A facile and efficient route to one-pot synthesis of new cyclophanes using vinamidinium salts

Article abstract of DOI:10.1039/d0ra10548a

In this study, an efficient method for the synthesis of new cyclophanes (5a-f,6a-g) through the condensation of 1,4-phenylenedimethanamine (3) or 2,3,5,6-tetramethylbenzene-1,4-diamine (4) with 2-substituted vinamidiniums (2a-g) is described. The cyclopha

Full text of DOI:10.1039/d0ra10548a

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A facile and efficient route to one-pot synthesis of
new cyclophanes using vinamidinium salts†
Cite this: RSC Adv., 2021, 11, 13666
Nooshin Golzar, Abdolmohammad Mehranpour * and Najmeh Nowrouzi
In this study, an efficient method for the synthesis of new cyclophanes (5a–f, 6a–g) through the
condensation of 1,4-phenylenedimethanamine (3) or 2,3,5,6-tetramethylbenzene-1,4-diamine (4) with 2-
substituted vinamidiniums (2a–g) is described. The cyclophane derivatives are obtained in good to
excellent yields in the presence of acetic acid in refluxing acetonitrile after 15 h. The structure of new
Received 15th December 2020
Accepted 26th March 2021
DOI: 10.1039/d0ra10548a
1
13
rsc.li/rsc-advances
compounds was validated based on their spectral data ( H NMR, C NMR, IR) and elemental analysis.
5
4
55
asymmetric catalysis, insulating plastics, organic elec-
Introduction
56
57,58
59
tronics, metal capture
and supramolecular chemistry.
1
The structure of a vast range of macromolecules conrmed that Besides, since cyclophane structure is the main foundation unit
60–62
the design and construction of macrocyclic compounds has in many biologically active natural products (Fig. 1),
their
been one of the most important reasons for improvement in design and application is a special interest of groups working in
supramolecular science. A well-known group of macrocyclic
compounds are cyclophanes and their particular chemistry has
2
attracted the attention of researchers, recently and has been
broadly discussed within the eld of modern supra-molecular
3,4
5–42
chemistry. Cyclophanes
are constrained organic mole-
cules consisting of aromatic ring(s) as well as aliphatic unit(s).
The aromatic rings support the rigidity of their structure, while
the aliphatic unit(s) create bridge(s) between the aromatic rings
and cause the exibility of the whole structure.
Due to their special structure, they are considered as an
4
3–47
important class of compounds in “host–guest” chemistry
and supramolecular assembly.
48–51
On the other hand, the clear
structure and high strain of cyclophanes has contributed in
52,53
a large number of applications such as pharmaceuticals,
Fig. 1 Natural products containing the cyclophane skeleton.
Department of Chemistry, Faculty of Sciences, Persian Gulf University, Bushehr,
7
†
1
5169, Iran. E-mail: ammehranpour@hotmail.com
Electronic supplementary information (ESI) available. See DOI:
0.1039/d0ra10548a
Scheme 1 Reported methods for the synthesis of cyclophanes.
13666 | RSC Adv., 2021, 11, 13666–13673
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methods. Therefore, designing better routes and improving
conditions to achieve cyclophanes is still needed.
Vinamidinium salts are examples of stabilized alkenes by
“push–pull” inuences between the electron-donating amino
group and the electron-withdrawing ammonium group. They
can easily undergo condensation reaction with bifunctional
nucleophiles to form heterocycles. During past years, our group
has been investigated the utilization of vinamidinium salts for
67–76
the synthesis of heterocyclic compounds
(Scheme 2).
Results and discussion
Scheme 2 Application of vinamidinium salts in organic synthetic
chemistry.
In continuation of these studies and due to the importance of
cyclophanes in different branches of sciences, we decided to
investigate the one-pot synthesis of cyclophanes from vinami-
dinium salts (Scheme 3). To the best of our knowledge, vina-
midinium salts have not yet been applied for preparing
cyclophanes.

elds including biological, medicinal and organic chemistry.
Moreover, cyclophanes are attractive in the area of theoretical
chemistry due to their particular topology and intra-molecular
interactions.
As shown in Scheme 3, the procedure is done in two-step: (i)
synthesis of the 2-substituted vinamidinium salts (2a–g) by the
So far, several methods have been reported for the synthesis
Vilsmeier–Arnold formylation of the substituted acetic acids
63–66
of cyclophanes compounds
(Scheme 1). In some instances,
67–76
(1a–g) as explained in authors previous work;
and (ii)
cyclophanes are formed in low yields and also with side prod-
ucts. Some procedures require many steps or harsh reaction
conditions such as high-pressure, and difficult separation
synthesis of cyclophane derivatives (5a–f, 6a–g) by the reaction
of 2-substituted vinamidinium salts (2a–g) with 1,4-
Table 1 Effect of the different reaction parameters on the reaction of
1
,4-phenylenedimethanamine (3) with ((E)-N-(3-(dimethylamino)-2-
(
(
naphthalen-1-yl)allylidene)-N-methylmethanaminium
2f))
perchlorate
a
Entry
Condition
Solvent
Time (h)
Yield (%)
1
2
3
4
5
6
7
8
9
AcOH (3 mmol)
AcOH (3 mmol)
AcOH (3 mmol)
AcOH (3 mmol)
AcOH (3 mmol)
AcOH (3 mmol)
AcOH (3 mmol)
EtOH/reux
MeOH/reux
24
24
15
24
24
24
24
24
24
24
15
24
24
43
36
90
35
Trace
—
45
—
—
CH
CHCl
CH Cl
3
CN/reux
/reux
/reux
3
2
2
Toluene/reux
ꢀ
DMF/100 C
Et
3
N (3 mmol)
CH
CH
CH
CH
CH
CH
3
3
3
3
3
3
CN/reux
CN/reux
CN/reux
CN/reux
CN/reux
CN/reux
i-Pr
2
NEt (3 mmol)
1
1
1
1
0
1
2
3
—
—
AcOH (4 mmol)
AcOH (2 mmol)
AcOH (1 mmol)
90
64
40
a
Isolated yield.
Scheme 3 Synthesis of cyclophanes.
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2021 The Author(s). Published by the Royal Society of Chemistry
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phenylenedimethanamine (3) or 2,3,5,6-tetramethylbenzene- phenylenedimethanamine (3) or 2,3,5,6-tetramethylbenzene-
1,4-diamine (4) by applying acetic acid in acetonitrile as solvent. 1,4-diamine (4) in reuxing acetonitrile in the presence of ace-
In the rst step, vinamidiniums were isolated as the tic acid for 15 h to manage the cyclophane derivatives (5a–f, 6a–
perchlorate salts and used directly without additional purica- g). To provide the best reaction conditions in second step, the
tion for the synthesis of cyclophanes. reaction of vinamidinium salt 2f with 1,4-phenylenedimethan-
As illustrated in Scheme 3, the symmetrical vinamidinium amine (3) was chosen as model reaction and the impacts of
salts (2a–g) were able to react with 1,4- solvents and catalysts were investigated. The obtained results
Table 2 The synthesis of cyclophane derivatives from the reaction of 2-substituted vinamidinium salts (2a–g) (1.0 mmol), 1,4-phenyl-
enedimethanamine (3) (1.0 mmol) in the presence of AcOH (3.0 mmol) in CH CN (8.0 mL) at reflux conditions
3
+
a
Entry
1
R or R
Yield (%)
87
90
2
3
83
88
4
5
90
a
Isolated yield.
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are summarized in Table 1. When EtOH and MeOH were low yields (43% and 36%, respectively) aer 24 h (Table 1,
applied as the solvent and the mixture was subjected to reux in entries 1 and 2). In a modied protocol, the reaction was carried
the presence of AcOH, the desired product, 5f, was achieved in out in reuxing acetonitrile. In this case, remarkable
Table 3 The synthesis of cyclophane derivatives from the reaction of 2-substituted vinamidinium salts (2a–g) (1.0 mmol), 2,3,5,6-tetrame-
thylbenzene-1,4-diamine (4) (1.0 mmol) in the presence of AcOH (3.0 mmol) in CH CN (8.0 mL) at reflux conditions
3
+
a
Entry
1
R or R
Yield (%)
77
86
2
3
80
82
4
5
6
81
90
87
7
a
Isolated yield.
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improvement of yield was observed (Table 1, entry 3). No better the system, we applied 2,3,5,6-tetramethylbenzene-1,4-diamine
results were obtained when the reaction was carried out in (4) as bifunctional nucleophile and investigated the formation
DMF, CHCl , CH Cl or toluene (Table 1, entries 4–7). There- of new cyclophanes.
3
2
2
fore, the subsequent reactions were carried out in CH CN.
2,3,5,6-Tetramethylbenzene-1,4-diamine (4) was also toler-
3
Aer choosing the solvent, the model reaction was con- ated well in this procedure to give the desired products (Table
ducted under neutral and basic conditions. As shown in entries 3).
8
and 9 of Table 1, in the presence of basic catalysts such as
triethylamine and ethyldiisopropylamine, the desired product a reasonable mechanism for the synthesis of cyclophane
f, was not achieved. In neutral conditions also, no product was compounds (5a–f, 6a–g) in the presence of AcOH is illustrated in
formed (Table 1, entry 10). Increasing the amount of AcOH did Scheme 4.
According to our previous works and above results,
5
not affect the reaction appreciably, while, decreasing the
The reaction proposed by the initial attack of the amino
amount of AcOH, resulted the product in lower yield (Table 1, group in 1,4-phenylenedimethanamine (3) or 2,3,5,6-
entries 11–13). So, acidic media is critical to the success of the tetramethylbenzene-1,4-diamine (4) to protonated vinamidi-
reaction.
nium salt. Then, removal of dimethylamine occurs, followed by
We then applied the obtained optimized conditions for the the nucleophilic attack of second molecule of amine on the
reaction of different vinamidinium salts with 1,4-phenyl- obtained iminium salt to produce intermediate A. The loss of
enedimethanamine (3). The results are listed in Table 2.
the second dimethylamine molecule produces intermediate B.
The results demonstrated that the variety of vinamidinium The reaction of this intermediate with the second molecule of
salts were successfully employed in this process, affording novel vinamidinium salt, followed by the loss of two dimethylamine
cyclophanes in high yields in suitable reaction times.
molecules and intramolecular nucleophilic cyclization, yields
Aer successful application of 1,4-phenylenedimethan- the desired cyclophane.
amine (3) in cyclophane synthesis, to enhance the generality of
Conclusion
In this study, an efficient and applicable protocol has been
developed for the synthesis of novel cyclophanes by the reaction
of 2-substituted vinamidinium salts with 1,4-phenyl-
enedimethanamine or 2,3,5,6-tetramethylbenzene-1,4-diamine
in the presence of acetic acid.
This protocol has several advantages such as: simple and
one-step procedure, absence of by-products, inexpensive cata-
lyst, normal atmospheric conditions, high to excellent yields
and easy purication of the products. Furthermore, the prod-
ucts are well-known, stable solids and have a long shelf-life
when stored in an anhydrous environment.
Experimental section
General procedure for the synthesis of cyclophane derivatives
(5a–f, 6a–g)
To a ame dried one-necked round-bottomed ask equipped
with magnetic stirring and reux condenser, 2-substituted
vinamidinium salts (2a–g) (1.0 mmol), 1,4-phenyl-
enedimethanamine (3) or 2,3,5,6-tetramethylbenzene-1,4-
diamine (4) (1.0 mmol), AcOH (3.0 mmol) and CH CN (8.0
3
mL) were added. The mixture was allowed to reux for 15 h in
an oil bath. Aer completion of the reaction, distilled H O (20
2
mL) was added to the mixture. The resulting precipitate was
gathered, washed with Et
2
O (3 ꢁ 3 mL). Finally, the precipitate
was washed with 2-propanol (3 ꢁ 3 mL) and dried under
ꢀ
vacuum at 80 C to afford the corresponding cyclophanes.
Conflicts of interest
Scheme 4 The proposed mechanism for the synthesis of cyclophanes
in the presence of AcOH.
There are no conicts of interest to declare.
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