A convenient method for synthesis of terpyridines: Via a cooperative vinylogous anomeric based oxidation

Article abstract of DOI:10.1039/d0ra04461j

The presented study is the first report of the synthesis of terpyridines in the presence of a nanomagnetic catalyst instead of harmful reagents. Herein, Fe3O4&at;O2PO2(CH2)2NH3+CF3CO2- as a retrievable nanocatalyst with magnetic properties was applied for the multi-component reaction between acetylpyridine derivatives (2 or 3 or 4-isomer), aryl aldehydes and ammonium acetate under conventional heating conditions in the absence of any solvent. The derived terpyridines were obtained with acceptable yields and brief reaction times via a cooperative vinylogous anomeric based oxidation route. Fe3O4&at;O2PO2(CH2)2NH3+CF3CO2- showed a high capability for recovery and reuse in the mentioned reaction.

Full text of DOI:10.1039/d0ra04461j

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PAPER
A convenient method for synthesis of terpyridines
via a cooperative vinylogous anomeric based
oxidation†
Cite this: RSC Adv., 2020, 10, 25828
*
Fatemeh Karimi, Meysam Yarie
and Mohammad Ali Zolfigol
The presented study is the first report of the synthesis of terpyridines in the presence of a nanomagnetic
ꢀ
catalyst instead of harmful reagents. Herein, Fe3O4@O2PO2(CH2)2NH3+CF3CO2 as
nanocatalyst with magnetic properties was applied for the multi-component reaction between
acetylpyridine derivatives (2 or or 4-isomer), aryl aldehydes and ammonium acetate under
a retrievable
3
Received 19th May 2020
Accepted 29th June 2020
conventional heating conditions in the absence of any solvent. The derived terpyridines were obtained
with acceptable yields and brief reaction times via a cooperative vinylogous anomeric based oxidation
DOI: 10.1039/d0ra04461j
ꢀ
route. Fe3O4@O2PO2(CH2)2NH3+CF3CO2 showed a high capability for recovery and reuse in the
rsc.li/rsc-advances
mentioned reaction.
Introduction
Nowadays, immobilizing catalytically homogeneous species onto
the surface of core–shell materials with magnetic cores for the
preparation of nanomagnetic heterogeneous catalysts has
attracted enormous interest. The insoluble and paramagnetic
natures of these kinds of catalysts,1–6 provide efficient and simple
isolation of them from the reaction mixture with an externally
applied magnetic eld. Because of their retrievability, high
surface area, biocompatibility and possibility of modication of
the surface of the magnetic nanoparticles with both organic and
inorganic compounds, these catalysts have found comprehensive
and signicant uses among academic and industrial scien-
tists.7–11 They are robust catalysts which have been applied in
various kinds of organic synthesis.12–23
Scheme 1 Anomeric effect leads to more stability axial conformer 2-
diphenylphosphinoyl 1,3-dithiane.42,43
In conformity with the principles of green chemistry, such as
increase the efficiency of chemical reactions, the atomic
economy, reduce derivatives, decrease the utilization of organic
solvents and waste production, simplify processes and design
for energy efficiency, multi-component reactions (MCRs) have
been presented and extended as a powerful method for the
preparation of structurally diverse drug-like compounds
(expansion of large chemical libraries of drug-like
compounds).24–32
Anomeric effect is an important stereoelectronic phenom-
enon which had been described as the axial superiority for an
electronegative substituent (acceptor group) positioned adja-
cent to a donor group (lone pairs) rather than equatorial
Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University,
Hamedan, 6517838683, Iran. E-mail: mzolgol@yahoo.com
† Electronic supplementary information (ESI) available. See DOI:
10.1039/d0ra04461j
Scheme 2 Stability of bis-peroxides due to the anomeric effect.
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Katritzky et al. by low temperature X-ray crystallography have
been shown that facile C–N bond dissociation of the benzo-
triazole residue in compound C, have been related to a vinyl-
ogous anomeric effect (VAE) (Scheme 4).54
Based on above mentioned facts, “cooperative anomeric
and/or vinylogous anomeric based oxidation” terms represent
a new mechanistic vision and major driving force for the
oxidative aromatization of some susceptible heterocyclic mole-
cules. Recently, these concepts have been reviewed.55,56
Scheme 3 Anomeic effect in tetrahydropyrane versus a vinylogous
anomeric effect in pyran.54
Pyridines are a privileged category of N-heteroaromatics
found in numerous natural and synthetic compounds with
a wide range of biological, pharmaceutical, agrochemical and
physiological applications such as anti-ulcer,57 antineoplastic,58
antimicrobial,59–62 antiviral,63 antitubercular,64 antitumor,65–69
and cardiotonic70 properties. Among these compounds, terpyr-
idines (tpys) by reason of their p-stacking ability, directional H-
bonding and coordination properties are outstanding building
blocks in supramolecular chemistry.71 In addition, terpyridines
(tpys) have been applied broadly in various elds such as
molecular biology,72,73 antitumor chemo-therapeutics,74 photo-
sensitization,75 and asymmetric catalysis.76 Also, they are able to
coordinate to a variety of transition-metal ions as ligands and
form the corresponding complexes.77–79 A class of these ligands
is becoming popular as a building block for the assembly of
coordination polymers and networks.80–95 Therefore, the
construction of novel terpyridines and/or methodologies has
attracted many attentions. So far many protocols were reported
for the synthesis of these valuable compounds.96–104 Traditional
protocols for synthesis of tpys have many drawbacks such as
multi-step procedure, the use of microwave irradiation, a long
reaction time, low yield, utilization of organic solvents like
glycol and harmful reagents for environment such as sodium or
potassium hydroxide and acetic acid. Therefore, the presenta-
tion of more efficient and greener methods for the synthesis of
tpys is highly desirable.
Scheme 4 VAE causes facile C–N bond dissociation of the benzo-
triazole residue.
position.33–39 In the other hand, this concept is a kind of nega-
tive hyperconjugation can lead sharing of the electron density
from lone-pair orbital to a vacant anti-bonding sigma orbital (n
/ s*) (Scheme 1).40,41
Anomeric effect has a potent role to explain some eccentric
phenomena in the chemistry knowledge. For instance, anome-
ric effect justies why bis-peroxides A and B can be more ther-
modynamically stable than mono-peroxides, and can even melt
ꢁ
without decomposition at 131 and 142 C, respectively. Anom-
alous stability of these compounds is associated with strong
anomeric nO/s*CꢀO interactions in two peroxide groups which
separated by a one-atom bridge (Scheme 2).44
The anomeric effect can also be extended through double
bonds in what has been named the vinylogous anomeric effect
(VAE). The VAE had been applied for the stereoelectronic sup-
ported interactions of unshared electron pairs to vacant anti-
bonding sigma orbitals (n / s*) over four bonds (Scheme 3).45–53
For overcome to these demerits, for the rst time we applied
a recoverable nanocatalyst with magnetic properties instead of
harmful reagent for one-pot synthesis of tpys under conven-
tional heating conditions in the absence of any solvent. Also, we
ꢀ
Scheme 5 Construction of terpyridines in the presence a catalytic amount of Fe3O4@O2PO2(CH2)2NH3+CF3CO2
.
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Table 1 Influence of the different parameters on construction of terpyridine 1aa
Temperature
(ꢁC)
Load of catalyst
(mg)
Entry
Solvent
Time (min)
Yieldb (%)
1
—
—
—
—
—
—
—
80
100
120
140
120
120
120
Reux
Reux
Reux
Reux
Reux
Reux
10
10
10
10
15
5
—
10
10
10
10
10
10
90
60
50
50
50
60
90
90
90
90
90
90
90
60
75
80
78
80
65
30
40
40
43
35
Trace
Trace
2
3c
4
5
6
7
8
H2O
EtOH
CH3CN
EtOAc
CH2Cl2
n-Hexane
9
10
11
12
13
a
Reaction conditions: benzaldehyde (1.0 mmol, 0.106 g), 4-acetyl-pyridine (2.0 mmol, 0.242 g) and ammonium acetate (2.0 mmol, 0.154 g).
Reported yields are referred to isolated yields. The achieved data for testing the model reaction under air, nitrogen and argon atmospheres
b
c
are similar.
generalize the presented protocol by applying various isomer of and argon atmospheres. The results under air, nitrogen and
acetylpyridine (2 or 3 or 4-isomer) and introduce a new mech- argon atmospheres are same (Table 1, entry 3).
anistic route (CVABO) for the synthesis of tpys. In this paper, to
Aerwards, the scope, limitations and generality of the pre-
develop the concept of “cooperative vinylogous anomeric based sented protocol developed by applying different aryl aldehydes,
oxidation (CVABO)”105–110 and in continuation of our efforts to acetylpyridine (2, 3 and 4-isomers) and ammonium acetate
+
ꢀ
develop new protocols for the synthesis of pyridine deriva- using of Fe3O4@O2PO2(CH2)2NH3 CF3CO2 as a recoverable
tives,106–110 we investigated the catalytic performance of catalyst under the optimal qualications. As disclose in Table 2,
+
ꢀ
Fe3O4@O2PO2(CH2)2NH3 CF3CO2 in construction of terpyr- all desired molecules were synthesized in brief times with
idins (Scheme 5).
acceptable yields.
In separate study, the possibility of recycling
a
+
ꢀ
Fe3O4@O2PO2(CH2)2NH3 CF3CO2 was probed by the model
reaction between benzaldehyde, 4-acetylpyridine and ammo-
nium acetate in 50 minute. Aer each individual run, hot ethanol
was added to the reaction mixture to dissolve unreacted starting
materials and target product. Thus the insoluble nanocatalyst
conveniently isolated from the reaction mixture utilizing
a magnet bar. Then, the reusable catalyst was utilizable aer
washing with ethanol and drying for subsequent run. As depicted
in Fig. 1, it can be inferred that the catalyst has good recovery
capability for reusing test.
Results and discussion
The reusable nano magnetic catalyst with ionic liquid tags
namely Fe3O4@O2PO2(CH2)2NH3 CF3CO2 was synthesized
according to our recently reported procedure.106
+
ꢀ
In rst step, for determine the optimal reaction conditions,
we chose condensation between of benzaldehyde, 4-acetylpyr-
idine and ammonium acetate as a model reaction. For obtain-
ing the appropriate conditions, effective parameters including
various solvents, temperature and amount of catalyst were
exactly probed. Based on the obtained data as summarized in
Table 1, the highest experimental yield and lowest reaction time
was achieved in the presence of 10 mg catalyst at 120 ꢁC in the
absence of any solvent (Table 1, entry 3). In addition to, for
demonstration of the last step of the proposed mechanism, the
optimized reaction conditions were performed under nitrogen
A suggested plausible reaction mechanism for the prepara-
tion of desirable molecule 2a via a cooperative vinylogous
anomeric based oxidation mechanism is portrayed in Scheme ꢀ6.
+
Initially, in the presence of Fe3O4@O2PO2(CH2)2NH3 CF3CO2
,
enolic form of 3-acetylpyridine attacked to activated benzalde-
hyde to produce intermediate A. In continuation, chalcone
intermediate
A is attacked by second molecule of 3-
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Table 2 Fe3O4@O2PO2(CH2)2NH3+CF3CO2ꢀ catalyzed synthesis of terpyridinesa
a
Reaction condition: aryl aldehyde (1.0 mmol), acetylpyridine derivatives (2.0 mmol, 0.242 g) and ammonium acetate (2.0 mmol, 0.154 g), solvent
free, 120 ꢁC, catalyst ¼ 10 mg. Reported yields are referred to isolated yields.
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without further purication. The reaction progress and purity
of the prepared structures were monitored by TLC performed
with silica gel SIL G/UV 254 plates. FT-IR spectra were recorded
on a PerkinElmer Spectrum Version 10.02.00 using KBr
pellets. The 1H NMR (301 MHz) and 13C NMR (76 MHz) spectra
were recorded on a Bruker spectrometer (d in ppm) using
DMSO-d6 as solvent with chemical shis measured relative to
Si(CH3)4 as internal standard. Melting points were determined
with a Buchi B-545 melting point apparatus in open capillary
tubes.
ꢀ
Fig. 1 The reusing test of Fe3O4@O2PO2(CH2)2NH3+CF3CO2
General procedure for synthesis of
+
ꢀ
Fe3O4@O2PO2(CH2)2NH3 CF3CO2
acetylpyridine in enolic form to afford intermediate B. Aer-
wards, the enamine intermediate C is produced from the reac-
tion of ammonium acetate and intermediate B. In the next step,
through intramolecular nucleophilic attack, intermediate C
converted to intermediate D. In the last step, lone pair electrons
of N atom through C–C double bonds interact with a vacant
The reusable nano magnetic catalyst with ionic liquid tags
namely Fe3O4@O2PO2(CH2)2NH3 CF3CO2 was synthesized
according to our recently reported protocol.106
+
ꢀ
General procedure for the synthesis of terpyridines
anti-bonding
orbital
of
C–H
bond
To a mixture of aromatic aldehydes (1.0 mmol), acetylpyridine
derivatives (2.0 mmol, 0.242 g) and ammonium acetaꢀte (2.0 mmol,
ðnN/s*CꢀH and pC¼C/sC* ꢀHÞ and weaken it which favored
hydride transfer and H2 releasing from intermediate D to
generate the aromatized molecule 2a. The achieved data from
optimization of reaction under argon and nitrogen atmo-
spheres veried our suggestion for oxidation and aromatization
of intermediate D.
+
0.154 g), 10 mg of Fe3O4@O2PO2(CH2)2NH3 CF3CO2 was added.
The result mixture was stirred in the absence of any solvent at
ꢁ
120 C for suitable times (Table 2). The progress of reaction was
checked by TLC (n-hexane/ethylacetate as eluent). Aer comple-
tions of reactions, for separation of the catalyst, hot ethanol was
added to the reaction mixtures. Then, insoluble nanocatalyst
conveniently isolated from the reaction mixture utilizing a magnet
bar. It was washed with ethanol and reused for subsequent reac-
tion. Finally, the solvent was removed and the crude solids ob-
Experimental
General
The commercially available chemicals were obtained from tained were puried using ethanol. The desired products were
Fluka and Merck chemical companies and used as received obtained in acceptable isolated yields as presented in Table 2.
Scheme 6 A proposed reaction mechanism for preparation of target molecule 2a via a cooperative vinylogous anomeric based oxidation
mechanism.
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155.7, 154.9, 149.5, 149.3, 137.5, 137.5, 129.49, 129.4, 126.9,
124.5, 120.9, 118.0, 25.5.
Selected spectral data
40-(2-Thiophenyl)-4,20:60,400-terpyridine (1b). A light green
solid, mp ¼ 242–244 ꢁC. FT-IR (KBr, n, cmꢀ1): 3035, 1592, 1557,
1538, 1403, 828. 1H NMR (301 MHz, DMSO) dppm: 8.80 (d, 4H, J
¼ 6 Hz, pyridine), 8.40 (s, 2H, pyridine), 8.32 (d, 4H, J ¼ 6 Hz,
pyridine), 8.20 (d, 1H, J ¼ 3 Hz, thiophene), 7.88 (d, 1H, J ¼ 3 Hz,
thiophene), 7.34 (t, 1H, J ¼ 3 Hz, thiophene). 13C NMR (76 MHz,
DMSO) dppm: 155.1, 150.9, 145.5, 144.3, 140.4, 129.7, 129.4,
128.4, 121.6, 117.5.
40-(4-Chlorophenyl)-4,20:60,400-terpyridine (1e). A white solid,
mp ¼ 260–262 ꢁC. FT-IR (KBr, n, cmꢀ1): 3035, 1592, 1559, 1493,
1389, 1092, 812. 1H NMR (301 MHz, DMSO) dppm: 8.80 (d, 4H, J
¼ 6 Hz, pyridine), 8.53 (s, 2H, pyridine), 8.36 (d, 4H, J ¼ 6 Hz,
pyridine), 8.20 (d, 2H, J ¼ 6 Hz, aromatic), 7.69 (d, 2H, J ¼ 6 Hz,
aromatic). 13C NMR (76 MHz, DMSO) dppm: 155.0, 150.9, 149.4,
145.7, 136.1, 135.2, 129.9, 129.6, 121.7, 119.4.
40-Phenyl-3,20:60,300-terpyridine (2a). A white solid, mp ¼ 205–
207 ꢁC. FT-IR (KBr, n, cmꢀ1): 3034, 1595, 1558, 1483, 1390, 803.
1H NMR (301 MHz, DMSO) dppm: 9.55–9.54 (m, 2H, pyridine),
8.75–8.71 (m, 4H, pyridine), 8.40 (s, 2H, pyridine), 8.15–8.12 (m,
2H, aromatic), 7.64–7.56 (m, 5H, aromatic). 13C NMR (76 MHz,
DMSO) dppm: 155.2, 150.6, 150.4, 148.8, 137.6, 135.0, 134.5,
130.1, 129.6, 128.0, 124.3, 118.0.
Conclusions
In conclusions, for the rst time a nanomagnetic catalyst was
applied for one-pot preparation of terpyridines. In this study,
+
ꢀ
the catalytic performance of Fe3O4@O2PO2(CH2)2NH3 CF3CO2
as a retrievable nanocatalyst with magnetic properties was
investigated for the synthesis of terpyridines through a multi-
component reaction between various isomer of acetylpyridine,
aryl aldehyds and ammonium acetate under conventional
heating and solvent-free reaction conditions with acceptable
yields and brief times. For nal step of the mechanistic route for
the synthesis of target molecules we suggested a cooperative
vinylogous anomeric based oxidation mechanism as a new
+
ꢀ
mechanistic route. Also, Fe3O4@O2PO2(CH2)2NH3 CF3CO2
showed excellent reusability in the investigated multi-
component reactions. Other advantage of presented protocol
are overcoming to drawbacks of traditional procedures such as
multi-step procedure, use of microwave irradiation, long reac-
tion time, low yield, utilization of organic solvents like glycol
and harmful reagents for environment such as sodium or
potassium hydroxide and acetic acid.
40-(2-Thiophenyl)-3,20:60,300-terpyridine (2b). A white solid, mp
¼ 194–195 ꢁC. FT-IR (KBr, n, cmꢀ1): 3055, 1603, 1547, 1428, 1024,
805, 695. 1H NMR (301 MHz, DMSO) dppm: 9.50 (s, 2H, pyridine),
8.73–8.67 (m, 4H, pyridine), 8.30 (s, 2H, pyridine), 8.17 (dd, 1H, J1
¼ 3.6 Hz, J2 ¼ 0.9 Hz, thiophene), 7.85 (dd, 1H, J1 ¼ 4.8 Hz, J2 ¼
0.6 Hz, thiophene), 7.60 (dd, 2H, J1 ¼ 7.8 Hz, J2 ¼ 4.8 Hz, pyridine),
7.33 (dd, 1H, J1 ¼ 5.1 Hz, J2 ¼ 3.9 Hz, thiophene). 13C NMR (76
MHz, DMSO) dppm: 155.3, 150.7, 148.7, 143.9, 140.7, 134.9, 134.19,
129.4, 129.3, 128.2, 124.3, 116.1.
Conflicts of interest
There are no conicts to declare.
Acknowledgements
We thank the Bu-Ali Sina University and Iran National Science
Foundation (INSF) (Grant Number: 98001912) for nancial
support.
40-(4-Methoxyphenyl)-3,20:60,300-terpyridine (2c).
A
white
solid, mp ¼ 128–130 ꢁC. FT-IR (KBr, n, cmꢀ1): 3031, 1597, 1541,
1
1489, 812. H NMR (301 MHz, DMSO) dppm: 9.53 (s, 2H, pyri-
dine), 8.71 (s, 4H, pyridine), 8.35 (s, 2H, pyridine), 8.11 (d, 2H, J
¼ 6 Hz, aromatic), 7.59 (s, 2H, aromatic), 7.15 (d, 2H, J ¼ 3 Hz,
Notes and references
aromatic), 3.88 (s, 3H, OMe). 13C NMR (76 MHz, DMSO) dppm
:
¨
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40-(4-Chlorophenyl)-3,20:60,300-terpyridine (2e). A white solid,
mp ¼ 202–204 ꢁC. FT-IR (KBr, n, cmꢀ1): 3044, 1609, 1577, 1545,
1497, 1420, 1024, 803, 701. 1H NMR (301 MHz, DMSO) dppm
:
9.53 (s, 2H, pyridine), 8.73–8.70 (m, 4H, pyridine), 8.40 (s, 2H,
pyridine), 8.17 (d, 2H, J ¼ 9 Hz, aromatic), 7.65 (d, 2H, J ¼ 9 Hz,
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