Friedlander synthesis of quinolines promoted by polymer-bound sulfonic acid

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Friedlander Synthesis of Quinolines
Promoted By Polymer-bound Sulfonic
Acid
Behrooz Malekia, Esmail Rezaei Sereshta & Zahra Ebrahimia
a Department of Chemistry, Hakim Sabzevari University, Sabzevar,
Khorasan, Iran
Published online: 18 Mar 2015.
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To cite this article: Behrooz Maleki, Esmail Rezaei Seresht & Zahra Ebrahimi (2015) Friedlander
Synthesis of Quinolines Promoted By Polymer-bound Sulfonic Acid, Organic Preparations
and Procedures International: The New Journal for Organic Synthesis, 47:2, 149-160, DOI:
10.1080/00304948.2015.1005986
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Organic Preparations and Procedures International, 47:149–160, 2015
Copyright Ó Taylor & Francis Group, LLC
ISSN: 0030-4948 print / 1945-5453 online
DOI: 10.1080/00304948.2015.1005986
Friedlander Synthesis of Quinolines Promoted By
Polymer-bound Sulfonic Acid
Behrooz Maleki, Esmail Rezaei Seresht, and Zahra Ebrahimi
Department of Chemistry, Hakim Sabzevari University, Sabzevar,
Khorasan, Iran
Quinolines and their derivatives are very important biologically and occur widely in natu-
ral products. Members of this family have displayed interesting physiological activities
and found major applications in medicinal chemistry, as anti-malarial,1–2 anti-bacterial,3–4
anti-inflammatory,5–6 anti-hypertensive,7–8 anti-platelet, and tyrosine kinase inhibiting
agents.9–13 They are also useful for the preparation of nano- and meso-structures having
enhanced electronic and photonic properties.14–15 Moreover, quinolines are also employed
in the fields of bioorganic,16 bioorganometallic processes17 and industrial organic chemis-
triy.18 Therefore, the exploration of efficient synthetic methods to construct the quinoline
framework has continually drawn great attention for many decades.
Among these methods, the Friedlander annulations is one of the simplest and most
direct approaches for the synthesis of quinolines. It involves the acid-, base-catalyzed or
thermal condensation between o-aminoarylketones and aldehydes with another carbonyl
compound possessing a reactive a-methylene group followed by cyclodehydration.19–23 It
has been shown that acid catalysis is more effective than base catalysts for the Friedlander
annulation. In recent years, Bronsted and Lewis acids such as ionic liquids,24–26 sulfamic
acid,27 hydrochloric acid,28 zirconium tetrakisdodecyl sulfate [Zr(DS)4],29 silica sulfuric
acid,30–31 silica supported phosphomolybdic acid [PMA.SiO2],32 nanocrystalline aluminium
oxide,33 dodecylphosphonic acid (DPA),34 poly(N-bromoethylbenzene-1,3-disulfonamide)
[PBBS] or N,N,N0,N0-tetrabromobenzene-1,3-disulfonamide [TBBDA],35 zinc triflate,36
nano-flake ZnO,37 CsxH3¡xPW12O40 heteropoly salts,38 Yb(OTf)3,39 nanosized MCM-41
supported ionic liquid [(BSPY)HSO4/MCM-41],40 o-benzendisulfonimide41 and nano-
crystalline sulfated zirconia42 have been utilized. However, many of these methods suffer
from harsh reaction conditions, long reaction times, low yields, expensive reagents, tedious
work-up procedures. The main disadvantage of nearly all existing methods is that the cata-
lysts cannot be recovered and reused. For these reasons, the use of solid and heterogeneous
catalysts has received considerable attention in organic synthesis. This extensive application
of heterogeneous catalysts can make the process more efficient from both the environmental
and economic points of view when the catalyst can be easily recycled.43–45
There are no previous report describing the use of Poly(AMPS-co-AA) in organic
transformations.46–48 and it has been shown to possess several advantages such as low
toxicity and cost, ease of handling and high catalytic activity as a potential green catalyst.
Received April 14, 2014; in final form November 6, 2014.
Address correspondence to Behrooz Maleki, Department of Chemistry, Hakim Sabzevari Uni-
versity, Sabzevar, Khorasan, Iran. E-mail: malekibehrooz@gmail.com
149

150
Maleki et al.
Scheme 1
We now disclose a novel, green, facile and convenient method for the preparation of quin-
oline from o-aminoaryl ketones or aldehydes and various ketones catalyzed by poly
(AMPS-co-AA) under solvent-free conditions at 110ꢀC (Scheme 1).
In order to determine the optimum conditions, the effect of temperature on the rate of
the reaction was studied first for the preparation of 3a from the two-component condensa-
tion of ethyl acetoacetate with o-aminobenzophenone under solvent-free conditions
(Table 1, Entries 1–4). At 110ꢀC, the reaction proceeded smoothly with near complete
conversion to product. Further increase in temperature to 120 and 130ꢀC did not acceler-
ate rate or improve the yield. The study to determine optimal amount of Poly (AMPS-co-
AA), was carried out by varying the amount of the catalyst (Entries 5, 6). The maximum
yield was obtained with 0.06 g. Further increases in amount of Poly (AMPS-co-AA) did
not have any significant effect on the yield. In absence of the catalyst, no products could
be detected even after 1h.
We next established the generality of these conditions using different types of
a-methylene carbonyl compounds with o-aminoaryl ketones to produce the correspond-
ing quinolines under solvent-free conditions (Table 2).
Table 1
Screening of the Reaction Conditions for the Synthesis of 3a
Entry
Poly (AMPS-co-AA) (g)
Temp. (ꢀC)
Times (min)
Yield (%)
1
2
3
4
5
6
7
0.06
0.06
0.06
0.06
0.08
0.03
—
100
110
120
130
110
110
110
15
10
10
10
10
20
60
68
84
68
50
80
72
a
—
a No reaction.

Friedlander Synthesis of Quinolines
151
Table 2
The Heterogeneous Synthesis of Quinolines using Poly(AMPS-co-AA)
mp (ꢀC)
o-Aminoaryl
ketones or
aldehydes
a-Methylene
Yield
(%)
Time
(min)
Found
Lit.
ketones
Quinoline
84
10
100–101
100–10140
80
80
90
95
90
10
10
60
10
10
108–110
134–135
140–142
156–158
190–192
108–10940
133–13537
138–14137
15926
189–19137
(Continued on next page)

152
Maleki et al.
Table 2
The Heterogeneous Synthesis of Quinolines using Poly(AMPS-co-AA) (Continued)
mp (ꢀC)
o-Aminoaryl
ketones or
aldehydes
a-Methylene
Yield
(%)
Time
(min)
Found
107–109
Lit.
ketones
Quinoline
97
70
107–10931
86
60
160–161
—
86
70
93–94
—
Et2CO
84
20
96–97
95–9638
(Continued on next page)

Friedlander Synthesis of Quinolines
153
Table 2
The Heterogeneous Synthesis of Quinolines using Poly(AMPS-co-AA) (Continued)
mp (ꢀC)
o-Aminoaryl
ketones or
aldehydes
a-Methylene
Yield
(%)
Time
(min)
Found
145–146
Lit.
ketones
Quinoline
EtMeCO
80
20
14438
76
60
176–177
174–17534
89
30
174–176
17238
86
70
89
10
20
15
102–104
154–155
97–98
102–10440
15440
97–9840
(Continued on next page)

154
Maleki et al.
Table 2
The Heterogeneous Synthesis of Quinolines using Poly(AMPS-co-AA) (Continued)
mp (ꢀC)
o-Aminoaryl
ketones or
aldehydes
a-Methylene
Yield
(%)
Time
(min)
Found
Lit.
ketones
Quinoline
70
25
161–162
162–16340
90
10
185–186
18529
95
15
208–209
209–21130
65
45
126–127
128–13031
94
50
137–139
—
(Continued on next page)

Friedlander Synthesis of Quinolines
155
Table 2
The Heterogeneous Synthesis of Quinolines using Poly(AMPS-co-AA) (Continued)
mp (ꢀC)
o-Aminoaryl
ketones or
aldehydes
a-Methylene
Yield
(%)
Time
(min)
Found
93–95
Lit.
ketones
Quinoline
82
40
91–9339
86
88
40
40
98–99
78–79
96–9920
76–7720
92
40
206–207
203–20520
90
40
191–192
190–19220

156
Maleki et al.
Table 3
Comparison of Methods for the Synthesis of Quinolines.
Entry
Quinolines 3
Conditions
Time (min) Yield (%)
3a
Zr(DS)4/EtOH:H2O(1:2)/Reflux29
Silica sulfuric acid/100ꢀC/ Solvent-Free30
PMA.SiO2/EtOH/Reflux32
Nanocrystalline Al2O3/CHCl3/Reflux33
DPA/90ꢀC/Solvent-Free34
Zinc triflate /MWI/Solvent-Free36
Nano-flake ZnO /100ꢀC/Solvent-Free37
(BSPY)HSO4/MCM-41/100ꢀC/Solvent-Free40
o-Benzendisulfonimide/80ꢀC/Solvent-Free41
Nano-crystalline SZ/EtOH/Reflux42
This work
180
55
72
87
94
98
90
90
85
93
93
84
84
80
98
84
63
87
78
90
90
92
90
98
82
87
95
60
180
30
4/5
210
70
180
110
10
3d
PMA.SiO2/EtOH/Reflux32
Nanocrystalline Al2O3/CHCl3/Reflux33
PBBS/100ꢀC/Solvent-Free35
70
180
390
240
90
Nano-flake ZnO /100ꢀC/Solvent-Free37
(BSPY)HSO4/MCM-41/100ꢀC/Solvent-Free40
Nano-crystalline SZ/EtOH/Reflux42
This work
SO3H-functionalized ionic liquid/70ꢀC/ H2O26
Sulfamic acid/60ꢀC/Solvent-Free27
Zr(DS)4/EtOH:H2O(1:2)/Reflux29
Nanocrystalline Al2O3/CHCl3/Reflux33
CsxH3-xPW12O40/100ꢀC/Solvent-Free38
(BSPY)HSO4/MCM-41/100ꢀC/Solvent-Free40
This work
110
60
3e
300
75
360
180
30
40
10
The insolubility of the Poly (AMPS-co-AA) catalyst in ethanol provided an easy
method for its separation from the product. After the addition of 96% ethanol to the thick
reaction mixture, the insoluble catalyst was filtered off (suction), dried at 110ꢀC and was
re-used three times without substantial decrease in yields (84–75%) of 3a. The products
were isolated by simple evaporation of the filtrate and purified by crystallization from eth-
anol. It is important to note that acid-sensitive functional groups in the substrates (Table 2,
3v–3z) remain unaffected. Unlike previous procedures, our method does not require the
use of either hazardous acids or harsh reaction conditions; it has several advantages such
as higher yields, shorter reaction times, and simple experimental and work-up procedures.
In addition, polymer-like condensation products resulting from the self-condensation of
o-aminoaryl ketones and aldehydes were not found.14–17
In order to demonstrate the efficiency of our method, we compared our results with
some selected catalyst that have been reported in the recent literature. Table 3 indicates
that it is more efficient as a green, heterogeneous catalyst in terms of reaction times and
yields.

Friedlander Synthesis of Quinolines
157
Experimental Section
IR spectra were recorded as KBr pellets on a Shimadzu 435-U-04 spectrophotometer. 1H
and 13C NMR spectra were obtained using Bruker DRX-300 Avance spectrometer in
DMSO-d6 or CDCl3 using TMS as an internal reference. Melting points were determined
in open capillary tubes in a Stuart BI Branstead Electrothermal Cat No: IA9200 apparatus
and are uncorrected.
Preparation of Catalyst
Cross-linked N,N-methylene bis-acrylamide (MBA, 2 g) was added to a mixture of 2-
acrylamido-2-methylpropanesulfonic acid (AMPS, 10 g) and acrylic acid (AA, 10 ml) in
100 ml distilled water. The mixture was vigorously stirred (magnetic stirrer) at room tem-
perature for 10 min. Then, the solution was added to a three-neck flask equipped with a
mechanical stirrer (Heidolph RZR 2021, three blade propeller type). The flask was
immersed in a thermo-stated water bath at 70ꢀC and an inert gas (nitrogen) was gently
bubbled into the solution to remove any oxygen. After 15 min, an ammonium persulfate
solution (APS, 0.2 g in 2 ml H2O) was added to the mixture, and the mixture was stirred
(200 rpm) for 20 min. Methanol (40 mL) was added and the mixture was stirred gently
for 72 hrs in order to remove any unreacted monomer. After decantation of the methanol,
the product was broken up into small pieces (mortar and pestle), dried in an oven at
110ꢀC for five hours and then powdered (mortar and pestle). The powdered polymer was
stored protected from moisture, heat and light.46–48
General Procedure for the Synthesis of Quinolines
To mixture of a-methylene carbonyl compounds (1.2 mmol) and o-aminoaryl ketones or
aldehydes (1 mmol) was added cross-linked poly(AMPS-co-AA) (0.06 g) [for solid sub-
strates 0.1 ml of ethanol was added] and the mixture was heated on an oil bath at 110ꢀC
for the time show in Table 2. Upon completion of the reaction as indicated by TLC (hex-
ane:ethyl acetate, 8:2), the appropriate amounts of hot EtOH (96%, 5 ml) was added and
the mixture stirred for 10 min. After separation of the catalyst by filtration, the filtrate
was concentrated in vacuum to remove the ethanol. The residue was washed with cold
water and crystallized from hot ethanol (3 ml) to afford the pure products characterized
by comparison between their mp, IR and NMR data with those of authentic samples.
Analytical Data for New Compounds
1
2-(4-Nitrophenyl)-4-phenylquinoline (3h), IR: 3052, 1600, 1580; H NMR (300 MHz,
DMSO-d6): d 7.57–7.64 (m, 5H), 7.83–7.91 (m, 2H), 8.18–8.22 (m, 2H), 9.36–9.39 (d,
2H), 9.61–9.64 (d, 2H); 13C NMR (75 MHz, DMSO-d6): d 119.30, 123.97, 125.38,
125.50, 120,76, 128.52, 128.78, 129.68, 130.00, 130.33, 132.29, 144.45, 148.09, 149.18,
153.47.
Anal. Calcd. for C21H14N2O2: C, 77.29; H, 4.33; N, 8.58. Found: C, 77.31; H, 4.32;
N, 8.61.
2-(4-Fluorophenyl)-4-phenylquinoline (3i), IR: 3085, 1600, 1560; 1H NMR
(400 MHz, CDCl3): 7.48–7.55 (m, 7H), 7.74–7.78 (m, 2H), 7.89–7.91 (d, 1H), 8.14–8.16
(d, 2H), 8.21–8.23 (d, 1H); 13C NMR (100 MHz, DMSO-d6): d 118.92, 125.70, 125.84,

158
Maleki et al.
126.56, 128.52, 128.65, 129.02, 129.71, 130.09, 135.58, 138.04, 138.27, 148.78, 149.44,
155.54.
Anal. Calcd. for C21H14FN: C, 84.26; H, 4.72; N, 4.68 Found: C, 84.29; H, 4.70; N,
4.65.
1
6-Chloro-2-(4-fluorophenyl)-4-phenylquinoline (3u), IR: 3085, 1600, 1560; H-
NMR (300 MHz, DMSO-d6): d 7.33–7.39 (t, 2H), 7.55–7.63 (m, 5H), 7.75 (s, 1H), 7.79–
7.83 (d, 1H), 8.10 (s, 1H), 8.14–8.17 (d, 1H), 8.37–8.42 (t, 2H); 13C NMR (100 MHz,
DMSO-d6): d 120.03, 124.50, 126.51, 127.56, 128.73, 128.84, 128.92, 129.44, 129.62,
130.46, 131.77, 132.17, 137.77, 139.22, 147.25, 148.25, 157.07.
Anal. Calcd. for C21H13ClFN: C, 75.56; H, 3.92; N, 4.28. Found: C, 75.56; H, 3.90; N
4.32.
Acknowledgment
The authors are thankful to the Research Council of Hakim Sabzevari University for
financial support.
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