Synthesis of Seleno Oxindoles via Electrochemical Cyclization of N-arylacrylamides with Diorganyl Diselenides

Article abstract of DOI:10.1002/adsc.202001192

The tandem cyclization of acrylamide with diselenides facilitated by electrochemical oxidation was successfully developed. This strategy provided an environmentally friendly method for the construction of C?Se bond. A series of seleno oxindoles with pharmacological activity were obtained by using this well-designed tandem cyclization strategy. The in vitro antitumor activity of the compounds was also screened through MTT assay. Results showed that the seleno oxindoles exhibited better antitumor activity than other oxindole derivatives. (Figure presented.).

Full text of DOI:10.1002/adsc.202001192

Title: Synthesis of Seleno Oxindoles via Electrochemical Cyclization of
N-arylacrylamides with Diorganyl Diselenides
Authors: Xin-Yu Wang, Yuan-Fang Zhong, Zu-Yu Mo, Shi-Hong Wu,
Yanli Xu, Hai-Tao Tang, and Ying-ming Pan
This manuscript has been accepted after peer review and appears as an
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content of this Accepted Article.
To be cited as: Adv. Synth. Catal. 10.1002/adsc.202001192
Link to VoR: https://doi.org/10.1002/adsc.202001192

Advanced Synthesis & Catalysis
10.1002/adsc.202001192
COMMUNICATION
DOI: 10.1002/adsc.202((will be filled in by the editorial staff))
Synthesis of Seleno Oxindoles via Electrochemical Cyclization
of N-arylacrylamides with Diorganyl Diselenides
a
a
b
a
b
Xin-Yu Wang, Yuan-Fang Zhong, Zu-Yu Mo, Shi-Hong Wu, Yan-Li Xu, Hai-Tao
a
a,
Tang, and Ying-Ming Pan *
a
State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and
Pharmaceutical Sciences of Guangxi Normal University, Guilin 541004, People’s Republic of China. E-mail:
panym@mailbox.gxnu.edu.cn
Pharmacy School of Guilin Medical University, Guilin, 541004 People’s Republic of China
b
Received: ((will be filled in by the editorial staff))
Supporting information for this article is available on the WWW under http://dx.doi.org/10.1002/adsc.201######.((Please
delete if not appropriate))
Abstract: The tandem cyclization of acrylamide with heterocyclic units also have unique biological
diselenides facilitated by electrochemical oxidation was activities, such as antitumor, antibacterial, anti-
successfully developed. This strategy provided an
environmentally friendly method for the construction of C–
inflammatory, antiviral, cardiovascular protection,
and immune regulation, and other biological activities
Se bond. A series of seleno oxindoles with pharmacological
activity were obtained by using this well-designed tandem
cyclization strategy. The in vitro antitumor activity of the
compounds was also screened through MTT assay. Results
showed that the seleno oxindoles exhibited better antitumor
activity than other oxindole derivatives.
[16]
(
Figure 1).
Therefore, introducing a selenium
functional group into oxindoles presents an attractive
research direction; however, only a few chemists
[17]
have undertaken such an activity. Various selenium
reagents, such as elemental selenium, selenium
dioxide, selenium sulfonate, potassium selenocyanate,
Keywords: Electrochemical synthesis; Cross-coupling and N-(phenylseleno)phthalimide, have been used for
[18]
reaction; Oxindole skeletons.
the construction of organic selenium compounds.
Nevertheless, most selenization reactions usually
suffer from harsh or complex reaction conditions. As
a result, diselenide, a stable and readily available
selenium reagent, has emerged as an alternative for
constructing selenium compounds.
Oxindoles are preferential heterocyclic structural
motifs that are widely present in numerous natural
[1]
products and pharmaceutical agents,
such as
isatin,[ alatonisine, strychnofoline, AKI-001,
2]
[3]
[4]
[5]
In 2014, Fu and coworkers described the
ammonium-persulfate-mediated radical oxidative
[6]
[7]
HIV protease inhibitors, and AG-041R (Figure 1).
As a result of the excellent properties of this
framework, the functionalization and synthesis of the
oxindole scaffold have attracted considerable interest
from synthetic organic chemists.[ Two strategies,
namely, the functionalization of a pre-existing
oxindole skeleton by introducing new functional
groups[ and the assembly of a new oxindole ring
cyclization
of
N-arylacrylamides
with
N-
(
phenylseleno)phthalimide and obtained several
[17]
seleno oxindoles selectively. However, this method
requires the use of excess oxidants and complex
selenium reagents.
8]
9]
Figure 1 Representative oxindole structures
[10-14]
from acyclic precursors, are commonly used.
Generally, the latter approach has much subatantial
potential for the rapid acquisition of diversity in the
functionalized oxindoles. Many functional groups,
such as sulfonyl,[ trifluoromethyl, phosphoryl,
10]
[11]
[12]
substituted alkyl,[13] and aryl,
[14]
have been
successfully incorporated into the oxindole
framework through this route.
Selenium is an indispensable trace element in the
[15]
human body. Selenium compounds that containing
1
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Advanced Synthesis & Catalysis
10.1002/adsc.202001192
In recent years, organic electrochemical synthesis has
been widely considered as a sustainable, benign, and
eco-friendly synthetic tool that can realize the
oxidation reaction through electron transfer and can
be used to replace traditional oxidizing additives.
This strategy has also been applied by Lei to achieve
the electrochemical synthesis of seleno dihydrofurans
and oxazolines.[ Inspired by these studies and our
When we attempted to reduce the amount of 1a to 0.6
eq., 3a was only afforded in 68% yield (entry 2). The
research has indicated that HFIP can be used to
[25]
stabilize radicals. We observed that the yield was
slightly diminished to 60% when CH CN was used as
a solvent (Table 1, entry 3). Then, a series of
3
n
supporting electrolytes, such as Bu
4
NBF
4
and
19]
n
Bu
4
NClO
4
, was screened (Table 1, entries 4 and 5).
[20-24]
previous research on electrosynthesis,
we
Platinum plates or graphite rods were applied to both
electrodes to test the electrode effect (Table 1, entries
6–8). We also changed the anode and cathode, but
none of the tested materials could increase the yield
of 3a. Changing the operating current (10 or 20 mA)
was proven to be minimally efficient (Table 1, entries
9 and 10). When the temperature was changed to
conducted an electrochemical cyclization reaction
between N-arylacrylamides and diselenides to obtain
seleno oxindole products. These products belong to a
new class of compounds with better anticancer
activity than compared with traditional oxindole
derivatives and organic selenides.
6
0 °C or 100 °C, 3a was observed in 64% or 57%
We began our investigation with diphenyl
diselenide 1a and N-arylacrylamide 2a as substrates.
After considerable effort, an optimal yield of product
yield, respectively (Table 1, entries 11 and 12).
Control experiments showed that no target product
was produced in the absence of electricity (Table 1,
entry 13).
3
a was obtained in 85% under constant current (15
n
mA) for 2 h in the presence of Bu
CH
:2 as the cosolvent (Table 1, entry 1).
4
NPF
6
and using
3
CN/1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) =
With the optimized reaction conditions, we
subjected the alkyl/aryl diselenides 1a–1h and N-
arylacrylamide 2a to electrochemical cyclization to
obtain the corresponding products 3a–3h in Scheme 1.
The diaryldiselenides with electron-donating (−Me)
and electron-withdrawing (−Cl and −Br) substituents
were reacted with N-arylacrylamide to provide the
desired products 3b–3d in 74%–81% yields. In
addition, 1,2‐ di(naphthalen‐ 2‐ yl)diselane and 1,2-
8
Table 1 Optimization of the reaction conditionsa
di([1,1′-biphenyl]-4-yl)diselane
provided
the
corresponding products 3e–3f in 77%–80% yields.
Dimethyl diselenide could also provide the target
product 3g with a yield of 39%. Nevertheless, when
Entry
Variation from standard conditions
None
Yield b
85%
68%
60%
67%
46%
62%
57%
77%
59%
60%
64%
57%
0
1
2
3
4
5
6
7
8
9
1,2-di(thiophen-2-yl)diselane was used as the
1a (0.6 eq.) was used
substrate, the corresponding adduct 3h was not
obtained. A scaled-up reaction was conducted to
verify the practical application of electrochemical
cyclization. When 6 mmol 2a was used to react with
3
CH CN
nBu
nBu
NBF
NClO
instead of Bu
n
NPF
NPF
4
4
4
6
n
4
4
instead of Bu
4
6
1a, adduct 3a was isolated in 80% yield.
C−C
We extended the substrate range of N-
Pt−Pt
arylacrylamide under standard conditions. As shown
in Scheme 2, the electron-donating and electron-
withdrawing groups on the para-position of the two
different aromatic rings of N-arylacrylamide all
worked well with diselenides, providing the
corresponding selenium-containing oxindole products
in considerable yields (3i–3l, 3m–3p). The two
C(+)−Pt(−)
10 mA instead of 15 mA
20 mA instead of 15 mA
60 °C instead of 80 °C
100 °C instead of 80 °C
No electricity
1
1
1
1
0
1
2
3
isomers 3k
1
and 3k were generated when 3-methyl-
2
substituted substrate 2d reacted with 1a. This result
might be caused by the regioselectivity of the
cyclization. The reaction of the N-substituted
acrylamide with diphenyl diselenide could also
proceed smoothly. For example, when phenyl- and
benzyl-substituted acrylamides were subjected to
electrolysis under the standard conditions, the
aReaction conditions: undivided cell, graphite rod cathode
(
Φ 6 mm), Pt plate anode (1 cm × 1 cm), constant current =
n
1
5 mA, 1a (0.2 mmol), 2a (0.2 mmol), Bu
equiv), CH CN/HFIP (10 mL, v/v = 4:1), 80 °C, 2 h.
Isolated yields.
4 6
NPF (2.0
3
b
2
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Advanced Synthesis & Catalysis
10.1002/adsc.202001192
Scheme 3 Substrate scopea
corresponding adducts 3q and 3r were generated in
80% and 84% yields, respectively. The tricyclic
oxindole 3s was obtained in 77% yield.
Scheme 1 Substrate scope of diselenidesa
a
Reaction conditions: undivided cell, graphite rod cathode
(
1
Φ 6 mm), Pt plate anode (1 cm × 1 cm), constant current =
n
5 mA, 1a (0.2 mmol), 2a (0.2 mmol), Bu
4
NPF
6
(2.0
3
equiv), CH CN/HFIP (10 mL, v/v = 4:1), 80 °C, 2 h
a
Reaction conditions: undivided cell, graphite rod cathode
Scheme 4 One-pot, two-step synthesis of seleno oxindolesa
(
Φ 6 mm), Pt plate anode (1 cm × 1 cm), constant current =
n
1
5 mA, 1a (0.2 mmol), 2a (0.2 mmol), Bu
equiv), CH CN/HFIP (10 mL, v/v = 4:1), 80 °C, 2 h.
undivided cell, constant current = 100 mA, 1a (6 mmol),
4 6
NPF (2.0
3
b
n
2
a (6 mmol), Bu
4 6 3
NPF (3 mmol), CH CN/HFIP (70 mL,
v/v = 4:1), 80 °C, 10 h.
Scheme 2 Substrate scope of acrylamidesa
a
Reaction conditions: (1) aniline (1 mmol), methylacryloyl
chloride (1.2 mmol), and triethylamine (1.2 mmol) in dry
n
DCM (10 mL) at 0 °C for 6 h; (2) 1a (1 mmol) Bu
4
NPF
6
(
2.0 equiv), CH
3
CN/HFIP (10 mL, v/v = 4:1), 80 °C, 3 h,
yield of isolated products.
The electrochemical selenization cyclization was
not restricted to N-arylacrylamides. N-
arylcinnamamide 4 was successfully converted into
-methyl-4-phenyl-3-(phenylselanyl)-3,4-
dihydroquinolin-2(1H)-one 4a , and 1-methyl-4-
phenylquinolin-2(1H)-one 4a was obtained with a
yield of 50% (Scheme 3, a). N-acetyl-protected 5a
was not detected, whereas seleno hydrolysate 5a was
1
1
2
2
1
obtained with a yield of 67% (Scheme 3, b). However,
the target products were not detected when we used
diorganyl ditelluride or diorganyl disulfide as
substrates.
aReaction conditions: undivided cell, graphite rod cathode
(
1
Φ 6 mm), Pt plate anode (1 cm × 1 cm), constant current =
n
5 mA, 1a (0.2 mmol), 2a (0.2 mmol), Bu
4 6
NPF (2.0
equiv), CH CN/HFIP (10 mL, v/v = 4:1), 80 °C, 2 h.
3
3
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Advanced Synthesis & Catalysis
10.1002/adsc.202001192
Anilines are more stable than acrylamides and are
commercially available. These advantages contribute
to their wildly use in organic synthesis. Therefore, a
one-pot, two-step pattern of reaction was conducted.
The amine in methylene chloride was treated with
acryloyl chloride to obtain the expected acrylamide.
After the solvent was removed, the reaction residue
was subjected to constant current electrolysis in the
presence of 1a to obtain the corresponding adducts
(
Scheme 4). The one-pot, two-step reaction, which
avoided the isolation and purification of intermediate
acrylamides, was proven to be a practical protocol.
Several control experiments were performed to
gain further understanding of the mechanism of the
method. As shown in Scheme 5, 3a was not detected
when electrolysis was performed in the presence of
2.0 equiv. of TEMPO or BHT (Scheme 5, a). We also
conducted a controlled experiment in a divided cell,
and product 3a was detected in the anode oxidation
with a yield of 75% (Scheme 5, b), indicating that the
reaction could be completed directly in anode
oxidation. Further investigation revealed that 2a
could produce the desired product 3a in the presence
of PhSeCl (Scheme 5, c). Therefore, the phenyl
selenium cation pathway possibly existed. The
detailed experimental results are described in the
Supporting Information (Scheme S1). In addition,
two substrates were subjected to cyclic voltammetry
experiments (Figure 2). An evident oxidation peak of
substrate 2a could be observed at 1.67 V. Diphenyl
diselenide 1a presented an oxidation peak at 1.44 V.
Additionally, 82% yield was obtained when the
Figure 2 Cyclic voltammograms
reaction was performed under N
, d). Therefore, this process was confirmed to be an
electro-oxidation process.
2
conditions (Scheme
5
Scheme 6 Proposed mechanism
On the basis of the abovementioned results and
reported literature,[ a possible mechanism for the
electrochemical cyclization is presented in Scheme 5.
The reaction could be initiated by the formation of
seleno radical A and selenium cation B via anodic
oxidation. Thereafter, the radical addition of A to 2a
provided the radical intermediate C, and the
intramolecular cyclization of intermediate C resulted
in the radical intermediate D. Further anodic
oxidation and deprotonation led to the formation of
product 3a (path I). We could not rule out the ionic
pathway. The addition of B to the double bond of 2a
could generate intermediate F, for which further
oxidative cyclization and deprotonation led to the
formation of product 3a (path II).
26]
We used the MTT method to screen the in vitro
cytotoxicities of the seleno oxindole compounds
against four cancer cell lines (HeLa, T-24, MGC-803,
and HepG-2) with 5-fluorouracil (5-FU) as a positive
control to investigate the antitumor activity of the
synthesized compounds (Table 2). The corresponding
Scheme 5 Control experiments
4
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Advanced Synthesis & Catalysis
10.1002/adsc.202001192
products 6a and 6b were prepared through the Acknowledgements
reaction
of
N-arylamides
with
sodium
We thank the National Natural Science Foundation of China
trifluoromethylsulfite and sodium phenylsulfinyl, and
their antitumor activities were screened. The results
showed that the seleno oxindole products had a better
antitumor activity than other oxindole skeletons 6a
and 6b. The antitumor activity of compound 3r was
better than that of the positive control 5-FU.
Compound 3r exhibited a favorable anticancer
activity toward HeLa and T-24 cell lines with IC50
values of 10.5 ± 0.8 and 15.4 ± 1.1 μM, respectively.
We also studied the antitumor mechanism of
compound 3r on HeLa, and the results are presented
in the Supporting Information (Figures S2–S5).
(
22061003, 21861006, 21861015), Guangxi Natural Science
Foundation of China (2016GXNSFEA380001,
019GXNSFAA245027), Guangxi Key R&D Program (No.
2
AB18221005), Science and Technology Major Project of
Guangxi (AA17204058-21), Guangxi science and technology
base and special talents (guike AD19110027) and the
Student Innovation trainning program (202010602236) for
financial support.
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Advanced Synthesis & Catalysis
10.1002/adsc.202001192
COMMUNICATION
Synthesis
of
Seleno
Oxindoles
of
via
N-
Electrochemical
Cyclization
Arylacrylamides with Diorganyl Diselenides
Adv. Synth. Catal. Year, Volume, Page – Page
a
a
b
Xin-Yu Wang, Yuan-Fang Zhong, Zu-Yu Mo,
a
b
a
Shi-Hong Wu, Yan-Li Xu, Hai-Tao Tang, and
a,
Ying-Ming Pan *
7
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