Visible light induced radical cascade cyclization of: Ortho -cyanoarylacrylamides with phosphine oxides for the preparation of phosphorylated quinoline-2,4(1 H,3 H)-dione

Article abstract of DOI:10.1039/d1nj03579g

Visible light induced cascade cyclization of ortho-cyanoarylacrylamides with phosphine oxides for the preparation of phosphorylated quinoline-2,4(1H,3H)-dione. Products with moderate to good yields were efficiently isolated. A radical mechanism was propos

Full text of DOI:10.1039/d1nj03579g

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DOI: 10.1039/D1NJ03579G
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Visible light induced radical cascade cyclization of ortho-
cyanoarylacrylamides with phosphine oxides for the preparation
of phosphorylated quinoline-2,4(1H,3H)-dione
Received 00th January 20xx,
Accepted 00th January 20xx
a
a
a
a
b
DOI: 10.1039/x0xx00000x
Yuan-Yuan Sun, Jing-Cheng Song, Shao-Hui Yang, Zu-Li Wang, * En-Xuan Zhang, Qing-Qing
a
a
Han, Shan Yue
www.rsc.org/
3
2
spiro[4,5]trienones,33
Visible light induced cascade cyclization of ortho- substituted
cyanoarylacrylamides with phosphine oxides for the preparation sulfur-containing compounds
of phosphorylated quinoline-2,4(1H,3H)-dione. Products with
moderate to good yields were efficiently isolated. Radical
mechanism was proposed for this transformation.
dihydroisoquinolones,
3
4
and so on35-38 have been
3
9-43
reported. In line with our interests in radical chemistry,
herein, visible light induced radical cascade cyclization of ortho-
cyanoarylacrylamides with phosphine oxides for the preparation
of phosphorylated quinoline-2,4(1H,3H)-dione was efficiently
realized.
Quinoline-2,4-dione scaffolds are central core in a large number
1
-
of natural products, pharmaceuticals and agrochemicals.
In order to find the optimized reaction conditions, the reaction
5
Additionally, they are also intermediates for the synthesis of
of
N-(2-cyanophenyl)-N-methylmethacrylamide
and
bioactive and novel heterocyclic compounds.6, 7As
a
diphenylphosphine oxide was chosen as a model reaction for
this investigation. To our delight, the desired product was
consequence, the development of efficient and novel protocols
for their construction has aroused great interest over the past
decades.8-11Among these reported synthetic methods, the radical
cascade cyclization reactions were proved to be the most
effective methods. For example, the copper-catalyzed cascade
isolated in 29% yield using CHCl
3
as solvent, 4CzIPN as
photocatalyst and LPO (Dilauroyl peroxide) as oxidation (table 1,
entry 1). The use of THF as solvent led to 84% yield (table 1,
entry 2). The reactions which conducted in dioxane or DCE
generated the corresponding products in 71-76% yields (table 1,
entries 3-4). Solvents containing halogen and ether solvents may
be favorable for the reaction. Poor yields of the products were
obtained when the reaction was performed in DMF, DMSO,
toluene. Most of the substrates were unreacted and only trace of
unknown side products was detected in these reactions (table 1,
entries 5-7). Photocatalyst also play an important role in this
reaction. To our disappointment, no desired products was
addition/cyclization
phosphonylated, carbonylated, methylated,
for
the
synthesis
of
1
2
13
14
1
5
trifluoromethylated and sulfonated quinoline-2,4(1H,3H)-
diones was described by Li group. The difluorinated quinoline-
2,4-diones were efficiently prepared by Shi group and Lu
group.17 However, new versatile and practical methods for the
synthesis of various substituted quinoline-2,4(1H,3H)-diones are
still desirable.
1
6
Visible light has proved to be highly economical and eco-friendly
[Acr+-Mes]ClO4-,
isolated when Eosin Y,
3 2
Ru(bpy) Cl ,
1
8-22
energy source.
Organic transformations induced by visible
tetrabromofluorescein or Eosin B was subjected to this reaction
entries 8-12). Subsequently, we examined the effect of oxidant
on this reaction. Encouraged by this result, we investigated the
effect of different oxidants for this reaction. It revealed that BPO
2
3-28
light have obtained much progress in recent years.
Among
(
these reactions, radical cascaded cyclization reactions for the
synthesis of various substituted heterocyclic products induced
by visible light have received much attention. At present, visible
light induced cyclization reactions for the preparation of
(
dibenzoyl peroxide) could delivered the desired in moderate
2
9
30
yield (table 1, entry 16). Low yields of the products were
isolated when DCP (dicumyl peroxide), TBHP (t-
butylhydroperoxide), TBPB (tert-butyl peroxybenzoate) or
DTBP (di-tert-butyl peroxide) was used as oxidant (table 1,
entries 14-15, 17-18). No reaction could proceed in the presence
of PIDA (table 1, entry 13). Visible light, photocatalyst nitrogen
protection and oxidant was crucial for this reaction, because no
desired product was isolated when the reaction was performed
in the absence of any of them (table 1, entries 22-25)
azepane cores,
trifluoromethylated
2-amino-1,4-naphthoquinone derivatives,
3
1
dihydroisoquinolinones, phosphoryl-
a. College of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural
University, Qingdao 266109, PR China
[
wangzulichem@163.com; wangzuli09@tsinghua.org.cn]
b.
Asymchem Life Science (Tianjin) Co., Ltd.,Tianjin 300457, China
†
Footnotes relating to the title and/or authors should appear here.
Electronic Supplementary Information (ESI) available: [details of any
supplementary information available should be included here]. See
DOI: 10.1039/x0xx00000x
This journal is © The Royal Society of Chemistry 20xx
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View Article Online
DOI: 10.1039/D1NJ03579G
Table 2. Reaction Scopes a,b
Table 1. Optimization Studies a
O
N
CN
O
O
O O
N
P
O O
N
P
O O
N
P
O
conditions
P
+
Ph
P
H
Ph
Ph
O
N
Ph
O
F
O
Cl
O
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
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7
8
9
0
1
2
3
4
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7
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9
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
C2, 75%
C3,65%
A
B
C1
C1, 84%
b
Entry Potocatalyst
Oxidant Solvent
Yield (%)
29
84
1
2
3
4
5
6
7
8
9
1
1
1
1
1
1
1
1
1
2
2
2
2
4CzIPN
4CzIPN
4CzIPN
4CzIPN
4CzIPN
4CzIPN
4CzIPN
LPO
LPO
LPO
LPO
LPO
LPO
LPO
LPO
LPO
LPO
LPO
LPO
PIDA
DCP
TBHP
BPO
TBPB
DTBP
LPO
-
CHCl
THF
Dioxane 71
3
F
O O
N
P
O O
N
P
O O
P
F
O
Br
O
N
O
DCE
DMF
DMSO
Toluene
THF
THF
THF
THF
THF
THF
THF
THF
THF
THF
THF
THF
THF
THF
THF
76
C6,71%
C4, 62%
C5, 68%
Trace
Trace
Trace
N.D.
N.D.
N.D.
N.D.
N.D.
N.D.
11
13
74
38
23
N.D.
trace
N.D.
N.D.
Cl
O O
P
O O
N
P
Br O O
P
Eosin Y
+
-
[Acr -Mes]ClO
4
N
O
O
N
O
0
1
2
3
4
5
6
7
8
2
3
4
5
Ru(bpy)
3
Cl
2
C9,92%
C7, 64%
C8,59%
Tetrabromofluorescein
Eosin B
4CzIPN
4CzIPN
4CzIPN
4CzIPN
4CzIPN
4CzIPN
4CzIPN
4CzIPN
-
O O
N
P
Br O O
P
F
O O
N
P
O
N
O
O
C10, 79%
C12, 83%
C11, 81%
c
O O
N
P
O O
N
P
O O
N
P
LPO
LPO
d
4CzIPN
Br
O
F
O
Cl
O
C13, 89%
C14, 93%
C15, 88%
aReaction conditions: A (0.1mmol), B (0.1mmol), PC (5 mol%), oxidant (2.0
equiv), solvent (2 ml) for 24 under PC photocatalyst,
4CzIPN=1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene, LPO
dilauroyl peroxide, N.D. = not detected. b Isolated yield. c dark. d Under Air.
OMe
h
N
2
.
=
=
O O
N
P
O O
P
O O
N
P
OMe
Cl
F
O
N
O
O
C16, 90%
C17, 83%
Under the optimized reaction conditions, the scope of a variety
of ortho-cyanoarylacrylamides and phosphine oxides was
investigated. Ortho-cyanoarylacrylamides possessing various
electron-withdrawing groups such as F, Cl, Br on the phenyl ring
show good performance and afforded the corresponding
products in 59-84% yields (C1-C8). Products bearing these
groups are favorable for their further modification. Additionally,
ortho-cyanoarylacrylamides modified by electron-donating
methyl group was also effective for this reaction, providing the
product with 92% yield (C9). Next, the effect of substituents on
phenyl group of phosphine oxides was also examined. To our
delight, phenyl ring containing methyl, methoxyl and dimethyl
group all suitable for this reaction. The substrates were
successfully converted to the desired products with good to
excellent yields (C10-C19). It is worthwhile to note that products
whit high yields were isolated when di(naphthalen-2-
yl)phosphine oxide and diethyl phosphonate were examined
C18, 92%
OEt
O O
P
O O
P
OEt
O O
N
P
N
O
N
O
C19, 91%
O
C20, 90%
C21, 80%
O O
P
O O
P
N
O
N
O
Bn C23, 66%
Bn C22, 89%
a
Reaction conditions: ortho-cyanoarylacrylamides (0.1mmol),
phosphine oxides (0.1mmol), 4CzIPN (5 mol%), LPO (2.0equiv), white
LEDs (10 W) for 24 h under N
2
.
(
C20-C21). For the substituent on nitrogen of ortho-
cyanoarylacrylamides, benzyl group was also applicable for the
reaction, give the desired product with 66-88% yields (C22-C23)
In order to gain some insight to the mechanism of this
transformation, some control experiments were conducted. No
2
| J. Name., 2012, 00, 1-3
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target product was isolated when radical scavenger 2,2,6,6-
tetramethyl-1piperidinyloxy (TEMPO), butylated laboratory.
hydroxytoluene (BHT) or 1,1-Diphenylethylene(3.0equiv) was
added in the model reaction (Scheme 1). These results indicated
that a radical process was involved in this reaction.
other complicated molecules are currently undeVriewwaAyrticilne Onoliuner
DOI: 10.1039/D1NJ03579G
This work was supported by the National Natural Science
Foundation of China (21772107), Shandong Province Key
Research and Development Plan (No. 2019GSF108017). We
also thank Cai-Zhen Ding, Yan-Li Wang and Hong-Di Yang for
their useful help
O
CN
O
O
O
TEMPO(3.0equiv)
standard conditions
N
O
P
(a)
+
Ph
P
H
Ph
+
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
Ph
O
Ph
N
Ph
N
P
Ph
O
no reaction
Detected by HRMS
OH
tBu
tBu
O
CN
O
O
P
Conflicts of interest
O
BHT(3.0equiv)
+
Ph
Ph
P
H
H
Ph
(b)
Ph
O
+
Ph
N
Ph
standard conditions
N
P
O
Ph
“There are no conflicts to declare”.
trace
Detected by HRMS
O
N
CN
O
O
O
O
1,1-Diphenylethylene(3.0equiv)
standard conditions
Ph
P
P
+
P
Ph
Ph (c)
Ph
O
+
N
Ph
Notes and references
‡
Ph
Ph
no reaction
Detected by HRMS
Footnotes relating to the main text should appear here. These
might include comments relevant to but not central to the
Scheme 1. Control experiments.
matter under discussion, limited experimental and spectral data,
and crystallographic data.
§
§
§
Based on the above mentioned results and previous reports,44-47
etc.
a plausible reaction mechanism was described for this reaction
(Scheme 2). Initially, the ground state of 4CzIPN is converted
into the excited state 4CzIPN* under the irradiation of visible
light. Then the SET reaction between tri-coordinated isomer B1
of diphenylphosphine oxide and the excited 4CzIPN* occurred to
give phosphoryl radical B2 and the radical anion 4CzIPN . Then
carbon-centered radical was formed via the addition reaction of
phosphoryl radical B2 and carbon-carbon double bond of A,
which was followed by cyclization to deliver intermediate A2.
1
.
.
S. Han, F.-F. Zhang, H.-Y. Qian, L.-L. Chen, J.-B. Pu, X. Xie
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2
-.
3
.
Next, imine intermediate A3 was generated from A2 via H 4.
abstraction. Finally, hydrolysis of imine intermediate A3 by
water delivered the desired product C1.
5
6
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.
N
O
A. Klásek, V. Mrkvička, A. Pevec and J. Košmrlj, J. Org.
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N
O
O
A
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Cyclization
N
P
O
Ph
Ph
B2
2
003-2011
N
PPh2
A1
8
.
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O
OH
SET
Ph
PPh2
P
[4CzIPN]
H-abstraction
Ph
B1
9.
N
O
A2
4CzIPN]*
LPO
[
NH
O
O
O
O
P
visible light
10.
SET
PPh2
PPh2
Ph H Ph
4CzIPN
hydrolysis
N
O
N
O
B
[LPO]
1
1
1
1
1
1
1.
2.
3.
4.
5.
6.
A3
C1
Scheme 2. Proposed reaction mechanism.
In conclusion, we have developed a simple and practical protocol
for the efficient synthesis of a series of phosphorylated quinoline-
2
,4(1H,3H)-dione. In the presence of visible light, products with
moderate to high yields were obtained. Further studies on the
reaction mechanism and expansion of the scope of the reaction to
3
58, 3616-3626
F. Ding, Y. Fang, Y. Jiang, K. Lin and L. Shi, Chem Asian J,
018, 13, 636-640
2
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