Highly efficacious preparation of 3,3′-(arylmethylene)-bis(2-hydroxynaphthoquinone) derivatives catalyzed by a nanorod-structured organic–inorganic hybrid material

Article abstract of DOI:10.1007/s11164-020-04375-6

Abstract: A nanorod-structured organic–inorganic hybrid material namely nanorod-[SiO₂–Pr–Im–SO₃H][CF₃CO₂] (N-[SPIS][TFA]) has been applied as a highly efficacious, dual-functional, and recoverable catalyst for t

Full text of DOI:10.1007/s11164-020-04375-6

Research on Chemical Intermediates (2021) 47:1349–1358
https://doi.org/10.1007/s11164-020-04375-6
Highly efcacious preparation
oꢀ 3,3′‑(arylmethylene)‑bis(2‑hydroxynaphthoquinone)
derivatives catalyzed by a nanorod‑structured
organic–inorganic hybrid material
Abdolkarim Zare1 · Jaleh Atashrooz · Mohammad Mehdi Eskandari
1
2
Received: 14 June 2020 / Accepted: 19 December 2020 / Published online: 11 January 2021
©
The Author(s), under exclusive licence to Springer Nature B.V. part of Springer Nature 2021
Abstract
A nanorod-structured organic–inorganic hybrid material namely nanorod-[SiO –
2
Pr–Im–SO H][CF CO ] (N-[SPIS][TFA]) has been applied as a highly efca-
3
3
2
cious, dual-ꢀunctional, and recoverable catalyst ꢀor the solvent-ꢀree preparation oꢀ
3
,3’-(arylmethylene)-bis(2-hydroxynaphthoquinone) {3,3′-(arylmethylene)-bis(2-
hydroxynaphthalene-1,4-dione)} derivatives in high yields and relatively short
times. The one-pot pseudo-multi-component reaction oꢀ 2-hydroxynaphthoquinone
(
2-hydroxynaphthalene-1,4-dione) (2 eq.) and arylaldehydes (1 eq.) has been used
ꢀ
or the preparation oꢀ these compounds.
Graphic abstract
O
O
O
OH
O
OH HO
Ar
N-[SPIS][TFA]
Solvent-free,110°C
2
+
Ar
H
O
O
O
CF COO
3
The reaction times: 50-75 min
Yields: 78-96%
O
SO H
N-[SPIS][TFA]=
N
3
O
Si
N
O
Keywords 3,3′-(arylmethylene)-bis(2-hydroxynaphthoquinone) · Organic–inorganic
hybrid material · Nanorod-[SiO –pr–im–SO H][CF CO ]; (N-[SPIS][TFA]) ·
2
3
3
2
Pseudo-multi-component reaction · Solvent-ꢀree
Supplementary Inꢀormation The online version oꢀ this article (https://doi.org/10.1007/s11164-020-
4375-6) contains supplementary material, which is available to authorized users.
0
*
Abdolkarim Zare
abdolkarimzare@pnu.ac.ir; abdolkarimzare@yahoo.com
Extended author inꢀormation available on the last page oꢀ the article
Vol.:(012
1
3456789)
3

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A. Zare et al.
Introduction
Compounds bearing naphthoquinone moiety are oꢀ importance, since they have a wide
range oꢀ biological, pharmaceutical, and industrial applications [1–14]. For exam-
ple, they show antioxidant [1], antiꢀungal [1], antiplatelet [2], antibacterial [3], anti-
malarial [4], anti-inꢁammatory [5], antithrombotic [6], anti-proliꢀerative [7], antiviral
[
8], antitumor [9], CDC25 phosphatase inhibitor [10], anti-allergic [11], and antimi-
crobial [12] activities. Moreover, these compounds can be utilized as pigments [13,
4]. 3,3′-(Arylmethylene)-bis(2-hydroxynaphthoquinone) {3,3′-(arylmethylene)-bis(2-
1
hydroxynaphthalene-1,4-dione)} derivatives are a kind oꢀ naphthoquinone-containing
compounds, which can be prepared via the one-pot pseudo-multi-component reaction
oꢀ 2-hydroxynaphthoquinone (2-hydroxynaphthalene-1,4-dione) (2 eq.) and arylalde-
hydes (1 eq.) in the presence oꢀ a catalyst [15–22]. It is worth noting that a ꢀew catalysts
have been reported ꢀor the reaction oꢀ 2-hydroxynaphthoquinone (2 eq.) and arylalde-
hydes (1 eq.) leading to 3,3′-(arylmethylene)-bis(2-hydroxynaphthoquinone) deriva-
tives; so, it is highly desirable to introduce new efcacious catalysts ꢀor this reaction.
Hybrid materials are composed ꢀrom at least two diꢂerent constituents wherein inor-
ganic and organic constituents are put together by special interactions, and increase the
synergistic oꢀ their ꢀunctional properties [23]. They have attracted much attention in
diverse scientiꢃc, industrial, and pharmaceutical ꢃelds [23–45]. Hybrid materials have
been applied as electrode [24], sensor [25], antitumor [26], and platꢀorm ꢀor in vitro
cell manipulation [27]. Furthermore, they have been used ꢀor decomposition oꢀ hazard-
ous organic industrial pollutants in aqueous medium [28], energy storage [29], drug
delivery [30], and bioimaging [30]. Organic–inorganic hybrid materials have been,
especially, used as catalysts in organic synthesis [31–52]. Among the diverse inorganic
compounds [31–55], silica is usually preꢀerable to utilize as inorganic component ꢀor
production oꢀ hybrid materials, due to possessing some unbeatable characteristics, con-
sisting oꢀ saꢀety, eco-ꢀriendly nature, appropriate thermal and chemical stability, low
cost, non‐corrosiveness, simple ꢀunctionalization, having large surꢀace-to-volume ratio
(
nanomaterials), and easy isolation ꢀrom reaction medium [35–46].
Solvent-ꢀree conditions [56–61] and multi-component reactions [62–67] are practi-
cal, well-known, useꢀul and green technique which has been used in organic synthesis;
their advantages have been mentioned in the literature [56–67].
Considering the above topics, we have introduced a highly efcacious method ꢀor
the preparation oꢀ 3,3′-(arylmethylene)-bis(2-hydroxynaphthoquinone) derivatives via
the one-pot pseudo-three-component reaction oꢀ 2-hydroxynaphthoquinone (2 eq.)
and arylaldehydes (1 eq.) using a nanorod-structured organic–inorganic hybrid catalyst
namely nanorod-[SiO –Pr–Im–SO H][CF CO ] (N-[SPIS][TFA]) under solvent-ꢀree
2
3
3
2
conditions.
1
3

Highly efcacious preparation oꢀ…
1351
Experimental
Materials and instruments
The reactants and solvents were bought ꢀrom Fluka or Merck Chemical Compa-
nies. Nanorod-[SiO –Pr–Im–SO H][CF CO ] (N-[SPIS][TFA]) was synthesized
2
3
3
2
according to our recently published procedure in this Journal (Scheme 1) [35].
To identiꢀy the synthesized 3,3′-(arylmethylene)-bis(2-hydroxynaphthoquinone)
derivatives, their melting points/spectral data were compared with those reported
in the literature. Thin layer chromatography (TLC) (silica gel SIL G/UV 254
plates) was used ꢀor observation oꢀ the reactions progress. FT-IR was run on
1
13
Bruker instrument (model: Tensor 27, Germany). H and C NMR were recorded
on Bruker Avance DPX, FT-NMR spectrometer. Melting points were measured
using a Thermo Scientiꢃc 9200 instrument in open capillary tubes. Mass spectra
were obtained by a Shimadzu GC–MS-QP 1100 Ex device.
General procedure for the preparation
of 3,3′‑(arylmethylene)‑bis(2‑hydroxynaphthoquinone) derivatives
A mixture oꢀ 2-hydroxynaphthoquinone (2 mmol, 0.348 g), aldehyde (1 mmol ꢀor
solid aldehydes; 1.1 mmol ꢀor liquid ones), and N-[SPIS][TFA] (0.020 g) was
vigorously stirred by a small rod at 110 °C. Aꢀter completing the reaction (as
observed by TLC), EtOAc (30 mL) was added, stirred ꢀor 2 min under reꢁux con-
ditions, ꢀollowed by centriꢀugation and decanting to isolate the unsolvable cata-
lyst (which was washed by EtOAc, dried and used ꢀor the next run). The EtOAc
resulted ꢀrom the decanting was evaporated, and the precipitate (crude product)
was puriꢃed by recrystallization ꢀrom EtOH/H O.
2
Note: Selected spectral data and original spectrums oꢀ the products have been
presented in supplementary material.
Toluene
Si(OEt3)
Nanorod silica
N
NH
N
N
+
Cl
Si(OEt)
3
Reflux,12h
EtOAc, Reflux,18 h
_
_
HCl
EtOH
Cl
O
O
O
O
ClSO
3
H
CF
r.t.
3
COOH
60°C
3
SO H
Si
N
N
O
Si
N
N
CH
2
Cl , 0 °C, 3h
2
O
1
2 h
_
HCl
CF
3
COO
N
O
O
O
3
SO H
Si
N
(
N-[SPIS][TFA])
Scheme 1 The synthesis oꢀ N-[SPIS][TFA]
1
3

1352
A. Zare et al.
O
O
O
O
OH HO
O
O
CHO
OH
N-[SPIS][TFA]
Solvent-free
Different conditions
2
+
NO
2
NO
2
Scheme 2 The model reaction
Table 1 The results on
optimization oꢀ the reaction
conditions (Scheme 2)
Entry
The catalyst
amount (g)
Temp. (°C)
Time (min)
Yield (%)
1
2
3
4
5
6
–
110
110
110
110
100
115
50
50
50
45
50
50
17
81
93
93
79
93
0.015
0.020
0.025
0.020
0.020
Results and discussion
Initially, the reaction oꢀ 2-hydroxynaphthoquinone (2 mmol) and 4-nitrobenzal-
dehyde (1 mmol) was examined in the absence oꢀ catalyst and also using diꢂerent
amounts oꢀ nanorod-[SiO –Pr–Im–SO H][CF CO ] (N-[SPIS][TFA]) at a range
2
3
3
2
oꢀ 100–115 °C under solvent-ꢀree conditions (Scheme 2), in order to optimize the
reaction conditions relative to the catalyst amount and temperature. The results are
summarized in Table 1. Examining the reaction in the absence oꢀ catalyst at 110 °C
aꢂorded low yield oꢀ the desired 3,3′-(arylmethylene)-bis(2-hydroxynaphthoqui-
none) (Table 1, entry 1). The optimized conditions were attained when 0.020 g oꢀ the
catalyst was applied at 110 °C; in these conditions, the desired 3,3′-(arylmethylene)-
bis(2-hydroxynaphthoquinone) was produced in 93% aꢀter 50 min (Table 1, entry
3
). Increasing the temperature up to 115 °C did not improve the reaction results
(
Table 1, entry 6). Increment oꢀ the catalyst amount up to 0.025 g slightly decreased
the reaction time (Table 1, entry 4); nevertheless, 0.020 g was chosen as the optimal
catalyst amount; because perꢀorming the reaction using ꢀewer amount oꢀ the catalyst
is more economical.
Aꢀter acquiring the optimal conditions, various derivatives oꢀ
3
,3′-(arylmethylene)-bis(2-hydroxynaphthoquinone) were prepared through the
reaction oꢀ 2-hydroxynaphthoquinone (2 eq.) and diꢂerent arylaldehydes (1 eq.);
the results are reported in Table 2. As it can be observed in Table 2, all products
were obtained in good to excellent yields and in relatively short times. When
1
3

Highly efcacious preparation oꢀ…
1353
Table 2 The solvent-ꢀree synthesis oꢀ 3,3′-(arylmethylene)-bis(2-hydroxynaphthoquinone) derivatives
O
O
O
O
O
O
OH
O
OH HO
Ar
N-[SPIS][TFA]
Solvent-free,110 °C
2
+
Ar
H
a
Product No
Ar
Time (min)
Yield (%)
M.p. (ºC) [lit.]
1
2
3
4
5
6
7
8
9
C H
4-ClC H
4-FC H
4-BrC H
55
75
75
75
60
60
50
75
60
50
96
92
83
96
78
91
93
84
92
94
208–210 (202–204) [16]
181–183 (180–182) [16]
174–176 (177–178) [20]
196–198 (195–197) [20]
205–207 (200–202) [20]
154–156 (151–152) [19]
179–181 (177–178) [18]
178–180 (143–145) [19]
223–225 (220–222) [17]
171–173 (170–172) [18]
6
5
6
4
6
4
6
4
2,4-Cl C H
2
6
3
3-O NC H
2
6
4
4-O NC H
2
6
4
3,4-(CH O) C H
4-CH OC H
4-CH C H
3 6 4
3
2
6
3
3
6
4
1
0
aIsolated yield
benzaldehyde was used as aldehyde substrate, the related product was synthesized
in excellent yield (Table 2, product 1). Among the halogen-bearing aldehydes,
4
-chloro and 4-bromobenzaldehyde gave high to excellent yields; however, 4-ꢁuoro
and 2,4-dichlorobenzaldehyde aꢂorded good yields (Table 2, products 2–5). When
aldehydes containing electron-withdrawing substituents (3-nitro and 4-nitrobenza-
ldehyde) were applied in the reaction, the corresponding products were obtained in
high yields (Table 2, products 6 and 7). Among the aldehydes possessing electron-
donating substituents, 4-methoxy and 4-methylbenzaldehyde gave the desired prod-
ucts in high yields; but, 3,4-dimethoxybenzaldehyde aꢂorded the corresponding
product in good yield (Table 2, products 8–10). Considering the obtained results, it
can be said that N-[SPIS][TFA] is a highly efcacious and general catalyst ꢀor the
preparation oꢀ 3,3′-(arylmethylene)-bis(2-hydroxynaphthoquinone) derivatives.
Recoverability and reusability oꢀ N-[SPIS][TFA] were studied ꢀor the synthesis
oꢀ 3,3′-(arylmethylene)-bis(2-hydroxynaphthoquinone) 1. The catalyst was recov-
ered as mentioned in the experimental section. It was reusable ꢀor two times with
negligible decrement oꢀ the yield and increment oꢀ the reaction time (Fig. 1, runs
2
and 3). Nevertheless, the reaction yield was decreased to 85% in third recycling
(
Fig. 1, run 4).
N-[SPIS][TFA] can act as a dual-ꢀunctional catalyst; SO H is an acidic group,
3
and triꢁuoroacetate is a weak basic group [35]. Based on this theme and the lit-
erature [16, 20], a reasonable mechanism was proposed ꢀor the synthesis oꢀ
1
3

1354
A. Zare et al.
Fig. 1 The reusability results oꢀ N-[SPIS][TFA]
3
,3′-(arylmethylene)-bis(2-hydroxynaphthoquinone) derivatives (Scheme 3). The cata-
lyst can ꢀacilitate all steps oꢀ the reaction, its roles, which are clearly illustrated in the
mechanism, consist oꢀ: (1) activation oꢀ the electrophiles by the SO H to react with
3
the nucleophiles (Scheme 3, steps 1 and 3), (2) activating the nucleophiles by the tri-
ꢁ
uoroacetate anion to react with the electrophiles (Scheme 3, steps 1 and 3), (3) help
ꢀ
or elimination oꢀ H O (Scheme 3, step 2), and (4) acceleration oꢀ tautomerization
2
(
Scheme 3, step 4).
In another study, the results and the reaction conditions oꢀ N-[SPIS][TFA] ꢀor
the production oꢀ compound 1 were compared with those oꢀ the reported catalysts
(
Table 3). As Table 3 demonstrates, the reaction yield oꢀ N-[SPIS][TFA] was higher
than the other catalysts, and the reaction time oꢀ our catalyst was shorter than some
reported catalysts. Moreover, in our work, the reaction has been perꢀormed under
solvent-ꢀree conditions. Nevertheless, the reaction temperature in our work is higher
than the others.
Conclusions
Brieꢁy, we have developed
a
new protocol ꢀor the preparation oꢀ
3
,3′-(arylmethylene)-bis(2-hydroxynaphthoquinone) derivatives ꢀrom 2-hydrox-
ynaphthoquinone and arylaldehydes. The advantages oꢀ this protocol consist oꢀ
efcacy, wide scope, high yields, relatively short reaction times, application oꢀ
solvent-ꢀree conditions, and a nanorod-structured organic–inorganic hybrid cata-
lyst (and consequently possessing the advantages oꢀ these two), studying a reaction
that have been scarcely reported in the literature, simple puriꢃcation oꢀ the products
using recrystallization, recoverability oꢀ the catalyst and good agreement with green
chemistry principles.
1
3

Highly efcacious preparation oꢀ…
1355
F
3
C
O
H
O
N
N
3
SO H
O
O
O
O
OH
O
O
Ar
O
N-[SPIS][TFA]
O
Step 1
Ar N-[SPIS][TFA]
H
Ar
H
CF
3
COO
N
O
S
H
N
O
O
CF
3
COO
H
O
S
H
O
O
O
O
O
N
N
Ar
O
Ar
N-[SPIS][TFA]
H
Step 2
_
O
O
2
H O
O
N
N
SO H
3
F3C
O
H
O
O
O
O
Ar
O
O
O
O
O
N-[SPIS][TFA]
Ar
Step 3
O
OH
O
CF COO
O
H
O
S
3
O
N
N
O
Ar
Ar
O
O
O
O
H
Tautomerization
Step 4
OH
O
H
OH HO
O
O
O
O
The product
O
S
O
N
N
O
CF COO
3
Scheme 3 The reaction mechanism
1
3

1356
A. Zare et al.
Table 3 The synthesis oꢀ compound 1 using N-[SPIS][TFA] and the reported catalysts
Catalyst
Conditions
Time (min) Yield (%) Reꢀerences
N-[SPIS][TFA]
LiCl
Solvent-ꢀree, 110 °C
55
720
15
5
96
83
90
91
87
85–92
92
88
89
–
H O, reꢁux
[16]
[17]
[18]
[18]
[19]
[20]
[21]
[22]
2
H SO
H O/EtOH, reꢁux
2
4
2
LiCl
LiCl
H O, 25 °C, ultrasonic irradiation
2
H O, 75 °C, microwave irradiation 15
2
a,b
H O/[bmim][BF ]
90 °C
240–360
2
4
Sulꢀamic acid
Lipase
O-Carboxymethyl chitosan H O/MeOH, 70 °C
H O/EtOH, r.t
960
120
50
2
EtOH, 60 °C
2
a
1
-Butyl-3-methylimidazolium tetraꢁuoroborate
b
In this research, compound 1 has not been synthesized; thus, we tabulated the ranges oꢀ the reaction
times and yields
Acknowledgements The authors appreciate Research Council oꢀ Payame Noor University ꢀor the support
oꢀ this work.
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Aꢀliations
Abdolkarim Zare1 · Jaleh Atashrooz · Mohammad Mehdi Eskandari
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1
Department oꢀ Chemistry, Payame Noor University, PO Box 19395-3697, Tehran, Iran
2
Nanotechnology Research Center, Research Institute oꢀ Petroleum Industry (RIPI), PO
Box 1485733111, Tehran, Iran
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