Efficient and highly selective production of 10,11-dihydrochromeno[4,3-b]chromene-6,8(7H,9H)-diones using a mesoporous silica-based nanocatalyst

Article abstract of DOI:10.1007/s11164-019-03913-1

Abstract: An efficient and highly selective protocol for the production of 10,11-dihydrochromeno[4,3-b]chromene-6,8(7H,9H)-dione derivatives has been developed. The one-pot multi-component condensation of arylaldehydes with 4-hydroxycoumarin and dimedone

Full text of DOI:10.1007/s11164-019-03913-1

Research on Chemical Intermediates
https://doi.org/10.1007/s11164-019-03913-1
Efcient and highly selective production of 10,11‑
dihydrochromeno[4,3‑b]chromene‑6,8(7H,9H)‑diones
using a mesoporous silica‑based nanocatalyst
Alireza Kohzadian1 · Abdolkarim Zare1
Received: 28 January 2019 / Accepted: 20 June 2019
© Springer Nature B.V. 2019
Abstract
An efcient and highly selective protocol for the production of 10,11-dihydrochromeno
[4,3-b]chromene-6,8(7H,9H)-dione derivatives has been developed. The one-pot
multi-component condensation of arylaldehydes with 4-hydroxycoumarin and dime-
done in the presence of a mesoporous acidic nanocatalyst, namely nano-N,N,N′,N′-
tetramethyl-N-(silica-n-propyl)-N′-sulfo-ethane-1,2-diaminium chloride (nano-
[TSPSED][Cl]2) selectively aforded the mentioned compounds in high yields and
in relatively short reaction times. The nanocatalyst was reusable for four times with-
out signifcant loss of activity. Our catalyst was better than the reported catalysts
in terms of three or more of these factors: the reaction temperatures, times, yields,
turnover number and turnover frequency.
Graphic abstract
EtOAc, Reflux
O
O
O
O
O
Ar
H
O
Ar
O
+
O
HO
Time = 180-240 min
Yield = 84 - 95%
O
C l
N
Me
Me
SO3H
Cl
N
O
O
O
The nanocatalyst
=
Si
Me
Me
Electronic supplementary material The online version of this article (https://doi.org/10.1007/s1116
4-019-03913-1) contains supplementary material, which is available to authorized users.
Extended author information available on the last page of the article
Vol.:(0123456789)
1 3

A. Kohzadian, A. Zare
Keywords 10,11-Dihydrochromeno[4,3-b]chromene-6,8(7H,9H)-dione · Multi-
component reaction · Mesoporous silica-based nanocatalyst · Nano-N,N,N′,N′-
tetramethyl-N-(silica-n-propyl)-N′-sulfo-ethane-1,2-diaminium chloride (nano-
[TSPSED][Cl]2) · 4-Hydroxycoumarin · Dimedone
Introduction
Nanocatalysis, as a vital part of “sustainable technology and organic transforma-
tions”, is an attractive, useful and growing research feld, and has been applied
in approximately all kinds of catalytic organic reactions [1–18]. In this process,
enhanced surface area of the active component of nanocatalyst increases the impact
between starting materials and catalyst, and consequently a nanocatalyst behaves as
a homogeneous catalyst; on the other hand, insolubility of nanocatalyst in reaction
media causes easy separation from the reaction mixture, and this behavior is like het-
erogeneous catalysts [1–18]. Thus, nanocatalysts have benefts of both homogeneous
and heterogeneous catalysts. Some types of nanocatalysts include organic nanopar-
ticles [6], graphene-based [7], core–shell [8, 9], nano mixed metal oxides [10], and
solid-supported [11–18] nanocatalysts. Among them, solid-supported nanocatalysts
(and particularly silica-base ones) have been broadly utilized in organic synthesis,
because of possessing various benefts such as simple functionalization, high activ-
ity, safety, non-corrosiveness, high selectivity, large surface area, suitable thermal
and chemical stability, low density, easy recyclability, tunability of nano-size, and
easy separation from the reaction media [11–18].
Multi-component reactions (MCRs), as an efcient protocol for preparation of com-
plex molecules, have attracted much attention in combinatorial, organic and medici-
nal chemistry. MCRs in which a heterocycle core produces, are of great interest, since
essential components of many drugs and biologically active compounds are heterocy-
clic scafolds. They are defned as reactions wherein three or more small-molecular-
weight building blocks are combined in one operation leading to a single product with
high selectivity and combinatorial efectuality. Additionally, MCRs save time, decrease
energy consuming, improve raw materials consumption, minimize or prevent synthesis
of waste/by-products, and reduce utilization of volatile organic solvents [19–23]. Thus,
the use of this technique has good compliance with green chemistry protocols, and its
application is easier and more economical compared with classical multi-step reactions.
Heterocyclic compounds bearing coumarin core are of importance, because they
have a variety of pharmaceutical and biological properties [24], including antimicro-
bial [25], antiallergic [26], antiasthmatic [27], antinociceptive [27], anti-HIV [28],
antioxidant [29], antitumor [30], antibacterial [31], antifungal [32], anticoagulant [33],
anti-infammatory [34], and antiviral [35] activities. On the other hand, a chromene
component is often a signifcant structural scafold of biologically active and natu-
ral molecules. This moiety exists in tocopherols, favonoids, alkaloids and anthocya-
nins; chromene derivatives have also played increasing roles in synthetic strategies for
favorable compounds in the feld of drug chemistry [36–40].
1 3

Efcient and highly selective production of…
Interestingly, 10,11-dihydrochromeno[4,3-b]chromene-6,8(7H,9H)-diones possess
both biologically important moieties, i.e., coumarin and chromene. Some catalysts have
been reported for the production of these compounds by the one-pot multi-component
reaction of arylaldehydes, 4-hydroxycoumarine and cyclic-1,3-dicarbonyl compounds;
e.g., Fe(DS)3 [36], Mg(ClO4)2 [41], 1,3-dimethyl-2-oxo-1,3-bis(4-sulfobutyl)imidazo-
lidine-1,3-diium hydrogen sulfate ([DMDBSI].2HSO4) [42], nano-silica sulfuric acid
(nano-SSA) [43], CuO nanoparticles [44], H3BO3 [45], I2/HOAc [46], 1-butyl-3-meth-
ylimidazolium hexafuorophosphate ([bmim][PF6]) [47], and p-toluene sulfonic acid (p-
TSA) [48]. Nevertheless, most of these methods sufer from at least one or more of the
following disadvantages: moderate yield, long reaction time, employing large amount
of catalyst, harsh reaction conditions and non-recyclability of catalyst. Moreover, the
reaction of arylaldehydes, 4-hydroxycoumarine and cyclic-1,3-dicarbonyl compounds,
leading to 10,11-dihydrochromeno[4,3-b]chromene-6,8(7H,9H)-diones, has been
barely reported in the literature.
Bearing in mind the above topics, we report here our results on the efectual
and highly selective preparation of 10,11-dihydrochromeno[4,3-b]chromene-
6,8(7H,9H)-diones by the one-pot multi-component reaction of arylaldehydes with
4-hydroxycoumarin and dimedone (5,5-dimethylcyclohexane-1,3-dione) using
nano-N,N,N′,N′-tetramethyl-N-(silica-n-propyl)-N′-sulfo-ethane-1,2-diaminium
chloride (nano-[TSPSED][Cl]2) as a reusable mesoporous acidic nanocatalyst. It is
noteworthy that our protocol has none of the abovementioned drawbacks at all.
Experimental
Materials and apparatuses
All chemicals were purchased from Merck or Fluka Chemical Companies. All
known compounds were identifed by comparison of their melting points and/
or spectral data with those reported in the literature. The reactions progress was
monitored by thin-layer chromatography (TLC) on silica gel SIL G/UV 254
plates. Melting points were recorded on a Büchi B-545 apparatus in open capil-
1
lary tubes. H NMR (500 MHz) and 13C NMR (125 MHz) were run on a Bruker
Avance DPX, FT-NMR spectrometer. Mass spectra were obtained by Shimadzu
GC–MS-QP 1100 EX. The morphologies and particles sizes of samples were
characterized by feld emission scanning electron microscopy (FE-SEM), model
MIRA3TESCAN-XMU. A transmission electron microscope (TEM), model Zeiss
EM900, 80 keV, was used to measure the size and shape of particles.
Procedure for the production of nano‑[TSPSED][Cl]2
A mixture of N,N,N′,N′-tetramethylethane-1,2-diamine (0.58 g, 5 mmol), (3-chlo-
ropropyl) trimethoxysilane (0.99 g, 5 mmol) and toluene (15 mL) in a 50 mL
round-bottomed fask connected to a refux condenser, was stirred for 12 h under
1 3

A. Kohzadian, A. Zare
refux conditions; afterward, the solvent (toluene) was evaporated under vacuum
at 95 °C to give I. In the next step, I was reacted with nano-silica gel (0.30 g,
5 mmol) in refuxed EtOAc (15 mL) for 8 h; the formed precipitate was separated
by centrifuging and decanting, washed by EtOAc (2 × 5 mL), and dried under
vacuum at 80 °C to aford II. Subsequently, II was added gradually to a stirring
solution of chlorosulfonic acid (0.58 g, 5 mmol) in CH2Cl2 (10 mL) at 10 °C (in
an ice-bath), and stirred for 2 h at room temperature. The solvent was removed
by centrifuging and decanting, and the residue was triturated with dichlorometh-
ane (3 × 10 mL), and dried under vacuum at 80 °C to give nano-[TSPSED][Cl]2
as a pale yellow precipitate (Scheme 1) [14]. The catalytic species loading on
the silica surface was found to be 1.32 mmol/g [14]. The FE-SEM (feld emis-
sion scanning electron microscopy) and TEM (transmission electron microscopy)
micrographs of the nanocatalyst are shown in Figs. 1 and 2.
General procedure for the preparation of 10,11‑dihydrochromeno[4,3‑b]
chromene‑6,8(7H,9H)‑diones using nano‑[TSPSED][Cl]2
A mixture of 4-hydroxycoumarin (1 mmol), aromatic aldehyde (1 mmol), dimedone
(1 mmol) and nano-[TSPSED][Cl]2 (0.02 g, 2.64 mol%) was added to ethyl acetate
(2 mL), and the resulting mixture was refuxed. After completion of the reaction (as
monitored by TLC), and cooling the mixture to room temperature, EtOAc (30 mL)
was added, refuxed for 2 min, and the insoluble catalyst was separated by centrifu-
gation and decanting (the catalyst was washed by EtOAc (2×3 mL), dried and used
for next run). The EtOAc resulting from the decanting was evaporated, and the solid
residue was recrystallized from EtOH (95%) to aford the pure product.
Selected spectral data of the products
Product 1a FT-IR (KBr) νmax (cm−1): 1186 and 1364 (C–O stretching), 1489 and
1506 (C=C stretching, aromatic), 1605 (C=C stretching, aliphatic), 1665 (C=O
Cl
Toluene
Reflux,12h
NMe2
NMe2
+
Cl
Si(OMe)3
(MeO)3Si
N
Me Me
(I)
Me2N
Cl
O
ClSO3H
CH2Cl2
NMe2
Silica
EtOAc, Reflux, 8h
O
Si
N
Me Me
(II)
O
_
3MeOH
Cl
N
Me
Me
SO3H
Cl
O
O
O
Si
N
Me Me
(Nano-[TSPSED][Cl]2)
Scheme 1 The production of nano-[TSPSED][Cl]2
1 3

Efcient and highly selective production of…
Fig. 1 The FE-SEM image of
nano-[TSPSED][Cl]2
Fig. 2 The TEM micrograph of
nano-[TSPSED][Cl]2
stretching, ester), 1716 (C=O stretching, ketone), 2869 (C–H symmetric stretching,
aliphatic), 2933 (C–H asymmetric stretching, aliphatic), 3085 (C–H stretching, aro-
1
matic). H NMR (500 MHz, DMSO-d6) δ (ppm): 0.96 (3H, s, CH3), 1.07 (3H, s,
1 3

A. Kohzadian, A. Zare
CH3), 2.14 (1H, d, J=16.1 Hz, CH2-C=C), 2.31 (1H, d, J=16.1 Hz, CH2-C=C),
2.70–2.78 (2H, Distorted AB system, CH2-C=O), 4.67 (1H, s, methine CH), 7.13
(1H, t, J=6.8 Hz, HAr), 7.21–7.26 (4H, m, HAr), 7.43 (2H, q, J=8.4 Hz, HAr), 7.67
(1H, t, J=8.1 Hz, HAr), 7.91 (1H, d, J=7.8 Hz, HAr). 13C NMR (125 MHz; DMSO-
d6) δ (ppm): 27.3, 29.1, 32.6, 33.6, 47.4, 50.6, 106.4, 113.7, 114.4, 117.2, 123.3,
125.4, 127.4, 128.8, 129.0, 133.4, 143.4, 152.5, 154.3, 160.6, 163.3, 196.6.
Product 1c FT-IR (KBr) νmax (cm−1): 1174 and 1348 (symmetric and asym-
metric stretching of NO2), 1186 and 1363 (C–O stretching), 1455 and 1529 (C=C
stretching, aromatic), 1606 (C=C stretching, aliphatic), 1659 (C=O stretch-
ing, ester), 1721 (C=O stretching, ketone), 2868 (C–H symmetric stretching,
aliphatic), 2959 (C–H asymmetric stretching, aliphatic), 3065 (C–H stretching,
1
aromatic). H NMR (500 MHz CDCl3) δ (ppm): 0.92 (s, 3H, CH3), 1.01 (3H, s,
CH3), 2.08 (1H, d, J = 16.3 Hz, CH2-C=C), 2.18 (1H, d, J = 16.3 Hz, CH2-C=C),
2.55–2.65 (2H, Distorted AB system, CH2-C=O), 4.81 (1H, s, methine CH), 7.16
(1H, d, J = 8.2 Hz, HAr), 7.25 (1H, t, J = 7.8 Hz, HAr), 7.30 (1H, t, J = 7.9 Hz, HAr),
7.45–7.47 (1H, m, HAr), 7.60 (1H, d, J = 7.8 Hz, HAr), 7.76 (1H, d, J = 7.9 Hz,
HAr), 7.85 (1H, d, J = 8.2 Hz, HAr), 7.99 (1H, t, J = 1.9 Hz, HAr).
Product 1g FT-IR (KBr) νmax (cm−1): 1170 and 1353 (C–O stretching), 1489
and 1608 (C=C stretching, aromatic), 1623 (C=C stretching, aliphatic), 1663
(C=O stretching), 1725 (C=O stretching), 2867 (C–H symmetric stretching, ali-
phatic), 2922 (C–H asymmetric stretching, aliphatic), 3085 (C–H stretching aro-
1
matic). H NMR (500 MHz, DMSO-d6) δ (ppm): 0.95 (3H, s, CH3), 1.06 (3H, s,
CH3), 2.09 (1H, d, J = 16.1 Hz, CH2-C=C), 2.29 (1H, d, J = 16.1 Hz, CH2-C=C),
2.66–2.75 (2H, Distorted AB system, CH2-C=O), 5.01 (1H, s, methine CH), 7.06
(1H, t, J = 7.6 Hz, HAr), 7.23 (1H, t, J = 7.1 Hz, HAr), 7.28 (1H, d, J = 6.7 Hz, HAr),
7.39–7.47 (3H, m, HAr), 7.67 (1H, t, J = 8.3 Hz, HAr), 7.92 (1H, d, J = 7.9 Hz,
HAr); 13C NMR (125 MHz, DMSO-d6) δ (ppm): 27.2, 29.2, 32.4, 34.9, 47.3, 50.6,
104.2, 113.4, 117.1, 123.4, 125.3, 127.4, 128.1, 129.2, 133.5, 133.6, 138.2, 138.9,
140.0, 152.6, 154.6, 160.2, 163.4, 196.5. Mass m/z: 451 (M+), 452 (M+ + 1).
Results and discussion
For optimization of the reaction conditions, the reaction of 3-nitrobenzaldehyde
(1 mmol), 4-hydroxycoumarin (1 mmol) and dimedone (1 mmol) was selected as a
model reaction (Scheme 2), and infuence of various factors including solvent type,
solvent amount, and amount of nano-N,N,N′,N′-tetramethyl-N-(silica-n-propyl)-
N′-sulfo-ethane-1,2-diaminium chloride (nano-[TSPSED][Cl]2) on the reaction
was investigated; the results are briefed in Table 1. For choosing the best reaction
media, the reaction was examined in diferent amounts of solvents such as ethyl ace-
tate, ethanol, acetonitrile and acetone in refux conditions, and under solvent-free
conditions; the best results were obtained in 2 mL of ethyl acetate (Table 1, entry
2). Investigating the infuence of the catalyst amount showed that 0.02 g of nano-
[TSPSED][Cl]2 was the optimal catalyst loading for this reaction (Table 1, entry 2),
and higher catalyst loading could not improve the results. In another study, we tried
1 3

Efcient and highly selective production of…
CHO
O
O
O
OH
O
O
O
NO2
Nano-[TSPSED][Cl]2
Different conditions
+
+
O2N
O
O
Scheme 2 The model reaction
Table 1 Optimization of the reaction conditions on the reaction of 3-nitrobenzaldehyde (1 mmol),
4-hydroxycoumarin (1 mmol) and dimedone (1 mmol)
Entry
Solvent
Solvent
Temp. (°C)
The catalyst
amount (g)
Time (min)
Yielda (%)
amount (mL)
1
2
3
4
5
6
7
8
9
10
EtOAc
EtOAc
EtOAc
EtOH
EtOH
EtOH
MeCN
Acetone
–
1
2
3
2
2
3
3
3
–
–
Refux
Refux
Refux
Refux
Refux
Refux
Refux
Refux
80
0.01
0.02
0.03
0.01
0.02
0.03
0.03
0.03
0.03
0.03
180
180
180
240
240
180
180
180
45
79
94
92
37
61
90
47
40
56
68
–
100
45
aIsolated yield
to prepare the catalyst by modifcation of the sequences mentioned in Scheme 1.
For this purpose, at frst, nano-silica was reacted with (3-chloropropyl)trimethoxysi-
lane, and the obtained intermediate was treated with N,N,N′,N′-tetramethylethane-
1,2-diamine; fnally, the produced intermediate from the second step was reacted
by chlorosulfonic acid to give the catalyst. The reaction of 3-nitrobenzaldehyde
(1 mmol), 4-hydroxycoumarin (1 mmol) and dimedone (1 mmol) was examined
using this catalyst (0.02 g) in refuxed ethyl acetate (2 mL); in these conditions, the
desired product was obtained in 85% after 180 min. Thus, the method mentioned in
Scheme 1 was better than this method, for the synthesis of nano-[TSPSED][Cl]2.
After obtaining the optimum reaction conditions in terms of solvent type, sol-
vent amount and the catalyst amount, high efcacy, generality and selectiv-
ity of nano-[TSPSED][Cl]2 for this reaction were proved by examining the con-
densation of diverse arylaldehydes with 4-hydroxycoumarin and dimedone; the
acquired results are presented in Table 2. As the data of this Table specify, nano-
[TSPSED][Cl]2 was highly efective, general and selective; because all aldehydes
(i.e., aromatic aldehydes bearing electron-withdrawing, electron-releasing and
halogen substituents on ortho, meta or para positions) aforded the corresponding
1 3

A. Kohzadian, A. Zare
Table 2 The production of 10,11-dihydrochromeno[4,3-b]chromene-6,8(7H,9H)-diones using nano-
[TSPSED][Cl]2
OH
O
O
O
O
O
O
Nano-[TSPSED][Cl]2
EtOAc, Reflux
Ar
+
+
Ar
H
O
O
O
Comp. no.
Ar
Time (min)
Yielda (%)
M.p., °C
Found
Reported
1a
1b
1c
1d
1e
1g
1g
1h
1i
C6H5
240
240
180
240
240
240
240
240
240
240
240
95
88
94
91
84
89
90
86
92
89
92
223–225
233–235
240–243
200–202
186–188
249–251
227–229
233–235
229–231
248–250
247–249
220–222 [41]
235–240 [44]
240–245 [44]
202–205 [44]
188–190 [43]
250–252 [43]
–
233–235 [43]
230–232 [43]
250–252 [41]
248–250 [41]
2-O2NC6H4
3-O2NC6H4
4-O2NC6H4
4-MeOC6H4
4-FC6H4
2-BrC6H5
3-BrC6H5
2-ClC6H4
1j
2,4-Cl2C6H3
4-ClC6H4
1k
aIsolated yield
10,11-dihydrochromeno[4,3-b]chromene-6,8(7H,9H)-diones in high isolated yields
and in relatively short reaction times.
According to the literature, the possible products in the reaction of arylaldehydes
with 4-hydroxycoumarin and dimedone can be 10,11-dihydrochromeno[4,3-b]
chromene-6,8(7H,9H)-diones (1) [41–48], bis-coumarins (2) [49] and 9-aryl-1,8-di-
oxo-octahydroxanthenes (3) [50] (Scheme 3). Nano-[TSPSED][Cl]2 was highly
selective for the synthesis of 10,11-dihydrochromeno[4,3-b]chromene-6,8(7H,9H)-
diones; compounds 1a, 1c, 1g, 1i and 1j were obtained as almost sole products; how-
ever, one side-product (in trace yield) was produced beside the other compounds.
A plausible mechanism, considered by the literature [44, 46, 48], is
illustrated in Scheme 4. Nano-[TSPSED][Cl]2 catalyzes the synthesis of
10,11-dihydrochromeno[4,3-b]chromene-6,8(7H,9H)-diones by achieving two roles:
(1) activation of carbonyl groups to accept nucleophilic attack (steps 1, 3 and 4), and
(2) promoting removal of H2O molecule (steps 2 and 5); these roles are obviously
shown in Scheme 4.
1 3

Efcient and highly selective production of…
OH
O
O
O
O
O
O
Ar
+
+
+
Ar
H
O
O
O
(1)
O
Ar
O
Ar
OH
HO
+
O
(3)
O
O
O
(2)
O
Scheme 3 The possible products which can form by the reaction of arylaldehydes, 4-hydroxycoumarin
and dimedone
To demonstrate the merit of our catalyst with respect to the reported ones, these
catalysts were compared in terms of the reaction temperature, time, yield, turnover
number (TON) and turnover frequency (TOF), in the synthesis of compound 1c; this
comparison is displayed in Table 3. As it can be seen in this Table, nano-[TSPSED]
[Cl]2 was better than the other catalysts in terms of three or more of these factors:
the reaction temperature, time, yield, TON and TOF. Moreover, in our work, micro-
wave energy has not been used, and our protocol has none of the mentioned draw-
backs (in the introduction section) at all.
Recyclability of the nano-[TSPSED][Cl]2 was studied for the reaction of
3-nitrobenzaldehyde with 4-hydroxycoumarin and dimedone to prepare compound
1c. The nanocatalyst was recycled according to the procedure mentioned in the
experimental section. The catalyst was reusable for four times with negligible loss of
its activity (Fig. 3).
Conclusions
In summary, we have reported a new practical procedure for the synthesis of
10,11-dihydrochromeno[4,3-b]chromene-6,8(7H,9H)-dione derivatives via the
one-pot three-component condensation of diverse arylaldehydes with 4-hydroxy-
coumarin and dimedone using nano-[TSPSED][Cl]2. The advantages of the pre-
sented method are efciency, generality, high selectivity, high yields of the prod-
ucts, relatively short reaction times, ease of workup and purifcation procedures,
and usage of nanotechnology.
1 3

A. Kohzadian, A. Zare
OH
O
O
OH
O
H
O
Nanocatalyst
O
Ar Nanocatalyst
O
O
Step1
Ar
O
Ar
H
H
S
O
O
H
H
O
O
O
O
O
S
O
O
Ar
Ar
Nanocatalyst
_
H2O
O
O
O
Step2
O
O
OH
S
H
O
O
OH
O
O
O
Ar
Ar
Nanocatalyst
Step3
O
O
O
O
O
S
O
H
O
HO
O
O
H
O
O
O
Ar
Ar
Nanocatalyst
Step4
O
O
O
O
H
O
S
O
O
O
H
O
O
O
O
O
O
O
H
Ar
Ar
Ar
Step6
Step5
O
O
O
O
O
The product
Scheme 4 The proposed mechanism for the synthesis of 10,11-dihydrochromeno[4,3-b]chromene-
6,8(7H,9H)-diones using nano-[TSPSED][Cl]2
1 3

Efcient and highly selective production of…
1 3

A. Kohzadian, A. Zare
250
200
150
100
50
Time (min)
Yield (%)
220
200
180
180
180
94
94
91
90
88
0
Run 1
Run 2
Run 3
Run 4
Run 5
Fig. 3 The results of reusing nano-[TSPSED][Cl]2
Acknowledgements Financial support of this work by the Research Afair Ofce of Payame Noor Uni-
versity is gratefully acknowledged.
References
1. M. Kazemi, M. Ghobadi, Nanotechnol. Rev. 6, 549 (2017)
2. R.K. Sharma, R. Gaur, M. Yadav, A. Goswami, R. Zbořil, M.B. Gawande, Sci. Rep. 8, 1901 (2018)
3. V. Somjit, M.W.C. Man, A. Ouali, P. Sangtrirutnugul, V. Ervithayasuporn, ChemistrySelect 3, 753
(2018)
4. S.B. Singh, P.K. Tandon, J. Energy Chem. Eng. 2, 106 (2014)
5. T. Yang, L. Wei, L. Jing, J. Liang, X. Zhang, M. Tang, M.J. Monteiro, Y. Chen, Y. Wang, S. Gu, D.
Zhao, H. Yang, J. Liu, G.Q.M. Lu, Angew. Chem. Int. Ed. 56, 8459 (2017)
6. A.R. Moosavi-Zare, M.A. Zolfgol, V. Khakyzadeh, C. Böttcher, M.H. Beyzavi, A. Zare, A. Hasan-
inejad, R. Luque, J. Mater. Chem. A 2, 770 (2014)
7. C. Wang, D. Astruc, Prog. Mater Sci. 94, 306 (2018)
8. Z. Shahamat, F. Nemati, A. Elhampour, Res. Chem. Intermed. 44, 6649 (2018)
9. H. Veisi, A. Nikseresht, A. Rostami, S. Hemmati, Res. Chem. Intermed. 45, 507 (2019)
10. H. Huang, X. Wang, E. Tervoort, G. Zeng, T. Liu, X. Chen, A. Sologubenko, M. Niederberger, ACS
Nano 12, 2753 (2018)
11. V.N. Mahire, G.P. Patil, A.B. Deore, P.G. Chavan, H.D. Jirimali, P.P. Mahulikar, Res. Chem.
Intermed. 44, 5801 (2018)
12. A. Fihri, D. Cha, M. Bouhrara, N. Almana, V. Polshettiwar, Chemsuschem 5, 85 (2012)
13. A. Zare, M. Merajoddin, A.R. Moosavi-Zare, M. Zarei, M.H. Beyzavi, M.A. Zolfgol, Res. Chem.
Intermed. 42, 2365 (2016)
14. A. Zare, M. Sadeghi-Takallo, M. Karami, A. Kohzadian, Res. Chem. Intermed. 45, 2999 (2019)
15. Q. Li, T. Zhou, H. Yang, ACS Catal. 5, 2225 (2015)
16. L. Wei, S. Yan, H. Wang, H. Yang, NPG Asia Mater. 10, 899 (2018)
17. M. Rezaei, K. Amani, K. Darvishi, Catal. Commun. 91, 38 (2017)
18. M.A. Abarghooei, R. Mohebat, Z. Karimi-Jaberi, M.H. Mosslemin, Catal. Commun. 105, 59 (2018)
19. M.-M. Li, C.-S. Duan, Y.-Q. Yu, D.-Z. Xu, Dyes Pigm. 150, 202 (2018)
20. A.R. Bhat, R.S. Dongre, J. Taiwan Inst. Chem. Eng. 56, 191 (2015)
21. N. Irannejad-Gheshlaghchaei, A. Zare, S.S. Sajadikhah, A. Banaei, Res. Chem. Intermed. 44, 6253
(2018)
22. V. Estévez, M. Villacampa, J.C. Menéndez, Chem. Soc. Rev. 43, 4633 (2014)
23. H. Naeimi, A. Didar, J. Mol. Struct. 1137, 626 (2017)
1 3

Efcient and highly selective production of…
24. J. Neyts, E.D. Clercq, R. Singha, Y.H. Chang, A.R. Das, S.K. Chakraborty, S.C. Hong, S.-C. Tsay,
M.-H. Hsu, J.R. Hwu, J. Med. Chem. 52, 1486 (2009)
25. Z.H. Chohan, A.U. Shaikh, A. Rauf, C.T. Supuran, J. Enzyme Inhib. Med. Chem. 21, 741 (2006)
26. J. Yamahara, M. Kozuka, T. Sawada, H. Fujimura, K. Nakano, T. Tomimatsu, T. Nohara, Chem.
Pharm. Bull. 33, 1676 (1985)
27. P. Anand, B. Singh, N. Singh, Bioorg. Med. Chem. 20, 1175 (2012)
28. H. Zhao, N. Neamati, H. Hong, A. Mazumder, S. Wang, S. Sunder, G.W. Milne, Y. Pommier, T.R.
Burke, J. Med. Chem. 40, 242 (1997)
29. S. Stanchev, G. Momekov, F. Jensen, I. Manolov, Eur. J. Med. Chem. 43, 694 (2008)
30. M. Suzuki, K. Nakagawa-Goto, S. Nakamura, H. Tokuda, S.L. Morris-Natschke, M. Kozuka, H.
Nishino, K.-H. Lee, Pharm. Biol. 44, 178 (2006)
31. O. Kayser, H. Kolodziej, Z. Naturforsch. 54c, 169 (1999)
32. G. Yang, Q. Jin, C. Xu, S. Fan, C. Wang, P. Xie, Int. J. Biol. Macromol. 106, 179 (2018)
33. Y.L. Garazd, E. Kornienko, L. Maloshtan, M. Garazd, V. Khilya, Chem. Nat. Compd. 41, 508
(2005)
34. C.A. Kontogiorgis, D.J. Hadjipavlou-Litina, J. Med. Chem. 48, 6400 (2005)
35. J.R. Hwu, R. Singha, S.C. Hong, Y.H. Chang, A.R. Das, I. Vliegen, E. De Clercq, J. Neyts, Antivir.
Res. 77, 157 (2008)
36. K. Pradhan, S. Paul, A.R. Das, Tetrahedron Lett. 54, 3105 (2013)
37. M.N. Elinson, A.S. Dorofeev, S.K. Feducovich, S.V. Gorbunov, R.F. Nasybullin, N.O. Stepanov,
G.I. Nikishin, Tetrahedron Lett. 47, 7629 (2006)
38. W. Sun, L.D. Cama, E.T. Birzin, S. Warrier, L. Locco, R. Mosley, M.L. Hammond, S.P. Rohrer,
Bioorg. Med. Vhem. Lett. 16, 1468 (2006)
39. A.V. Stachulski, N.G. Berry, A.L. Low, S.L. Moores, E. Row, D.C. Warhurst, I.S. Adagu, J.-F. Ros-
signol, J. Med. Chem. 49, 1450 (2006)
40. J.-P. Gesson, N. Fonteneau, M. Mondon, S. Charbit, H. Ficheux, F. Schutze, US Patent, 6, 965, 039
B2 (2005)
41. H. Emtiazi, M.A. Amrollahi, S. Afr, J. Chem. 67, 175 (2014)
42. Z. Chen, Q. Zhu, W. Su, Tetrahedron Lett. 52, 2601 (2011)
43. S.E.S. Ebrahimi, P. Ghadirian, H. Emtiazi, A. Yahya-Meymandi, M. Saeedi, M. Mahdavi, H. Nadri,
A. Moradi, B. Sameem, M. Vosooghi, Med. Chem. Res. 25, 1831 (2016)
44. K.T. Patil, L. Walekar, S. Undare, G. Kolekar, M.B. Deshmukh, P. Choudhari, P.V. Anbhule, Ind. J.
Chem. 55, 1151 (2016)
45. N.C. Ganguly, S. Roy, P. Mondal, Synth. Commun. 44, 433 (2014)
46. X.-J. Sun, J.F. Zhou, S.-J. Zhi, Synth. Commun. 42, 1987 (2012)
47. P. Iniyavan, S. Sarveswari, V. Vijayakumar, Res. Chem. Intermed. 41, 7413 (2015)
48. H. Anaraki-Ardakani, R. Ghanavatian, M. Akbari, World Appl. Sci. J. 22, 802 (2013)
49. S.S. Kauthale, S.U. Tekale, K.M. Jadhav, R.P. Pawar, Mol. Divers. 20, 763 (2016)
50. A. Zare, H. Asvar, F. Zarei, M. Khalili, Z. Kordrostami, A.R. Moosavi-Zare, V. Khakyzadeh, J.
Appl. Chem. Res. 10, 59 (2016)
Publisher’s Note Springer Nature remains neutral with regard to jurisdictional claims in published
maps and institutional afliations.
Afliations
Alireza Kohzadian1 · Abdolkarim Zare1
*
Abdolkarim Zare
abdolkarimzare@pnu.ac.ir; abdolkarimzare@yahoo.com
1
Department of Chemistry, Payame Noor University, P.O. Box 19395-3697, Tehran, Iran
1 3