Ag2Cr2O7 nanoparticles: An eco-friendly and reusable catalyst for synthesis of pyrano[c]chromenediones and [1,3]dioxolo[g]chromeneones in aqueous media at ambient temperature

Article abstract of DOI:10.1002/jccs.201900488

An efficient and green protocol for the synthesis of 4-aryl-3,4-dihydro-2H,5H-pyrano[3,2-c]chromene-2,5-diones and 8-aryl-7,8-dihydro-6H-[1,3]dioxolo[4,5-g]chromene-6-ones through the Ag₂Cr₂O₇ nanoparticles catalyzed cyclo

Full text of DOI:10.1002/jccs.201900488

Received: 12 December 2019
DOI: 10.1002/jccs.201900488
Revised: 27 February 2020
Accepted: 16 April 2020
A R T I C L E
Ag2Cr2O7 nanoparticles: An eco-friendly and reusable
catalyst for synthesis of pyrano[c]chromenediones and [1,3]
dioxolo[g]chromeneones in aqueous media at ambient
temperature
Mitra Ebrahimi | Shahrzad Abdolmohammadi
| Reza Kia-Kojoori
Department of Chemistry, Islamic Azad
Abstract
University, Tehran, Iran
An efficient and green protocol for the synthesis of 4-aryl-3,4-dihydro-2H,5H-
pyrano[3,2-c]chromene-2,5-diones and 8-aryl-7,8-dihydro-6H-[1,3]dioxolo
[4,5-g]chromene-6-ones through the Ag2Cr2O7 nanoparticles catalyzed
cyclocondensation reaction of active methylene compounds including
4-hydroxycoumarin or 3,4-methylenedioxyphenol, aromatic aldehydes, and
meldrum's acid in water at ambient temperature was described. This method
demonstrates several advantages compared with methods that are currently
employed such as a mild reaction conditions, simple work-up, good to excel-
lent yields, avoiding toxic catalyst and hazardous solvent, and recovery and
reuse of the catalyst.
Correspondence
Shahrzad Abdolmohammadi, Department
of Chemistry, East Tehran Branch,
Islamic Azad University, P.O. Box
18735-138, Tehran, Iran.
Email: s.abdolmohamadi@yahoo.com, s.
abdolmohamadi@iauet.ac.ir
Funding information
Islamic Azad University
K E Y W O R D S
[1,3]dioxolo[g]chromeneones, aqueous media, environmentally benign procedure, pyrano[c]
chromenediones, recyclability of catalyst, silver(I) dichromate (Ag2Cr2O7 NPs)
1 | INTRODUCTION
acronycine (lung, colon and ovary cancer),[24] and seselin
(skin cancer)[25] (Figure 1).
The chromene ring system is presumably the most well-
known heterocycle, a common and significant core struc-
ture in a variety of natural and nonnatural pharmacologi-
cal agents.[1] Interest on the discover of new procedures
for the synthesis of chromene derivatives has been con-
tinously increasing as they possess important biological
properties such as antioxidant,[2,3] antibacterial,[4–6]
antimicrobial,[7–9] antiviral,[10] antifungal,[11] anti-
inflammatory,[12] anticancer,[13–17] hypotensive,[18] local
anesthetic, antiarrhythmic,[19] and cognitive enhancing
activity.[20] Several examples which exhibit anticancer
activity and are mainly found in natural products (iso-
lated from plants) include tephrosin (lung cancer),[21]
calanone (leukemia and cervical carcinoma)[22,23]
Recently, considerable attention has been paid to
develop the utilities of nanoscale metal salts as catalysts
in organic reactions because they have been found to
influence the chemical and physical properties of the
bulk material.[26–33] The diverse silver nanostructure salts
are extensively applied in different fields.[34] However,
there is no report on the application of silver(I) dichro-
mate (Ag2Cr2O7 NPs) as catalyst in any organic synthesis.
These facts encouraged us to investigate and evaluate the
catalytic ability of Ag2Cr2O7 NPs as a new efficient het-
erogeneous catalyst for either exclusive synthesis of
the pyrano[c]chromenedione and [1,3]dioxolo[g]chro-
meneone derivatives. According to the literature survey,
several procedures have been reported to catalyze the
© 2020 The Chemical Society Located in Taipei & Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
J Chin Chem Soc. 2020;1–8.
http://www.jccs.wiley-vch.de
1

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EBRAHIMI ET AL.
SCHEME 1 Synthesis of pyrano[c]chromenedione and [1,3]
dioxolo[g]chromeneone derivatives
FIGURE 1 Representative of naturally chromene-containing
compounds with anticancer activity
formation of these compounds, some of them include the
use of catalysts such as proline,[35] CeCl3.7H2O,[36] basic
alumina,[37] CuI NPs.[38] While most of these catalysts
are helpful to construct the products in good yields, but
these methods, unfortunately, have certain limitations
such as long reaction times, harsh reaction conditions,
and utilization of hazardous chemicals.
With this background in mind, and in continuation of
our earlier efforts to develop new facile and efficient
routes in heterocyclic synthesis,[39] herein we would like
to report an efficient and simple approach to synthesize
4-aryl-3,4-dihydro-2H,5H-pyrano[3,2-c]chromene-
FIGURE 2 SEM images of the Ag2Cr2O7 NPs
As revealed in Figure 2, the SEM image of the synthe-
sized Ag2Cr2O7 NPs confirmed the formation of bundles
nanorod-shaped nanoparticles with the average particle
size of about 40 nm.
2,5-diones 5 and 8-aryl-7,8-dihydro-6H-[1,3]dioxolo[4,5-g]
chromene-6-ones
cyclocondensation reaction of active methylene com-
pounds including 4-hydroxycoumarin or
6 via an environmentally benign
1
The EDS spectra of the synthesized Ag2Cr2O7 NPs, is
given in Figure 3. As shown in Figure, the presence of
Ag, Cr, and S as the main elemental components is
observed. The appearance of sulfur element in this spec-
trum is due to the SDS adsorbed on the nanoparticles.
Figure 4 shows the FTIR spectrum of the synthesized
Ag2Cr2O7 NPs. The characterization peak at 886 cm−1
can be attributed to the Cr O stretching vibrations. The
broad peak at 3,436 cm−1 is also corresponded to the
O H stretching vibrations of water molecules adsorbed
on the surface of Ag2Cr2O7 NPs. The very weak peaks at
2,928, 2,853, and 1,092 cm−1 are due to the C H and
S O stretching bonds of SDS.
3,4-methylenedioxyphenol 2, aromatic aldehydes 3, and
meldrum's acid 4 using Ag2Cr2O7 NPs as a new, efficient,
and recyclable heterogeneous catalyst in water at ambi-
ent temperature (Scheme 1).
2 | RESULTS AND DISCUSSION
The preliminary effort has been made to prepare the
Ag2Cr2O7 NPs catalyst according to a simple precipitation
route reported by Salavati-Niasari et al.[40] The
nanostructures of the synthesized Ag2Cr2O7 NPs were
characterized by scanning electron microscopy (SEM),
energy-dispersive X-Ray spectroscopy (EDS), Fourier
transform infrared (FT-IR) spectroscopy, and X-Ray dif-
fraction (XRD) analysis.
As can be seen in the XRD pattern of the synthesized
Ag2Cr2O7 NPs (Figure 5), all the obtained diffraction
peaks corresponded to the Ag2Cr2O7 NPs, which can be
readily supported by JCPDS file No. 01-0963.

EBRAHIMI ET AL.
3
SCHEME 2 Synthesis of 5c from the reaction of
4-hydroxycoumarin, 4-chlorobenzaldehyde, and meldrum's acid
under various reaction conditions
amounts of the Ag2Cr2O7 NPs as catalyst were tried in
water at ambient temperature. It was observed that 10 mol
% of catalyst is sufficient for this conversion (Table 1, entries
2–4). Next, the influence of the temperature was tested, and
it was apparent that using 10 mol% of catalyst and under
refluxing gave the same yield of the desired product in
shorter reaction time (Table 1, entries 3 and 5). The replace-
ment of water with other organic solvents such as EtOH,
CH3CN, CH2Cl2, and DMF in the model reaction led to
moderate conversions of the particular reactants (Table 1,
entries 3 and 6–9).
FIGURE 3 EDS analysis of the Ag2Cr2O7 NPs
In order to determine the scope and limitation of this
reaction, various substituted aromatic aldehydes were
conducted with meldrum's acid and 4-hydroxycoumarin
or
3,4-methylenedioxyphenol,
to
obtain
the
corresponding products 4a–g and 6a–g in high yields
under optimized conditions (Table 2). Because of the vol-
atile nature of many aliphatic aldehydes and also lower
activity of those compared to aromatic ones, we used only
aromatic aldehydes for mentioned reaction. However, ali-
phatic aldehydes gave only trace yields of products
on TLC.
FIGURE 4 FTIR spectrum of the Ag2Cr2O7 NPs
The reusability of the Ag2Cr2O7 NPs as catalyst was
then investigated for the synthesis of 5c under the opti-
mized reaction conditions. The recovered catalyst was
able to recycle five times without significant loss of activ-
ity (Figure 6). It should be noted that a slight weight loss
of catalyst was also detected during recycling process.
Although the reaction occurred at ambient temperature,
it may be related to the slow decomposition of Ag2Cr2O7
in water.
FIGURE 5 XRD spectra of the Ag2Cr2O7 NPs
A proposed reaction mechanism for the formation of
pyrano[c]chromenediones 5 through Ag2Cr2O7 NP-catalyzed
cyclocondensation reaction of 4-hydroxycoumarin, aromatic
aldehydes, and meldrum's acid is illustrated in Scheme 3.
Ag2Cr2O7 NPs play the role of bifunctional Lewis acid-Lewis
base catalyst for the formation of alkene 8, readily prepared
in situ from Knoevenagel condensation of Meldrum's
acid 4 and aromatic aldehyde 3, which proceed via
intermediate 7. Then, 4-hydroxycoumarin adds to
To select the optimization reaction conditions, a typical
reaction of 4-hydroxycoumarin (1), 4-chlorobenzaldehyde
(3c), and meldrum's acid (4) was examined for the synthesis
of compound 5c under various reaction conditions
(Scheme 2 and Table 1). Performing the reaction without
any catalyst under refluxing in water, gave only 67% of
product 5c after 5 hr (Table 1, entry 1). Then, different

4
EBRAHIMI ET AL.
TABLE 1
Synthesis of
Entry
Nanocatalyst (mol%)
None
Solvent
H2O
Temp. (ꢀC)
Time (hr)
Yield (%)a
4-(4-chlorophenyl)-3,4-dihydro-2H,5H-
pyrano[3,2-c]chromene-2,5-dione 5c
under different conditions
1
2
3
4
5
6
7
8
9
Reflux
r.t.
5
67
88
95
94
95
73
66
48
78
Ag2Cr2O7 (5 mol%)
Ag2Cr2O7 (10 mol%)
Ag2Cr2O7 (15 mol%)
Ag2Cr2O7 (10 mol%)
Ag2Cr2O7 (10 mol%)
Ag2Cr2O7 (10 mol%)
Ag2Cr2O7 (10 mol%)
Ag2Cr2O7 (10 mol%)
H2O
3
H2O
r.t.
2
H2O
r.t.
2
H2O
Reflux
r.t.
1
EtOH
CH3CN
CH2Cl2
DMF
2.5
3
r.t.
r.t.
3
r.t.
2
aIsolated yield.
TABLE 2
Ag2Cr2O7 NPs catalyzed synthesis of pyrano[c]chromenedione and [1,3]dioxolo[g]chromeneone derivatives in water at
ambient temperature
M.p (ꢀC)
Active methylene
compounds
Product
5a
Ar
Time (hr)
Yield (%)a,b
Obsd.
Lit.
C6H5
1
1
1
1
1
1
1
2
2
2
2
2
2
2
2
2
2
2
2
2
2
2
3
3
3
3
3
3
98
97
95
98
95
95
96
96
96
97
97
93
94
95
168–170
210–212
196–197
207–209
146–147
193–194
181–183
130–132
162–164
200–202
208–210
128–129
155–157
139–141
169–171[35]
212–214[35]
197–199[35]
—
143–145[35]
192–195[35]
180–182[35]
133–134[36]
160–161[36]
205–2,061[36]
—
5b
2-Cl-C6H4
4-Cl-C6H4
4-OH-C6H4
4-OCH3-C6H4
2-CH3-C6H4
3-NO2-C6H4
C6H5
5c
5d
5e
5f
5g
6a
6b
2-Cl-C6H4
4-Cl-C6H4
4-OH-C6H4
4-OCH3-C6H4
2-CH3-C6H4
3-NO2-C6H4
6c
6d
6e
129–130[36]
6f
—
6g
142–143[36]
aIsolated yield.
bReaction conditions: A mixture of 4-hydroxycoumarin (1) or 3,4-methylenedioxyphenol (2) (1 mmol), an aromatic aldehyde 3 (1 mmol),
meldrum's acid (4, 1 mmol), and Ag2Cr2O7 NPs (43.2 mgr, 10 mol%) in H2O (3 ml) was sttring at room temperature for appropriate times.
alkene 8 in a Michael-type addition to give intermedi-
ate 9. The cyclization of 9 followed by elimination of
acetone generates product 5 after decarboxylation of
intermediate 10. The formation of [1,3]dioxolo[g]chro-
meneones 6 can be explained similarly.
3 | CONCLUSION
In this research, an efficient and green method for the
synthesis of pyrano[c]chromenediones and [1,3]dioxolo
[g]chromeneones using Ag2Cr2O7 NPs as an new efficient
and recyclable heterogeneous catalyst was developed.
Compared with previous methods,[35–38] this new
approach provides several advantages like higher yields,
avoiding toxic catalyst and hazardous solvent, recovery
and reuse of the catalyst, simple work-up, and treatment
under milder reaction conditions.
Confirmation of the structures of compounds 5(a–g)
1
and 6(a–g) were established with IR, H NMR and 13C
NMR spectroscopic data and also by elemental analyses.
Spectroscopic data have been given in general procedure
section. The synthesized catalyst was fully characterized
by SEM, EDS, FTIR, and XRD techniques.

EBRAHIMI ET AL.
5
using Cu Kα radiation (λ = 1.54 Å).The microscopic mor-
phology of the catalyst was revealed using scanning electron
microscope (SEM, Philips, XL-30) equipped with energy-
dispersive X-ray analysis system (EDS).
4.1 | General procedure for the
preparation of Ag2Cr2O7 NPs catalyst
The catalyst was prepared according to the literature
method.[40] To a magnetically stirred mixture of AgNO3
(2 mmol) in 40 ml of distilled water, a solution of sodium
salicylate (2 mmol) in an equal volume of distilled water
was added dropwise and the resulted mixture was contin-
ued to be stirred at 80ꢀC for about 30 min. Afterward, the
produced precursor silver(I) salicylate, [Ag(HSal)] as a
white precipitate was filtered and washed with distilled
water and ethanol several times to remove impurities. In
the next step, precursor silver(I) salicylate, [Ag(HSal)]
(4 mmol) and sodium dodecyl sulfate (SDS) (0.05 g) as
shape controller were dissolved in 50 ml of distilled water
and then, a previously prepared solution of (NH4)2Cr2O7
(2 mmol) in 20 ml of distilled water, was added dropwise
into the above mixture under strong magnetic stirring for
20 min. Subsequently, the obtained precipitate of
Ag2Cr2O7 NPs was vacuum-filtered, washed in ethanol,
and dried in a vacuum oven at 50ꢀC for about 20 hr.
FIGURE 6 Reusability of the Ag2Cr2O7 NPs as catalyst
toward synthesis of 5c
4.2 | General method for the preparation
of compounds 5a–g and 6a–g
A mixture of 4-hydroxycoumarin 1 or 3,4-methylene-
dioxyphenol 2 (1 mmol), arylaldehyde 3 (1 mmol), mel-
drum's acid (4, 1 mmol), and Ag2Cr2O7 NPs (43.2 mgr,
10 mol%) in H2O (3 ml) was magnetically stirred at room
temperature. After completion of the reaction (monitored by
TLC), the reaction mixture was filtered and the residue was
dissolved in hot ethanol (3 ml) and then centrifuged for
5 min at 2,000–3,000 rpm to recover the catalyst. The recov-
ered catalyst was washed three times with EtOH and then
dried in a vacuum oven at 50ꢀC for reuse. The pure product
was obtained by cooling the ethanol solution to room tem-
perature, diluted with 1 ml H2O, and allowed to crystallize.
SCHEME 3 The proposed mechanism
4 | EXPERIMENTAL
All of the chemical materials used in this work were pur-
chased from Merck and Fluka and used without further
purification. Melting points were determined on an Electro-
thermal 9,100 apparatus. IR spectra were obtained on a
Bruker, Equinox 55 FT-IR spectrometer. H NMR and 13C
4.3 | Selected spectroscopic data
1
NMR spectra were recorded on a Bruker DRX-500
AVANCE at 500 and 125 MHz, respectively, using TMS as
internal standard and DMSO-d6 as solvent. Elemental ana-
lyses were carried out on Foss-Heraeus CHN-O-rapid ana-
lyzer instruments. Powder X-ray diffraction data were
determined on a Rigaku D-max C III, X-ray Diffractometer
4.3.1 | 4-Phenyl-3,4-dihydro-2H,5H-
pyrano[3,2-c]chromene-2,5-dione (5a)
White powder, yield 0.293 g (98%), m. p. 168–170ꢀC (lit:
169–171ꢀC[35]). IR (KBr): νmax = 1,784, 1,702, 1,659,

6
EBRAHIMI ET AL.
1,087 cm−1
.
1H NMR (500 MHz, DMSO-d6): δ = 3.13
1,102 cm−1
.
1H NMR (500 MHz, DMSO-d6): δ = 3.10
(1 H, d, J = 16.1 Hz, H-3), 3.20 (1 H, d, J = 16.1 Hz, H-
30), 4.52 (1 H, s, H-4), 7.28 (3 H, m, HAr), 7.29 (1 H, d,
J = 7.0 Hz, HAr), 7.34 (1 H, d, J = 7.0 Hz, HAr), 7.39
(2 H, m, HAr), 7.61 (1 H, t, J = 7.2 Hz, HAr), 7.91 (1 H, d,
J = 7.4 Hz, HAr) ppm. 13C NMR (125 MHz, DMSO-d6):
δ = 36.8, 37.1, 105.6, 113.2, 116.9, 122.8, 126.3, 128.1,
128.8, 130.3, 133.2, 141.2, 154.1, 156.7, 160.1, 163.9 ppm.
Anal. calcd. for C18H12O4 (299.29): C 72.24, H 4.04;
found: C 72.19, H 4.12%.
(1 H, d, J = 16.0 Hz, H-3), 3.19 (1 H, d, J = 16.0, Hz H-
30), 3.71 (3 H, s, OCH3), 4.50 (1 H, s, H-4), 6.79 (2 H, d,
J = 8.4 Hz, HAr), 7.17 (2 H, d, J = 8.4 Hz, HAr), 7.37
(2 H, m, HAr), 7.69 (1 H, t, J = 8.0 Hz, HAr), 7.88 (1 H, d,
J = 8.1 Hz, HAr) ppm. 13C NMR (125 MHz, DMSO-d6):
δ = 34.8, 36.7, 56.1, 105.9, 114.1, 116.6, 117.5, 125.8,
127.8, 130.7, 132.8, 152.3, 156.2, 158.5, 159.1, 160.9,
164.1 ppm. Anal. calcd. for C19H14O5 (322.32): C 70.80, H
4.38; found: C 70.65, H 4.16%.
4.3.2 | 4-(2-Chlorophenyl)-3,4-dihydro-
2H,5H-pyrano[3,2-c]chromene-
2,5-dione (5b)
4.3.5 | 4-(3-Nitrophenyl)-3,4-dihydro-
2H,5H-pyrano[3,2-c]chromene-
2,5-dione (5g)
White powder, yield 0.317 g (97%), m. p. 210–212ꢀC (lit:
212–214ꢀC[35]). IR (KBr): νmax = 1,792, 1,701, 1,623,
White powder, yield 0.324 g (96%), m. p. 181–183ꢀC (lit:
180–182ꢀC[35]). IR (KBr): νmax = 1,781, 1,719, 1,645,
1
1,100 cm−1
.
1H NMR (500 MHz, DMSO-d6): δ = 3.12
1,506, 1,491, 1,119 cm−1. H NMR (500 MHz, DMSO-d6):
(1 H, d, J = 15.0 Hz, H-3), 3.18 (1 H, d, J = 15.0 Hz, H-
30), 4.59 (1 H, s, H-4), 6.95 (1 H, d, HAr, J = 8.5), 7.15
(1 H, t, J = 7.2, Hz HAr), 7.23 (1 H, t, J = 7.2 Hz, HAr),
7.43 (3 H, m, HAr), 7.66 (1 H, t, J = 7.9, Hz HAr), 7.95
(1H, d, J = 7.9, Hz HAr) ppm. 13C NMR (125 MHz,
DMSO-d6): δ = 33.5, 35.0, 104.8, 113.4, 117.1, 122.9,
124.7, 126.9, 127.6, 129.5, 130.7, 133.2, 133.5, 135.9, 153.5,
158.7, 160.3, 163.6 ppm. Anal. calcd. for C18H11ClO4
(326.73): C 66.17, H 3.39; found: C 65.90, H, 3.31%.
δ = 2.86 (1 H, d, H-3, J = 15.9 Hz), 3.44 (1 H, d, H-30,
J = 15.9 Hz), 4.27 (1 H, s, H-4), 6.52 (4 H, m, HAr), 7.04
(1 H, t, J = 7.5 Hz, HAr), 7.39 (2 H, m, HAr), 7.77 (1 H, d,
J = 7.4 Hz, HAr) ppm. 13C NMR (125 MHz, DMSO-d6):
δ = 36.1, 37.0, 107.1, 114.1, 115.4, 120.6, 121.0, 123.3,
125.8, 130.4, 131.1, 134.0, 142.3, 145.9, 153.5, 158.7, 161.0,
166.0 ppm. Anal. calcd. for C18H11NO6 (337.29): C 64.01,
H 3.29, N 4.15; found: C 63.89, H 3.14, N 4.23%.
4.3.6 | 8-Phenyl-7,8-dihydro-6H-[1,3]
dioxolo[4,5-g]chromene-6-one (6a)
4.3.3 | 4-(4-Hydroxyphenyl)-3,4-dihydro-
2H,5H-pyrano[3,2-c]chromene-
2,5-dione (5d)
White powder, yield 0.258 g (96%), m. p. 130–132 ꢀ C (lit:
133–134ꢀC[36]). IR (KBr): νmax = 2,995, 2,904, 2,856,
White powder, yield 0.302 g (98%), m. p. 207–209ꢀC. IR
1,716, 1,668, 1,554, 1,512, 1,370, 1,149 cm−1 1H NMR
.
1
(KBr): νmax = 3,499, 1,768, 1,716, 1,644, 1,115 cm−1. H
(500 MHz, DMSO-d6): 2.90 (1 H, d, J = 15.9 Hz, H-7,),
3.05 (1 H, d, J = 15.9 Hz, H-70), 4.25 (1 H, s, H-8), 5.93
(1 H, d, J = 1.2 Hz, H-2), 5.95 (1 H, d, J = 1.2 Hz, H-20),
6.40 (1H, s, HAr), 6.68 (1 H, s, HAr), 7.10–7.13 (2 H, m,
HAr), 7.23–7.30 (3 H, m, HAr) ppm. 13C NMR (125 MHz,
DMSO-d6): δ = 37.0, 40.1, 99.3, 101.6, 107.4, 117.5, 119.9,
128.4, 129.6, 140.4, 144.4, 145.6, 146.5, 167.3 ppm. Anal.
calcd. for C16H12O4 (268.27): C 71.64, H 4.51; found: C
71.59, H 4.32%.
NMR (500 MHz, DMSO-d6): δ = 2.96 (1 H, d, J = 15.6 Hz,
H-3), 3.48 (1 H, d, J = 15.6, Hz H-30), 4.36 (1 H, s, H-4), 6.75
(2 H, d, J = 6.8 Hz, HAr), 7.05 (2 H, d, J = 7.0 Hz, HAr),
7.46 (2 H, m, HAr), 7.70 (1 H, d, J = 6.6 Hz, HAr), 7.84
(1 H, d, HAr, J = 6.8 Hz), 9.45 (s, 1 H, OH) ppm. 13C NMR
(125 MHz, DMSO-d6): δ = 35.4, 37.3, 107.5, 114.2, 116.5,
116.6, 117.5, 123.3, 125.6, 131.0, 133.8, 153.4, 157.6, 157.7,
161.1, 166.1 ppm. Anal. calcd. for C18H12O5 (308.29): calcd.
C 70.13, H 3.92; found: C 70.27, H 4.08%.
4.3.7 | 8-(4-Chlorophenyl)-7,8-dihydro-
6H-[1,3]dioxolo[4,5-g]chromene-6-one (6c)
4.3.4 | 4-(4-Methoxyphenyl)-3,4-dihydro-
2H,5H-pyrano[3,2-c]chromene-
2,5-dione (5e)
White powder, yield 0.294 g (97%), m. p. 200–202ꢀC
(lit: 205–206ꢀC[36]). IR (KBr): νmax = 3,046, 2,916,
1
White powder, yield 0.306 g (95%), m. p. 146–147ꢀC (lit:
143–145ꢀC[35]). IR (KBr): νmax = 1,774, 1,705, 1,668,
2,882, 1,720, 1,673, 1,574, 1,519, 1,361, 1,152 cm−1. H
NMR (500 MHz, DMSO-d6): δ = 2.88 (1 H, d,

EBRAHIMI ET AL.
7
J = 16.0 Hz, H-7,), 3.04 (1 H, d, J = 16.0 Hz, H-70), 4.23
(1 H, s, H-8), 5.99 (1 H, d, J = 1.0 Hz, H-2), 5.97 (1 H,
d, J = 1.0 Hz, H-20), 6.41 (s, 1H, HAr), 6.66 (1 H, s,
HAr), 7.11 (2 H, d, J = 8.3 Hz, HAr), 7.36 (2 H, d,
J = 8.3 Hz, HAr) ppm. 13C NMR (125 MHz, DMSO-d6):
δ = 36.5, 39.8, 99.4, 101.2, 107.3, 116.5, 128.2, 129.0,
132.3, 139.4, 144.0, 146.1, 147.8, 167.7 ppm. Anal.
calcd. for C16H11ClO4 (302.72): C 63.48, H 3.66; found:
C 63.30, H 3.78%.
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4.3.8 | 8-(4-Hydroxyphenyl)-7,8-dihydro-
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4.3.9 | 8-(2-Methylphenyl)-7,8-dihydro-
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ACKNOWLEDGMENTS
We are grateful to the East Tehran Branch Islamic Azad
University Research Council for the financial support of
this work.
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ORCID
Shahrzad Abdolmohammadi https://orcid.org/0000-
0001-8187-9624
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SUPPORTING INFORMATION
Additional supporting information may be found online
in the Supporting Information section at the end of this
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