Nickel oxide nanoparticles catalyzed synthesis of poly-substituted quinolines via Friedlander hetero-annulation reaction

Article abstract of DOI:10.1016/j.cclet.2014.06.026

Reusable acidic nickel oxide nanoparticles have been synthesized, characterized and applied as a catalyst to convert 2-aminoaryl ketones and β-ketoesters/ketones into the corresponding quinolines in good yields with high selectivity. This could serve as a

Full text of DOI:10.1016/j.cclet.2014.06.026

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Chinese Chemical Letters xxx (2014) xxx–xxx
Contents lists available at ScienceDirect
Chinese Chemical Letters
journal homepage: www.elsevier.com/locate/cclet
1
2
Original article
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4
Nickel oxide nanoparticles catalyzed synthesis of poly-substituted
quinolines via Friedlander hetero-annulation reaction
*
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Q1 B. Palakshi Reddy, P. Iniyavan, S. Sarveswari, V. Vijayakumar
Centre for Organic and Medicinal Chemistry, VIT University, Vellore 632014, India
A R T I C L E I N F O
A B S T R A C T
Article history:
Reusable acidic nickel oxide nanoparticles have been synthesized, characterized and applied as a catalyst
to convert 2-aminoaryl ketones and -ketoesters/ketones into the corresponding quinolines in good
Received 26 April 2014
Received in revised form 12 May 2014
Accepted 29 May 2014
Available online xxx
b
yields with high selectivity. This could serve as a simple and convenient procedure for the Friedlander
annulations.
ß 2014 V. Vijayakumar. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights
reserved.
Keywords:
o-Aminoaryl ketones
NiO NPs
Friedlander annulation
Quinolines
7
8
1. Introduction
reaction time, etc. Thus, a simple and environmentally benign 33
procedure with an inexpensive and readily available reagent is 34
9
Quinolines are an important class of heterocycles due to their
wide range of pharmacological properties such as antimalarial,
anti-inflammatory, anti-asthmatic, antibacterial, antihyperten-
sive, tyro-kinase PDGF-RTK inhibitory activities. The derivatives
of quinolines are also used as synthetic building blocks in the
synthesis of heterocycles [1–6]. The classical methods to synthe-
size quinolines require harsh reaction conditions and the yields are
unsatisfactory in most cases [7]. The Friedlander annulation, which
involves the condensation of an aromatic 2-amino aldehyde/
ketone with ketone/aldehyde containing active methylene group
followed by cyclization, is the simplest and most straightforward
synthetic method for the synthesis of quinoline derivatives,
especially for the highly substituted three-functionalized quino-
lines [8]. Hydrochloric acid, sulfuric acid, p-toluenesulfonic acid
and PPA have been employed as catalysts for this conversion
[9–12]. Some of the methods reported for the synthesis of
quinolines also involve the use of catalysts such as SnCl2, BiCl3,
I2 [12,13], montmorillonite KSF clay [14], ionic liquids [15],
Bi(OTf)3 [16], Y(OTf)3 [17], silver dodecatungstophosphate [18],
silica sulfuric acid, sulfamic acid, neodymium nitrate [19,20],
dodecylphosphonic acid (DPA) [21], proline [22], silica supported
phosphomolybdic acid [23], and sodium ethoxide [24]. However,
most of these methods suffered from certain drawbacks such as
harsh reaction conditions, use of expensive catalysts, and long
desirable, which prompted us to test the feasibility of NiO 35
nanoparticles (NiO NPs) as a catalyst for the synthesis of quinolines 36
without any co-catalysts or additives. Hence in continuation of our 37
earlier effort on quinolines [25–33] syntheses, herein we report an 38
efficient, cost effective and environmentally benign procedure for 39
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
the synthesis of multi-substituted quinolines (Scheme 1).
40
2. Experimental
41
42
2.1. General
Chemicals were purchased from Sigma Aldrich, Fluka and used 43
as received. IR spectra were recorded using an AVATAR 330 44
equipped with a DTGS detector. NMR spectra were recorded on a 45
Bruker AMX-400 instrument in CDCl3 using TMS as an internal 46
reference. Mass spectra were recorded either on an ABI QSTAR XL 47
ESI-TOF Mass spectrometer (Sciex Model) or an LC–MS using 48
Agilent 1200 series LC and Micromass zQ spectrometer. Melting 49
points were determined in open capillaries and were uncorrected. 50
Powder X-ray diffraction analysis was carried out using a Bruker 51
D8 Advance diffractometer and lanthanum hexaboride (LaB6) was 52
used to calibrate the instrument before analysis.
53
2.2. Synthesis of the catalyst
54
To a solution of 2.3 g of Ni(NO3)2ꢀ6H2O in 10 mL distilled water, 55
*
Corresponding author.
E-mail address: kvpsvijayakumar@gmail.com (V. Vijayakumar).
10 mL of 15% NaOH was added drop wise with constant stirring. 56
http://dx.doi.org/10.1016/j.cclet.2014.06.026
1001-8417/ß 2014 V. Vijayakumar. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
Please cite this article in press as: B. Palakshi Reddy, et al., Nickel oxide nanoparticles catalyzed synthesis of poly-substituted quinolines
via Friedlander hetero-annulation reaction, Chin. Chem. Lett. (2014), http://dx.doi.org/10.1016/j.cclet.2014.06.026

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B. Palakshi Reddy et al. / Chinese Chemical Letters xxx (2014) xxx–xxx
Scheme 1. Synthesis of poly-substituted quinolones.
57
58
59
After 15 min the obtained products were collected by centrifuga-
tion, washed thoroughly with distilled water and dried at 100 8C.
Then the dried sample was heated at 400 8C for 3 h.
2.4. Test to determine the morphology of NiO NPs
87
To determine the morphologies, the image of NiO NPs was
taken using a scanning electron microscope (SEM) (Carl Zeiss
oxford instrument) at various magnifications. The SEM micro-
graphs (Fig. 2.) at lower magnification clearly revealed that the
formation of well dispersed rod shaped nickel oxide nanostruc-
tures. SEM demonstrates that all the particles were in the size
range of less than 100 nm.
88
89
90
91
92
93
94
60
2NaOHðsÞ ! 2NaþðaqÞ þ 2OHꢁðaqÞ
612
63
NiðNO3Þ2ꢀ6H2OðsÞ ! Ni2þðaqÞ þ 2NO3ꢁðaqÞ þ 6H2OðaqÞ
Ni2þðaqÞ þ 2OHꢁðaqÞ þ xH2OðaqÞ ! NiðOHÞ2ꢀxH2OðsÞ #
NiðOHÞ2ꢀxH2OðsÞ ! NiðOHÞ2ðsÞ þ xH2OðgÞ "
NiðOHÞ2ðsÞ ! NiOðsÞ þ H2OðgÞ "
645
66
678
69
2.5. General procedure for the synthesis of quinoline derivatives
95
To a mixture of 2-aminoaryl ketone (1 mmol) and
a
-methylene
96
97
98
99
100
101
102
103
104
105
106
107
701
72
carbonyl compound (1 mmol) in ethanol (5 mL) was added NiO
NPs (10 mol%) and the mixture was refluxed. The progress of the
reaction was monitored by TLC analysis. After the completion of
the reaction, the reaction mixture was dissolved in ethanol to
recover the catalyst by filtration and solvent was removed under
reduced pressure. The obtained products were recrystallized using
chloroform, characterized by IR, 1H, 13C NMR and mass spectral
data. The melting points and spectral data for the known
compound are found to be identical to the values reported in
the literature and for newly reported compounds the data are
given below.
734
75
2.3. Test to determine the phase formation of NiO NPs
76
77
78
79
80
81
82
83
84
85
86
The synthesized NiO NPs were characterized using an XRD
Bruker D8 Advance Diffractometer (Bruker AXS, Germany) with
˚
Cu K
a radiation (l = 1.54 A). The XRD pattern of NiO NPs
powder samples was recorded over a 2u range of 10–908, which
revealed that the synthesized NiO NPs were crystalline (Fig. 1).
The XRD pattern showed four distinct diffraction peaks at 37.05,
43.19, 62.67, 75.12 and 79.02, which could be assigned to
(1 1 1), (2 0 0), (2 2 0), (3 1 1) and (2 2 2) of cubic NiO NPs,
respectively, and were in agreement with the database of
Joint Committee on Powder Diffraction Standards (JCPDS No.
01-089-7130).
3. Results and discussion
108
By considering the advantageous surface characteristics of NiO
NPs, we decided to investigate the behavior of different
109
110
(200)
160
JCPDS: 01-089-7130
140
(111)
(220)
120
100
(311)
80
60
40
20
(222)
1
2
3
4
5
6
7
8
2θ
Fig. 1. XRD pattern of synthesized NiO nanoparticles.
Fig. 2. SEM micrograph of synthesized NiO nanoparticles.
Please cite this article in press as: B. Palakshi Reddy, et al., Nickel oxide nanoparticles catalyzed synthesis of poly-substituted quinolines
via Friedlander hetero-annulation reaction, Chin. Chem. Lett. (2014), http://dx.doi.org/10.1016/j.cclet.2014.06.026

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Table 1
98
Optimization the reaction conditions under various solvents and various
concentrations of the NiONPs catalyst for the representative compound 3a.a
96
94
92
90
88
86
Entry
Solvent
Catalyst
(mol%)
Time
Conversion
(%)
(min)
1
2
3
4
5
6
7
Acetonitrile
Toluene
10
10
240
300
300
240
150
150
300
58
Trace
65
THF
10
Dichloromethane
Ethanol
10
68
10
97
Ethanol
20
10b
97
Ethanol
92
a
Reaction conditions: 2-aminobenzophenone (1 mmol), ethylacetoacetate
(1 mmol), NiO NPs (10 mol%).
b
Commercially available NiO.
1
2
3
4
5
Reusability of NiO NPs
111
112
113
114
115
116
117
118
119
120
121
122
123
124
125
126
127
128
129
130
131
132
133
134
135
136
137
138
139
140
141
142
143
2-aminoaryl ketones with various simple ketones, cyclic ketones
and
b-keto esters in the presence of NiO NPs as a catalyst. The
Fig. 4. Reusability of NiO NPs.
compound 3a has been taken as a representative example and it
was synthesized by treating 2-aminobenzophenone with ethyl
acetoacetate in the presence NiO NPs as a catalyst in various
solvents. Ethanol served as a better solvent than other solvents
such as toluene, acetonitrile, dichloromethane and THF. After
finding the suitable solvent the concentration of the catalyst was
varied and optimized as 10 mol%. The yields of the products were
found to be lower at lower amount than the optimized amount of
catalyst and it remains unaffected above the optimized amount of
the catalyst and reaction duration. The best results were obtained
with10 mol% of the catalyst in ethanol (Table 1).
However, in the absence of NiO NPs, the reaction did not
proceed even after long duration (10–12 h). Unlike other methods,
the present procedure does not require either strong acids or high
temperature to afford quinoline derivatives. This method has
several advantages such as shorter reaction time with higher
yields, cleaner product profiles, and simpler experimental and
workup procedures. The reaction was carried out with different
carbonyl compounds and 2-aminoaryl ketones to establish the
generality and scope of the method. The obtained products were
recrystallized using chloroform, characterized by IR, 1H NMR, 13C
NMR and mass spectral data. All the spectral data are given as
Supporting information. It was observed that the reactions of
2-amino benzophenone, 2-amino-5-chlorobenzophenone, 2-ami-
no-20,5-dichlorobenzophenone and 2-amino-5-nitrobenzophe-
none with various carbonyl compounds including cyclic, acyclic
Moreover, in most of the cases, 2-aminobenzophenone and 144
2-amino-5-chlorobenzophenone in comparison with 2-amino- 145
20,5-dichlorobenzophenone and 2-amino-5-nitrobenzophenone 146
afforded the corresponding quinolines in shorter reaction time.
147
The NiO NPs indeed displayed better activity compared to the 148
commercially available NiO since the NiO NPs have Lewis acid sites 149
(Ni2+) and Lewis base sites (O2ꢁ). Thus, a Lewis base site (O2ꢁ) of 150
NiO NPs deprotonate the
site (Ni2+) can activate the carbonyl group for the imine formation 152
(Fig. 3). 153
The efficacy of the NiO NPs as a catalyst was compared with that 154
of other reported catalysts such as Bi(OTf)3, Y(OTf)3, Ag3PW12O40 155
a-methylene group, and the Lewis acid 151
,
NaHSO4ꢀSiO2 and KSF clay using 3a as a representative example 156
and found to be equally efficient. The results given in Table 3 157
clearly reveal that the present protocol (using NiO NPs) could serve 158
as a better method than the existing methods.
159
The NiO catalyst can be recovered easily, since it is insoluble in 160
organic solvents. Furthermore, we investigated the reusability of 161
the catalyst. After the completion of the reaction, the catalyst has 162
been recovered by filtration, washed three times with 5 mL of 163
methanol, dried at 100 8C overnight, and then subjected to a 164
second run of the reaction with the same substrates. Fig. 4 shows 165
that the yields of 3a in the second and third runs were almost 166
identical to that in the first use. In every case, greater than 92% of 167
the NiO NPs was easily recovered from the reaction mixture by 168
filtration. In the fourth and fifth runs 93% yield of 3a was obtained. 169
Fig. 5 revealed that even after the fifth run the morphology of the 170
b
-diketones, aliphatic and aromatic
b-diketones, ketones and
b
-ketoesters proceeded efficiently and the desired products were
obtained in high yields in short reaction time. The reaction
duration and the yields are given in Table 2. In addition, this
method is equally effective for both cyclic and acyclic ketones.
NiO NPs was not affected much.
171
Fig. 3. Plausible mechanism.
Please cite this article in press as: B. Palakshi Reddy, et al., Nickel oxide nanoparticles catalyzed synthesis of poly-substituted quinolines
via Friedlander hetero-annulation reaction, Chin. Chem. Lett. (2014), http://dx.doi.org/10.1016/j.cclet.2014.06.026

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B. Palakshi Reddy et al. / Chinese Chemical Letters xxx (2014) xxx–xxx
Table 2
Nano-NiO2 catalyzed synthesis of polysubstituted quinolines.a
Entry
1
Amino ketone
Ketone
Quinoline
Time (h)
2.0
Yield (%)b
97
Mp (8C)
1a
2a
3a
9610
2
2b
3b
2.0
96
10610
3
2c
3c
2.5
93
11310
4
5
6
2d
2e
2f
3d
3e
3f
3.0
3.0
2.5
90
88
89
>280
250
74
7
2g
3g
3.0
92
13910
8
2h
3h
3.0
91
15810
9
2i
3i
2.5
94
19110
Please cite this article in press as: B. Palakshi Reddy, et al., Nickel oxide nanoparticles catalyzed synthesis of poly-substituted quinolines
via Friedlander hetero-annulation reaction, Chin. Chem. Lett. (2014), http://dx.doi.org/10.1016/j.cclet.2014.06.026

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Table 2 (Continued )
Entry
10
Amino ketone
1b
Ketone
2a
Quinoline
Time (h)
2.0
Yield (%)b
96
Mp (8C)
3j
11212
11
2b
3k
2.0
95
13623
12
2c
3l
2.5
95
15210
13
2d
3m
3.0
94
198–200
14
2e
3n
3.0
92
200
15
2f
3o
2.5
95
106–110
16
2g
3p
2.5
91
16212
17
2h
3q
2.0
92
18723
18
2j
3r
3.0
89
122–124
19
2i
3s
2.0
93
210–21223
Please cite this article in press as: B. Palakshi Reddy, et al., Nickel oxide nanoparticles catalyzed synthesis of poly-substituted quinolines
via Friedlander hetero-annulation reaction, Chin. Chem. Lett. (2014), http://dx.doi.org/10.1016/j.cclet.2014.06.026

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B. Palakshi Reddy et al. / Chinese Chemical Letters xxx (2014) xxx–xxx
Table 2 (Continued )
Entry
20
Amino ketone
Ketone
2b
Quinoline
Time (h)
3.0
Yield (%)b
91
Mp (8C)
1c
3t
129
21
2a
3u
3.0
94
102
22
2h
3v
3.0
93
180
23
1d
2a
3w
3.0
94
97
24
2h
3x
3.5
92
168
a
Reaction conditions: Amino ketone (1 mmol), ketone (1 mmol) and NiO NPs at reflux conditions.
Isolated yields.
b
Fig. 5. XRD pattern of used NiO nanoparticles (after the five runs).
Please cite this article in press as: B. Palakshi Reddy, et al., Nickel oxide nanoparticles catalyzed synthesis of poly-substituted quinolines
via Friedlander hetero-annulation reaction, Chin. Chem. Lett. (2014), http://dx.doi.org/10.1016/j.cclet.2014.06.026

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In summary, a new method has been developed for the
synthesis of poly-substituted quinolines under Friedla¨nder hetero-
annulation conditions using NiO NPs as a heterogeneous and
reusable catalyst. The advantages of this method are the efficiency,
generality, high yields with short reaction time, low cost, clean
product profile, simplicity, ease of preparation of the catalyst, ease
of product isolation, and compliance with the green chemistry
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The authors are thankful to the VIT University for providing the
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Appendix A. Supplementary data
255
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synthesis of 6-chloro-3-(3-arylacryl oyl)-2-methyl-4-phenylquinolines and their 257
conversion to 6-chloro-3-(1-phenyl-5-aryl-4,5-dihydro-1H-pyrazol-3-yl)-2- 258
187
188
189
Supplementary data associated with this article can be found, in
the online version, at http://dx.doi.org/10.1016/j.cclet.2014.
06.026.
methyl-4-phenylquinolines, J. Chin. Chem. Soc. 59 (2012) 66–71.
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Please cite this article in press as: B. Palakshi Reddy, et al., Nickel oxide nanoparticles catalyzed synthesis of poly-substituted quinolines
via Friedlander hetero-annulation reaction, Chin. Chem. Lett. (2014), http://dx.doi.org/10.1016/j.cclet.2014.06.026