Tandem cyclocondensation-Knoevenagel-Michael reaction of phenyl hydrazine, acetoacetate derivatives and arylaldehydes

Article abstract of DOI:10.1039/c4nj01079e

In this work, a novel N-bromo sulfonamide reagent, namely N,2-dibromo-6-chloro-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine-7-sulfonamide 1,1-dioxide (DCDBTSD), is synthesized and fully characterized by IR, UV, ¹H and ¹³C NMR, XRD, TG/DTG as well as mass spectra. The presented N-bromo sulfonamide is used as a new and highly efficient catalyst for the synthesis of 4,4′-(arylmethylene)-bis(3-methyl-1-phenyl-1H-pyrazol-5-ol)s via one-pot pseudo five component condensation reaction of phenylhydrazine, acetoacetate derivatives and arylaldehydes. Mechanistically, Br⁺ ions, which are generated by the catalyst, can catalyze this reaction in neutral media. This methodology offers several advantages, such as use of non-toxic and inexpensive materials, high yields, short reaction times and clean workup.

Full text of DOI:10.1039/c4nj01079e

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Tandem cyclocondensation-Knoevenagel–Michael
reaction of phenyl hydrazine, acetoacetate
derivatives and arylaldehydes†
Cite this:DOI: 10.1039/c4nj01079e
a
a
b
Ardeshir Khazaei,* Fatemeh Abbasi and Ahmad Reza Moosavi-Zare*
In this work, a novel N-bromo sulfonamide reagent, namely N,2-dibromo-6-chloro-3,4-dihydro-2H-
benzo[e][1,2,4]thiadiazine-7-sulfonamide 1,1-dioxide (DCDBTSD), is synthesized and fully characterized by
1
13
IR, UV, H and C NMR, XRD, TG/DTG as well as mass spectra. The presented N-bromo sulfonamide is
Received (in Porto Alegre, Brazil)
0
2
8th June 2014,
used as a new and highly efficient catalyst for the synthesis of 4,4 -(arylmethylene)-bis(3-methyl-1-
Accepted 13th August 2014
phenyl-1H-pyrazol-5-ol)s via one-pot pseudo five component condensation reaction of phenylhydrazine,
+
acetoacetate derivatives and arylaldehydes. Mechanistically, Br ions, which are generated by the catalyst,
DOI: 10.1039/c4nj01079e
can catalyze this reaction in neutral media. This methodology offers several advantages, such as use of
non-toxic and inexpensive materials, high yields, short reaction times and clean workup.
www.rsc.org/njc
1
4
15
16
17
such as [Dsim] AlCl
(
4
,
[pyridine–SO
3
H]Cl, THSB, SASPSPE,
1
. Introduction
18
AP-SiO2) and N-(3-silicapropyl)-N-methyl imidazolium hydrogen
19
Multi-component reactions (MCRs) play an important role in sulfate ([Sipmim]HSO4). However, some of the reported methods
combinatorial chemistry because of the ability to synthesize suffer from some disadvantages such as low yield, long reaction
target compounds with greater efficiency and atom economy by time, toxic and corrosive solvent, strong acidic and basic media,
generating structural complexity in a single step from three or and use of toxic, corrosive, expensive and large amounts of
more reactants. Also, MCRs offer some advantages of simplicity catalysts. However, limited methods have been reported for the
1
–3
and synthetic efficiency over conventional chemical reactions
and lead to the formation of interesting heterocyclic rings.
synthesis of these compounds by one-pot pseudo five component
condensation reaction of phenylhydrazine, acetoacetate derivatives
20,21
Heterocycles are popularly known for displaying a wide range of and arylaldehydes.
biological properties, and among the heterocyclic ring systems, pounds, the introduction of a milder, faster and more eco-friendly
pyrazolone derivatives have a wide range of unique biological method accompanied with higher yields is still needed.
Because of the importance of these com-
4
activities. Some of the pyrazolone derivatives are an interesting
A large group of compounds generically called N-halo
class of bioactive drugs in the pharmaceutical and agrochemical reagents are used as potentially reactive intermediates. These
0
industry. Among them, bis(pyrazolyl)methanes including 4,4 -(aryl- compounds are widely applied in organic transformations and
methylene)-bis(3-methyl-1-phenyl-1H-pyrazol-5-ol)s are applied as in the chemistry of natural compounds. Some specific features
5
6
7
anti-inflammatory, antipyretic, gastric secretion stimulatory,
of N-halo reagents including the high activity of the N–X bond
8
9
10
antidepressant, antibacterial and antifilarial agents. Moreover, and the various modes of splitting of this bond have led to their
these compounds have been used as fungicides, pesticides
11
12
22
wide application in organic synthesis. Based on the above facts and
13
and insecticides.
in continuation of our previous studies on the application of N-halo
0
23–31
The most common protocol for the preparation of 4,4 -(aryl- reagents in organic synthesis,
we have recently introduced
methylene)-bis(1H-pyrazol-5-ol)s is three-component condensa- a new N-halo reagent, namely N,2-dibromo-6-chloro-3,4-dihydro-2H-
tion reaction of aldehydes with 3-methyl-1-phenyl-5-pyrazolone. benzo[e][1,2,4]thiadiazine-7-sulfonamide 1,1-dioxide (DCDBTSD), as
This protocol was reported in the presence of various catalysts an efficient and novel catalyst (Scheme 1 and Fig. 1).
Herein, we have utilized N,2-dibromo-6-chloro-3,4-dihydro-
2
H-benzo[e][1,2,4]thiadiazine-7-sulfonamide 1,1-dioxide as an efficient
a
Faculty of Chemistry, Bu-Ali Sina University, Hamedan 6517838683, Iran.
E-mail: Khazaei_1326@yahoo.com; Fax: +98 8138257407; Tel: +98 8138282807
Department of Chemistry, University of Sayyed Jamaleddin Asadabadi, Asadabad,
0
and homogeneous catalyst for the synthesis of 4,4 -(arylmethylene)-
bis(3-methyl-1-phenyl-1H-pyrazol-5-ol)s via one-pot pseudo five
component condensation reaction of phenyl hydrazine (2 eq.)
and b-ketoester derivatives (2 eq.) with aromatic aldehydes
b
6
541835583, Iran. E-mail: moosavizare@yahoo.com; Fax: +98 81323237451;
Tel: +98 81323237450
†
Electronic supplementary information (ESI) available. See DOI: 10.1039/c4nj01079e (1 eq.) at 80 1C under solvent-free conditions (Scheme 2).
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Scheme 1 The preparation of N,2-dibromo-6-chloro-3,4-dihydro-2H-
benzo[e][1,2,4]thiadiazine-7-sulfonamide 1,1-dioxide (DCDBTSD).
Fig. 2 IR spectra of (a) DCDBTSD and (b) hydrochlorothiazide.
Fig. 1 The structure of N,2-dibromo-6-chloro-3,4-dihydro-2H-benzo[e]-
[1,2,4]thiadiazine-7-sulfonamide 1,1-dioxide (DCDBTSD).
Fig. 3 TG/DTG diagrams of DCDBTSD.
multi-stage decomposition pattern in DCDBTSD. Therefore,
DCDBTSD could be used as catalyst below 200 1C, and it
decomposes above 255 1C.
XRD patterns of the catalyst (DCDBTSD) were studied in the
domain of 5–901 (Fig. 4). As shown in Fig. 4, XRD patterns
exhibited diffraction lines of a high crystalline nature at 2y E
0
Scheme 2 The synthesis of 4,4 -(arylmethylene)-bis(3-methyl-1-phenyl-
1
H-pyrazol-5-ol)s using DCDBTSD.
9
5
.201, 18.501, 20.801, 27.901, 29.501, 33.701, 38.801, 47.501, and
8.701 and several small lines in the 25–601 range.
2
. Results and discussion
After full characterization of DCDBTSD, we examined the catalytic
activity of the catalyst in the preparation of 4,4 -(arylmethyl-
1
13
0
The structure of DCDBTSD was studied by IR, UV, H and
C
NMR, XRD, TG/DTG as well as mass spectra. The spectral data ene)-bis(3-methyl-1-phenyl-1H-pyrazol-5-ol)s. For this purpose, the
are as follows: IR (KBr): 3377, 3232, 1579, 1495, 1362, 1308, condensation of ethylacetoacetate (2 mmol) and phenyl hydrazine
ꢀ1 1
1
(
(
244, 1147, 1058, 1025, 794, 716, 675, 579, 545 cm ; H NMR (2 mmol) with 4-chlorobenzaldehyde (1 mmol), as a model reaction,
400 MHz, DMSO-d ): d (ppm) 4.70 (s, 2H), 6.85 (s, 1H), 7.20
s, 1H), 7.88 (s, 1H), 8.07 (s, 1H); C NMR (100 MHz, DMSO-d6):
6
1
3
d (ppm) 55.08, 107.26, 110.65, 122.57, 127.55, 136.34, 142.14;
+
MS: m/z = 455 (M ). The IR spectrum of the catalyst and
hydrochlorothiazide has been depicted in Fig. 2. Comparison
of hydrochlorothiazide and DCDBTSD spectra illustrated that
two sharp peaks of N–H groups of hydrochlorothiazide at 3363
ꢀ
1
and 3169 cm were eliminated in DCDBTSD. These differences
prove that the sulfonamide hydrogen of N–H groups in hydro-
chlorothiazide is replaced with two N–Br groups in DCDBTSD.
In another study, thermal gravimetric (TG) and derivative
thermal gravimetric (DTG) analyses of DCDBTSD were carried
out in the range of 30–618 1C, with a rate of temperature increase
ꢀ1
of 10 1C min in a nitrogen atmosphere. The corresponding
diagrams are shown in Fig. 3. In the TG pattern, we observed a chlorothiazide.
Fig. 4 XRD patterns of DCDBTSD in comparison with that of hydro-
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Table 1 Optimization of the amount of DCDBTSD and the reaction are summarized in Table 2. As Table 2 indicates, all aldehydes
0
temperature for the preparation of 4,4 -((4-chlorophenyl)methylene)-
(
including benzaldehyde and arylaldehydes bearing halogens,
bis(3-methyl-1-phenyl-1H-pyrazol-5-ol)
electron-withdrawing substituents) were successfully reacted
with 3-methyl-1-phenyl-5-pyrazolone derivatives (obtained from the
reaction of b-ketoester and phenyl hydrazine) to produce the corres-
Catalyst
a
amount Temperature Time Yield
(mol%) (1C) (min) (%)
Entry Catalyst
0
ponding 4,4 -(arylmethylene)-bis(3-methyl-1-phenylpyrazol-5-ol)
1
2
3
4
5
6
7
8
9
1
1
1
No catalyst
Hydrochlorothiazide 10
HBr
—
80
80
80
80
80
80
80
80
60
70
90
100
180
180
180
50
60
40
50
50
120
90
40
42
34
45
65
70
80
77
75
60
70
78
75
derivatives in good to excellent yields and in relatively short
reaction times. The presented method was successfully used for
arylaldehydes with various groups in different positions such as
halides, nitro and naphthyl.
20
5
7.5
10
12.5
15
10
10
10
10
DCDBTSD
DCDBTSD
DCDBTSD
DCDBTD
DCDBTSD
DCDBTSD
DCDBTSD
DCDBTSD
DCDBTSD
0
1
2
40
a
Isolated yield.
was examined in the presence of different quantities of DCDBTSD,
in the range of 60–100 1C under solvent-free conditions (Scheme 1).
The results are displayed in Table 1. As Table 1 indicates, higher
yield and shorter reaction time were obtained using 10 mol% of the
catalyst at 80 1C under solvent-free conditions. No improvement in
the reaction results was observed on increasing the amount of the
catalyst and the temperature. Also, the solvent-free condensation was
examined at 80 1C without catalyst, with hydrochlorothiazide and
hydrobromic acid and it was observed that the reaction did not
progress even after a long reaction time (3 h).
After optimization of the reaction conditions, to explore the
efficiency and the scope of the presented protocol, b-ketoester
derivatives (2 mmol) and phenyl hydrazine (2 mmol) were
treated with structurally diverse aromatic aldehydes in the
presence of DCDBTSD as catalyst. The corresponding results
0
Table 2 Synthesis of 4,4 -(arylmethylene)-bis(3-methyl-1-phenylpyrazol-
5-ol)s using DCDBTSD at 80 1C
a
Entry R Ar
Et
Time (min)/yield (%) M.p. (1C) (L)
1
4
1
2
3
4
5
6
7
8
9
1
1
1
1
1
1
1
1
1
1
2
2
2
C
6
H
5
100/74
90/75
45/71
35/73
50/85
60/82
40/80
50/81
100/77
35/77
70/80
80/79
40/76
55/78
40/76
105/75
65/83
70/80
40/80
95/79
85/74
70/73
160–162 (168–170)1
217–218 (221–223)
232–234
4
Et 2-NO
Et 3-NO
Et 4-NO
Et 2-ClC
Et 3-ClC
Et 4-ClC
Et 2,3-DiClC
Et 2,4-DiClC
Et 4-Cl-3-NO
Et 2-FC
Et 4-FC
Et 4-BrC
Et 4-CF
2
2
2
C
C
C
6
6
6
H
H
H
4
4
4
1
4
4
4
4
228–230 (229–231)1
6
6
6
H
H
H
4
235–236 (235–236)
1
4
4
153–154 (150–152)1
209–210 (213–215)
243–244
6
H
H
C
3
3
2
1
6
219–221 (227–229)1
5
0
1
2
3
4
5
6
7
8
9
0
1
2
2
6
H
4
232–235 (232–238)
157–159
6
H
H
4
1
9
6
4
180–181 (181–183)2
0
6
H
4
185–186 (183–184)
223–224
3
C
6
H
5
1
5
4
4
4
4
0
9
0
Et 2-Naphthyl
Me C
204–206 (203–207)1
6
H
5
160–162 (168–170)1
235–236 (235–236)
Me 2-ClC
Me 3-ClC
Me 4-ClC
Me 2,4-DiClC H
6 3
Me 4-FC
6
6
6
H
H
H
4
4
4
1
153–154 (150–152)1
209–210 (213–215)2
219–221 (227–229)1
180–181 (181–183)
6
H
4
2
Me 4-BrC
6
H
4
185–186 (183–184)
0
Scheme 3 The plausible mechanism for the synthesis of 4,4 -(arylmethyl-
ene)-bis(3-methyl-1-phenyl-1H-pyrazol-5-ol)s using DCDBTSD.
a
Isolated yield.
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ꢀ
1
Since DCDBTSD contains bromine atoms which are bonded to 3380 and 3253 cm (related to catalyst). This result proves that
+
nitrogen atoms in the heterocyclic ring, by in situ generation of Br
the catalyst was completely recovered during the reaction and the
from the catalyst, the reaction is catalyzed. So, in a proposed proposed mechanism was confirmed.
25,32–34
reaction mechanism which is supported by the literature,
UV spectra were another piece of evidence to confirm the
we suggest that b-ketoester and the catalyst produce intermediates production of activated forms (I and II or VI and V). UV studies
I and II (Scheme 3). Then, phenyl hydrazine attacks I and II and were recorded in tetrahydrofuran as solvent. The maximum of
intermediate III is obtained by the removal of one molecule of absorption for ethylacetoacetate, methylacetoacetate, benzaldehyde
alcohol and is then converted to IV after tautomerization. Inter- and catalyst appeared at 290, 290, 289 and 333 nm respectively.
mediate VII is formed via condensation of IV with VI or V (the But lmax of the complexes of ethylacetoacetate, methylacetoacetate
+
activated forms of aldehyde following reaction with catalyst). The and aldehyde with Br ions, which are generated by the addition
next step is the Michael addition of another intermediate of IV to of DCDBTSD to ethylacetoacetate, methylacetoacetate and benzal-
VII to give VIII. Finally, after the tautomeric proton shift, the dehyde, was observed at 281, 285 and 282 nm respectively (Fig. 6).
corresponding product and catalyst are obtained.
There are some references which confirm the regeneration
To prove the formation of intermediates I and II or VI and V, of N-halo reagents after the reaction. These references clearly
+
b-ketoester and benzaldehyde were reacted with catalyst at mention that the Br ion is connected again to the structure of
80 1C separately, and then IR and UV spectra of the carbonyl
groups in the reaction mixture were recorded and compared with
those in ethylacetoacetate, methylacetoacetate and benzaldehyde:
ꢀ
1
IR (Nujol): lmax (cm ) of CQO in ethylacetoacetate (from 1721 to
714), methylacetoacetate (from 1717 to 1711) and benzaldehyde
from 1704 to 1692) decreased in the reaction mixture (Fig. 5).
1
(
Also, the IR spectra of these complexes showed two sharp peaks at
Fig. 6 UV spectra of (a) ethylacetoacetate, (b) methylacetoacetate, and
+
Fig. 5 IR spectra of (a) ethylacetoacetate, (b) methylacetoacetate, and
(c) benzaldehyde, DCDBTSD and complexes of them and Br (I and II or VI
(
c) benzaldehyde and a mixture of them and DCDBTSD.
and V) at 80 1C in tetrahydrofuran.
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for 20 min. After this time, to the solution of hydrochlorothia-
zide, which was kept under stirring, bromine (0.08 mL, 3 mmol)
was slowly added over a period of 15 min at 0 1C. The insoluble
brominated catalyst was removed by filtration and washed with
H O (10 mL) to give N,2-dibromo-6-chloro-3,4-dihydro-2H-
2
benzo[e][1,2,4]thiadiazine-7-sulfonamide 1,1-dioxide (DCDBTSD)
in 90% yield (0.82 g).
4.3. Catalyst characterization
1
13
The H NMR (400 MHz) and C NMR (100 MHz) spectra were
recorded on a Bruker-NMR spectrometer (d in ppm).
IR spectra were recorded on a Shimadzu FTIR-470 spectro-
photometer.
Fig. 7 UV spectra of DCDBTSD and the reaction mixture at 80 1C in
tetrahydrofuran.
Mass spectra were obtained using an Agilent Technologies
(HP) 5973 network mass selective detector (MSD) operating at
2
5,33–35
an ionization potential of 70 eV.
Thermal gravimetric (TG) and differential thermal gravimetric
(DTG) analyses were carried out using a Perkin Elmer instrument
catalyst.
To investigate that the presented catalyst was
completely regenerated during the reaction and then proceeded
to catalyze the synthesis of 4,4 -(arylmethylene)-bis(3-methyl-1-
0
(
Model: Pyris 1). TG/DTG analysis: 30 to 618 1C, rate of temperature
phenyl-1H-pyrazol-5-ol)s, we recorded the UV spectra of the
catalyst and the reaction mixture in tetrahydrofuran as solvent
respectively. We observed that the maximum of absorption in
the UV spectrum of the catalyst (333 nm) was similar to that
observed for the reaction mixture. Based on this, it is clear that
DCDBTSD was recovered unchanged after the completion of the
reaction (Fig. 7) and the proposed mechanisms were acceptable.
ꢀ
1
increase 10 1C min , nitrogen atmosphere.
Melting points were recorded in open capillary tubes using
Stuart Scientific melting point apparatus.
The crystal structure of synthesized materials was deter-
mined using an X-ray diffractometer (Ital structure ADP 2000
XRD) at ambient temperature.
0
4
.4. General procedure for the synthesis of 4,4 -(arylmethylene)-
3
. Conclusions
bis(3-methyl-1-phenyl-1H-pyrazol-5-ol)s using N,2-dibromo-6-
chloro-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine-7-sulfonamide
In summary, we have reported an efficient and practical procedure
for the synthesis of 4,4 -(arylmethylene)-bis(3-methyl-1-phenyl-
pyrazol-5-ol)s via one-pot pseudo five component condensation of
phenyl hydrazine (2 mmol) and b-ketoester derivatives (2 mmol)
with aromatic aldehydes (1 mmol) using N,2-dibromo-6-chloro-3,4-
dihydro-2H-benzo[e][1,2,4]thiadiazine-7-sulfonamide 1,1-dioxide
1,1-dioxide (DCDBTSD)
0
A mixture of b-ketoester (2 mmol), phenyl hydrazine (2 mmol)
and DCDBTSD (0.0455 g, 10 mol%) in a 10 mL round-bottomed
flask connected to a reflux condenser was stirred at 80 1C for
30 s and then aromatic aldehyde (1 mmol) was added to the
reaction mixture and the reaction was continued for the appropriate
time. After completion of the reaction, as monitored by TLC, the
reaction mixture was cooled to room temperature and recrystallized
from ethanol (95%).
(DCDBTSD) as a new and homogeneous organic catalyst at 80 1C
under solvent-free and neutral conditions. The catalyst is fully
1
13
characterized by IR, H and C NMR, XRD, TG/DTG as well as
mass spectra. The advantages of the presented method are
efficiency, generality, high yield, short reaction time, cleaner
reaction profiles, ease of product isolation and simplicity.
Acknowledgements
The authors gratefully acknowledge the support of this work by
the Research Affairs Office of Bu-Ali Sina University (Grant number
32-1716 entitled development of chemical methods, reagent and
molecules) and the University of Sayyed Jamaleddin Asadabadi.
4
. Experimental
4.1. Materials
All chemicals were purchased from Merck or Fluka chemical
companies. The known products were identified by comparison
of their melting points and spectral data with those reported in
the literature.
Notes and references
1
Multicomponent Reactions, ed. J. Zhu and H. Bienayme,
Wiley, Weinheim, 2005.
4
.2. Catalyst preparation
ꢀ1
A solution of sodium hydroxide (6 mol L , 1 mL) was added
dropwise with stirring into a round bottomed flask (50 mL)
containing hydrochlorothiazide (0.6 g, 2 mmol) in distillated
water (2 mL) over a period of 10 min at room temperature. After
the addition was completed, the reaction mixture was stirred
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