 812, 764. H NMR spectrum, δ, ppm:
.95 s (3H, CH ), 1.14 s (3H, CH ), 2.22–2.35 m (2H,
–1
23
17
2
+
1
[M + H ].
1
0
3
3
12-(4-Methoxyphenyl)-8,9,10,12-tetrahydro-
CH ), 2.61 s (2H, CH ), 5.81 s (1H, CH), 7.35–7.44 m
2
2
benzo[a]xanthen-11-one (1m). Yield 88%, mp 180–
–
1
(
8
4
4H, ArH), 7.80–7.87 m (4H, ArH), 7.94 d (1H, J =
.4 Hz, ArH), 8.11 s (1H, ArH). ESI-MS, m/z. Found:
22.1378. C H O N. Calculated: 422.1368. [M + Na ].
1
1
81°C. IR spectrum, ν, cm : 3056, 2960, 1661, 1376,
1
222, 832, 753. H NMR spectrum, δ, ppm: 1.92–2.10
+
25
21
4
m (2H, CH ), 2.38–2.48 m (2H, CH ), 2.66–2.76 m
2
2
(
(
7
2H, CH ), 3.69 s (3H, OCH ), 5.69 s (1H, CH), 6.71 d
2 3
General procedure for synthesis of compounds
j–1o. A catalytic amount of Fe(III) tetranitrophthalo-
cyanine immobilized on activated carbon (5 mol %)
was added to a mixture of aromatic aldehyde
1 mmol), 1,3-cyclohexanedione (0.146 g, 1.2 mmol),
2H, J = 8.8 Hz, ArH), 7.23–7.44 m (5H, ArH), 7.74–
.78 t (2H, J = 8.8 Hz, ArH), 7.95 d (1H, J = 8.4 Hz,
ArH). ESI-MS, m/z. Found: 379.1305. C H O .
1
24
20
3
+
Calculated: 379.1310. [M + Na ].
(
β-naphthol (0.144 g, 1 mmol), two drops of con-
centrated hydrochloric acid, and ethyl alcohol (10 mL).
The reaction mixture was refluxed for ca 30 min upon
stirring. The catalyst was recovered by filtration fol-
lowed by repeated washing with ethanol and drying.
The liquid filtrate was cooled and crystallized. The
solid obtained was filtered off, dried and purified by
recrystallization from ethanol.
12-(4-Nitrophenyl)-8,9,10,12-tetrahydrobenzo[a]-
xanthen-11-one (1n). Yield 89%, mp 236–238°C. IR
–
1
spectrum, ν, cm : 3069, 2953, 1664, 1373, 1224, 810,
1
726. H NMR spectrum, δ, ppm: 1.94–2.07 m (2H,
CH ), 2.36–2.49 m (2H, CH ), 2.71–2.80 m (2H, CH ),
2
2
2
5.84 s (1H, CH), 7.36–7.44 m (5H, ArH), 7.51 d (2H,
J = 8.8 Hz, ArH), 7.80–7.82 t (2H, ArH), 8.04 d (1H,
J = 8.8 Hz, ArH). ESI-MS, m/z. Found: 394.1052.
+
C H O N. Calculated: 394.1055. [M + Na ].
2
3
17
4
1
2-Phenyl-8,9,10,12-tetrahydrobenzo[a]xanthen-
1
1-one (1j). Yield 93%, mp 188–190°C. IR spectrum,
12-(3-Nitrophenyl)-8,9,10,12-tetrahydrobenzo[a]-
–
1
ν, cm : 3053, 2955, 1651, 1594, 1373, 1226, 748, 680.
xanthen-11-one (1o). Yield 86%, mp 232–234°C. IR
1
–1
H NMR spectrum, δ, ppm: 1.95–2.08 m (2H, CH2),
spectrum, ν, cm : 3072, 2963, 1656, 1371, 1226, 954,
1
2
.34–2.50 m (2H, CH ), 2.62–2.78 m (2H, CH ), 5.74 s
837, 748. H NMR spectrum, δ, ppm: 1.94–2.10 m
2
2
(
1H, CH), 7.05–7.08 t (1H, J = 7.4 Hz, ArH), 7.16–
(2H, CH ), 2.35–2.50 m (2H, CH ), 2.66–2.83 m (2H,
2
2
7
7
.19 t (2H, J = 7.6 Hz, ArH), 7.32–7.44 m (5H, ArH),
.75–7.79 t (2H, J = 7.0 Hz, ArH), 7.96 d (1H, J =
CH ), 5.84 s (1H, CH), 7.36–7.42 m (4H, ArH), 7.80–
7.84 m (4H, J = 8.8 Hz, ArH), 7.94 d (1H, J = 8.4 Hz,
2
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 86 No. 4 2016

9
38
HUANG et al.
ArH), 8,09 s (1H, ArH). ESI-MS, m/z. Found: 394.1054.
6. Ghodsi, M.Z., Negar, L., and Alireza, B., Sci. Iranica,
013, vol. 20, p. 580.
+
2
C H O N. Calculated: 394.1055. [M + Na ].
2
3
17
4
7
8
9
. Dharma Rao, G.B., Kaushik, M.P., and Halve, A.K.,
Tetrahedron Lett., 2012, vol. 53, p. 2741.
CONCLUSIONS
The highly efficient and green method of synthesis
of xanthene derivatives catalyzed by Fe(III) tetra-
nitrophthalocyanine immobilized on activated carbon
in ethanol has been developed. The simple procedure,
short reaction time, efficient recovery, and non-toxicity
of the catalyst are the advantages of the method.
. Li, J.J., Tang, W.Y., Lu, L.M., and Su, W.K., Tetra-
hedron Lett., 2008, vol. 49, p. 7117.
. Farhad, S., Somayeh, A.D., and Ali M.K., C. R. Chimie,
2
013, vol. 16, p. 207.
1
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1
1
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ACKNOWLEDGMENTS
2. Hassankhani, A., Mosaddegh, E., and Ebrahimipour, S.Y.,
We gratefully acknowledge financial support from
the Industrial Research Project of Shaanxi Science and
Technology Department (2014K08-29), National Basic
Science Personnel Training Fund (J1103311 and
J1210057) and Scientific Research Foundation of
Northwestern University.
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