Ultrasound-promoted regio and chemoselective synthesis of pyridazinones and phthalazinones catalyzed by ionic liquid [bmim]Br/AlCl3

Article abstract of DOI:10.1016/j.ultsonch.2011.11.008

The first ultrasound-promoted multicomponent synthesis of pyridazinones and phthalazinones from arenes, cyclic anhydrides and ArNHNH₂ in the presence of an efficient recyclable catalyst, [bmim]Br/AlCl₃, in high yield and short reaction time is reported.

Full text of DOI:10.1016/j.ultsonch.2011.11.008

Ultrasonics Sonochemistry 19 (2012) 740–744
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Ultrasonics Sonochemistry
journal homepage: www.elsevier.com/locate/ultsonch
Short Communication
Ultrasound-promoted regio and chemoselective synthesis of pyridazinones
and phthalazinones catalyzed by ionic liquid [bmim]Br/AlCl3
Leila Zare a,b, Nosrat Ollah Mahmoodi a, , Asieh Yahyazadeh a, Mohammad Nikpassand c
⇑
a Department of Organic Chemistry, University of Guilan, P.O. Box 1914, Rasht, Iran
b Payame Noor University, Shaft, Guilan, Iran
c Department of Chemistry, Rasht Branch, Islamic Azad University, Rasht, Iran
a r t i c l e i n f o
a b s t r a c t
Article history:
Received 15 April 2010
Received in revised form 21 September 2011
Accepted 7 November 2011
Available online 2 December 2011
The first ultrasound-promoted multicomponent synthesis of pyridazinones and phthalazinones from are-
nes, cyclic anhydrides and ArNHNH2 in the presence of an efficient recyclable catalyst, [bmim]Br/AlCl3, in
high yield and short reaction time is reported.
Ó 2011 Elsevier B.V. All rights reserved.
Keywords:
Pyridazinone
Phthalazinone
Arene
Cyclic anhydride
[bmim]Br/AlCl3
1. Introduction
reaction efficiency from both economic and ecological points of
view has given to this kind of procedures a remarkable synthetic
Pyridazinones are useful compounds with a broad array of bio-
logically activities. They possess notable hypertensive [1], platelet
aggregation inhibition [2], phosphodiesterase [3], antiasthmatic
[4], antisecretory and antiulcer [5], antidepressant [6], antibacte-
value and received great attention [21,22].
In recent years, ionic liquids have shown great promise as an
attractive alternative to conventional catalysts and solvents for
synthesizing organic chemicals [23–26]. The increased interest
for their investigations is mainly due to their green characteristics,
such as chemical and thermal stability, no measurable vapor pres-
sure, non-flammability, non-coordinating and solvation properties
[27]. They can be readily recycled, have profound effect on the
activity and selectivity in reactions and in some cases, facilitate
the isolation of products. Therefore, ionic liquids are considered
valuable substitute for volatile organic solvents. To the best of
knowledge, this is the first report on the ultrasound-promoted
multicomponent synthesis of pyridazinones and phthalazinones
from arenes, cyclic anhydrides and ArNHNH2 in the presence of
the efficient recyclable catalyst, [bmim]Br/AlCl3.
rial [7], antifongic [8],
a-adrenoceptor antagonists [9], analgesic
[10], antiinflammatory [11], antianemic [12], nephrotropic [13],
cardiotonic [14], anticancer [15], pesticidal and herbicidal [16]
properties.
Previously reported synthetic routes to synthesis of pyridazi-
nones include reaction of
alkylhydrazines or phenyl-hydrazines [17], condensation of Wittig
reagents with arylhydrazones or condensation of -ketoesters with
c-ketoacids and their derivatives with
a
hydrazinocarbonyl-acetic acid esters [18], catalytic reactions of
alkynes with arylhydrazines (hydrohydrazination) [19], condensa-
tion of hydrazine with appropriate substituted lactones [20].
Green chemistry has become a major driving force for organic
chemists to develop environmentally benign routes for the prepa-
ration of organic compounds. For example, the possibility of per-
forming reactions under ultrasound irradiation to enhance the
2. Materials and methods
2.1. Apparatus and analysis
For the ultrasound reactions, the ultrasound apparatus Astra 3D
(9.5 dm3, 45 kHz frequency, input power with heating, 305 W,
number of transducers, 2) from TECNO-GAZ was used. Chemicals
were purchased from Merck and Fluka and used as purchased.
⇑
Corresponding author.
E-mail address: mahmoodi@guilan.ac.ir (N.O. Mahmoodi).
1350-4177/$ - see front matter Ó 2011 Elsevier B.V. All rights reserved.
doi:10.1016/j.ultsonch.2011.11.008

L. Zare et al. / Ultrasonics Sonochemistry 19 (2012) 740–744
741
Melting points were measured on an Electro-thermal 9100 appara-
tus and are uncorrected. 1H NMR spectra were obtained on a Bru-
ker DRX 500, 250 and those of 13C NMR spectra on a Bruker DRX
125 Avance spectrometer in CDCl3 as solvent and with TMS as
internal standard. FT-IR spectra were recorded on a Shimadzu FT-
IR-8400S spectrometer. Elemental analyzes were recorded on a
Carlo-Erba EA1110CNNO-S analyzer.
C16H13ClN2O: C, 67.49; H, 4.60; N, 9.84. Found: C, 67.21; H, 4.58;
N, 9.81.
2.2.5. 2,6-Bis(4-methoxyphenyl)-4,5-dihydropyridazin-3(2H)-one 5
Red oil, IR (KBr, cmÀ1
) mmax 1683, 1595, 1490, 1326, 1H NMR
(500 MHz, CDCl3): 2.72–2.75 (2H, t, J = 8.5 Hz), 3.01–3.04 (2H, t,
J = 7.64 Hz), 3.81 (3H, s), 3.83 (3H, s), 6.90–6.94 (4H, m), 7.46–
7.48 (2H, d, J = 8.9 Hz), 7.72–7.74 (2H, d, J = 8.86 Hz); 13C NMR
(125 MHz, CDCl3): 23.23, 28.37, 55.81, 55.92, 114.24, 126.83,
128.07, 128.42, 134.95, 151.61, 158.50, 161.53, 165.86; Anal. Calcd.
for C18H18N2O3: C, 69.66; H, 5.85; N, 9.03. Found: C, 69.51; H, 5.69;
N, 9.45.
2.2. General procedure for the synthesis of pyridazinones and
phthalazinones
A mixture of anhydride (10 mmol), arenes (10 mmol) and
[bmim]Br/AlCl3 (20 mmol) were placed into Pyrex-glass open ves-
sel and irradiated in a water bath under silent condition by ultra-
sound (45 kHz) at 60 °C for the required reaction times (4–5 h).
The progress of the reaction was monitored by TLC (EtOAc: petro-
leum ether 1:4). Then the reaction mixture was cooled to room
temperature, and induced into two liquid phases (organic phase
and ionic liquid phase) by extracting with CHCl3. The ionic liquid
could be reused after the organic phase was extracted out with
CHCl3. The products 1–9 was purified by column chromatography
(EtOAc: petroleum ether 1:4) to furnish the desired pyridazinones
and phthalazinones. The pure products were collected in 65–75%
yields.
2.2.6. 2,4-Diphenylphthalazin-1(2H)-one 6
Light brown solid, mp 161–163 °C, IR (KBr, cmÀ1
) mmax 1656,
1580, 1487, 1325. 1H NMR (500 MHz, CDCl3): 7.40–7.43 (1H, t,
J = 7.3 Hz), 7.51–7.57 (5H, m), 7.69–7.70 (2H, d, J = 5.5 Hz), 7.78–
7.79 (2H, d, J = 7.6 Hz), 7.84–7.87 (3H, m), 8.66–8.67 (1H, d,
J = 7.4 Hz); 13C NMR (125 MHz, CDCl3): 126.18, 127.18, 128.08,
128.20, 129.11, 129.40, 129.87, 130.06, 131.98, 132.18, 133.59,
135.47, 142.43, 148.05, 159.37; Anal. Calcd. for C20H14N2O: C,
80.52; H, 4.73; N, 9.39. Found: C, 80.25; H, 4.51; N, 9.27.
2.2.7. 2-Phenyl-4-o-tolyl-2H phthalazin-1-one 7
Brown solid, mp 124–126 °C, IR (KBr, cmÀ1
) mmax 1662, 1595,
2.2.1. 2,6-Diphenyl-4,5-dihydropyridazin-3(2H)-one 1
1490, 1330, 1H NMR (500 MHz, CDCl3): 2.5 (3H, s), 7.37–7.42
(3H, m), 7.51–7.54 (2H, t, J = 8.0 Hz), 7.58–7.60 (2H, d, J = 7.9 Hz),
7.79–7.80 (2H, d, J = 7.7 Hz), 7.82–7.86 (m, 3H), 8.65–8.67 (1H, d,
J = 7.6 Hz); 13C NMR (125 MHz, CDCl3): 21.80, 126.26, 127.35,
128.00, 128.15, 129.11, 129.41, 129.65, 129.74, 129.88, 131.99,
132.62, 133.51, 139.67, 142.50, 148.07, 159.37; Anal. Calcd for
Off white solid, mp 92–94 °C, IR (KBr, cmÀ1
) mmax 1680, 1600,
1541, 1330, 1490; 1H NMR (500 MHz, CDCl3): 2.84 (2H, t,
J = 8.4 Hz), 3.15 (2H, t, J = 8.5 Hz), 7.30–7.33 (1H, m), 7.45–7.48
(5H, m), 7.64–7.66 (2H, d, J = 7.5 Hz), 7.85–7.86 (m, 2H); 13C
NMR (125 MHz, CDCl3): 23.33, 28.47, 125.31, 126.51, 127.00,
129.07, 130.42, 135.91, 141.68, 151.93, 165.69. Anal. Calcd. for
C21H16N2O: C, 80.75; H, 5.16; N, 8.97. Found: C, 80.35; H, 5.87;
C16H14N2O: C, 76.78; H, 5.64; N, 11.19. Found: C, 76.62; H, 5.77;
N, 8.43.
N, 11.10.
2.2.8. 4-(2,4-Dimethylphenyl)-2-phenyl-2H phthalazin-1-one 8
2.2.2. 6-(4-Methylphenyl)-4,5-dihydropyridazin-3(2H)-one 2
Brown solid, mp 156–158 °C, IR (KBr, cmÀ1
) mmax 1662, 1583,
Red oil, IR (KBr, cmÀ1 mmax 1680, 1595, 1492, 1326, 1H NMR
)
1492, 1330, 1H NMR (500 MHz, CDCl3): 2.25 (3H, s), 2.45 (3H, s),
7.17–7.19 (1H, d, J = 7.6 Hz), 7.21(1H, s), 7.30–7.31 (1H, d,
J = 7.5 Hz), 7.38–7.43 (2H, m), 7.50–7.53 (2H, t, J = 7.7 Hz), 7.76–
7.79 (3H, d, J = 7.8 Hz), 7.83–7.86 (1H, t, J = 7.3 Hz), 8.63–8.65
(1H, d, J = 7.8 Hz); 13C NMR (125 MHz, CDCl3): 20.28, 21.70,
126.17, 126.35, 127.07, 127.28, 127.98, 129.14, 130.30, 131.78,
131.98, 133.54, 133.74, 137.30, 139.54, 142.41, 148.42, 159.48;
Anal. Calcd. for C22H18N2O: C, 80.96; H, 5.56; N, 8.58. Found: C,
80.80; H, 5.57; N, 8.39.
(500 MHz, CDCl3): 2.4 (3H, s), 2.78 (2H, t, J = 8.5 Hz), 3.06 (2H, t,
J = 8.5 Hz), 7.27–7.30 (2H, d, J = 8.1 Hz), 7.32–7.35 (2H, t,
J = 7.4 Hz), 7.47–7.50 (2H, t, J = 7.6 Hz), 7.67–7.69 (2H, d,
J = 8.3 Hz), 7.75–7.77 (2H, d, J = 8.3 Hz); 13C NMR (125 MHz,
CDCl3): 21.86, 23.21, 125.33, 126.53, 126.96, 128.48, 128.97,
129.01, 129.82, 133.12, 140.71, 152.16, 165.87; Anal. Calcd. for
C17H16N2O: C, 77.25; H, 6.10; N, 10.60. Found: C, 77.26; H, 6.33;
N, 10.58.
2.2.3. 6-(2,4-Dimethylphenyl)-2-phenyl-4,5-dihydropyridazin-3(2H)-
one 3
2.2.9. 4-(2-Chlorophenyl)-2-phenyl-2H phthalazin-1-one 9
Brown solid, mp 164–165 °C, IR (KBr, cmÀ1
) mmax 1662, 1593,
Red oil, IR (KBr, cmÀ1 mmax 1677, 1600, 1494, 1326; 1H NMR
)
1569, 1490, 1323, 1139, 1H NMR (500 MHz, CDCl3): 7.40–7.43
(500 MHz, CDCl3): 2.4 (3H, s), 2.5 (3H, s), 2.8 (2H, t, J = 8.4 Hz),
3.0 (2H, t, J = 8.5 Hz), 7.10 (s, 1H), 7.12 (1H, s), 7.28–7.33 (m, 2H),
7.43–7.46 (2H, t, J = 8.2 Hz), 7.61–7.62 (2H, d, J = 7.6 Hz); 13C
NMR (125 MHz, CDCl3): 21.60, 21.61, 26.95, 28.74, 125.30,
126.93, 127.12, 128.93, 132.51, 134.02, 136.22, 139.66, 141.49,
155.60, 165.75; Anal. Calcd. for C18H18N2O: C, 77.67; H, 6.52. N,
10.06. Found: C, 77.56; H, 6.23; N, 10.18.
R3
NHNH2
[bmim]Br/AlCl3
R1
R1
O
O
O
N
N
N
R2
+
O
+
R2
2.2.4. 6-(4-Chlorophenyl)-2-phenyl-4,5-dihydropyridazin-3(2H)-one
4
R3
R3
1-
5
Red oil, IR (KBr, cmÀ1 mmax 1683, 1595, 1490, 1326, 1012, 1H
)
NHNH2
[bmim]Br/AlCl3
R1
O
R2
6
NMR (500 MHz, CDCl3): 2.8 (2H, t, J = 8.5 Hz), 3.06–3.10 (2H, t,
J = 8.5 Hz), 7.32–7.34 (1H, t, J = 7.3 Hz), 7.41–7.42 (2H, d,
J = 8.6 Hz), 7.46–7.49 (2H, t, J = 8.2 Hz), 7.62–7.63 (2H, d,
J = 7.4 Hz), 7.76–7.79 (2H, d, J = 8.62 Hz); 13C NMR (125 MHz,
CDCl3): 23.17, 28.31, 125.26, 125.39, 127.14, 127.91, 129.00,
129.29, 136.44, 141.59, 150.68, 165.53; Anal. Calcd. for
N
+
+
O
O
R1
O
R2
R3
9 -
Scheme 1. Multicomponent synthesis of pyridazinones and phthalazinones.

742
L. Zare et al. / Ultrasonics Sonochemistry 19 (2012) 740–744
Table 1
Multicomponent synthesis of pyridazinones and phthalazinones.
Entry
Productb
Reflux
Time (h)
11
Ultrasound
Time (h)
5
mp (°C)
Yielda(%)
52
Yielda(%)
65
1
92–94
N
N
O
N
2
3
10
57
63
4
75
72
Oil
Oil
N
H3C
H3C
Cl
O
11.5
4.5
CH3
N
N
O
4
5
12
54
65
5
4
65
72
Oil
Oil
N
N
O
OCH3
10.5
N
N
H3CO
O
6
12
45
5
65
161–163
N
N
O
7
8
10.5
68
62
4
75
71
124–126
156–158
N
N
H3C
O
11
4.5
CH3
N
N
H3C
O
9
12.5
58
5
69
164–166
N
N
Cl
O
a
Isolated yield.
b
Identified by spectroscopic analysis (IR, 1H NMR, 13C NMR and elemental analysis).
(1H, t, J = 7.4 Hz), 7.51–7.59 (m, 5H), 7.68–7.73 (2H, d, J = 7.2 Hz),
7.78–7.80 (2H, d, J = 7.6 Hz), 7.83–7.88 (2H, m), 8.66–8.67 (1H, d,
J = 7.5 Hz); 13C NMR (125 MHz, CDCl3): 126.27, 127.30, 128.08,
128.18, 129.07, 129.15, 129.40, 129.55, 129.66, 129.98, 132.08,
133.59, 135.48, 142.44, 148.04, 159.37; Anal. Calcd. for
3. Results and discussion
The remarkable catalytic activity together with easy availabil-
ity, operational simplicity of [bmim]Br/AlCl3 and our continued
interests for the development of efficient and environmentally
friendly procedures for the synthesis of heterocyclic com-
pounds [28–30] triggered us to synthesize pyridazinones and
C20H13ClN2O: C, 72.18; H, 3.94; N, 8.42. Found: C, 72.52; H, 3.57;
N, 8.27.

L. Zare et al. / Ultrasonics Sonochemistry 19 (2012) 740–744
743
eral advantages, such as virtue of their convergence, productivity,
ease of execution and work-up, the small amount of waste, short
reaction time, reusability of catalyst coupled with replacement of
any volatile organic solvent, since the ionic liquid plays dual roles
of Lewis acid catalyst and solvent.
O
O
O
[bmim]Br/AlCl3
R1
R2
O
O
O
R1
4. Conclusion
[bmim]Br/AlCl3
In conclusion, a convenient one pot [bmim]Br/AlCl3-catalyzed
synthesis of pyridazinones and phthalazinones from arenes, anhy-
drides and ArNHNH2 in high yield and short reaction time was
developed.
R2
[bmim]Br/AlCl3
O
O[bmim]Br/AlCl3
NH2
NH
O
R3
Acknowledgements
R1
N
N
R2
R3
+ H2O
O
We are thankful to the Research Council of University of Guilan
(RCUG) for the partial support of this work.
Scheme 2. Proposed mechanism for the multicomponent synthesis of pyridazi-
nones and phthalazinones.
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in the absence of ionic liquid/AlCl3 lead to no product after 24 h. A
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products in shorter reaction time and higher yields in comparison
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