A four-component synthesis of dihydropyrano[2,3-c]pyrazoles in a new water-based worm-like micellar medium

Article abstract of DOI:10.1016/j.tetlet.2014.04.122

Cocamidopropyl betaine (CAPB) as a biodegradable surfactant produces a new worm-like micellar medium for rapid synthesis of dihydropyrano[2,3-c]pyrazoles via a four-component reaction of aldehydes, ethyl acetoacetate, malononitrile, and hydrazine hydrate

Full text of DOI:10.1016/j.tetlet.2014.04.122

Accepted Manuscript
A four-component synthesis of dihydropyrano[2,3-c]pyrazoles in a new water-
based worm-like micellar medium
Fatemeh Tamaddon, Masoomeh Alizadeh
PII:
S0040-4039(14)00759-X
DOI:
http://dx.doi.org/10.1016/j.tetlet.2014.04.122
TETL 44584
Reference:
To appear in:
Tetrahedron Letters
Received Date:
Revised Date:
Accepted Date:
28 December 2013
14 April 2014
30 April 2014
Please cite this article as: Tamaddon, F., Alizadeh, M., A four-component synthesis of dihydropyrano[2,3-
c]pyrazoles in a new water-based worm-like micellar medium, Tetrahedron Letters (2014), doi: http://dx.doi.org/
1
0.1016/j.tetlet.2014.04.122
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A four-component synthesis of dihydropyrano[2,3-c]
pyrazoles in a new water-based worm-like micellar medium
Fatemeh Tamaddon*, Masoomeh Alizadeh
H
2
O
-
-
-
-
H O
2
H O
2
-
-
-
Hydrophilic medium
-
+
+
+
+
-
-
Hydrophobic core
Ph
+
+
+
O
+
CN
+
-
Ph
H
+
+
-
-
Me
Me
H
2
O
C
N
Ph
O
H
-
+
+
+
+
H
2
O
CN
NH
O
CN CAPB (0.02 mol%)
-
-
+
+
+
-
N
CN
H O, 50-60 °C
2
+
NH
+
+
O
Me
-
N
H
O
2
+
N
-
H O
+
+
EtO
H NNH .H O
2
2
2
-
+ + +
+
+
2
-
-
-
-
-
-
H O
2
-
-
2
H O

Tetrahedron Letters
1
TETRAHEDRON
LETTERS
Pergamon
A four-component synthesis of dihydropyrano[2,3-c]pyrazoles in
a new water-based worm-like micellar medium
*
Fatemeh Tamaddon , Masoomeh Alizadeh
Department of Chemistry, Yazd University, Yazd 89195-741, Iran
Abstract—Cocamidopropyl betaine (CAPB) as a biodegradable surfactant produces a new worm-like micellar medium for rapid synthesis
of dihydropyrano[2,3-c]pyrazoles via a four-component reaction of aldehydes, ethyl acetoacetate, malononitrile, and hydrazine hydrate at
5
0-60 °C. This zwitterionic surfactant was superior to anionic, cationic, and nonionic alternatives for accessing high yields of pure products
without the use of any organic solvent. While the reaction medium was reusable, simple isolation of products, mild reaction conditions, low
loading of CAPB for critical micelle concentration and short reaction times are additional advantages of this green procedure © 2014
Elsevier Science. All rights reserved
Advances in multicomponent reactions (MCRs) have
resulted in the rapid access to large libraries of bioorganic
molecules, the development of molecular designs, and
improvements in combinatorial chemistry. Due to the
OH
OH
1
O
Me
N
Me
N
benefits of MCRs, their combination with aqueous media
constitutes one of the highlighted subclasses of ideal
synthesis.
CN
NH
CN
NH
2
N
H
N
H
O
2
O
2
A
B
Despite its unique properties, the instability and low
solubility of organic compounds in water have restricted its
use as a solvent. These problems can be overcome by
3
Figure 1. Biologically active dihydropyrano[2,3-c]-pyrazoles: (A)
molluscicide, (B) inhibitor of human chk1 kinase.
4
5
using organic co-solvents, surfactants, hydrophilic
auxiliaries, and pH adjustment. Among these, surfactants
6
Pyranopyrazoles have been synthesized via the reaction of
tetracyanoethylene with 3-methyl-1-phenylpyrazolin-5-
one, or by the three-component reaction of a pyrazolone,
are very promising due to the reduction of water surface
tension,
7
17
superior dispersion/interaction of organic
8
18
compounds in water, and their role as phase-transfer
catalysts or micelle producers. Although surfactants are
categorized as nonionic, anionic, cationic, gemini, nano,
carbonyl compounds, and malononitrile. Recently, four-
component reactions of aldehydes, 1,3-dicarbonyl
compounds, malononitrile, and hydrazine have been
9
19
developed for the synthesis of pyranopyrazoles using L2 -2
and zwitterionic, the latter is more advantageous owing to
20
21
the presence of both cationic and anionic regions in a
molecule, large dipole moment, solubility at various pHs,
salinities, and lower critical micelle concentrations (CMC).
Moreover, zwitterionic surfactants create flexible micelles
with various spherical, cylindrical, bilayers, vesicles,
proline,
piperidine,24 morpholine,
triethylamine,
2
3
imidazole2, γ-alumina, cetyltrimethylammonium chloride
5
26
27
and glycine. However, more efficient
(CTACl),
I
2
,
syntheses of pyranopyrazoles using biocompatible catalysts
are desirable.
10
worm-like, and reverse shapes.
Cocamidopropyl betaine (CAPB) is a biodegradable
zwitterionic surfactant with viscoelastic properties that
1
1
12
13
28
The anti-inflammatory, molluscicidal, antimicrobial,
anticancer, fungicidal, analgesic, vasodilator, hypotensive,
self-assembles into flexible worm-like micelles, and
increases the viscosity of water via a fluid-like polymeric
1
4
15
hypoglycemic,
dihydropyrano[2,3-c]pyrazoles has resulted in the
development of their synthesis as one of the important
and kinase inhibitor properties
of
2
9
transient network. These significant properties result from
the presence of both positive and negative charges in the
molecule (Figure 2). CAPB has been used as a foam
booster, an28 emulsifier, an antistatic agent in hair
16
research topics of medicinal chemistry (Figure 1).
30
conditioners, and as carrier vehicles for drug delivery.
———
Corresponding author. Tel.: 00983518122666; fax: 00983518210644; e-mail:ftamaddon@yazduni.ac.ir.
*

2
Tetrahedron Letters
with previously reported water-based methods shows the
merit of the present protocol (Table 2).
O
CH3
N
O
C18H37
N
H
O
CH3
Table 1
Optimization of the reaction conditions
Figure 2. Cocamidopropyl betaine.
The unique properties of CAPB prompted us to use it in the
green synthesis of pyranopyrazoles via the four-component
reaction of aldehydes, ethyl acetoacetate, malononitrile,
and hydrazine hydrate in water at 50-60 °C (Scheme 1). To
the best of our knowledge, this is the first use of CAPB as a
catalyst or surfactant in aqueous organic reactions.
O
O
Me
Me
O
H
CN
CN
O
CN
NH
1
a
Conditions
2
N
+
O
OEt
3
H O
2
N
H
O
2
H
2
NNH
2
.H
2
O
A
4
Entry
Conditions
Time
Yield
(%)
74
R
Surfactant (type/mol%)/Temp. (°C)
-
a
CTAB (cationic/0.05)/50-60
b
SDS (anionic/0.05)/50-60
c
TritonX-100 (non-ionic/0.05)/50-60
(min)
260
110
65
25
40
35
10
8
R
Me
Me
N
H
O
1
2
3
4
5
6
7
8
9
CN
CN
CN
84
O
CAPB (0.02 mol%)
O, 50-60 °C
+
94
H
2
O
OEt
H NNH .H O
N
O
NH
2
90
H
R = Ar or aliphatic
d
TritonX-114 (non-ionic/0.05)/50-60
2
2
2
92
PEG-400 (non-ionic/0.05)/50-60
CAPB (zwitterionic/0.05)/50-60
CAPB (zwitterionic/0.04)/50-60
CAPB (zwitterionic/0.03)/50-60
CAPB (zwitterionic/0.02)/25-30
82
Scheme 1. CAPB-catalyzed synthesis of dihydro[2,3-c]pyranopyrazoles.
98
93
To optimize the conditions for the synthesis of the
dihydropyrano pyrazole A as a molluscicide, condensation
of furfural (1a), malononitrile, ethyl acetoacetate, and
hydrazine hydrate in the molar ratio 1:1:1:2 in water was
selected as a model reaction and screened with various
types of surfactants. As Table 1 shows, the best yield of 6-
amino-4-(furan-2-yl)-1,4-dihydro-3-methylpyrano[2,3-
c]pyrazole-5-carbonitrile (A) was obtained after two
minutes from the reaction with 0.02 mol% of CAPB in
water at 50-60 °C (Table 1, entry 11). The precipitated
product formed during the reaction was isolated in high
purity by addition of cold water and filtration. For a
reusability test, after completion of a model reaction in 10
mmol scale, the mixture was cooled and filtered. The
filtrate was used as the recycled reaction medium in the
second reaction run and compound A was isolated in the
same yield without significant changes in the reaction time
8
95
1
1
0
1
18
2
88
e
CAPB (zwitterionic/0.02)/50-60
95
f
12
13
14
CAPB (zwitterionic/0.02)/50-60
4
95
g
CAPB (zwitterionic/0.02)/50-60
8
94
CAPB (zwitterionic/0.02)/70-80
CAPB (zwitterionic/0.02)/80-90
12
15
97
1
a
5
90
Cetyltrimethylammonium bromide.
Sodium dodecyl sulfonate.
b
c
Polyethylene glycol p-(1,1,3,3-tetramethylbutyl)-phenyl ether
O) ) with average 9.5 ethylene oxide units.
O(CH CH
For the first reaction run.
For the reused reaction medium in the second run
For the reused reaction medium in the third run.
(
C
14
H
22O(C
2
H
4
n
d
C
8
H
18
C
6
H
4
2
2
O)7.5.
e
f
g
Table 2
Comparison of the efficiency of CAPB with other catalysts in water
(
Table 1, entries 11-13).
Ph
Me
From a mechanistic point of view, condensation of
hydrazine hydrate (4) with ethyl acetoacetate (2) and
subsequent tautomerization results in the formation of
enolate 8, while Knoevenagel condensation of
malononitrile (3) with furfural (1) provides the intermediate
CN
Conditions
PhCHO
Entry
+
2
+
3
+ 4
N
2
H O
N
H
O
NH2
Conditions
Isolated yield
Ref.
(%)
23
89
Catalyst/Temp./Time/(mol%/°C/min)
imidazole (50/80/20)
I2 (5/25/5)
6
. Michael addition of the intermediate 8 to electron-
deficient alkene generates intermediate 9, which
undergoes intramolecular cyclization to give the
pyranopyrazole A. This explanation is presented in Scheme
1
2
3
4
5
6
7
9
2
6
6
89
90
91
62
80
89
76
90
20
L-proline (5/reflux/10)
piperidine (10/r.t./5)
morpholine (10/r.t./30)
γ-alumina (10/reflux/50)
CTACl (20/90/240)
no catalyst (100/240)
glycine (2/r.t./5)
21
21
2.
24
25
Comparison of the results of the CAPB-catalyzed reaction
of benzaldehyde (1 mmol), malononitrile (1 mmol), ethyl
acetoacetate (1 mmol), and hydrazine hydrate (2 mmol)
19
27
1
1
0
1
CAPB (0.02/50-60/4)
96 this work

Tetrahedron Letters
3
O
O
C
N
H
6 CN
H2O
H2O
H
O
H2O
-
-
-
NH
-
H2O
-
-
-
N
7
-
+
+ +
+
H2O
+
O
-
+
+
NH
-
+
+
-
N
+
+
+
+
+
+
+
8
-
-
-
H
O
H2O
H2O
H2O
O
Hydrophobic
core
1
a
Me
N
-
O
CN CAPB (0.02 mol%)
H2O, 50-60 °C
CN
CN
+
-
2
+
-
+
+
-
O
OEt
3
H2O
+
+
-
C
+
+
-
N
H
H2NNH2.H2O
O
-
+ + + +
+
-
4
-
NH
-
H2O
9
H2O
-
-
-
-
H2O
H2O
Hydrophilic medium
O
O
H
Me
Me
N
CN
CN
N
N
H
NH2
N
O
NH2
O
5
Scheme 2. Cross section of the proposed worm-like micelle for CAPB in water.
To a mixture of aldehyde (2 mmol), malononitrile (2
mmol), ethyl acetoacetate (2 mmol), and hydrazine hydrate
(4 mmol) was added CAPB (0.02 mol%) in H O (1.5 mL)
and the mixture was stirred at 50-60 °C for the given times
(Table 3). After completion of the reaction (TLC
The superiority of CAPB in water is reflected in the short
reaction times and high product yields. The exceptional
properties of CAPB are responsible for this superiority and
the catalytic performance of CAPB can be due to the
formation of high performance viscoelastic worm-like
micelles that increase the polarity and viscosity of water
to provide a favorable medium to interaction of the organic
reactants or intermediates.
2
monitoring), cold H
product was filtered off and washed with H
2
O was added and the precipitated
O to give the
1
0
2
product. The structures of the dihydropyrano[2,3-
c]pyrazole products 5a-r were identified by comparison of
the spectroanalytical data those reported in the literature
(Table 3).
To check the scope and efficiency of the CAPB surfactant,
the reaction was performed under the optimized conditions
using various substituted aromatic, heteroaromatic, and
aliphatic aldehydes in water. The reactions proceeded
rapidly for aromatic aldehydes with electron-withdrawing
or electron-donating groups at different positions of the
ring (Table 3, entries 1-16) and the desired products were
isolated in excellent yields without any side product
formation in very short reaction times. While a few reports
are available on the synthesis of pyranopyrazoles from
1
6,24
aliphatic aldehydes,
enolizable aldehydes such as
acetaldehyde and butyraldehyde gave the desired products
in excellent yields (Table 3, entries 17 and 18).
In conclusion, this protocol offers benefits for the rapid
MCR synthesis of dihydropyrano[2,3-c]pyrazoles using
cocamidopropyl betaine (CAPB) as a biodegradable
surfactant in a new water-based worm-like micellar
medium at 50-60 °C. This zwitterionic surfactant was
superior to anionic, cationic, and nonionic surfactants for
access to pure products without the use of any organic
solvent. In addition, the reaction medium can be recycled.
General procedure for the preparation of 6-amino-1,4-
dihydro-3-methyl-4-substitutedpyrano[2,3-c]pyrazole-5-
carbonitriles

4
Tetrahedron Letters
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R
1
17; (g) Slobbe, P.; Ruijter, E.; Orru, R. V. A. Med. Chem.
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Me
Ph
Me
N
H
O
1
CN
CN
CN
O
CAPB (0.02 mol%)
4
2
+
H O , 50-60 °C
2
O
OEt
3
N
H
O
NH2
Synth. 2013, 10, 564.
2
.
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H NNH .H O
2
5a-r
2
2
4
Entry
R
Product Time
Yield Mp (°C)
a
Ref
(Lit.)
(
min) (%)
1
2
3
4
5
6
7
8
9
2-furyl
5a
5b
5c
5d
5e
5f
2
95
96
95
91
95
95
90
89
97
95
87
85
88
94
93
95
90
91
171-173
3
1
4
4
2
2
4
1
3
1
4
4
1
4
3
1
3
1
4
(
175-177)
C
6
H
5
4
244-246
2
2
3
3
2
3
3
3
2
2
3
2
1
3
3
3
2
(
244-245)
248-250
251-252)
221-225
222-224)
190-193
190-192)
234-236
234-235)
146-148
145-147)
175-178
176-177)
171-172
170-171)
223-224
223-224)
205-208
206-208)
171-173
170-172)
210-212
210-212)
223-225
223-224)
204-208
208-209)
225-228
220-223)
155-158
158-160)
140-142
143-145)
4-O
2-O
3-O
2
NC
6
6
6
H
H
H
4
4
4
3
(
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2
NC
NC
3
(
4
.
Elinson, M. N.; Ilovaisky, A. I; Merkulova, V. M.; Belyakov,
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931.
2
5
(
(
4-ClC
2-ClC
3-ClC
6
6
6
H
H
H
4
4
4
5
(
9
5g
5h
5i
5
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(
5
(
4-FC
6
H
4
4
(
1
1
1
1
1
1
1
1
0
1
2
3
4
5
6
7
8
3-BrC
6
H
4
5j
5
6
.
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(
2
4-H
3
CC
CC
6
6
H
4
4
5k
5l
9
7
.
(
3-H
3
H
9
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(
4-MeOC
6
H
4
5m
5n
5o
5p
5q
5r
9
(
4-HOC
2-HOC
3-HOC
6
6
6
H
4
H
4
H
4
5
(
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(
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CH
3
3
18
15
(
1
CH
2 2
CH CH
(
5
43.
a
All products were isolated in high purity by a simple filtration.
1
1
1
3. Makawana, J. A.; Mungra, D. C.; Patel, M. P.; Patel, R. G.;
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Acknowledgment
We acknowledge the research council of Yazd University.
2
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5
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