Copper(II) acetate monohydrate: an efficient and eco-friendly catalyst for the one-pot multi-component synthesis of biologically active spiropyrans and 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives under solvent-free conditions

Article abstract of DOI:10.1007/s11164-016-2565-0

Abstract: We have studied the catalytic ability of copper(II) acetate monohydrate as a mild, environmentally benign, natural and economical catalyst for the multi-component efficient synthesis of biologically active spiro-4H-pyran derivatives and 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives with excellent yields and short reaction times. The most important advantages of this procedure are its mild, non-toxic and inexpensive catalyst, one-pot synthesis, environmentally benign nature, solvent-free conditions, simple operational procedures, and highly efficient conditions. Graphical Abstract: [Figure not available: see fulltext.]

Full text of DOI:10.1007/s11164-016-2565-0

Res Chem Intermed (2016) 42:7841–7853
DOI 10.1007/s11164-016-2565-0
Copper(II) acetate monohydrate: an efficient and eco-
friendly catalyst for the one-pot multi-component
synthesis of biologically active spiropyrans and 1H-
pyrazolo[1,2-b]phthalazine-5,10-dione derivatives
under solvent-free conditions
Farzaneh Mohamadpour1 Malek Taher Maghsoodlou1
•
•
Reza Heydari1 Mojtaba Lashkari2
•
Received: 16 December 2015 / Accepted: 26 April 2016 / Published online: 30 June 2016
Ó Springer Science+Business Media Dordrecht 2016
Abstract We have studied the catalytic ability of copper(II) acetate monohydrate as a
mild, environmentally benign, natural and economical catalyst for the multi-component
efficient synthesis of biologically active spiro-4H-pyran derivatives and 1H-pyra-
zolo[1,2-b]phthalazine-5,10-dione derivatives with excellent yields and short reaction
times. The most important advantages of this procedure are its mild, non-toxic and
inexpensive catalyst, one-pot synthesis, environmentally benign nature, solvent-free
conditions, simple operational procedures, and highly efficient conditions.
Graphical Abstract
H2N
O
NC
O
O
O
or
Cu (OAC)2.H2O (15mol%)
Solvent free, 80°C
+
NC
CN
+
or
H2N
NC
O
O
O
O
N
H
O
N
H
O
NH2NH2 .H2O
+
O
O
O
Ar
N
N
O
Cu(OAC)2.H2O (20 mol %)
Solvent free, 80 °C
CN
NH2
CN
CN
Ar CHO
+
&
Malek Taher Maghsoodlou
mt_maghsoodlou@yahoo.com; mt_maghsoodlou@chem.usb.ac.ir
1
2
Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan,
P. O. Box 98135-674, Zahedan, Iran
Faculty of Science, Velayat University, Iranshahr, Iran
123

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F. Mohamadpour et al.
Keywords Copper(II) acetate monohydrate Á Spiro-4H-pyran derivatives Á 1H-
pyrazolo[1,2-b]phthalazine-5,10-dione derivatives Á Solvent-free conditions
Introduction
Nowadays, most research has been focused on the study of synthesising heterocyclic
compounds. Organic compounds containing nitrogen heterocyclic rings are important
compounds in medicinal chemistry. The synthesis of biologically active spiropyran
derivatives (spirooxindole) and 1H-pyrazolo[1,2-b]phthalazine-5,10-dione deriva-
tives have been given much attention because of their advantages in various biological
(Figs. 1, 2) and pharmaceutical fields, for example, as anti-HIV [1], anti-tubercular
[2], fungicidal [3], anticonvulsant [4] and anticancer [5, 6] agents; in addition, these
spirocycles are MDM2 inhibitors [7] and progesterone receptor modulators [8].
In recent decades, a number of methodologies for preparation of these compounds
have been reported that have included various catalysts such as [BMIm] BF4 [9], urea–
choline chloride [10], sulfated choline-based heteropolyanion [11], b-cyclodextrin
[12], lipase [13], CsF [14], carbon–SO3H [15], Et3N [16], [Bmim]OH [17],
ultrasound-assisted [18], NiCl2Á6H2O [19], PTSA/[Bmim]Br [20], CuI nanoparticles
[21], InCl3 [22, 23], STA [24], SBA-Pr–SO3H [25], PTSA [26], Ce(SO4)2Á4H2O [27]
and Cu(OAc)2/sodium L-ascorbate [28]. Some of these methodologies have
limitations such as a difficult work-up, toxic and expensive catalysts and solvents,
long reaction times and low yields.
Recently, increasing interest has been paid to the multi-component domino
reactions (MCRs) [29–40]. Because of their notable advantages such as atom
economy, environmental friendliness, low-cost, one-pot nature, simple work-up
they have become powerful tools in the synthesis of organic compounds possessing
biological and pharmaceutical properties.
Our recent research has focused on the development of clean and simple
methodologies with environmentally benign natures. Therefore, given that one of
the factors that reduces environmental pollution in synthesis of organics is solvent-
free conditions, we have developed multicomponent reactions under solvent-free
conditions.
In this regard, we have reported copper(II) acetate monohydrate for the synthesis
of spiro-4H-pyran derivatives and 1H-pyrazolo[1,2-b]phthalazine-5,10-diones via
Me
H
O
N
O
H
O
N
N
CO2Me
N
H
H
O
O
N
H
N
H
HO
O
N
H
Elacomine
Spirotryprostatin B
Pteropodine
Fig. 1 Some alkaloids containing a heterocyclic spirooxindole unit
123

Copper(II) acetate monohydrate: an efficient and…
OH
7843
CH3
O
OH CO2
NH
N
N
O
N
N
O
N
Me
Me
Cinnopentazone
Nigellicine derivatives
Fig. 2 Biologically active compounds with a two-ring junction nitrogen atom
MCRs under thermal and solvent-free conditions. The advantages of copper(II)
acetate monohydrate as a catalyst in organic compound synthesis are that it is
environmentally benign, economical, mild, inexpensive, non-toxic and highly
efficient [41–43].
Results and discussion
In this protocol, we have reported copper(II) acetate monohydrate as an efficient
catalyst under thermal and solvent-free conditions for simple, environmentally
benign synthesis of biologically active spiro-4H-pyran derivatives 4 from reaction
between isatin 1, malononitrile 2 and 1,3-dicarbonyl compounds/4-hydroxy-
cumarin/naphthlol 3 (Scheme 1).
In order to optimize the reaction conditions, the synthesis of compound 4a
(Table 3, entry 1) was used as a model reaction. The effect of different amounts of
catalyst on the reaction has been studied in this protocol. No product could be
detected in the absence of the catalyst even after 10 h (Table 1, entry 1). Good
yields were obtained in the presence of the catalyst. The best amount of catalyst was
15 mol% (0.03 g; Table 1, entry 4). The higher amount of catalyst did not increase
the yields products (Table 1, entry 5).
Also, the effect of temperature on the reaction has been investigated. At room
temperature, the product was not detected (Table 2, entry 1). The reaction was
CN
H2N
NC
CN
O
2
O
Cu (OAc)2.H2O(15mol%)
Solvent free,80°C
O
O
N
H
+
O
N
H
(4a-f)
1
3
Scheme 1 Synthesis of spiro-4H-pyran derivatives
123

7844
F. Mohamadpour et al.
Table 1 Optimization of the reaction condition for the synthesis of spiro-4H-pyran 4a
O
O
O
CN
CN
O
+
+
O
O
NH2
N
H
CN
O
N
H
Entry
Cu(OAc)2ÁH2O (mol%)
Time (h)
Product
Isolated yields (%)
1
2
3
4
5
Catalyst free
10
7
4a
4a
4a
4a
4a
–
5
49
71
86
88
10
15
20
6
4
4
Reaction condition: isatin, malononitrile, dimedone and copper(II) acetate monohydrate were heated at
80 °C for the appropriate time
Table 2 Effect of temperature on the synthesis of 4a
O
O
O
CN
CN
O
+
+
O
O
NH2
N
H
CN
O
N
H
Entry
Temperature (°C)
Time (h)
Isolated yields (%)
1
2
3
4
5
r.t.
40
10
6
–
41
67
86
87
60
5
80
4
100
4
Reaction condition: isatin, malononitrile and dimedone (1:1:1) with copper(II) acetate monohydrate
(15 mol%) were heated under various temperatures for the appropriate time and yields
investigated at various temperatures and a high yield of product was obtained at
80 °C (Table 2, entry 4).
In order to study this procedure, we synthesized a one-pot, three-component
condensation reaction of isatin (1.0 mmol), malononitrile (1.0 mmol) and com-
pounds 3 (1.0 mmol) in the presence of copper(II) acetate monohydrate (15 mol%)
as a mild catalyst under thermal and solvent-free conditions, and the results are
shown in Table 3.
After the successful synthesis of spiro-4H-pyran derivatives 4, we turned our
attention to the synthesis of spiro-4H-pyran derivatives from reaction between
acenaphthoquinone 5, malononitrile 2 and compounds 6 in the present of copper(II)
123

Copper(II) acetate monohydrate: an efficient and…
7845
Table 3 Copper(II) acetate monohydrate-catalyzed synthesis of spiropyrans
Entry
1
Isatin
3
Product
Time (h) Yield %a
86 [9]
4
O
O
O
O
O
N
H
O
NH2
CN
O
N
H
4a
2
6
79 [10]
O
OH
O
O
O
N
H
O
O
O
NH2
CN
O
N
H
4b
3
4
O
O
O
5
5
81 [15]
83 [10]
O
O
O
NH2
N
H
CN
O
N
H
4c
O
OH
O
N
O
H
NH2
CN
O
N
H
4d
4e
5
6
4.5
89 [9]
O
O
O
EtO
O
O
O
O
NH2
N
H
CN
O
N
H
4
81 [14]
O
O
O
Cl
O
O
N
O
H
NH2
Cl
CN
O
N
H
4f
a
Isolated yield
123

7846
F. Mohamadpour et al.
CN
CN
2
H2N
O
O
O
NC
O
Cu(OAc)2.H2O (15mol%)
Solvent free, 80°C
+
O
6
5
(7a-f)
Scheme 2 Synthesis of spiro-4H-pyran derivatives
acetate monohydrate (Scheme 2) and these compounds were synthesized under
similar conditions in good yields. The results are shown in Table 4.
Then, we turned our attention toward the synthesis of pyrazolo[1,2-b]phtha-
lazine-5,10-dione derivatives. In order to discern the optimal conditions, we
investigated the four components of phthalic anhydride 8, hydrazine monohydrate 9,
aromatic aldehydes derivatives 10 and malononitrile 2 in the presence of copper(II)
acetate monohydrate as an efficient, environmentally benign and natural catalyst
(Scheme 3).
In order to optimize the reaction conditions, the synthesis of compound 11a
(Table 7, entry 1) was used as a model reaction. The effect of different amounts of
catalyst on the reaction has been studied in this protocol. No product could be
detected in the absence of the catalyst even after 10 h (Table 5, entry 1). Good
yields were obtained in the presence of catalyst. The best amount of catalyst was
20 mol% (0.04 g; Table 5, entry 5). The higher amount of catalyst did not increase
the yields products (Table 5, entry 6).
Also, the effect of temperature on the reaction has been investigated. At room
temperature, the product was not detected (Table 6, entry 1). The reaction was
investigated at various temperatures and a high yield of product was obtained at
80 °C (Table 6, entry 4).
In order to study this procedure, we synthesized a series of compounds with
various types of electron-donating and electron-withdrawing aldehyde derivatives
such as Cl, Br, NO2, OH, OMe,….substituted banzaldehydes which gave excellent
yields. Also, the generality of this four-component condensation reaction was
studied by using copper(II) acetate monohydrate (20 mol%) via phthalic anhydride
(1.0 mmol), hydrazine monohydrate (1.0 mmol), the various aldehyde derivatives
(1.0 mmol) and malononitrile (1.0 mmol) under thermal and solvent-free condi-
tions, and the results are shown in Table 7.
Comparison of the catalytic ability of some catalysts reported in the literature for
the synthesis of spiro-4H-pyran and 1H-pyrazolo[1,2-b]phthalazine-5,10-dione
derivatives are shown in Tables 8 and 9. This study reveals that copper(II) acetate
monohydrate has shown its extraordinary potential to be an alternative cheap, cost-
effective, eco-friendly, efficient catalyst for the synthesis of these compounds. In
123

Copper(II) acetate monohydrate: an efficient and…
7847
Table 4 Copper(II) acetate monohydrate-catalyzed synthesis of spiro-4H-pyran
Entry
1
Acenaphthoquinone
7
Product
Time (h) Yield %a
O
O
O
5
84 [16]
O
O
O
O
O
O
NH2
CN
7a
7b
2
3
6
7
81 [16]
O
O
O
O
O
O
O
NH2
CN
OH
O
79 [16]
O
O
O
O
O
NH2
CN
7c
4
O
O
OH
4
82 [16]
O
O
NH2
CN
7d
5
6
O
O
O
O
O
O
O
6
6
87 [16]
78 [16]
OEt
O
O
O
O
NH2
CN
7e
O
HN
NH
HN
NH
O
O
O
O
O
NH2
CN
7f
a
Isolated yield
123

7848
F. Mohamadpour et al.
O
NH2NH2 .H2O
+
+
O
O
Ar
9
N
O
Cu(OAc)2.H2O (20 mol %)
Solvent free, 80 °C
CN
N
8
CN
NH2
O
Ar CHO
CN
2
(11a-o)
10
Scheme 3 Synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives
Table 5 Optimization of the reaction condition for the synthesis of pyrazolo[1,2-b]phthalazine-5,10-
dione 11a
O
O
Ph
CN
CN
N
N
O
+
NH2NH2 .H2O
CN
NH2
Ph CHO
+
+
O
O
Entry
Cu(OAc)2ÁH2O
Time (h)
Isolated
yields (%)
(mol%)
1
2
3
4
5
6
Catalyst-free
10
7
–
46
58
72
83
84
5
10
15
20
25
5
4
3
3
Reaction conditions: phthalic anhydride, hydrazine monohydrate, aromatic aldehydes derivatives and
malononitrile (1:1:1:1) and copper(II) acetate monohydrate were heated at 80 °C for the appropriate time
addition, the use of solvent-free conditions with excellent yields and short reaction
times are notable advantages of this presented methodology.
Experimental
General
Melting points of all compounds were determined using an Electrothermal 9100
apparatus. Also, proton nuclear magnetic resonance (1H NMR) analyses were
recorded on a Bruker DRX-400 Avance instrument with deuterated dimethyl
sulfoxide (DMSO-d6 ) as a solvent. In this article, all reagents and solvents were
purchased from Merck, Fluka and Acros chemical companies and were used without
further purification.
123

Copper(II) acetate monohydrate: an efficient and…
7849
Table 6 Effect of the reaction temperature on the synthesis of 11a
O
O
O
Ph
CN
N
N
O
+
NH2NH2 .H2O
CN
NH2
Ph CHO
+
+
CN
O
Entry
Temperature (°C)
Time (h)
Isolated yields (%)
1
2
3
4
5
r.t.
40
12
8
–
47
69
83
83
60
5
80
3
100
3
Reaction conditions: phthalic anhydride, hydrazine monohydrate, aromatic benzaldehyde and malonon-
itrile (1:1:1:1) with copper(II) acetate monohydrate (20 mol%) were heated under various temperatures
for the appropriate time
Table 7 Copper(II) acetate monohydrate-catalyzed synthesis of pyrazolo[1,2-b]phthalazine-5,10-dione
derivatives under solvent-free conditions
Entry
Ar
Product
Time (h)
Isolated
yields (%)
M.p. °C
M.p. °C Ref.
1
C6H5
11a
11b
11c
11d
11e
11f
3
5
5
3
3
5
5
4
3
4
5
3
3
5
4
83
76
81
85
89
85
78
82
86
83
74
86
87
73
78
269–271
265–267
256–258
250–252
265–267
271–273
244–246
254–256
265–267
228–230
268–270
247–249
251–253
272–274
266–268
270–272 [21]
265–267 [18]
257–259 [20]
250–252 [21]
264–266 [22]
269–271 [20]
244–246 [21]
253–255 [20]
263–265 [18]
228–229 [20]
270–272 [18]
248–251 [18]
253–255 [21]
270–272 [21]
266–267 [18]
2
4-Br–C6H4
2-Cl–C6H4
3-Me–C6H4
3-F–C6H4
3
4
5
6
3-O2N–C6H4
C4H3S
7
11g
11h
11i
8
3,4,5-(OMe)3–C6H2
4-F–C6H4
9
10
11
12
13
14
15
4-O2N–C6H4
3-Br–C6H4
3-OMe–C6H4
4-Me–C6H4
4-OH–C6H4
3-Cl–C6H4
11j
11k
11l
11m
11n
11o
General procedure for preparation of spiro-4H-pyran derivatives (4a–f)
and (8a–f)
A mixture of isatin/acenaphthoquinone (1.0 mmol), malononitrile (1.0 mmol) and
1,3-dicarbonyl compounds/4-hydroxycumarin/naphthlol 3 (1.0 mmol) in the pres-
ence of copper(II) acetate monohydrate as a mild, environmentally benign and
natural catalyst under thermal and solvent-free conditions was heated for the
123

7850
F. Mohamadpour et al.
Table 8 Comparison of the catalytic ability of some catalysts reported in the literature for the synthesis
of spiro-4H-pyran 4a
Entry
Catalyst
Conditions
Time/yield (%)
References
1
2
3
4
5
6
b-Cyclodextrin
Lipase
H2O, heating
5 h/90
[12]
EtOH, heating
EtOH, reflux
3 h/94
[13]
Carbon–SO3H
Et3N
3 h/81
[15]
EtOH, reflux
4 h/80
[16]
InCl3
MeCN, reflux
Solvent-free, heating
90 min/75
4 h/86
[23]
Cu(OAc)2ÁH2O
This work
Based on the three-component reaction of isatin, malononitrile and dimedone
Table 9 Comparison of the catalytic ability of some catalysts reported in the literature for the synthesis
of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives
Entry
Catalyst
Conditions
Time/yield (%)
References
1
2
3
4
5
6
NiCl2Á6H2O
CuI nanoparticles
InCl3
EtOH, reflux
3 h/87
[19]
MeCN, reflux
27 min/91
1.5 h/85
20 min/94
3 h/94
[21]
Water, reflux
[22]
STA
Solvent-free, heating
[Bmim]Br, heating
Solvent-free, heating
[24]
PTSA
[26]
Cu(OAc)2ÁH2O
3 h/83
This work
Based on the four-component reaction of benzaldehyde, phthalic anhydride, hydrazine monohydrate and
malononitrile
appropriate time. After completion of the reaction [as determined by thin layer
chromatography (TLC)], the mixture was cooled to room temperature (rt), the solid
products were filtered and then were recrystallized from ethanol to give pure
compounds (4a–f) and (7a–f). All products were characterized by comparison of
spectroscopic data (1HNMR). Spectra data of selected and known products are
represented below:
7-Amino-1,3-dimethyl-5-nitro-2,2,4-trioxo-1,2,3,4-tetra-hydrospiro[indoline-3,5-
pyrano[2,3-d]pyrimidine]-6-carbonitrile (4a) mp: 288–290 °C; 1H NMR
(400 MHz, DMSO-d6): 1.00 (3H, s, CH3), 1.03 (3H, s, CH3), 2.07–2.19 (2H, m,
CH2), 2.50–2.57 (2H, m, CH2), 6.79 (1H, d, J = 7.2 Hz, ArH), 6.89 (1H, t,
J = 7.2 Hz, ArH), 6.98 (1H, d, J = 6.8 Hz, ArH), 7.13 (1H, t, J = 6.4 Hz, ArH),
7.22 (2H, s, NH2), 10.38 (1H, s, NH).
2-Amino-7,7-dimethyl-2,5,6,7,8-tetrahydro-2H-spiro[acenaphthylene-1,4-chromene]-
3-carbonitrile (7a) mp: 270–272 °C; 1H NMR (400 MHz, DMSO-d6): 1.02 (3H, s,
CH3), 1.04 (3H, s, CH3), 2.04–2.13 (1H, m, CH2), 2.50–2.51 (1H, m, CH2), 2.63
(2H, s, CH2), 7.32 (2H, s, NH2), 7.37–7.85 (6H, m, ArH).
123

Copper(II) acetate monohydrate: an efficient and…
7851
General procedure for preparation of pyrazolo[1,2-b]phthalazine-5,10-
dione derivatives (11a–o)
A mixture of phthalic anhydride (8, 1.0 mmol), hydrazine monohydrate (9,
1.0 mmol) and copper(II) acetate monohydrate was heated for 2 h at 80 °C. Then,
aromatic aldehyde (10, 1.0 mmol) and malononitrile (12, 1.0 mmol) were added
and the mixture was heated for the appropriate time. After completion of the
reaction (as per TLC), the mixture was cooled to rt, the solid products were filtered
and then were recrystallized from ethanol to give pure compounds (11a–o). All
products were characterized by comparison of spectroscopic data (1HNMR).
Spectra data of selected and known products are represented below:
3-Amino-1-(2-thenaldehyde)-5,10-dihydro-5,10-dioxo-1H-pyrazolo[1,2-b]phtha-
lazine-2-carbonitrile (11g) mp: 244–246 °C; 1H NMR (400 MHz, DMSO-d6):
6.09 (1H, s, CHAr), 6.88–7.30 (4H, m, ArH), 7.96–8.28 (6H, m, NH2 and ArH).
3-Amino-1-(3,4,5-trimethoxyphenyl)-5,10-dihydro-5,10-dioxo-1H-pyrazolo[1,2-
b]phthalazine-2-carbonitrile (11h) mp: 254–256 °C; 1H NMR (400 MHz, DMSO-
d6): 3.66 (3H, s, OCH3), 3.76 (6H, s, 2 OCH3), 6.07 (1H, s, CHAr), 6.78 (2H, s,
ArH), 7.89–8.29 (6H, m, NH2 and ArH).
3-Amino-1-(4-fluorophenyl)-5,10-dihydro-5,10-dioxo-1H-pyrazolo[1,2-b]phtha-
lazine-2-carbonitrile (11i) mp: 265–267 °C; 1H NMR (400 MHz, DMSO-d6):
6.17 (1H, s, CHAr), 7.20 (2H, t, J = 8.8 Hz, ArH), 7.53–7.57 (2H, m, ArH),
7.96–8.26 (6H, m, NH2 and ArH).
3-Amino-1-(3-methoxyphenyl)-5,10-dihydro-5,10-dioxo-1H-pyrazolo[1,2-b]phtha-
lazine-2-carbonitrile (11l) mp: 247–249 °C; 1H NMR (400 MHz, DMSO-d6):
3.34 (3H, s, OCH3), 6.09 (1H, s, CHAr), 6.88–7.30 (4H, m, ArH), 7.83–8.26 (6H, m,
NH2 and ArH).
3-Amino-1-(4-methylphenyl)-5,10-dihydro-5,10-dioxo-1H-pyrazolo[1, 2-b]phtha-
1
lazine-2-carbonitrile (11m) mp: 251–253 °C; H NMR (400 MHz, DMSO-d6):
2.30 (3H, s, CH3), 6.10 (1H, s, CHAr), 7.18 (2H, d, J = 8.0 Hz, ArH), 7.34 (2H, d,
J = 8.0 Hz, ArH), 7.97–8.28 (6H, m, NH2 and ArH).
Conclusion
In summary, we have studied an efficient, environmentally benignm, natural and
economical catalyst for the one-pot, multi-component synthesis of spiro-4H-pyran
derivatives and pyrazolo[1,2-b]phthalazine-5,10-dione derivatives. Copper(II)
acetate monohydrate catalyzed synthesis of these bioactive compounds under
solvent-free and thermal conditions. The notable advantages of this methodology
are its use of a mild, non-toxic and inexpensive catalyst, its excellent yields and
short reaction times, its highly efficient yields, environmentally benign nature and
one-pot and solvent-free conditions.
123

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F. Mohamadpour et al.
Acknowledgments We gratefully acknowledge financial support from the Research Council of the
University of Sistan and Baluchestan.
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