Nicotinic acid-supported cobalt ferrite-catalyzed one-pot synthesis of substituted chromeno[3,4-b]quinolines

Article abstract of DOI:10.1002/aoc.5469

One-pot synthesis of substituted chromeno[3,4-b]quinoline derivatives was developed by three-component reaction of aldehydes, dimedone or 1,3-cyclohexadione, and 4-aminocoumarin in the presence of nicotinic acid-supported cobalt ferrite [CoFe₂O

Full text of DOI:10.1002/aoc.5469

Received: 9 October 2019
DOI: 10.1002/aoc.5469
Revised: 17 December 2019
Accepted: 18 December 2019
F U L L P A P E R
Nicotinic acid-supported cobalt ferrite-catalyzed one-pot
synthesis of substituted chromeno[3,4-b]quinolines
Mahdiye Foroughi Kaldareh
| Masoud Mokhtary
| Mohammad Nikpassand
Department of Chemistry, Rasht Branch,
Islamic Azad University, Rasht, Iran
One-pot synthesis of substituted chromeno[3,4-b]quinoline derivatives was
developed by three-component reaction of aldehydes, dimedone or
1,3-cyclohexadione, and 4-aminocoumarin in the presence of nicotinic acid-
supported cobalt ferrite [CoFe2O4@SiO2@Si(CH2)3Cl@NA] as a novel mag-
netic catalyst in chloroform at reflux conditions. Nicotinic acid-supported
cobalt ferrite was characterized via Fourier transform infrared spectroscopy,
X-ray diffraction, thermal gravimetric analysis, scanning electron micros-
copy, high-resolution transmission electron microscopy, energy-dispersive X-
ray spectroscopy, and vibrating sample magnetometry. Moreover, the cata-
lyst could be easily recovered by magnetic separation and recycled up to
five times without significant loss of its catalytic activity. The products
formed in excellent yields over appropriate reaction times under environ-
mentally friendly conditions. High efficiency and easy isolation of the cata-
lyst from products by simple magnetic attraction are some of the
considerable advantages of this procedure.
Correspondence
Masoud Mokhtary, Department of
Chemistry, Rasht Branch, Islamic Azad
University, Rasht, P.O. Box 3516-41335,
Iran.
Email: mmokhtary@iaurasht.ac.ir
K E Y W O R D S
4-aminocoumarin, chromeno[3,4-b]quinoline, cobalt ferrite, nanocatalyst, one-pot synthesis
1 | INTRODUCTION
in various applications, such as magneto-optical
devices,[14] magnetic hyperthermia,[15] and as contrast
The development of magnetic nanoparticles (MNPs) for
use as supports and exploration of their applications as
catalyst in organic synthesis is an important green
method as it is environmentally friendly and allows
sustainable separation. By enabling simple recovery of
MNPs from reaction media, different protocols involv-
ing surface modification, binding, and self-assembly
offer a broad scope of approaches for preparing mag-
netically retrievable nanoparticles.[1] In recent years,
the design and synthesis of nanomaterials with
improved catalytic properties for use in photocatalysis
and alcohol oxidation have been developed.[2–13] Cobalt
ferrite nanoparticles have attracted continuous interest
because of their unique properties and exceptionally
promising applications. Cobalt ferrite has been utilized
agent
for
magnetic
resonance
imaging.[16]
Aminocoumarin derivatives have a wide range of bio-
logical applications,[17,18] such as antibiotics,[19] fluores-
cent markers,[20] melanin-concentrating hormone
receptor antagonist,[21] inducing estrogenic activity,[22]
carbonic anhydrase class of inhibitors,[23] and
α-glucosidase inhibitors.[24] Organic compounds con-
taining 4-aminocoumarin scaffold are synthesized by
the reaction of 4-hydroxycoumarin, ammonia solution,
Meldrum's acid, and aromatic aldehydes in the pres-
ence of SBA-15-SO3H[25]; three-component reaction of
4-aminocoumarin, arylglyoxal monohydrates, and aro-
matic amines promoted by KHSO4 in toluene under
reflux condition[26]; three-component condensation of
4-aminocoumarin, aldehydes, and ethyl benzoylacetates
Appl Organometal Chem. 2020;e5469.
wileyonlinelibrary.com/journal/aoc
© 2020 John Wiley & Sons, Ltd.
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https://doi.org/10.1002/aoc.5469

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FOROUGHI KALDAREH ET AL.
SCHEME 1 Synthesis of chromeno[3,4-b]quinoline derivatives
SCHEME 2 Procedure for the synthesis of
CoFe2O4@SiO2@Si-(CH2)3Cl@NA nanocatalyst.
DMSO, dimethyl sulfoxide; TMOS, tetramethyl
orthosilicate
by POCl3 in dichloroethane under reflux conditions[27]
three-component domino condensation of 4-
aminocoumarins, arylglyoxal monohydrates, and vari-
ous nucleophilic substrates, such as arylamines,
malononitrile, ethyl cyanoacetate, and cyanoacetamide-
produced functionalized chromeno[4,3-b]pyrrol-4(1H)-
;
we herein report an efficient method for the synthesis
of chromeno[3,4-b]quinoline derivatives by the reaction
of aldehydes, dimedone or 1,3-cyclohexadione, and
4-aminocoumarin in the presence of nicotinic acid-
supported cobalt ferrite [CoFe2O4@SiO2@Si(CH2)3
Cl@NA] as a novel nanocatalyst in chloroform at
reflux conditions (Scheme 1). To the best of our
ones
nanoparticles as a solid acid catalyst under solvent-free
conditions[28]
oxidative aromatization of
in
the
presence
of
Fe3O4@SiO2-SO3H
knowledge,
the
CoFe2O4@SiO2@Si(CH2)3Cl@NA
;
nanocatalyst has so far not been addressed in the rele-
vant literature.
tetrahydrochromeno[4,3-b]quinoline derivatives by nit-
ric acid at ambient temperature[29]; two-component
coupling of 4-aminocoumarin and α,β-unsaturated
nitroalkene catalyzed by PEG–SO3H[30]
;
three-
component reaction of phenyl glyoxal, dimedone, and
4-amino coumarin to afford disubstituted chromeno
[4,3-b]pyrrole-4(1H)-one derivatives catalyzed by I2/
dimethyl sulfoxide (DMSO)[31]; synthesis of coumarin
fused to highly decorated indenodihydropyridyl and
dihydropyridyl derivatives in the presence of ( )lactic
acid/ethyl-L-lactate at 100 ꢀC[32]; and synthesis of
chromeno[4,3-b]quinoline derivatives in the presence of
catalytic amounts of Cu(II)–Schiff base/SBA-15 by con-
densation of arylaldehydes with 1,3-cyclohexadione and
then treating the obtained intermediates with
[33]
ꢀ
4-aminocoumarin in an autoclave at 200 C.
Despite
the potential utility of these methods, some suffer from
disadvantages such as long reaction times, low yields,
high reaction temperature, and the use of more corro-
sive catalyst. Because of the significance of chromeno
[3,4-b]quinoline derivatives in pharmaceutical indus-
tries, there exists a need to develop effective, one-pot,
and affordable procedures for the synthesis of these
compounds. Following our interest in the use of mag-
netically separable catalyst in organic synthesis,[34,35]
FIGURE 1 Fourier-transform infrared spectra: (a) CoFe2O4,
(b) CoFe2O4@SiO2, (c) CoFe2O4@SiO2@Si-(CH2)3Cl, and
(d) CoFe2O4@SiO2@Si-(CH2)3Cl@NA

FOROUGHI KALDAREH ET AL.
3 of 12
2 | EXPERIMENTAL
2.2 | Synthesis of CoFe2O4 nanoparticles
2.1 | Material and methods
First, FeCl3Á6H2O (6.5 g) and CoCl2Á4H2O (2.85 g) were
dissolved in distilled water (120 mL). After complete dis-
solution of the salts, NaOH (14.4 g) was dissolved in dis-
tilled water (120 mL) and added to the solution. The
resulting black solution was vigorously stirred for 2 hr at
All chemicals were purchased from Merck Chemical
Company, Darmstadt, Germany. Melting points (MPs)
were recorded on an electrothermal MP apparatus. The
nuclear magnetic resonance (NMR) spectra were
recorded in DMSO-d6 with TMS as the internal standard
on a Bruker Avance DRX 300-MHz spectrometer.
Fourier-transform infrared (FT-IR) spectra were deter-
mined on an SP-1100, P-UV-Com instrument. The satura-
tion magnetization was deduced based on the hysteresis
loop using a vibrating sample magnetometer (Meghnatis
Kavir Kashan Co., Kashan, Iran). The energy-dispersive
X-ray spectroscopy (EDS) analysis of the fabricated
nanocatalyst was performed using a Philips XL30 micro-
scope with an accelerating voltage of 20 kV. The field
emission scanning electron microscopy (FESEM) image
was obtained on a MIRA3 operated at an accelerating
voltage of 15 kV. Prior to FESEM and EDS studies, each
sample was gold sputtered. High-resolution transmission
electron microscopy (HRTEM) images were obtained on
an FEI (TEC9G20) operated at an accelerating voltage of
200 kV. The crystalline structure of the materials was
evaluated using a diffractometer (Philips) with Cu-Kα
radiation (λ = 1.54 Å). The thermal stability was deter-
mined by thermogravimetric analysis (TGA; Mettler
ꢀ
80 C under N2 atmosphere. The precipitated cobalt fer-
rite was then separated from the solution using a magnet
and washed several times with distilled water. Finally, a
stable black magnetic dispersion was obtained that was
dried in an oven.
ꢀ
Toledo) at a heating rate of 10 C/min from room tem-
perature to 600 ꢀC in an inert atmosphere. Products were
separated by simple filtration and identified by FT-IR, 1H
NMR, 13C NMR spectra, and elemental analysis.
FIGURE 3 Scanning electron microscopy image of the
CoFe2O4@SiO2@Si-(CH2)3Cl@NA nanocatalyst
FIGURE 2 X-ray diffraction patterns: (a) CoFe2O4@SiO2,
(b) CoFe2O4@SiO2@Si-(CH2)3Cl, and (c) CoFe2O4@SiO2@Si-
(CH2)3Cl@NA
FIGURE 4 Energy-dispersive X-ray spectroscopy spectrum of
the CoFe2O4@SiO2@Si-(CH2)3Cl@NA nanocatalyst

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FOROUGHI KALDAREH ET AL.
2.3 | Synthesis of CoFe2O4@SiO2
nanoparticles
2.6 | General procedure for the synthesis
of chromeno[3,4-b]quinoline derivatives
First, CoFe2O4 (1 g) nanoparticles were dispersed in a
distilled water and ethanol mixture (80:20 v/v%) using
ultrasound bath (15 min). Then, ammonia (2 mL,
28 wt%) and tetramethyl orthosilicate (2 mL) were
added dropwise to the mixture which was stirred
at 50 ꢀC for 2 hr. The obtained CoFe2O4@SiO2
nanoparticles were isolated using a magnet and then
washed with distilled water and ethanol, respectively,
and dried in an oven.
A mixture of aldehyde (1 mmol), 4-aminocoumarin
(2 mmol), dimedone or 1,3-cyclohexadione, and
Fe3O4@SiO2@Si-(CH2)3Cl@NA (0.02 g) was dissolved in
CHCl3 (5 mL) and heated under reflux conditions. The
progress of the reaction was monitored by thin-layer
chromatography
(ethyl acetate/n-hexane/methanol,
4:6:1). Upon completion of the reaction, the catalyst was
separated using an external magnet and the crude prod-
uct was recrystallized from ethanol (10 mL) to obtain the
pure chromeno[3,4-b]quinoline derivatives.
2.4 | Synthesis of CoFe2O4@SiO2@Si-
(CH2)3Cl nanoparticles
3 | RESULTS AND DISCUSSION
3.1 | Characterization of the catalyst
First, CoFe2O4@SiO2 (1 g) nanoparticles were dispersed
in toluene (50 mL) by ultrasound bath (15 min). After
that, (3-chloropropyl)triethoxysilane (2 mL) was gently
In this study, nicotinic acid-supported cobalt ferrite
[CoFe2O4@SiO2@Si(CH2)3Cl@NA] as a novel magnetic
ꢀ
added to the mixture and refluxed at 110 C for 24 hr.
The synthesized nanoparticles were separated using a
magnet, washed several times with toluene and water,
respectively, and finally the product was dried in
an oven.
2.5 | Synthesis of Fe3O4@SiO2@Si-
(CH2)3Cl@NA nanocatalyst
Nicotinic acid (1.5 g) was dissolved in DMSO (70 mL).
Then, CoFe2O4@SiO2@Si-(CH2)3Cl (1 g) nanoparticles
were added to the mixture and dispersed by ultrasound
bath (15 min). The mixture was then refluxed for 24 hr.
Finally, CoFe2O4@SiO2@Si-(CH2)3Cl@NA nanoparticles
were separated using a magnet and washed with DMSO
(50 mL) and dried in an oven.
FIGURE 6 Vibrating sample magnetometry curves:
(a) CoFe2O4@SiO2, (b) CoFe2O4@SiO2@Si-(CH2)3Cl, and
(c) CoFe2O4@SiO2@Si-(CH2)3Cl@NA nanocatalyst
FIGURE 5 High-resolution
transmission electron microscopy
images of the prepared
CoFe2O4@SiO2@Si-(CH2)3Cl@NA
magnetic nanoparticles

FOROUGHI KALDAREH ET AL.
5 of 12
FIGURE 7 Thermogravimetric analysis
thermogram of the CoFe2O4@SiO2@Si-
(CH2)3Cl@NA nanocatalyst. DTG, differential
thermogravimetry
nanocomposite was successfully prepared according to
procedure presented in Scheme 2.
3.3 | SEM analysis
The FT-IR spectra of the CoFe2O4, CoFe2O4@SiO2,
CoFe2O4@SiO2@Si-(CH2)3Cl, and CoFe2O4@SiO2@Si-
(CH2)3@NA are shown in Figure 1. The wavenumber
587 cm−1 corresponds to the stretching vibration of Co–
O, and bands at 1635 and 3408 cm−1 correspond to the
OH stretching vibration of hydroxides, which confirms
the formation of CoFe2O4 (Figure 1a).[36]. The band at
1087 cm−1 is related to the Si–O group of SiO2 in
CoFe2O4@SiO2 (Figure 1b), the band at 2931 cm−1 repre-
sents the CH2 stretching of propyl chloride in
CoFe2O4@SiO2@Si-(CH2)3Cl (Figure 1c), and bands at
1728 and 3416 cm−1 correspond to the C=O and OH
stretching of nicotinic acid in CoFe2O4@SiO2@Si-
(CH2)3Cl@NA, respectively (Figure 1d).
Surface morphological image of the Fe3O4@SiO2@Si-
(CH2)3Cl@NA nanocatalyst explored by a scanning elec-
tron microscope is presented in Figure 3. The average
size of the fine nonagglomerated particles was found to
be nearly 23 nm. This confirms the nanostructure of the
nanocatalyst.
In addition, the EDS spectrum of the
Fe3O4@SiO2@Si-(CH2)3Cl@NA nanocomposite shows
the presence of carbon (C), nitrogen (N), oxygen (O), sili-
con (Si), iron (Fe), and cobalt (Co) components in the
nanocomposite (Figure 4).
3.4 | HRTEM analysis
The structural information about the nicotinic acid-
3.2 | X-ray diffraction analysis
supported
cobalt
ferrite
[CoFe2O4/SiO2@Si
(CH2)3Cl@NA] was investigated by HRTEM. HRTEM
The X-ray diffraction (XRD) patterns of CoFe2O4@SiO2,
CoFe2O4@SiO2@Si-(CH2)3Cl, and CoFe2O4@SiO2@Si-
(CH2)3Cl@NA are presented in Figure 2. The XRD pat-
terns of CoFe2O4@SiO2, CoFe2O4@SiO2@Si-(CH2)3Cl,
and CoFe2O4@SiO2@Si-(CH2)3@NA illustrated main
peaks at 2θ = 30.12ꢀ, 35.45ꢀ, 43.3ꢀ, 53.89ꢀ, 57.20ꢀ, and
62.72ꢀ. The XRD patterns for CoFe2O4@SiO2@Si-
(CH2)3@NA revealed peaks indicative of pure CoFe2O4
nanoparticles with a spinel structure.[37] According to the
Debye–Scherrer equation for the full width at half maxi-
mum of the sharpest diffraction peak (311), the average
crystallite size for CoFe2O4@SiO2, CoFe2O4@SiO2@Si-
(CH2)3Cl, and Fe3O4@SiO2@Si-(CH2)3Cl@NA was
13, 18, and 19 nm, respectively.
TABLE 1 Synthesis of 4a using different solventsa
Entry
Solvent
Ethanol
Time (hr)
Yield (%)b
1
2
3
4
5
3
7
8
3
4
70
40
35
95
65
Ethyl acetate
n-Hexane
CHCl3
MeCN
aReaction conditions: 4-Cl-benzaldehyde (1 mmol), 4-aminocoumarin
(1 mmol), 1,3-cyclohexadione (1 mmol), and
CoFe2O4@SiO2@Si-(CH2)3Cl@NA (0.02 g)
under reflux conditions.
bYield refers to isolated products.

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FOROUGHI KALDAREH ET AL.
TABLE 2 Synthesis of chromeno[3,4-b]quinolines catalyzed by the Fe3O4@SiO2@Si-(CH2)3Cl@NA nanocatalysta
Entry
Ar
R
Product
4a
Time (hr)
Yield (%)b
Melting point (ꢀC)
1
H
3
95
216–218
2
H
4b
2.45
96
284–286
3
4
H
H
4c
4d
2.5
3
97
96
262–264
298–300
5
6
H
H
4e
4f
4
4
91
90
278–280
336–338
7
8
H
H
4g
4
92
90
335–337
304–306
4h
4.5
9
Me
Me
4i
4j
3
94
94
301–303
282–284
10
3.5
11
12
13
Me
Me
Me
4k
4l
4
5
4
92
90
91
348–350
160–161
300–302
4m
14
Me
4n
3
90
264–266
(Continues)

FOROUGHI KALDAREH ET AL.
7 of 12
TABLE 2 (Continued)
Entry
Ar
R
Product
Time (hr)
Yield (%)b
Melting point (ꢀC)
15
16
Me
Me
4o
4p
3
5
96
93
333–334
322–324
aReaction conditions: Aldehyde (1 mmol), 4-aminocoumarin (1 mmol), dimedone or 1,3-cyclohexadione (1 mmol), and CoFe2O4@SiO2@Si-(CH2)3Cl@NA
(0.02 g) in CHCl3 under reflux conditions.
bYield refers to isolated products.
images of the synthesized nicotinic acid-supported cobalt
ferrite show the formation of the CoFe2O4@SiO2@Si
(CH2)3Cl@NA core–shell nanostructure. The HRTEM
image of CoFe2O4/SiO2@Si(CH2)3Cl@NA shows highly
uniform crystalline spherical nanoparticles with grain
size of about 20–30 nm (Figure 5a).
3.5 | Vibrating sample magnetometry
analysis
Magnetic properties of CoFe2O4, CoFe2O4@SiO2,
CoFe2O4@SiO2@Si-(CH2)3Cl, and Fe3O4@SiO2@Si-
(CH2)3Cl@NA nanocatalyst were characterized by vibrat-
ing sample magnetometry. In general, magnetization
increased with increases in the magnetic field. The mag-
netic
hysteresis
loops
of
CoFe2O4@SiO2,
CoFe2O4@SiO2@Si-(CH2)3Cl, and CoFe2O4@SiO2@Si-
(CH2)3Cl@NA are provided in Figure 6a–c. The satura-
tion magnetization value of the pristine CoFe2O4@SiO2
nanoparticles was 35.47 emu/g. This high saturation
magnetization value indicates
structure. The saturation magnetization values of
CoFe2O4@SiO2@Si-(CH2)3Cl and Fe3O4@SiO2@Si-
a
good crystal
(CH2)3Cl@NA were 27.17 and 22.07 emu/g, respectively
(Figure 6c). Although the saturation magnetization of the
catalyst was lower than that of CoFe2O4@SiO2@Si-
(CH2)3Cl (Figure 6b), this was sufficient enough to
recover the catalyst easily from the reaction mixture.
SCHEME 3 Plausible mechanism for the synthesis of
chromeno[3,4-b]quinoline derivatives by CoFe2O4@SiO2@Si-
(CH2)3Cl@NA
FIGURE 8 Recyclability of the catalyst for the synthesis of 4a

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FOROUGHI KALDAREH ET AL.
TABLE 3 Comparison of Fe3O4@SiO2@Si-(CH2)3Cl@NA with some other catalysts for the synthesis of 4c and 4n
Entryproduct
Catalyst
Reaction conditions
200–220 ꢀC
Time/min
Yield (%)
Reference
[38]
4c
4c
4c
4n
4n
4n
–
45
5
45
70
97
72
78
90
[33]
Cu(II)–Schiff base/SBA-15
Fe3O4@SiO2@Si-(CH2)3Cl@NA
–
200 ꢀC
CHCl3/reflux
150
720
180
180
This work
[39]
n-PrOH/reflux
Ethyl-L-lactate/100 ꢀC
CHCl3/reflux
[32]
( )Lactic acid
Fe3O4@SiO2@Si-(CH2)3Cl@NA
This work
3.6 | Thermogravimetric analysis
The magnetic property of Fe3O4@SiO2@Si-
(CH2)3Cl@NA facilitates its efficient recovery from the
reaction mixture during work-up. The activity of the
recycled catalyst was also examined under the reaction
conditions. After the completion of reaction, the catalyst
was separated by an external magnet, washed with etha-
nol, and dried. The recovered catalyst was reused for five
consecutive cycles without significant loss in its catalytic
activity (Figure 8). However, beyond five runs the activity
of the catalyst was reduced, and thus required re-
functionalization with nicotinic acid.
To study the efficiency of the present method for the
synthesis of chromeno[3,4-b]quinoline derivatives, com-
pounds 4c and 4n were compared with some of those
reported in the literature (Table 3). As can be seen, when
all conditions including efficiency and reaction condi-
tions are considered, our results present a good compari-
son with previously reported data.
The thermal behavior of the Fe3O4@SiO2@Si-
(CH2)3Cl@NA nanocatalyst is presented in Figure 6.
According to the TGA thermogram of the nꢀanocatalyst, a
weight loss of about 9.67% occurred at 598 C (Figure 7).
Thus, the catalyst remains stable and decomposes only
above 600 ꢀC.
To optimize the reaction conditions, the reaction
between 4-chlorobenzaldehyde, 4-aminocoumarin, and
1,3-cyclohexadione was examined as a model reaction in
several solvents, including ethanol, n-hexane, ethyl ace-
tate, chloroform, and acetonitrile (Table 1). Among these,
chloroform under reflux conditions was more efficient
with respect to reaction time and yield of the desired
product (Table 1).
To investigate the effect of catalyst loading, the model
reaction was carried out in the presence of different
amounts of catalyst (0.01, 0.02, and 0.03 g). It was observed
that the variation of amount of CoFe2O4@SiO2@Si-
(CH2)3@NA had an effective influence, with 0.02 g identi-
fied to be the best amount of CoFe2O4@SiO2@Si-
(CH2)3Cl@NA, as this afforded the desired product in 95%
yields. After optimization of the reaction conditions, a
variety of chromeno[3,4-b]quinoline derivatives were syn-
thesized by Fe3O4@SiO2@Si-(CH2)3Cl@NA in CHCl3
under reflux conditions (Table 2, Entries 1–16). The reac-
tions worked well with all arylaldehydes with electron-
donating or electron-withdrawing substituent.
Mechanistic pathway indicates the catalytic role of
Fe3O4@SiO2@Si-(CH2)3Cl@NA in the synthesis of
chromeno[3,4-b]quinoline derivatives (Scheme 3). Elec-
trophilicity of the carbonyl group of aldehyde is increased
by hydrogen bonding with acidic hydrogen of the catalyst.
It is supposed that the reaction may proceed at first by the
4 | CONCLUSIONS
In this research, for the first time, Fe3O4@SiO2@Si-
(CH2)3Cl@NA as a recyclable magnetic nanocatalyst
was prepared. In the prepared Fe3O4@SiO2@Si-
(CH2)3Cl@NA nanostructure, the cobalt ferrite compo-
nent was responsible for the magnetic recyclable ability.
The silica shell as the intermediate layer aids in stabiliz-
ing and protecting the cobalt ferrite part. The outermost
nicotinic acid component acts as the catalyst for the one-
pot synthesis of chromeno[3,4-b]quinoline derivatives
by the reaction of aldehydes, dimedone or
1,3-cyclohexadione, and 4-aminocoumarin. FT-IR, EDS,
and XRD results as well as FESEM and HRTEM images
indicated that the Fe3O4@SiO2@Si-(CH2)3Cl@NA
nanocatalyst can be successfully prepared via the utilized
route. Furthermore, the Fe3O4@SiO2@Si-(CH2)3Cl@NA
nanocatalyst showed excellent recycling efficiency as well
as stability for at least five runs. The high efficiency, one-
pot synthesis, excellent yields over appropriate reaction
times, and affordable procedure are some of the advan-
tages of this method.
reaction
of
aldehyde
with
dimedone
or
1,3-cyclohexadione, which provides the desired
Knoevenagel intermediate I. Then, 4-aminocoumarin
attacks intermediate I to produce intermediate II. After-
ward, intermediate II is converted into intermediate III by
tautomerization. Finally, intermediate III generates prod-
uct IV by dehydration.

FOROUGHI KALDAREH ET AL.
9 of 12
Spectroscopic data for synthetic compounds are given
in the following sections.
143.0, 132.6, 129.6, 124.5, 123.7, 123.5, 117.3, 113.3, 111.4,
101.1, 37.0, 35.5, 26.8, 21.1. Anal. calcd for C22H16N2O5:
C 68.04, H 4.15, N 7.21; found: C 68.07, H 4.17, N 7.24.
4.1 | 7-(4-Chlorophenyl)-
7,10,11,12-tetrahydro-6H-chromeno[4,3-b]
quinoline-6,8(9H)-dione (4a)
4.4 | 7-(3-Nitrophenyl)-
7,10,11,12-tetrahydro-6H-chromeno[4,3-b]
quinoline-6,8(9H)-dione (4d)
MP: 216–218 C; FT-IR (KBr, ν, cm−1): 3435, 2958, 2929,
ꢀ
2866, 1727, 1632, 1473, 1361, 1280, 1174, 1129, 1073,
MP: 298–300 ꢀC; FT-IR (KBr, ν, cm−1): 3289, 3097,
2927, 1677, 1713, 1631, 1605, 1528, 1507, 1475, 1352,
1
1035, 919, 830, 756. H NMR (300 MHz, DMSO-d6): δ
1
9.80 (s, 1H, NH), 8.33 (d, J = 7.8 Hz, 1H, Ar–H), 7.64 (t,
J = 7.5 Hz, 1H, Ar–H), 7.39–7.49 (m, 2H, Ar–H),
7.27–7.37 (m, 4H, Ar–H), 5.00 (s, 1H, CH), 2.71–2.91 (m,
2H, CH2), 2.30–2.34 (m, 2H, CH2), 1.85–2.06 (m, 2H,
CH2). 13C NMR (75 MHz, DMSO-d6): δ 195.4, 160.8,
152.4, 151.5, 149.5, 141.9, 134.7, 132.1, 128.6, 124.3, 123.2,
117.2, 113.6, 112.8, 112.7, 102.9, 37.2, 33.3, 26.8, 21.3.
Anal. calcd for C22H16NO3Cl: C 69.94, H 4.27, N 3.71.
Found: C 70.03, H 4.30, N 3.77.
1167, 1246, 1186, 1142, 1075, 1031, 927, 760. H NMR
(300 MHz, DMSO-d6): δ 9.91 (s, 1H, NH), 8.35 (d,
J = 7.5 Hz, 1H, Ar–H), 8.10 (d, J = 7.8 Hz, 2H, Ar–
H), 8.08 (s, 1H), 8.00 (d, J = 7.5 Hz, 1H, Ar–H),
7.65–7.74 (m, 2H, Ar–H), 7.39–7.57 (m, 3H, Ar–H),
5.12 (s, 1H, CH), 2.75–2.91 (m, 2H, CH2), 2.26–2.36
(m, 2H, CH2), 1.90–2.06 (m, 2H, CH2). 13C NMR
(75 MHz, DMSO-d6): δ 195.5, 160.7, 152.8, 152.6, 148.3,
148.0, 143.0, 132.6, 130.0, 124.5, 123.5, 122.7, 117.3,
113.2, 111.5, 101.3, 36.9, 35.3, 26.8, 21.1. Anal. calcd
for C22H16N2O5: C22H16N2O5: C 68.04, H 4.15, N 7.21;
found: C 68.09, H 4.20, N 7.25.
4.2 | 7-(2,4-Dichlorophenyl)-
7,10,11,12-tetrahydro-6H-chromeno[4,3-b]
quinoline-6,8(9H)-dione (4b)
4.5 | 7-(4-Methoxyphenyl)-
7,10,11,12-tetrahydro-6H-chromeno[4,3-b]
quinoline-6,8(9H)-dione (4e)
MP: 284–286 C; FT-IR (KBr, ν, cm−1): 3285, 3085, 2952,
ꢀ
1704, 1633, 1605, 1505, 1475, 1359, 1245, 1180, 1140,
1073, 1036, 921, 846, 755. 1H NMR (300 MHz, DMSO-d6):
δ 9.78 (s, 1H, NH), 8.33 (d, J = 7.8 Hz, 1H, Ar–H), 7.64 (t,
J = 7.8 Hz, 1H, Ar–H), 7.37–7.49 (m, 4H, Ar–H), 7.27 (d,
J = 8.1 Hz, 1H, Ar–H), 5.27 (s, 1H, CH), 2.66–2.91 (m,
2H, CH2), 2.18–2.34 (m, 2H, CH2), 1.78–1.99 (m, 2H,
CH2). 13C NMR (75 MHz, DMSO-d6): δ 195.4, 160.3,
152.6, 143.0, 142.7, 134.1, 133.9, 132.6, 131.7, 128.8, 127.3,
124.4, 123.5, 117.3, 113.1, 111.5, 101.1, 37.1, 34.4, 26.8,
21.1. Anal. calcd for C22H15NO3Cl2: C 64.09, H 3.67, N
3.40. Found: C 64.11, H 3.70, N 3.38.
−1
ꢀ
MP: 278–280 C; FT-IR (KBr, ν, cm ): 3322, 3077, 2935,
2837, 1677, 1640, 1508, 1470, 1363, 1304, 1241, 1179, 1138,
1
1032, 920, 753. H NMR (300 MHz, DMSO-d6): δ 9.75 (s,
1H, NH), 8.32 (d, J = 7.5 Hz, 1H, Ar–H), 7.64 (t, J = 7.2 Hz,
1H, Ar–H), 7.39–7.49 (m, 2H, Ar–H), 7.12 (d, J = 7.8 Hz,
2H, Ar–H), 7.01 (d, J = 7.8 Hz, 2H, Ar–H), 4.98 (s, 1H,
CH), 3.68 (s, 3H, OMe), 2.73–2.89 (m, 2H, CH2), 2.30 (sbr,
2H, CH2), 1.89–2.01 (m, 2H, CH2). 13C NMR (75 MHz,
DMSO-d6): δ 195.4, 160.8, 158.1, 152.4, 151.8, 142.2, 138.7,
132.3, 129.1, 124.4, 123.3, 117.3, 113.8, 113.5, 112.6, 102.5,
56.1, 37.1, 33.7, 26.8, 21.2. Anal. calcd for C23H19NO4: C
73.98, H 5.13, N 3.75; found: 74.06, H 5.16, N 3.76.
4.3 | 7-(4-Nitrophenyl)-
7,10,11,12-tetrahydro-6H-chromeno[4,3-b]
quinoline-6,8(9H)-dione (4c)
MP: 262–264 C; FT-IR (KBr, ν, cm−1): 3314, 3093, 2949,
4.6 | 7-(4-Hydroxy-3-methoxyphenyl)-
7,10,11,12-tetrahydro-6H-chromeno[4,3-b]
quinoline-6,8 (9H)-dione (4f)
ꢀ
2868, 1677, 1634, 1604, 1513, 1469, 1347, 1243, 1167,
1202, 1136, 1110, 1049, 920, 896, 856, 822, 756. H NMR
1
(300 MHz, DMSO-d6): δ 9.89 (s, 1H, NH), 8.36 (d,
J = 7.5 Hz, 1H, Ar–H), 8.10 (d, J = 7.8 Hz, 2H, Ar–H),
7.66 (t, J = 7.2 Hz, 1H, Ar–H), 7.40–7.56 (m, 4H, Ar–H),
5.12 (s, 1H, CH), 2.72–2.92 (m, 2H, CH2), 2.30–2.34 (m,
2H, CH2), 1.90–2.01 (m, 2H, CH2). 13C NMR (75 MHz,
DMSO-d6): δ 195.4, 160.7, 153.6, 152.7, 152.6, 146.4,
MP: 336–338 C; (KBr, ν, cm−1): 3362, 3059, 2945, 1696,
ꢀ
1625, 1509, 1469, 1360, 1274, 1237, 1178, 1032, 902, 765. 1H
NMR (300 MHz, DMSO-d6): δ 9.72 (s, 1H, NH), 8.29 (d,
J = 7.5 Hz, 1H, Ar–H), 7.60 (t, J = 7.2 Hz, 1H, Ar–H),
7.37–7.46 (m, 2H, Ar–H); 6.88 (d, J = 1.5 Hz, 1H, Ar–H),

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FOROUGHI KALDAREH ET AL.
6.55–6.64 (m, 2H, Ar–H), 4.94 (s, 1H, CH), 2.66–2.90 (m,
2H, CH2), 2.31–2.34 (m, 2H, CH2), 1.91–2.08 (m, 2H, CH2).
13C NMR (75 MHz, DMSO-d6): δ 195.5, 160.0, 152.4, 151.8,
147.4, 145.5, 137.5, 132.2, 124.4, 123.3, 120.0, 117.2, 115.6,
113.6, 112.8, 112.4, 102.6, 56.0, 37.2, 33.7, 26.8, 21.3. Anal.
calcd for C23H19NO5: C 70.94, H 4.92, N 3.60; found: 70.96,
H 4.90, N 3.62.
1193, 1149, 1020, 919, 892, 842, 754. 1H NMR
(300 MHz, DMSO-d6): δ 9.96 (s, 1H, NH), 8.42 (d,
J = 6.6 Hz, 1H, Ar–H), 7.57 (t, J = 7.2 Hz, 1H, Ar–
H), 7.32–7.43 (m, 2H, Ar–H), 7.26 (sbr, 4H, Ar–H),
4.94 (s, 1H, CH), 2.61–2.77 (m, 2H, CH2), 2.24 (d,
J = 16.2 Hz, 1H, CH2), 2.05 (d, J = 16.2 Hz, 1H,
CH2), 1.06 (s, 3H, CH3), 0.92 (s, 3H, CH3). 13C NMR
(75 MHz, DMSO-d6): δ 195.1, 160.7, 152.5, 150.6, 145.2,
142.9, 132.4, 131.2, 130.1, 128.3, 124.4, 123.9, 117.2,
113.5, 110.8, 101.7, 50.5, 34.6, 32.6, 29.5, 26.9. Anal.
calcd for C24H20NO3Cl: C 71.02, H 4.97, N 3.45; found:
71.06, H 4.93, N 3.48.
4.7 | 7-(4-Hydroxyphenyl)-
7,10,11,12-tetrahydro-6H-chromeno[4,3-b]
quinoline-6,8(9H)-dione (4g)
MP: 335–337 ꢀC; (KBr, ν, cm−1): 3343, 2926, 1672,
1634, 1607, 1511, 1473, 1366, 1264, 1243, 1174, 1036,
923, 755. 1H NMR (300 MHz, DMSO-d6): δ 9.68 (s,
1H, NH), 9.17 (s, 1H, OH), 8.29 (d, J = 7.8 Hz, 1H,
Ar–H), 7.58 (t, J = 7.5 Hz, 1H, Ar–H), 7.34–7.44 (m,
2H, Ar–H), 7.03 (d, J = 8.1 Hz, 2H, Ar–H), 6.60 (d,
J = 8.1 Hz, 2H, Ar–H), 4.91 (s, 1H, CH), 2.65–2.89 (m,
2H, CH2), 2.30 (sbr, 2H, CH2), 1.86–2.06 (m, 2H, CH2).
13C NMR (75 MHz, DMSO-d6): δ 195.4, 160.8, 156.2,
152.4, 151.7, 142.0, 137.1, 132.1, 129.0, 124.3, 123.3,
117.2, 115.2, 113.5, 112.7, 102.7, 37.2, 33.5, 26.8, 21.2.
Anal. calcd for C22H17NO4: C 73.53, H 4.77, N 3.90;
found: 73.56, H 4.80, N 3.93.
4.10 | 10,10-Dimethyl-7-(3-nitrophenyl)-
7,10,11,12-tetrahydro-6H-chromeno[4,3-b]
quinoline-6,8 (9H)-dione (4j)
MP: 282–284 ꢀC; (KBr, ν, cm−1): 3221, 3089, 2930,
1727, 1651, 1604, 1509, 1471, 1366, 1345, 1290, 1235,
1192, 1149, 1044, 894, 760. 1H NMR (300 MHz,
DMSO-d6): δ 9.85 (s, 1H, NH), 8.33 (d, J = 6.6 Hz,
1H, Ar–H), 8.00 (m, 2H, Ar–H), 7.37–7.72 (m, 4H, Ar–
H), 5.07 (s, 1H, CH), 2.52–2.71 (m, 2H, CH2), 2.28 (d,
J = 15.6 Hz, 1H, CH2), 2.08 (d, J = 15.6 Hz, 1H,
CH2), 1.09 (s, 3H, CH3), 0.95 (s, 3H, CH3). 13C NMR
(75 MHz, DMSO-d6): δ 195.1, 160.7, 152.6, 150.8, 148.1,
148.0, 143.0, 135.1, 132.7, 130.0, 124.6, 123.6, 122.7,
121.8, 117.4, 113.3, 110.5, 101.4, 50.3, 35.5, 32.6, 29.5,
26.9. Anal. calcd for C24H20N2O5: C 69.22, H 4.84, N
6.73; found: 69.26, H 4.81, N 6.68.
4.8 | 7-(m-Tolyl)-7,10,11,12-tetrahydro-
6H-chromeno[4,3-b]quinoline-6,8(9H)-
dione (4h)
MP: 304–306 ꢀC; (KBr, ν, cm−1): 3309, 3042, 2947,
1685, 1634, 1606, 1572, 1506, 1475, 1362, 1241, 1189,
1169, 1142, 1040, 925, 754. 1H NMR (300 MHz,
DMSO-d6): δ 9.76 (s, 1H, NH), 8.32 (d, J = 7.5 Hz,
1H, Ar–H), 7.63 (t, J = 7.2 Hz, 1H, Ar–H), 7.39–7.48
(m, 2H, Ar–H), 6.92–7.13 (m, 4H, Ar–H), 4.98 (s, 1H,
CH), 2.71–2.91 (m, 2H, CH2), 2.52 (s, 3H, CH3),
2.23–2.32 (m, 2H, CH2), 1.90–2.02 (m, 2H, CH2). 13C
NMR (75 MHz, DMSO-d6): δ 195.4, 160.8, 152.5, 152.0,
146.3, 142.4, 137.3, 132.3, 128.7, 128.4, 127.3, 125.2,
123.4, 117.3, 113.5, 112.4, 102.3, 37.1, 34.5, 26.8, 21.6,
21.2. Anal. calcd for C23H19NO3: C 77.29, H 5.36, N
3.92; found: 77.33, H 5.38, N 3.90.
4.11 | 7-(4-Hydroxyphenyl)-
10,10-dimethyl-7,10,11,12-tetrahydro-6H-
chromeno[4,3-b]quinoline-6,8(9H)-dione
(4k)
MP: 348–350 ꢀC; (KBr, ν, cm−1): 3280, 3242, 3054,
2951, 1719, 1632, 1588, 1508, 1476, 1362, 1305, 1243,
1193, 1145, 1039, 1014, 920, 838, 756. 1H NMR
(300 MHz, DMSO-d6): δ 9.62 (s, 1H, NH), 9.17 (s, 1H,
OH), 8.27 (d, J = 7.2 Hz, 1H, Ar–H), 7.57 (t,
J = 8.4 Hz, 1H, Ar–H), 7.33–7.44 (m, 2H, Ar–H), 7.03
(d, J = 8.4 Hz, 2H, Ar–H), 6.59 (d, J = 8.4 Hz, 2H,
Ar–H), 4.86 (s, 1H, CH), 2.65 (sbr, 2H, CH2), 2.25 (d,
J = 16.2 Hz, 1H, CH2), 2.06 (d, J = 16.2 Hz, 1H,
CH2), 1.08 (s, 3H, CH3), 0.96 (s, 3H, CH3). 13C NMR
(75 MHz, DMSO-d6): δ 195.1, 160.7, 156.2, 152.4, 149.6,
142.1, 137.0, 132.1, 129.1, 124.4, 123.3, 117.2, 115.1,
113.5, 111.6, 102.7, 50.6, 33.8, 32.6, 29.6, 26.9. Anal.
calcd for C24H21NO4: C 74.40, H 5.46, N 3.62; found:
74.46, H 5.43, N 3.60.
4.9 | 7-(4-Chlorophenyl)-10,10-dimethyl-
7,10,11,12-tetrahydro-6H-chromeno[4,3-b]
quinoline-6,8(9H)-dione (4i)
MP: 301–303 ꢀC; (KBr, ν, cm−1): 3294, 3076, 2945,
1704, 1633, 1608, 1571, 1506, 1475, 1361, 1303, 1238,

FOROUGHI KALDAREH ET AL.
11 of 12
4.12 | 7-[4-(Dimethylamino)phenyl]-
10,10-dimethyl-7,10,11,12-tetrahydro-6H-
chromeno[4,3-b] quinoline-6,8(9H)-dione
(4l)
(d, J = 7.8 Hz, 2H, Ar–H), 6.7 (d, J = 7.8 Hz, 2H, Ar–
H), 4.90 (s, 1H, CH), 3.67 (s, 3H, OCH3), 2.52 (d,
J = 16.2 Hz, 2H, CH2), 2.11 (d, J = 16.2 Hz, 2H,
CH2), 1.08 (s, 3H, CH3), 0.97 (s, 3H, CH3). 13C NMR
(75 MHz, DMSO-d6): δ 195.1, 160.7, 158.1, 152.5, 149.8,
142.3, 138.6, 132.3, 129.1, 124.4, 123.3, 117.3, 113.8,
113.5, 111.5, 102.6, 55.3, 50.6, 33.9, 32.6, 29.5, 27.0.
Anal. calcd for C25H23NO4: C 74.80, H 5.77, N 3.49;
found: 74.76, H 5.73, N 3.52.
MP: 160–161 ꢀC; (KBr, ν, cm−1): 3297, 3073, 2957,
1696, 1661, 1511, 1477, 1345, 1312, 1242, 1196, 1150,
1
1106, 1053, 829, 753. H NMR (300 MHz, DMSO-d6): δ
9.83 (s, 1H, NH), 8.33 (d, J = 7.8 Hz, 1H, Ar–H), 8.10
(d, J = 8.4 Hz, 2H, Ar–H), 7.64 (t, 1H, J = 7.5 Hz,
Ar–H), 7.50 (d, J = 8.4 Hz, 2H, Ar–H), 7.38–7.47 (m,
2H, Ar–H), 5.07 (s, 1H, CH), 2.90 (s, 3H, NCH3), 2.74
(s, 3H, NCH3), 2.52–2.69 (m, 2H, CH2), 2.27 (d,
J = 16.2 Hz, 1H, CH2), 2.07 (d, J = 16.2 Hz, 1H,
CH2), 1.08 (s, 3H, CH3), 0.94 (s, 3H, CH3). 13C NMR
(75 MHz, DMSO-d6): δ 195.1, 162.7, 160.6, 153.5, 152.6,
150.8, 146.4, 143.2, 132.7, 129.6, 124.6, 123.7, 123.6,
117.4, 113.3, 110.3, 101.1, 50.4, 36.2, 35.7, 32.6, 31.2,
29.4, 27.0. Anal. calcd for C26H26N2O3: C 75.34, H
6.32, N 6.76; found: 75.36, H 6.28, N 6.78.
4.15 | 7-(2,4-Dichlorophenyl)-
10,10-dimethyl-7,10,11,12-tetrahydro-6H-
chromeno[4,3-b]quinoline-6,8(9H)-dione
(4o)
MP: 333–334 C; (KBr, ν, cm−1): 3288, 3071, 2956, 1718,
ꢀ
1689, 1604, 1508, 1475, 1364, 1240, 1198, 1149, 1045, 747.
1H NMR (300 MHz, DMSO-d6): δ 9.73 (s, 1H, NH), 8.31
(d, J = 7.5 Hz, 1H, Ar–H), 7.63 (t, J = 7.5 Hz, 1H, Ar–H),
7.28–7.48 (m, 5H, Ar–H), 5.25 (s, 1H, CH), 2.64 (sbr, 2H,
CH2), 2.29 (d, J = 16.0 Hz, 1H, CH2), 2.01 (d, J = 16.0 Hz,
1H, CH2), 1.08 (s, 3H, CH3), 0.94 (s, 3H, CH3). 13C NMR
(75 MHz, DMSO-d6): δ 194.9, 160.3, 152.6, 150.6, 143.2,
142.5, 134.0, 133.9, 132.6, 131.7, 128.9, 127.2, 124.5, 123.5,
117.3, 113.1, 110.2, 101.0, 50.5, 34.5, 32.4, 29.5, 26.9. Anal.
calcd for C24H19NO3Cl2: C 65.47, H 4.35, N 3.18; found:
65.50, H 4.36, N 3.22.
4.13 | 7-(2-Chlorophenyl)-10,10-dimethyl-
7,10,11,12-tetrahydro-6H-chromeno[4,3-b]
quinoline-6,8 (9H)-dione (4m)
MP: 300–302 ꢀC; (KBr, ν, cm−1): 3292, 3075, 2956,
1711, 1633, 1607, 1510, 1475, 1364, 1243, 1198, 1148,
1
1041, 1021, 757. H NMR (300 MHz, DMSO-d6): δ 9.72
(s, 1H, NH), 8.34 (d, J = 6.9 Hz, 1H, Ar–H), 7.63 (t,
J = 8.4 Hz, 1H, Ar–H), 7.40 (t, J = 8.1 Hz, 1H, Ar–
H), 7.36–7.39 (m, 2H, Ar–H),7.25 (dd, 1H, J = 7.5,
1.5 Hz, Ar–H), 7.17 (td, J = 7.2, 1.8 Hz, 1H, Ar–H),
7.10–7.15 (m, 1H, Ar–H), 5.28 (s, 1H, CH), 2.53 (sbr,
2H, CH2), 2.23 (d, J = 16.2 Hz, 1H, CH2), 2.00 (d,
J = 16.2 Hz, 1H, CH2), 1.08 (s, 3H, CH3), 0.95 (s, 3H,
CH3). 13C NMR (75 MHz, DMSO-d6): δ 194.8, 160.3,
152.6, 150.4, 143.3, 143.0, 133.1, 132.7, 132.5, 129.7,
128.2, 127.0, 124.4, 117.2, 113.2, 110.6, 101.4, 50.6, 34.7,
32.4, 29.5, 26.9. Anal. calcd for C24H20NO3Cl: C 71.02,
H 4.97 N 3.45; found: 70.96, H 4.93, N 3.48.
4.16 | 10,10-Dimethyl-7-(naphthalen-
1-yl)-7,10,11,12-tetrahydro-6H-chromeno
[4,3-b]quinoline-6,8(9H)-dione (4p)
MP: 322–324 C; (KBr, ν, cm−1): 3309, 3073, 2955, 1724,
ꢀ
1670, 1608, 1574, 1510, 1476, 1361, 1237, 1195, 1147,
1
1053, 1020, 897, 777. H NMR (300 MHz, DMSO-d6): δ
9.76 (s, 1H, NH), 8.80 (d, J = 8.7 Hz, 1H, Ar–H), 8.35 (dd,
J = 8.1, 1.2 Hz, 1H, Ar–H), 7.81 (dd, J = 8.1, 1.2 Hz, 1H,
Ar–H), 7.68 (dd, J = 7.2, 2.4 Hz, 1H, Ar–H), 7.56–7.61 (m,
2H, Ar–H), 7.42–7.51 (m, 2H, Ar–H), 7.31–7.38 (m, 3H,
Ar–H), 5.74 (s, 1H, CH), 2.71 (sbr, 2H, CH2), 2.24 (d,
J = 16.5 Hz, 1H, CH2), 1.95 (d, J = 16.5 Hz, 1H, CH2),
1.08 (s, 3H, CH3), 0.89 (s, 3H, CH3). 13C NMR (75 MHz,
DMSO-d6): δ 195.1, 160.8, 152.3, 149.5, 145.6, 142.2,
133.2, 131.3, 128.1, 127.2, 127.0, 126.1, 125.8, 125.7, 124.4,
123.4, 117.2, 113.5, 113.0, 103.9, 50.5, 32.5, 30.2, 29.7,
26.7. Anal. calcd for C28H23NO3: C 79.79, H 5.50, N 3.32;
found: 80.02, H 5.55, N 3.34.
4.14 | 7-(4-Methoxyphenyl)-
10,10-dimethyl-7,10,11,12-tetrahydro-6H-
chromeno[4,3-b]quinoline-6,8(9H)-dione
(4n)
MP: 264–266 ꢀC; (KBr, ν, cm−1): 3263, 3093, 2958,
1727, 1646, 1606, 1511, 1471, 1365, 1261, 1237, 1196,
1
1039, 1021, 752. H NMR (300 MHz, DMSO-d6): δ 9.68
ACKNOWLEDGMENTS
(s, 1H, NH), 8.32 (d, J = 7.5 Hz, 1H, Ar–H), 7.64 (t,
J = 7.2 Hz, 1H, Ar–H), 7.39–7.49 (m, 2H, Ar–H), 7.15
Financial support by Rasht Branch, Islamic Azad Univer-
sity is gratefully acknowledged.

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FOROUGHI KALDAREH ET AL.
B. Geddes, E. Govek, M. Patane, D. Fry, B. D. Dayton,
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L. C. Preusser, K. Marsh, L. Hernandez, H. L. Sham,
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ORCID
Mahdiye Foroughi Kaldareh https://orcid.org/0000-
0003-3723-6589
Masoud Mokhtary https://orcid.org/0000-0003-3763-
7139
Mohammad Nikpassand https://orcid.org/0000-0002-
9692-6849
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How to cite this article: Foroughi Kaldareh M,
Mokhtary M, Nikpassand M. Nicotinic acid-
supported cobalt ferrite-catalyzed one-pot synthesis
of substituted chromeno[3,4-b]quinolines. Appl
Organometal Chem. 2020;e5469. https://doi.org/10.
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