Catalytic application of a nano-molten salt catalyst in the synthesis of biological naphthoquinone-based compounds

Article abstract of DOI:10.1007/s11164-018-3264-9

In this investigation, a new application of 1H-imidazol-3-ium tricyanomethanide catalyst was explored. The catalyst presented a robust catalytic applicability for the preparation of naphthoquinone-based compounds under mild and green reaction conditions.

Full text of DOI:10.1007/s11164-018-3264-9

Res Chem Intermed
https://doi.org/10.1007/s11164-018-3264-9
Catalytic application of a nano‑molten salt catalyst
in the synthesis of biological naphthoquinone‑based
compounds
Meysam Yarie1 · Mohammad Ali Zolfgol1 · Saeed Babaee1 · Saeed Baghery1 ·
Diego A. Alonso2 · Abbas Khoshnood2
Received: 17 October 2017 / Accepted: 8 January 2018
© Springer Science+Business Media B.V., part of Springer Nature 2018
Abstract In this investigation, a new application of 1H-imidazol-3-ium tricy-
anomethanide catalyst was explored. The catalyst presented a robust catalytic appli-
cability for the preparation of naphthoquinone-based compounds under mild and
green reaction conditions. A wide range of aromatic aldehydes were able to react
with 2-hydroxynaphthalene-1,4-dione and 3-methyl-1-phenyl-1H-pyrazol-5(4H)-
one or malononitrile to aford the desired naphthoquinone-based molecules in short
time with high to excellent yields.
Graphical Abstract A good range of aromatic aldehydes were treated with
2-hydroxynaphthalene-1,4-dione (henna) and 3-methyl-1-phenyl-1H-pyrazol-5(4H)-
one or malononitrile to aford the desired henna-based target molecules in short
reaction time with good to excellent yields.
Electronic supplementary material The online version of this article (https://doi.org/10.1007/
s11164-018-3264-9) contains supplementary material, which is available to authorized users.
*
Meysam Yarie
myari.5266@gmail.com
Mohammad Ali Zolfgol
zolf@basu.ac.ir; mzolfgol@yahoo.com
Diego A. Alonso
diego.alonso@ua.es
Abbas Khoshnood
abbas.khoshnood@ua.es
1
2
Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University,
Hamedan 6517838683, Iran
Instituto de Síntesis Orgánica, and Departamento de Química Orgánica, Universidad de
Alicante, Apdo. 99, 03080 Alicante, Spain
1 3

M. Yarie et al.
R
R
O
CN
R
H2N
O
A
OH
Me
NC
NH
CN
or
O
O
O
HO
1a-n
B
HN
Solvent
6
mg
CN
free,
or
N
O
N
C
2a-g
H
Thermal
O
R
OH
O
O
O
R=
4-CN,
(OMe)2 4-N(Me)2
H, 4-Cl, 2-Cl, 2,4-Cl, 3-Br, 4-Br, 4-F,
3-NO 4-NO
,
,
4-Me, 4-OMe, 3,4-
2
2
O
O
,
,
3-OH,
Thiophen-2-yl
O
O
O
3a-f
OH
N
N
N
N
C
O
Me
B
A
Keywords 1H-imidazol-3-ium tricyanomethanide · Naphthoquinone-based
compounds · Nano-molten salt catalyst · Multicomponent reactions
Introduction
As building blocks of diverse naturally occurring products, henna-based organic
compounds have found a privileged position in heterocyclic chemistry. From a his-
torical standpoint, Lawsonia inermis (source of henna) has played a key role in reli-
gious customs and ordinary life style. Traditionally, ancient cultures widely used
henna for treatment of liver and digestive disease, leprosy, diabetes, ulcer as well as
protection of hands and feet against fungal pathogens [1, 2]. Also, plants containing
henna-based molecules have been employed in the therapy of cancer [3, 4]. Nowa-
days, henna-based materials, have found a special position in diferent felds of sci-
ence such as phytochemistry and medicinal chemistry [1, 2]. In addition to the myr-
iad prominent in vitro and in vivo therapeutic applications of henna, their derivatives
present pharmaceutical and medicinal versatility in the feld of drug chemistry, such
as, cytotoxic activity, anti-infammatory, antibacterial, anti-HIV, fungicidal, mol-
luscicidal, leishmanicidal, antimalarial, trypanocidal, and antitumoral bioactivities
[5–12]. Some bioactive heterocyclic compounds bearing the naphthoquinone moiety
as anthracycline drugs and naturally occurring products are depicted in Schemes 1
and 2 [1, 2, 13].
On the other hand, pyrazole-containing heterocyclic compounds have emerged
as interesting bioactive materials which a broad spectrum of pharmacological and
medicinal applicabilities comprising fungicidal [14], anticancer [15], vasodilatory
[16], antianginal [17], and antitumor bioactivities [18]. Therefore, it is believed that
the coexistence of both naphthoquinone and pyrazole segments in a given molecule
1 3

Catalytic application of a nano‑molten salt catalyst in the…
O
OH
O
Me
OH
O
O
OH
OH
O
O
CH2OH
OH
O
OH
O
CH2OH
OH
OMe O
OH
O
O
Me
OH
O
Me
O
OH
O
O
Me
OH
O
Me
OH
NH2
NH2
Idarubicin
NH2
Doxorubicin
Daunorubicin
Scheme 1 Antitumour anthracycline drugs
OH
O
O
Me
O
O
Me
O
O
OH
O
O
H
O
H
O
O
OH
D
Cl
Deoxydihydrokalafungin
Nanaomycin
Atovaquone
Scheme 2 Naturally occurring products bearing a naphthoquinone fragment
may provide new bioactivities or improve referred therapeutic features of them.
So a new eco-friendly approach to these versatile heterocyclic molecules is highly
valuable.
Ionic liquids and molten salts, due to their special character and various applica-
tions in the recent era of modern chemistry as catalyst, reagents, and solvents, have
attracted substantial consideration of researchers in the last decade [19–23]. Ionic
liquids can be considered as “designer species” due to their chemical and thermal
stability, solvating capability, vapor pressure, and other interesting properties which
can be adjusted by using diferent combinations of anions and cations to form task-
specifc ones [24–27].
One-pot multicomponent reactions have recently emerged as a versatile atom-
economy synthetic tool. This excellent alternative to the routine linear-type syn-
thetic procedures has been especially used in the construction of complex heterocy-
clic materials. Also, multicomponent reactions can arrange facile and uncomplicated
protocols to provide organic molecule libraries and diversity-oriented synthesis
(DOS) [28–32].
In this study, in order to mature our interest on the use of task-specifc ionic liq-
uids, molten salts, biologically based solid acids, and nanoparticles with ionic tags
as catalysts for the construction of biologically active heterocyclic materials [33–46],
herein we wish to report a new application of 1H-imidazol-3-ium tricyanomethanide
(ImITCM) as an efcient catalyst for the preparation of versatile, pharmaceutical
naphthoquinone-based target molecules under green and eco-friendly reaction con-
ditions (Scheme 3).
1 3

M. Yarie et al.
O
R
O
HO
N
N
N
Me
1a-n
N
Me
HO
O
R
O
H
O
O
O
NC
NH
CN
OH
NC
HN
6
mg
N
N
CN
2a-g
3a-f
R
Solvent free, Thermal
H2N
O
R
O
O
O
OH
R=
4-CN,
(OMe)2 4-N(Me)2
H, 4-Cl, 2-Cl, 2,4-Cl, 3-Br, 4-Br, 4-F,
3-NO 4-NO
,
,
4-Me, 4-OMe, 3,4-
2
2
O
O
O
,
,
3-OH,
Thiophen-2-yl
O
O
Scheme 3 ImITCM as a robust catalyst for the preparation of naphthoquinone-based target molecules
Results and discussion
Initially, ImITCM as a robust molten salt catalyst was prepared according to our pre-
viously reported method, as depicted in Scheme 4 [47]. The structural confrmation
was fully made and all provided spectra confrmed the synthesis of ImITCM catalyst
(see Electronic Supplementary Information).
After ensurance of catalyst preparation using proper technical skills, in order to
obtain the optimal conditions to perform the reactions, the reaction of benzaldehyde,
2-hydroxynaphthalene-1,4-dione, and 5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-
3-one was selected as the test reaction (Scheme 5). Over the model reaction, difer-
ent reaction parameters such as solvent, operational temperature, and load of molten
salt catalyst were screened. The obtained related data are embedded in Table 1.
Firstly, using the same amount of catalyst, it is found that 90 °C is the optimal reac-
tion temperature (Table 1, entries 1–3). Also, the model reaction was performed
in refuxing common laboratory solvents and the obtained data indicated that the
solvent-free condition is the best choice (Table 1, entries 4–7). Finally, the optimal
amount of catalyst is demonstrated to be 6 mg (Table 1, entries 8–10). From the
data in Table 1, it can be deduced that solvent-free conditions and using a catalytic
Scheme 4 Preparation route of
ImITCM catalyst
1 3

Catalytic application of a nano‑molten salt catalyst in the…
Scheme 5 Screening of the optimal reaction conditions over the model reaction
Table 1 Optimization of reaction conditions for the synthesis of naphthoquinone-based molecules
Entry
Solvent
Load of catalyst Temperature (°C)
(mg)
Time (min)
Yield (%)a
1
2
3
4
5
6
7
8
9
–
–
–
H2O
EtOH
CH3CN
n-Hexane
–
–
–
4
4
4
4
4
4
4
2
6
8
70
90
110
Refux
Refux
Refux
Refux
90
90
90
45
22
15
30
90
90
90
36
18
18
63
87
87
48
Trace
–
–
72
90
89
10
Reaction conditions: benzaldehyde (1 mmol, 0.106 g), 5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one
(1 mmol, 0.174 g), and 2-hydroxynaphthalene-1,4-dione (1 mmol, 0.174 g)
aIsolated yields
amount of catalyst at 90 °C are the optimal reaction conditions for the preparation of
naphthoquinone-based molecules (Table 1, entry 9).
Subsequently, with optimal reaction data in hand, in order to extend the capa-
bility of the catalyst, we focused on the generality and the scope of the presented
method for the synthesis of naphthoquinone-based heterocyclic molecules by using
a wide range of aromatic aldehydes (possessing electron-withdrawing, electron and
-donating components, and halogens) and other starting materials, as depicted in
Scheme 3. The obtained data as embedded in Table 2 confrm the versatility of the
presented procedure. All used starting materials interact with each other in a one-pot
multicomponent reaction to aford desired target molecules in short reaction times
with high to excellent yields.
Reusability of catalyst is one of the most outstanding advantages for
its application in various chemical processes. Thus, the reusability of
described catalyst was carried out successfully for three runs. For this pur-
pose the reaction of benzaldehyde, 2-hydroxynaphthalene-1,4-dione, and
1 3

M. Yarie et al.
Table 2 Synthesis of the naphthoquinone-based molecules in the presence of ImITCM under mild reac-
tion conditions
Entry
R
Product Structure of
naphthoquinone-
based molecules
Time
(min)
Yield
(%)a
M.p. (°C)
found
[Lit.]
[Ref.]
1
H
18
25
10
90
85
88
266–268
[267–268]
[48]
1a
1b
1c
2
3
2-Cl
4-Cl
250–252
[272–273]
[49]
262–263
[262–264]
[48]
4
5
4-F
25
13
74
92
256–258
[257–259]
[48]
1d
1e
4-OMe
253–254
[266–268]
[49]
6
3,4-
(OMe)2
40
91
235–237
[235–237]
[48]
1f
7
8
4-N(Me)2
21
17
83
74
210–212
[211–213]
[48]
1g
1h
Thiophen-
2-yl
238–240
[239–240]
[48]
1 3

Catalytic application of a nano‑molten salt catalyst in the…
Table 2 (continued)
9
2,4-Cl2
23
92
256–257
[257–258]
[48]
1i
1j
10
4-Me
22
89
264–266
[265–266]
[48]
11
12
3-OH
20
22
81
87
245–246
[new]
1k
1l
3-NO2
248–249
[266–268]
[48]
13
14
3-Br
45
15
88
89
214–215
[270–271]
[49]
1m
1n
4-CN
226–227
[273–274]
[49]
15
16
H
25
17
88
92
260–263
[260–263]
[50]
2a
2b
4-Cl
248–
251[250–
251] [50]
5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one was selected as a test reaction.
After each run, distillated water was added to the reaction mixture, stirred for a few
1 3

M. Yarie et al.
Table 2 (continued)
17
2-Cl
22
17
90
87
237–239
[235–237]
[50]
2c
18
4-F
240–245
[244–246]
[51]
2d
19
4-NO2
16
93
232–235
[232–234]
[50]
2e
20
21
3-NO2
4-Me
15
23
91
89
245–248
[247–250]
[50]
2f
240–243
[241–242]
[50]
2g
22
23
Thiophen-
2-yl
20
22
90
91
274–276
[274–276]
[52]
2h
3a
H
> 300
[300–302]
[53]
24
4-Cl
15
94
> 300
[330–332]
[53]
3b
1 3

Catalytic application of a nano‑molten salt catalyst in the…
Table 2 (continued)
25
4-F
20
84
269–272
[276–278]
[53]
3c
26
27
3-NO2
4-Me
15
21
93
86
> 300
[> 300]
[54]
3d
3e
> 300
[304–306]
[53]
28
29
4-OMe
14
22
91
88
> 300
[> 300]
[54]
3f
Thiophen-
2-yl
> 300
[263–265]
[55]
3g
Reaction condition: arylaldehydes (1 mmol), 5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one (1 mmol,
0.174 g) and 2-hydroxynaphthalene-1,4-dione (1 mmol, 0.174 g), Malononitrile (1 mmol, 0.066 g)
aIsolate yields
minutes, and decanted. After evaporation of the solvent, the ImITCM catalyst was
preserved for the next run. The resulted data presented in Fig. 1 illustrates that the
ImITCM catalyst can be reused for three times without signifcantly diminishing the
catalytic activity in comparison with its initial performance.
In a plausible mechanism for the synthesis of the target compound 1a as estab-
lished in Fig. 2, ImITCM as a nano-molten salt catalyst triggers the mechanistic
pathway by the activation of 2-hydroxynaphthalene-1,4-dione as a nucleophilic and
benzaldehyde as an electrophilic agent, respectively. The reaction proceeded by the
reaction of these two activated species to generate the related intermediate I. On the
other side, in the presence of the ImITCM catalyst, through a tautomerization pro-
cess, 5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one converted to its enol form
II. In the next step of the plausible mechanism, reaction of intermediates I and II
1 3

M. Yarie et al.
3
2
1
0
10
20
30
40
50
60
70
80
90
1
2
3
Isolated Yield (%)
Time (min)
90
90
88
18
20
22
Fig. 1 The successful reusability test of ImITCM as a nano-catalyst
via a Michael addition reaction yields the corresponding intermediate IV. Finally,
tautomerization of the intermediate IV in the presence of the catalyst generates the
target molecule 1a.
Conclusion
In this paper, a new application of ImITCM catalyst was explored. ImITCM pre-
sented a robust catalytic applicability for the preparation of naphthoquinone-based
compounds in green and mild reaction conditions. A wide range of aromatic alde-
hydes were treated with 2-hydroxynaphthalene-1,4-dione and 3-methyl-1-phenyl-
1H-pyrazol-5(4H)-one or malononitrile to aford the desired naphthoquinone-based
molecules in short time with high to excellent yields. Some distinguishing features
of the presented method include eco-friendly benign reaction conditions, a solvent-
less process, easy isolation and purifcation profle, and short reaction times with
high to excellent yields.
General method for the synthesis of ImITCM as a molten salt catalyst
The construction method and structural confrmation of the ImITCM as molten salt
catalyst were described in our previously reported study [47].
1 3

Catalytic application of a nano‑molten salt catalyst in the…
Fig. 2 Suggested plausible mechanism for the synthesis of target molecule 1a
General procedures for the synthesis of naphthoquinone‑based
molecules in the presence of ImITCM catalyst
To a mixture of aromatic aldehydes (1 mmol), 2-hydroxynaphthalene-1,4-dione
(1 mmol, 0.174 g) and one of the starting materials A, B, or C (1 mmol) in a round-
bottom fask, ImITCM (0.038 mmol, 6 mg) was added as molten salt catalyst. The
resulting mixture was exposed to the reaction in an oil bath at 90 °C for appropriate
times, as illustrated in Table 2. After completion of the reactions as indicated by
thin-layer chromatography TLC), in order to separate the catalyst, distillated water
was added to the reaction mixture and stirred for a few minutes. Then, the water-
containing catalyst was decanted and the catalyst recovered for the next run. Finally,
the desired products were recrystallized from EtOH to ofer the pure products in
high to excellent yields.
1 3

M. Yarie et al.
Selected spectral data
4‑(2‑Chlorophenyl)‑3‑methyl‑1‑phenyl‑1,4‑dihydrobenzo[6,7]chromeno[2,3‑c]
pyrazole‑5,10‑dione (1b)
Melting point = 250–252 °C.
FT-IR (KBr): ν (cm−1) = 3165, 3063, 1655, 1611, 1574, 1401, 1370, 837, 750,
691.
1H NMR (400 MHz, DMSO) δ (ppm) = 8.09–7.91 (m, 2H, aromatic), 7.87–7.76
(m, 2H, aromatic), 7.74–7.69 (m, 2H, aromatic), 7.52–7.42 (m, 3H, aromatic),
7.42–7.38 (m, 1H, aromatic), 7.34–7.20 (m, 3H, aromatic), 5.83 (s, 1H, CH), 2.08
(s, 3H, Me).
13C NMR (101 MHz, DMSO) δ (ppm) = 184.0, 182.1, 158.1, 147.9, 138.3,
137.0, 134.9, 133.6, 133.1, 132.3, 130.9, 130.8, 130.7, 129.9, 129.5, 129.4, 128.5,
127.1, 126.5, 126.1, 126.0, 124.4, 121.0, 120.2, 104.1, 33.3, 11.8.
4‑(4‑Methoxyphenyl)‑3‑methyl‑1‑phenyl‑1,4‑dihydrobenzo[6,7]chromeno[2,3‑c]
pyrazole‑5,10‑dione (1e)
Melting point = 253–254 °C.
FT-IR (KBr): ν (cm−1) = 3159, 3056, 2958, 1659, 1632, 1606, 1572, 1459, 1249,
1036, 757.
1H NMR (400 MHz, DMSO) δ (ppm) = 8.03 (dd, J = 7.5, 1.0 Hz, 1H, aromatic),
7.96 (dd, J = 7.5, 1.0 Hz, 1H, aromatic), 7.85–7.75 (m, 2H, aromatic), 7.72–7.65
(m, 2H, aromatic), 7.48 (t, J = 8.0 Hz, 2H, aromatic), 7.29 (t, J = 7.5 Hz, 1H, aro-
matic), 7.12 (d, J = 8.5 Hz, 2H, aromatic), 6.81 (d, J = 8.5 Hz, 2H, aromatic), 5.77
(s, 1H, CH), 3.70 (s, 3H, OMe), 2.26 (s, 3H, Me).
13C NMR (101 MHz, DMSO) δ (ppm) = 184.4, 182.5, 158.0, 147.8, 134.7,
133.6, 132.4, 131.6, 131.0, 129.6, 128.6, 126.6, 126.5, 126.0, 125.7, 120.7, 114.0,
105.4, 55.4, 32.1, 11.4.
4‑(3‑Hydroxyphenyl)‑3‑methyl‑1‑phenyl‑1,4‑dihydrobenzo[6,7]chromeno[2,3‑c]
pyrazole‑5,10‑dione (1k)
Melting point = 245–246 °C.
FT-IR (KBr): ν (cm−1) = 3550, 3177, 3099, 1659, 1609, 1593, 1485, 1375, 974,
771, 729, 691.
1H NMR (400 MHz, DMSO) δ (ppm) = 9.18 (br. s, 1H, OH), 8.04 (dd, J = 7.5,
1.2 Hz, 1H, aromatic), 7.98 (dd, J = 7.5, 1.4 Hz, 1H, aromatic), 7.88–7.76 (m, 2H,
aromatic), 7.72–7.69 (m, 2H, aromatic), 7.50 (t, J = 8.0 Hz, 2H, aromatic), 7.31 (t,
J = 7.5, 1H, aromatic), 7.05 (t, J = 8.0, 1H, aromatic), 6.69–6.60 (m, 2H, aromatic),
6.57 (d, J = 8.0 Hz, 1H, aromatic), 5.78 (s, 1H, CH), 2.28 (s, 3H, Me).
13C NMR (101 MHz, DMSO) δ (ppm) = 184.5, 182.4, 157.7, 147.9, 141.4,
134.7, 133.6, 132.4, 131.0, 129.6, 129.5, 126.6, 126.5, 126.0, 125.5, 120.7, 118.3,
114.5, 113.4, 105.2, 32.7, 11.4.
1 3

Catalytic application of a nano‑molten salt catalyst in the…
4‑(3‑Bromophenyl)‑3‑methyl‑1‑phenyl‑1,4‑dihydrobenzo[6,7]chromeno[2,3‑c]
pyrazole‑5,10‑dione (1m)
Melting point = 214–215 °C.
FT-IR (KBr): ν (cm−1) = 3156, 3074, 1660, 1634, 1595, 1501, 1416, 1286, 1054,
758, 690.
1H NMR (400 MHz, DMSO) δ (ppm) = 8.05–7.94 (m, 1H, aromatic), 7.85–7.74
(m, 1H, aromatic), 7.69–7.67 (m, 3H, aromatic), 7.51–7.36 (m, 5H, aromatic),
7.31–7.22 (m, 3H, aromatic), 4.98 (s, 1H, CH), 2.31 (s, 3H, Me).
13C NMR (101 MHz, DMSO) δ (ppm) = 184.1, 182.8, 160.5, 147.8, 146.8,
145.4, 143.4, 137.4, 134.7, 130.9, 130.2, 129.6, 129.5, 126.7, 126.4, 122.0, 121.2,
120.8, 104.6, 104.1, 33.2, 11.9.
4‑(3‑Methyl‑5, 10‑dioxo‑1‑phenyl‑1,4,5,10‑tetrahydrobenzo[6,7]
chromeno[2,3‑c]pyrazol‑4‑yl)benzonitrile (1n)
Melting point = 226–227 °C
FT-IR (KBr): ν (cm−1) = 3165, 3062, 2228, 1658, 1640, 1606, 1572, 1501, 1374,
1281, 954, 727.
1H NMR (400 MHz, DMSO) δ (ppm) = 8.03 (dd, J = 7.5 Hz, 1H, aromatic),
7.99–7.93 (m, 2H, aromatic), 7.86–7.64 (m, 6H, aromatic), 7.51–7.43 (m, 3H, aro-
matic), 7.32–7.27 (t, J = 7.5 Hz 1H, aromatic), 5.88 (s, 1H, CH), 2.27 (s, 3H, Me).
13C NMR (101 MHz, DMSO) δ (ppm) = 184.0, 182.7, 147.8, 146.8, 136.4,
134.7, 133.5, 132.5, 131.2, 129.6, 128.8, 126.6, 126.4, 126.0, 124.5, 120.9, 119.5,
109.1, 103.8, 33.3, 11.6.
Acknowledgements We thank Bu-Ali Sina University and the Iran National Science Foundation
(INSF) for fnancial support (grant no. 940124), and Iran’s National Elites Foundation for recognizing our
research group.
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