V2O5 based quadruple nano-perovskite as a new catalyst for the synthesis of bis and tetrakis heterocyclic compounds

Article abstract of DOI:10.1002/aoc.4783

In this article, we presented a novel, efficient and facile approach for using strontium titanate supported catalyst in organic synthesis. Bis and tetrakis of coumarin, indole and xanthene derivatives can effortlessly have prepared using V₂O

Full text of DOI:10.1002/aoc.4783

Received: 1 November 2018
DOI: 10.1002/aoc.4783
Revised: 11 December 2018
Accepted: 12 December 2018
F U L L P A P E R
V O based quadruple nano‐perovskite as a new catalyst for
2
5
the synthesis of bis and tetrakis heterocyclic compounds
1
2,3
4
Tamer K. Khatab | Amr Mohamed Abdelghany
| Hanan A. Soliman
1
Organometallic and Organometalloid
In this article, we presented a novel, efficient and facile approach for using
strontium titanate supported catalyst in organic synthesis. Bis and tetrakis of
coumarin, indole and xanthene derivatives can effortlessly have prepared using
V O /perovskite nanoparticles (NPs) under solvent‐free condition. V O /perov-
Chemistry Department, National Research
Centre, 33 El‐Behouth St., Dokki, 12622
Cairo, Egypt
2
Spectroscopy Department, Physics
2
5
2 5
Division, National Research Centre, 33 El‐
Behouth St., Dokki, 12622 Cairo, Egypt
skite in (NPs) was prepared and identified using Fourier transform infrared
spectroscopy (FTIR), X‐ray diffraction (XRD) and scanning electron micro-
scope supported with energy dispersive X‐ray (SEM/EDAX). Calculated crystal
size was from the intense XRD peaks was found to range between 50–60 nm in
agreement with that obtained from the transmission electron microscopic
investigation. EDAX analysis and mapping images reveal a homogenous distri-
bution of all constituents with their calculated ratios in the synthesized
catalyst.
3
Basic Science Department, Horus
University, International Coastal Road,
New Damietta, Kafr Saad, Damietta
Governorate, Egypt
4
Photochemistry Department, National
Research Centre, 33 El‐Behouth St.,
Dokki, 12622 Cairo, Egypt
Correspondence
Amr Mohamed Abdelghany, Spectroscopy
Department, Physics Division, National
Research Centre, 33 El‐Behouth St.,
Dokki, 12622, Cairo, Egypt.
KEYWORDS
coumarin, dimedone, indole, perovskite, vanadium oxide
Email: a.m_abdelghany@yahoo.com
[
3]
[4]
1
| INTRODUCTION
Hwang et al. also, Sébastien Royer et al. in their
extended reviews described the key role and conditions
to use Perovskite oxide catalysis. They also reported their
activity and stability to be used for electrochemical con-
versions spanning nitrogen, carbon, and oxygen
chemistries.
The first known perovskite crystal form is a calcium tita-
nium oxide mineral (CaTiO ). This type of compounds
3
occurs, which have the same type of crystal structure as
XII 2 + VI 4+ 2−
[1]
(
A
B X 3), known as the perovskite structure.
The symbol A which refers to cation is often an alkaline
earth (Sr, Ba, Ca), an alkali (Na, K) or a rare earth (La,
Sm, Pr) can be attached to 12 oxygen anions. The symbol
B which refers to cation is characteristically as a smaller
transition metal cation residing octahedral gaps in the oxy-
gen content. From this perovskite consist of a large number
of metallic elements and all these elements are arranged in
very stable phases. Perovskites are mixed‐metal oxides that
are attracting much scientific and application interest
owing to their low price, and thermal stability, which often
depend on bulk and surface characteristics. Perovskite‐
type oxides have acid–base, adsorption, as well as redox
Coumarins, naturally present in many classes of
plants are the memberships of oxygen‐containing hetero-
cyclic compounds. Industrially, Coumarins expansively
[
5]
employed as cosmetic, laser dye stabilizer and food addi-
[
5,6]
tives.
Also, considered as an important biologically
and pharmaceutical active scaffold, after the detections
of them being antibiotic, analgesic, anti‐inflammatory,
antitumor, anticoagulant, anti‐HIV, antihypertensive
[
7,8]
and anti‐arrhythmia agents.
Indole scaffold is plentifully existed in natural alka-
loids and presented in the human body as an essential
amino acid tryptophan also found in plants which regu-
late the plant growth in the form of hormone indole‐3‐
[
2]
properties, which lead to attractive catalytic properties.
Appl Organometal Chem. 2019;e4783.
wileyonlinelibrary.com/journal/aoc
© 2019 John Wiley & Sons, Ltd.
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https://doi.org/10.1002/aoc.4783

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KHATAB ET AL.
acetic acid. Indoles have diverse biological activity. 9–11]
The third scaffold is xanthenes which used as sensitizers
in photodynamic therapy (PDT) for destroying the tumor
[
2.2.2 | Fourier transform infrared
FTIR experimental data were measured using Thermo
[
12]
cells. Xanthenes also used in cosmetics and pigments,
Scientific Nicolet iS10, in the spectral range 4000–
[
13]
−1
−1
in the dye industry,
in laser technology because of
400 cm with a step 2 cm in both absorbance and
transmittance modes. Represented data is an average of
triplicate measured samples subjected to 32 scans.
[14]
their spectroscopic properties.
range of biological activity.
Also, they have a wide
Due to the industrial
[15]
importance and wide biological, and pharmacological
importance of the targeted scaffolds, several methods
have been reported for the synthesis of bis and tetrakis
of coumarin, indole, and xanthene. Heterogeneous cata-
lysts were employed to accelerate the condensation reac-
tion of aldehydes with coumarin, indole, and dimedone
but most of these methods have many drawbacks. Which
require hazard solvents, hard work up conditions and
2
.2.3 | Scanning electron microscopy
(SEM)
The prepared catalyst morphology was characterized
using a high resolution (SEM JEOL, Quanta FEG). To
minimize sample‐charging effects resulting from the used
electron beam, the studied sample was coated with a thin
layer of gold (3.5 nm).
[16,17]
coast catalyst preparation.
Improvements in these
conditions required the development of efficient, cost‐
effective, safe, mild and environmentally procedures syn-
thesis. Over the years the concept of green chemistry is
making researchers discover and develop various new
strategies.
2.2.4 | Chemicals and apparatus
Melting points are uncorrected. The NMR spectra were
recorded with a Bruker 300 MHz spectrometer instru-
ment in DMSO. The chemical shifts (δ) were measured
in ppm. Mass spectra were recorded on an Agilent LC–
MS spectrometer (pump quaternary 1200 Series, quadru-
ple MSD 6110). LC column into multimode (ESI + APCI)
ion source of MSD. Thin layer chromatography (TLC)
was performed on Merck silica gel GF254 plates and visu-
alized by UV‐light (254 nm) and all chemical were pur-
chased from Sigma‐Aldrich.
Presented work aims to introduce V O (transition
2
5
metal oxide) based quadruple nano‐perovskite as a new
catalyst for the synthesis of bis and tetrakis heterocyclic
compounds.
2
2
| EXPERIMENTAL
.1 | Catalyst preparation
Strontium titanate SrTiO nano‐powders have been suc-
3
cessfully prepared through a pre‐calculated amount of
strontium carbonate and titanium dioxide supplied
2.2.5 | General procedure and structure
elucidation
(Sigma Aldrich Co.). Thermal combustion route was
employed for perovskite material preparation at 1100 °C
for 6 hr. After synthesis, the prepared material was fully
characterized. 10 wt% of V O were added to perovskite
The reaction was started by mixing aldehyde (10 mmol)
and 4‐hydroxycumarin, indole or dimedone (20 and
40 mmol), the V O /perovskite (0.1 g 10 mol %) was
2
5
2 5
material suspended in 100 ml CHCl . The mixture was
added and the mixture was allowed to stir at 50 °C. The
reaction was monitored by TLC tells reaction completion.
Ethyl acetate (20 ml) was added to the reaction mixture.
Then, the mixture was filtered off and the extract was
vaporized then the residue was recrystallized to give the
pure product.
3
vigorously stirred at room temperature for 2 hr. The final
solution was kept in a closed oven at 40 °C until all sol-
vent residuals were evaporated.
2
.2 | Catalyst characterization
.2.1 | X‐ray diffraction
Example for spectral data:
2
3,3′‐
(benzo
[d][1,3]dioxol‐5‐ylmethylene)bis(4‐
hydroxy‐2H‐chromen‐2‐one) (3f)
−
1
1
X‐ray diffraction scans (XRD) recorded using
PANalyticalXPert PRO XRD system occupied with copper
Kα radiation (λ = 1.540 Å) with a tube operating voltage
of about 30 kV. All measurements were recorded within
Bragg angle (2θ) (5°‐70°).
Mp. = 262 °C; IR (cm , KBr): 3031, 1663; H NMR
(CDCl ; 300 MHz): δ 3.6 (2H, s, O–CH –O), 5.8 (1H, s,
3
2
13
CH) and 7.6–8.5 (11H, m,Ar ‐H); C NMR (CDCl3,
75 MHz): δ 152.4, 147.8, 144.6, 133.7, 132.3, 124.8, 124.2,
119.7, 117.3, 115.9, 107.6, 107.6, 104.2, 100.9 and 53.8;

KHATAB ET AL.
3 of 8
analysis: calcd. For C H O , C, 68.42; H, 3.53. Found: C,
32.88, 50.24, 111.47, 125.46, 127.56, 127.63, 147.15,
149.32, 194.36. Anal. Calcd for C H O : C, 78.83; H,
26
16 8
6
8.56; H, 3.71.
23
26 3
7.48; O, 13.70; Found: C, 78.92; H, 7.59.
3
,3′‐(3‐chloro‐3‐(4‐chlorophenyl)prop‐2‐ene‐1,1‐diyl)
bis(4‐hydroxy‐2H‐chromen‐2‐one) (3j)
Mp. = 234 °C; IR (cm , KBr): 2934, 1711, 1627; H NMR
1,4‐bis(3,3,6,6‐Tetramethyl‐1,8‐dioxo‐2,3,4,5,6,7‐
hexahydroxanthene‐9‐yl)benzene. (7j)
−
1
1
−
1
(
CDCl ; 400 MHz): δ 3.5(brs,1H, OH), 5.1(d,1H, CH), 6.01
M.p. >300 °C; IR (KBr, cm ) ν max = 2957, 2872, 1667,
3
−
1 1
(d, 1H, =CH), 7.37 (t, 2H, ArH), 7.46–7.53 (m, 4H, Ar ‐H),
1624 cm ; H NMR (400 MHz, CDC1 ): δ = 0.99 (s, 12H,
3
7
.62(t, 1H, ArH), 7.7 2(t, 1H, ArH), 7.88(d, 2H, ArH),
4 CH ), 1.09 (s, 12H, 4 CH ), 2.20 (s, 8H, 4CH ), 2.39 (dd,
3
3
2
8
.00(d, 1H, ArH), 8.13(d, 1H, ArH), 11,92 (brs, 1H, OH);
8H, 4CH ), 4.73 (s, 2H, CH), 7.10 (s, 4H, ArH). Anal.
2
1
3
C NMR (CDCl , 75 MHz): δ 160.9, 156.2,152.68,
calcd. For C H O : C, 77.14; H, 7.44. Found: C, 77.28;
3
40 46 6
1
1
52.45, 146.46 134, 132.92, 132.69, 131.47, 129.18,
26.55, 125.09,124.37, 123.2, 116.7, 114.3 and 101.5; anal-
H, 7.26.
ysis: calcd. For: C H16C O , C, 63.92; H, 3.18; Cl, 13.98;
27
l2 6
O, 18.92. Found: C, 63.5 2; H, 3.0 8; Cl, 13.5 8.
3
| RESULTS AND DISCUSSION
.1 | XRD experimental data
4
‐(bis(4‐hydroxy‐2‐oxo‐2H‐chromen‐3‐yl)methyl)
benzaldehyde (3 k)
3
−
1
Mp. = 175 °C; IR (cm , KBr): 3021, 2934, 2605,1667, 1611;
1
H NMR (CDCl ; 400 MHz): δ 6.04 (s, 1H, CH), 7.41 (m,
XRD pattern of both perovskite material and sample that
3
6
1
1
1
3
H, ArH), 7.6–6.85 (m, 6H, Ar ‐H), 9.91(s, 1H, CHO),
loaded with 10% V O5 were shown in (Figure 1).
2
13
2,92 (brs, 2H, 2OH); C NMR (CDCl , 75 MHz): δ
Obtained data was compared to that observed by different
authors and with that obtained from Joint Committee on
Powder Diffraction Standards (JCPDS) (JCPDS no. 84–
3
90.8, 162.8, 161.9, 150.2, 133.8, 128.3, 125.4, 123.2, 116.4,
04.3 and 36.2; analysis: calcd. For: C H O ,C,70.91; H,
26
16 7
.66; O, 25.43. Found: C, 70.56; H, 3.42.
0444) for cubic strontium titanate SrTiO and (JCPDS
3
no. 72–2041) tetragonal Sr TiO .
2
4
3
, 3′,3″,3″‐ (1,4‐phenylenebis (methanetriyl))tetrakis(4‐
Obtained data reveals the presence of crystalline sin-
hydroxy‐2H‐chromen‐2‐one (3 l)
gle phase of SrTiO with a sharp diffraction peaks at
25.75, 32.5, 39.94, 46.5, 57.7 and 67.8 attributed to (100),
(110), (111), (200), (211) and (220) diffraction planes of
3
−
1
1
Mp. = 272 °C; IR (cm , KBr): 3021, 2930, 1655, 1617; H
NMR (CDCl ; 400 MHz): δ 6.04 (s, 1H, CH), 7.11 (d, 4H,
3
13
ArH), 7.6–6.85 (m,16H, Ar ‐H), 11,92 (brs, 2H, 2OH);
C
cubic strontium titanate phase (SrTiO ) (JCPDS card no.
3
NMR (CDCl , 75 MHz): δ 162.82, 161.9 152.2, 141.8,
84–0444).
3
1
28.3, 125.8, 123.2, 116.7, 107.3 and 36.8; analysis: calcd.
The crystallite size of synthesized catalyst was calcu-
lated by X‐ray line broadening route according to the
well‐known Scherrer formula:
For: C H O ,C,70.78; H, 3.51; O, 25.71. Found: C,
44
26 12
7
8.56; H, 3.31.
1
,4‐bis (di(1H‐indol‐3‐yl)methyl) benzene (5j)
1
Mp.183–184 °C; H NMR (400 MHz, CDCl ) 7.38–7.35 (m,
3
8
H, ArH), 7.25–7.21 (m, 8H, ArH), 7.14 (d, 4H, ArH), 7.01
13
(d, 4H, ArH), 6.25–6.23 (m, 4H, ArH), 5.75 (s, 2H).
C
NMR (75 MHz, CDCl ) 141.6, 136.7, 128.6, 127.1, 123.6,
3
1
21.8, 120.0, 119.7, 119.0, 111.1, 39.9. Anal. calcd for
C H N C, 84.78; H, 5.34; N, 9.89; found, C, 84.9 8; H,
40
30 4
5
.1 4; N, 9.6 9.
3
,4,6,7‐tetrahydro‐3,3,6,6‐tetramethyl‐9‐phenyl‐2H‐xan-
thene‐1,8(5H,9H)‐dione (7a)
M. P.: 203–204 °C; IR (KBr, Cm ) ν max = 2950, 1660,
−
1
1
1
(
2
(
648, 1360, 1200, 1162, 1141, 998, 694. H NMR
300 MHz, DMSO‐d6): δ: 0.90 (s, 6H), 1.04 (s, 6H), 2.07–
.10 (d, 2H), 2.25–2.28 (d, 2H), 2.51–2.60 (m, 3H), 4.53
s, 1H), 7.09–7.12 (t, 1H), 7.17–7.18 (d, 1H), 7.20–7.23 (t,
FIGURE 1 XRD pattern of both perovskite material and sample
that loaded with 10% V O
2 5
13
3
H). C NMR (DMSO, 75 MHz), δ: 26.45, 29.13, 32.14,

4
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KHATAB ET AL.
k λ
β cos θ
3.3 | Scanning electron microscope (SEM)
DXRD ¼
Scanning electron microscopy measurements supported
with mapping analysis (Figure 3) were performed to
investigate distribution, the actual percentage of the cata-
lyst constituent along with their morphology.
Analysed EDAX data (Figure 4) support the idea of
presence small unavoidable traces of carbonate partner
in combination with other constituents and their respec-
tive ratios comparable to the starting materials with vari-
ation about ±0.6%. analysed data and net weights are
presented in Table 1.
Where λ is the X‐ray wavelength, k is the constant
usually equal to 0.9), θ is the diffraction angle and β is
the full width at half maximum (FWHM) in radian. It
was observed that the calculated crystallite size of pure
synthesized perovskite material ranged between
(
5
5:60 nm which increased to 50:65 nm in case of perov-
skite material loaded with vanadium pentoxide.
3.2 | Fourier transforms infrared (FTIR)
spectra
3.4 | Transmission electron microscope
(
TEM)
FTIR normalized absorption spectra for the prepared cat-
alyst. Obtained spectra reveal the presence of a prominent
Transmission electron micrographs with diffraction pat-
tern Figure (5) shows the formation of crystalline cubic
structure with the nearly the same dimension previously
obtained using X‐ray diffraction.
−
1
intensified peak at about 487 cm attributed to the Ti‐O
−
1
stretching vibrations. The band at 658, 936 cm attrib-
uted to Ti‐O bending and O‐Ti‐O stretching vibration
−
1
respectively. A very small absorption band at 1441 cm
can be assigned to C=O vibration arisen from extremely
small unavoidable traces of carbonate (Figure 2).
3.5 | Organic synthesis
Heterogeneous catalytic reactions for design and synthe-
sis of heterocyclic compounds play an important role in
[
18–20]
our group,
and so, this work was presented. The
reaction started by optimization step to measure the effi-
ciency of the prepared catalyst in organic synthesis espe-
cially in the preparation of polynuclear organic moieties
and after the data obtained from this step we found that
the best reaction condition as follows: The reaction is
started by mixing two moles of 4‐hydroxycoumarin and
one mole of benzaldehyde in the presence of V O /perov-
2
5
skite (NPs) at 60–70 °C under dry condition Scheme 1
and on the way to prove the effectiveness of the synthe-
sized catalyst we make comparable series of the same
reaction and change the type of catalyst as perovskite,
V O , and V O /perovskite respectively in the reaction
2
5
2 5
FIGURE 2 Collective FTIR spectra
between 4‐hydroxycoumarin and benzaldehyde. The
FIGURE 3 (a) Magnified SEM image (b) mapping analysis

KHATAB ET AL.
5 of 8
FIGURE 4 EDAX analysis of prepared catalyst
TABLE 1 EDAX data for the studied sample
The obtained results encouraged us to explore the effi-
cacy of this procedure for the synthesis of various bis or
tetrakis coumarin. The results are shortened in (scheme 2
and Table 2).
Element Weight % Atomic % Net Int. Net Int. Error
C
19.09
3.48
27.26
0.68
34.60
38.00
20.46
96.30
0.00
0.02
0.03
0.01
0.02
0.00
Sr
Ti
V
This type of electrophilic substitution expanded by the
reaction of 2 or 4 moles of indole with various aldehydes to
obtain bis or tetrakis indolylmethanes. The reaction condi-
tion also proceeded smoothly under solventless conditions
using the prepared catalyst V O /perovskite at 60‐70 °C.
9.77
30.5
5.40
1.82
O
62.26
66.75
2
5
The results are shortened in (Scheme 3 and Table 3).
In continuation to explore the efficacy of our prepared
catalyst in the synthesis of polynuclear organic moieties
the xanthenes and bisxanthenes were prepared by mixing
2
or 4 moles of dimedone and various aldehydes in the
presence of catalytic amount of the prepared catalyst
under solventless conditions at 60‐70 °C. The results are
shortened in (Scheme 4 and Table 4).
The data in the Table 2, 3 and 4 showed that generally
the efficacy of electrophilic attack reaction from carbonyl
group of aldehydes at coumarin, indole and dimedone
affected as follows: The inductive effect of electron with-
drawing group makes activation for the aldehydic car-
bonyl group and plays a positive rule in decreasing the
FIGURE 5 TEM show the quadrable structure of the prepared
NPs catalyst
reaction time like in (OMe, Br, Cl, CN, NO ). The structure
2
elucidation of bis and tetrakis of coumarin, indole and
xanthene derivatives as a targeted product were allocated
on the basis of reported melting point and spectral analy-
1
3
ses. Figure 6 introduce an exemplified chart of C for 3j.
The suggested mechanism for the V O /perovskite
2
5
catalysed synthesis of bis and tetrakis of coumarin,
indole and xanthene derivatives (II) was discussed in
SCHEME 1 Synthesis of biscoumarins
(
Scheme 5). The aldehydic carbonyl group was activated
observed reaction yields percent were found as traces, 70,
by the prepared catalyst and this facile the nucleophilic
attack by β‐vinylic position. After that, dehydration
occurs to forms the intermediate (I) that was activated
9
7
0% respectively after 20 to 60 minutes stirring at 60‐
0 °C under solvent‐free conditions.

6
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KHATAB ET AL.
SCHEME 2 Synthesis of various
biscoumarins and tetrakiscoumarins
TABLE 2 Synthesis of various bis and tetrakis coumarins
Entry
Ar
Products
Time (min)
Yield ℅
M.p. (found, lit.)
[
21]
1
2
3
4
5
6
7
8
9
benzaldehyde
3a
3b
3c
3d
3e
3f
20
25
25
25
20
25
20
25
20
30
45
60
90
90
90
92
93
90
90
85
90
85
85
80
226, 228
[
21]
4‐Methoxybenzaldehyde
4‐Bromobenzaldehyde
244, 242–244
[
[
22]
21]
267, 266
252, 252
4‐Chlorobenzaldehyde
[
22]
4‐hydroxybenzaldehyde
piperonal
222, 222–223
[
[
[
21]
21]
22]
262, 260
233, 232
268, 269
4‐Nitrobenzaldehyde
3g
3h
3i
4‐Methylbenzaldehyde
[
21]
Thiophene‐2‐carboxaldehyde
3‐chloro‐3‐(4‐chlorophenyl) acrylaldehyde
Terphthalaldehyde
210, 210–212
234–236
10
11
12
3j
3k
3l
175–177
Terphthalaldehyde +4 moles of hydroxycoumarin
272–274
SCHEME 3 Synthesis of various
bisindoles and tetrakisindoles
TABLE 3 Synthesis of bis and tetrakis indoles
Entry
Ar
Product
Time (min)
Yield %
Mp (°C)
Lit. mp (°C)
[
[
[
[
[
[
[
[
[
[
19]
19]
23]
23]
19]
19]
23]
23]
23]
24]
1
2
3
4
5
6
7
8
9
Benzaldehyde
5a
5b
5c
5d
5e
5f
35
33
27
35
25
25
30
28
30
40
93
92
90
90
95
90
90
91
89
85
123–125
191–193
121–122
186–188
220–222
110–112
187–188
138–139
155–156
185
124–125
190–192
120–122
187–188
220–222
110–112
188–190
136–138
154–156
183–184
4‐Methoxybenzaldehyde
4‐Chlorobenzaldehyde
4‐Methylbenzaldehyde
4‐Nitrobenzaldehyde
4‐Bromobenzaldehyde
2,4Dimethoxybenzaldehyde
3,5‐Dimethoxybenzaldehyde
3,4‐Dichlorobenzaldehyde
Terphthaldehyde
5g
5h
5i
1
0
5j

KHATAB ET AL.
7 of 8
SCHEME 4 Synthesis of various
xanthenes and bisxanthenes
TABLE 4 Synthesis of xanthenes and bisxanthenes
Entry
Aldehyde
Product
Time (min.)
Yield %
Mp. (°C)
Lit. Mp. (°C)
[
25]
1
2
3
4
5
6
7
8
9
Benzaldehyde
7a
7b
7c
7d
7e
7f
40
35
30
35
25
25
30
30
30
35
90
90
92
88
95
95
90
92
85
85
203–204
240–242
230–232
216–218
226–227
230
205
[
[
[
[
[
[
[
[
26]
26]
26]
25]
26]
26]
25]
25]
4‐Methoxybenzaldehyde
4‐Chlorobenzaldehyde
4‐Methylbenzaldehyde
4‐Nitrobenzaldehyde
4‐Bromobenzaldehyde
2,4‐Dimethoxybenzaldehyde
3,4,5‐Trimethoxybenzaldehyde
4‐cyanobenzaldehyde
Terphthaldehyde
238–240
230–232
215–217
225–226
232–234
206–208
198–200
214–216
7g
7h
7i
205–206
200
215
[
27]
1
0
7j
>300
>300
FIGURE 6 NMR chart of 3j

8
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KHATAB ET AL.
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[
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[
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[
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| CONCLUSIONS
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2
5
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cient application for this new catalyst the bis and tetrakis
of coumarin, indole, and xanthene derivatives were pre-
pared by a facile, clear and easy separated reaction. Com-
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excellent yield under mild reaction condition, also, this
protocol has features that are environmentally friendly,
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