Silver-mediated radical phosphorylation/cyclization of: N -allylbenzamides to access phosphoryl-substituted dihydroisoquinolones

Article abstract of DOI:10.1039/c9nj02833a

A silver-mediated phosphorylation/cyclization of N-allylbenzamides with phosphine oxides for the synthesis of phosphoryl-substituted dihydroisoquinolones was developed. This protocol features broad substrate scope, experimental simplicity, high efficiency

Full text of DOI:10.1039/c9nj02833a

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DOI: 10.1039/C9NJ02833A
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Silver-Mediated Radical Phosphorylation/Cyclization of N-
Allylbenzamides to Access Phosphoryl-Substituted
Dihydroisoquinolones
Received 00th January 20xx,
Accepted 00th January 20xx
Xiao-Ceng Liu,a,# Kai Sun,a,# Qi-Yan Lv,a,b Xiao-Lan Chen,a,* Yuan-Qiang Sun,a,* Yu-Yu Peng,c
DOI: 10.1039/x0xx00000x
Ling-Bo Qu,a Bing Yu,a,b*
A
silver-mediated
phosphorylation/cyclization
of
N- considerable
attention
of
synthetic
chemists
and
allylbenzamides with phosphine oxides for the synthesis of pharmacologists.8 Inspired by previous elegant works and our
phosphoryl-substituted dihydroisoquinolones was developed. interest in green chemistry and radical reactions,9 we herein
This protocol features broad substrate scope, experimental present a novel and efficient silver-mediated strategy, by which
simplicity, high efficiency, step-economy, and facile scalability.
a large variety of phosphoryl-substituted dihydroisoquinolones
were prepared via the reaction of N-allylbenzamides and
phosphine oxides (Scheme 1b).
Dihydroisoquinolones, as privileged structure of alkaloids, have
been widely found in complex natural products, biomolecules and
pharmaceuticals, which display extraordinary promising biological
activities such as anti-tumor, anti-nausea, anti-inflammatory and
even their wide applications in cancer diagnosis.1 Consequently,
increasing efforts have been devoted to the development of novel
and efficient methods to access diverse functionalized
dihydroisoquinolones in recent years.2 Among the reported of
methods, radical cascade cyclization strategies3 have proved to be
efficient and attractive routes for the synthesis of
dihydroisoquinolones from N-allylbenzamides with simple operation
and high step-economy.4 For example, radicals including
Scheme 1. The construction of dihydroisoquinolones
•CRR’(OH), CF3, SO2Ar, C(O)Ar, and alkyl radical have been
successfully applied for the radical cascade reactions (Scheme 1a).5
These above-mentioned elegant strategies suggested that N-
allylbenzamides has tremendous potential for the construction of
novel dihydroisoquinolones derivatives.
Phosphorus-containing groups as important structural
moieties are widespread in drugs, active molecules, pesticides
and functional materials.6 It is well known that medicinal
properties, biological responses as well as material functions
could be effectively modified by introducing phosphorus
substituents.7 Consequently, the installation of phosphorus
substituents into valuable frameworks has attracted
•
•
•
We commenced our investigations using N-methyl-N-(2-
methylallyl)benzamide (1a) and diphenylphosphine oxide (2a
)
as model substrates to optimize the conditions, as summarized
in Table 1. Gratifyingly, by employing 2 equiv of AgNO3, the
reaction of substrate 1a with diphenylphosphine oxide 2a was
smoothly performed in DMSO for 8 h to afford the desired
phosphoryl-substituted dihydroisoquinolones 3a in 46% yield
(entry 1). Encouraged by this exciting result, several different
solvents, including CH3CN, DCM, THF, MeOH, toluene,
acetone, 1,4-dioxane as well as DMF, were examined to
improve the reaction efficiency (entries 2-9). Much to our
delight, when the reaction was performed in CH3CN, a
satisfactory yield (76%) was obtained (entry 2). Furthermore,
different silver salts, including AgOAc, AgSbF6, Ag2O, AgF2,
AgOTf, and Ag3PO4 were screened (entries 10-16). As a result,
we found that AgNO3 was the most effective reagent for this
reaction among all the Ag salts tested. Afterward, the amount of
AgNO3 was investigated. It was found that the yield markedly
increased from 30% to 76% along with the increase of the
amount of AgNO3 from 1 equiv to 2 equiv (entry 17 vs and
entry 2), and then, a slight decrease was observed by
a.College of Chemistry, Zhengzhou University, Zhengzhou 450001, China. Email:
chenxl@zzu.edu.cn, bingyu@zzu.edu.cn.
b.Henan Nonferrous Metals Geological Exploration Institute, Zhengzhou 450052,
Henan Province, China
c. Hunan Provincial Key Laboratory of Materials Protection for Electric Power and
Transportation, Changsha University of Science & Technology, Changsha 410114,
China
# Xiao-Ceng Liu and Kai Sun contributed equally
Electronic Supplementary Information (ESI) available: [details of any
supplementary information available should be included here]. See
DOI: 10.1039/x0xx00000x
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Table 2. Substrate scope for phosphoryl-substituted dihydroisoquinolonesa
continuous increasing the amount of AgNO3 to 3 equiv (entry
18). Investigation of temperature and reaction time was also
conducted, and the results showed that 80 °C and 8 h were still
the best choices (entries 19-21). The experiment without silver
salt implied that AgNO3 is necessary for this transformation
(entry 22). Attempts to lower the loading of AgNO3 failed and
the yield of 3a decreased significantly (See Supporting
Information for details).10 After extensive experimentation, the
optimized reaction conditions were established as follows: 1a
(0.5 mmol), 2a (1 mmol), AgNO3 (2 equiv), CH3CN (3 mL)
under 80 °C for 8 h.
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DOI: 10.1039/C9NJ02833A
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Table 1. Optimization of the reaction conditionsa,b
entry
1
2
3
4
5
6
7
8
metal salt (equiv)
AgNO3 (2)
AgNO3 (2)
AgNO3 (2)
AgNO3 (2)
AgNO3 (2)
AgNO3 (2)
AgNO3 (2)
AgNO3 (2)
AgNO3 (2)
Ag2CO3 (1)
AgOAc (2)
AgSbF6 (2)
Ag2O (1)
Solvent
DMSO
CH3CN
DCM
Yield (%)
46
76 (74)b
11
THF
20
MeOH
toluene
acetone
1,4-dioxane
DMF
N.D.
N.D.
N.D.
26
trace
trace
trace
trace
21
9
10
11
12
13
14
15
16
17
18
19c
20d
21e
22
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
AgF2 (2)
19
AgOTf (2)
Ag3PO4 (0.67)
AgNO3 (1)
AgNO3 (3)
AgNO3 (2)
AgNO3 (2)
AgNO3 (2)
----
N.D.
N.D.
30
72
55
25
68.
N.D.
a Reaction conditions: 1 (0.5 mmol), 2 (1 mmol), AgNO3 (2 equiv), CH3CN (3 mL)
under 80 °C for 8 h. Isolated yields were given.
bearing methyl, ethyl, iso-propyl, and cyclopropyl groups on N-
position and halides on phenyl ring were also converted into the
target products 3k-o in good yields (69-78%). Afterward, N-methyl-
N-(2-methylallyl)benzamide (1a) was employed to react with
various organophosphorus reagents. To our delight, diarylphosphine
oxides, bearing different substituents were smoothly react with 1a to
access the desired products 3p-t in moderate to good yields (63-
75%). When ethyl phenylphosphinate was employed as phosphorus
reagent, the desired product 3u was isolated in 77% yield. Moreover,
five dialkyl H-phosphonates, including dimethyl H-phosphonate,
diethyl H-phosphonate, di-iso-propyl H-phosphonate, di-iso-butyl H-
phosphonate as well as di-tert-butyl H-phosphonate were found to be
suitable in this protocol, giving the corresponding target products
3v-z in moderate yields (46-60%). However, when N-allyl-N-
methylbenzamide was employed as reaction substrate, the desired
products 3aa were only obtained in 21% yield. Moreover, N-methyl-
N-(2-phenylallyl)benzamide was not suitable for this reaction.
a Reaction conditions: 1a (0.5 mmol), 2a (1 mmol), silver salt, solvent (3 mL)
under 80 °C for 8 h. N.D. = Not detected. Yields were determined by 31P
NMR using trioctylphosphine oxide as internal standard. b Isolated yield. c At
60 °C . d For 4 h. e For 12 h.
With the optimized reaction conditions in hand, we next
evaluated the substrate scope of this silver-mediated
transformation by examining various N-allylbenzamides
1 and
phosphine oxide components , and the results are summarized
2
in Table 2. As can be seen, different N-allylbenzamides, with
either electron-donating groups (-Me, -OMe) or electron-
withdrawing groups (-Cl, -Br, -I, -CN), reacted smoothly with
diphenyl phosphine oxide 2a to access the corresponding
phosphoryl-substituted dihydroisoquinolones 3a-j in moderate
to excellent yields (48-84%). It should be noted that N-
allylbenzamides which bear electron-donating groups gave slightly
higher yields compared to those with electron-withdrawing
substituents. Additionally, different N-substituted allylbenzamides
Furthermore, the scalability of this novel protocol was
investigated by performing the model reaction in 10 mmol scale.
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Pleasingly, it is found that the reaction proceeded smoothly by to produce the radical intermediate 6 with the formation of C-P bond.
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affording 3a in 65% isolated yield (Scheme 2).
Then, radical intermediate 6 underwent an inDtrOamI: 1o0l.e1c0u3l9a/rCc9yNcJl0iz2a8t3io3An
to generate the radical intermediate 7, which was further oxidized to
the carbocation intermediate 8 by Ag(I) via a single electron transfer
(SET) process. Finally, intermediate 8 was immediately converted
into the product 3a by deprotonation.
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Scheme 2. Gram-scale synthesis of 3a
Conclusions
In conclusion, we have developed a novel and straightforward
protocol by which a large variety of phosphoryl-substituted
dihydroisoquinolones were prepared via the radical cascade
reaction of easily available N-allylbenzamides and phosphine
oxides in the presence of AgNO3. This simple and step-
economy procedure has displayed broad substrate scope, good
scalability and high efficiency under mild reaction conditions.
Further exploration of this synthetic strategy will be conducted
in due course.
To gain deep mechanistic insight into this transformation,
several control experiments were conducted. As shown in
Scheme 3, when the model reaction was performed respectively
in the presence of two widely used radical scavengers like
TEMPO (2,2,6,6-tetramethyl-1-piperidinyloxy) or BHT (2,6-di-
tert-butyl-4-methylphenol), the reactions were remarkably
suppressed, suggesting that a radical pathway might be
involved in the reaction process. Moreover, when BHT was
added into the model reaction under optimized reaction
conditions, the adduct
4 was successfully detected by high-
resolution mass spectrometry (HRMS), implying that
diphenylphosphoryl radical was produced in these cyclization
reactions.
Conflicts of interest
There are no conflicts to declare.
Acknowledgements
We acknowledge the Centre of Advanced Analysis
&
Computational Science (Zhengzhou University) for the
characterization and financial support from NSFC (21501010),
China Postdoctoral Science Foundation (2019M652561), Key
Research Projects of Universities in Henan Province (19A350011)
and Hunan Provincial Key Laboratory of Materials Protection for
Electric Power and Transportation (2019CL03).
Notes and references
Scheme 3. Control experiments
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New Journal of Chemistry
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DOI: 10.1039/C9NJ02833A
Table of Content
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Silver-Mediated Radical Phosphorylation/Cyclization of N-Allylbenzamides to
Access Phosphoryl-Substituted Dihydroisoquinolones
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Xiao-Ceng Liu,a,# Kai Sun,a,# Qi-Yan Lv,a,b Xiao-Lan Chen,a,* Yuan-Qiang Sun,a,* Yu-Yu Peng,c Ling-Bo Qu,a
Bing Yu,a,b,
*
aCollege of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001, China. Email: chenxl@zzu.edu.cn,
bingyu@zzu.edu.cn.
bHenan Nonferrous Metals Geological Exploration Institute, Zhengzhou 450052, Henan Province, China
cHunan Provincial Key Laboratory of Materials Protection for Electric Power and Transportation, Changsha University of Science &
Technology, Changsha 410114, China
O
O
R2
O
AgNO3 (2 equiv)
N
R1
H P R3
R4
+
N
R2
R1
CH3CN, 80 °C, 8 h
O
R
R
P R3
R4
+ Wide substrate scope
+ Step-economy
+ Experimental simplicity
+ Facile scalability