Photocatalyst-free visible-light-promoted quinazolinone synthesis at room temperature utilizing aldehydes generatedin situ viaC=C bond cleavage

Article abstract of DOI:10.1039/d0ob02268c

This is the first report on a facile tandem route for synthesizing quinazolinones at room temperature from various aminobenzamides andin situ-generated aldehydes. The latter was formedviaC=C bond cleavage, and the overall reaction proceeded using molecular oxygen as a clean oxidant in the absence of a photocatalyst. Visible light, which was indispensable for the entire course of the reaction, played multiple roles. It initially cleaved styrene to an aldehyde, then facilitated its cyclization with ano-substituted aniline, and finally promoted the dehydrogenation of the cyclized intermediate. The previous step provided the feedstock for the next step in the reaction, thereby preventing volatilization, oxidation, and polymerization of the aldehyde. Thus, the overall process is simple, environmentally benign, and economically feasible.

Full text of DOI:10.1039/d0ob02268c

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DOI: 10.1039/D0OB02268C
ARTICLE
Photocatalyst-free visible-light-promoted quinazolinone synthesis
at room temperature utilizing aldehydes generated in situ via C=C
bond cleavage
Received 00th January 20xx,
Accepted 00th January 20xx
DOI: 10.1039/x0xx00000x
Zongbo Xie, Jin Lan, Liyuan Yan, Xuehua Chen, Qian Li, Jia Meng and Zhanggao Le
This is the first report on a facile tandem route for synthesizing quinazolinones at room temperature from various
aminobenzamides and in-situ-generated aldehydes. The latter was formed via C=C bond cleavage, and the overall reaction
proceeded using molecular oxygen as a clean oxidant in the absence of a photocatalyst. Visible light, which was
indispensable for the entire course of the reaction, had multiple roles. It initially cleaved styrene to an aldehyde, then
facilitated its cyclization with an o-substituted aniline, and finally promoted dehydrogenation of the cyclized intermediate.
The previous step provided the feedstock for the next step in the reaction, thereby preventing volatilization, oxidation,
and polymerization of the aldehyde. Thus, the overall process is simple, environmentally benign, and economically
feasible.
nanocomposites,45 ionic liquids,
46,
47
scandium triflate (III),48 β-
cyclodextrin-SO H, enzymes, and metals51, 52 have been utilized
4
9
50
Introduction
3
as catalysts to prepare these compounds, as have catalyst-free
Carbon−carbon bond cleavage is a formidable challenge in the field
of organic syntheses owing to the remarkable stability of this
ubiquitous bond. Specifically, the C=C bond cleavage has been
extensively studied and applied in organic syntheses for a long
5
3
methods. In recent years, synthesis of quinazolinones via
5
4
condensation of o-aminobenzamides with ketoalkynes
styrenes have also been reported.
or
5
5
1
-3
4-7
8-14
time. Several methods, such as ozonolysis, use of metals,
1
5, 16
and electrochemical reactions,
can be used to cleave this bond.
Previous works
O
O
1
7
18
In recent years, many photocatalysts such as CdS, eosin Y,
NH2
CHO
NH
1
9
20
R1
Acid, metal, or ionic liquids
ref. 36-53
R1
2
V O
5
/g-C
3
N
4
,
and BiVO
4
have been used to accomplish this bond
+
R2
NH2
N
O
cleavage.
R2
O
O
Quinazolinones are fundamental components in numerous clinical
medicines that exhibit diverse biological and pharmacological
TFA (3 equiv)
R3
NH
NH
NH2
R1
R1
R2
+
N , Toluene, 90 °C
2
N
O
NH2
O
ref. 54
2
1
22
activities,
including
antimalarial,
antimicrobial,
anticonvulsant,
R2
2
3
anti-inflammatory,24,
25
26
antihypertensive,
R3
anticancer, antitumor,28-30 anti-diabetic, dihydrofolate reductase-
2
7
NH2
Iodine (20 mol%)
R1
R1
R2
+
DMSO, 110 °C
ref. 55
N
3
1-35
NH2
inhibitory, and kinase inhibitory activities.
Owing to their
R2
relevance in the physiological system, extensive research on the
synthesis of this class of compound has been conducted. Among the
reported synthetic strategies, the method involving the reaction of
an o-substituted aniline with an aldehyde seems to be the most
This work
R1
O
N
O
O2
R3
Blue LED
NH
R1
NH2
NH2
R2
DMSO
3
6
commonly used strategy. Various compounds as cellulose-SO
3
H,
R2
3
7
38
2
-morpholinoethanesulfonic acid,
L-proline nitrate,
SiO
2
41
-
Photocatalyst-free
Visible light as eco-friendly energy source
In situ formed acetaldehyde
3
9
40
H
3
PW12O
40
,
zirconium (IV) chloride, chiral phosphoric acids,
Oxygen as a clean oxidant
Room temperature synthesis
ascorbic acid,42 thiamine hydrochloride (VB
),
43
p-TSA,44
1
One pot tandem reaction
Scheme 1. Existing routes and our method (this work) for the synthesis of
quinazolinones.
Jiangxi Province Key Laboratory of Synthetic Chemistry, School of Chemistry,
Biology and Material Science, East China University of Technology, Nanchang
3
30013, China
Despite the significant progress in quinazolinones synthesis, it is
Electronic Supplementary Information (ESI) available: [details of any
supplementary information available should be included here]. See DOI:
1
0.1039/x0xx00000x
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O rP gl ea na si ce &d Bo i on mo to al e dc juu l sa tr mC ha er mg i ins ts ry
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ARTICLE
Journal Name
highly desirable to develop a green and safe, metal-free and
View Article Online
DOI: 10.1039/D0OB02268C
catalyst-free
method
that
can
circumvent
O
N
O
catalyst , oxidant
Solvent , Time
NH
NH2
NH2
1a
2a
3a
Table 1. Optimization of reaction conditionsa
Entrya
Photocatalyst
Eosin Y
Rose bengal
Solvent
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
Oxidant (equiv.)
Molar ratio of 1a:2a
Time (h)
24
24
24
24
24
24
24
24
24
24
24
24
24
24
24
24
24
24
24
24
24
24
24
30
36
40
48
Yield (%)b
trace
NR
1
2
3
4
5
6
7
8
9
Air
Air
Air
Air
Air
Air
Air
1:2
1:2
1:2
1:2
1:2
1:2
1:2
1:2
1:2
1:2
1:2
1:2
1:2
1:2
1:2
1:2
1:2
1:2
1:2
1:2.5
1:3
1:3.5
1:4
1:3.5
1:3.5
1:3.5
1:3.5
Ru(bpy)
3
Cl
2
NR
NR
12
Eosin B
9-Fluorenone
Diphenylmethanone
11
c
d
e
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
8/ NR / NR / NR
N
O
2
NR
30
20
trace
20
trace
21
2
1
1
1
1
1
1
1
1
1
1
2
2
2
2
2
2
2
2
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
TBHP (1)
DTBP (1)
H
2
O
2
(1)
BPO (1)
(1)
(1)
2
K S
2
O
8
(NH
4
)
2
S
2
O
8
29
CH
3
CN
O
O
O
O
O
O
O
O
O
O
O
O
2
NR
NR
NR
NR
40
41
46
48
48
EtOH
2
2
H O
2
2
2
2
2
2
2
2
2
2
DMF
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
55
71
71
a
Reaction conditions: 1a (0.20 mmol), 2a (0.40–0.80 mmol), photocatalyst (5.0 mol%), solvent (1.5 mL), irradiation: 18 W LED; b Isolated yield; c in the dark; d white
LED; e green LED; NR = No reaction. TBHP: tert-Butyl hydroperoxide; DTBP: Di-tert-butyl peroxide; BPO: Dibenzoyl peroxide; K
= potassium persulfate; (NH
ammonium persulfate; O = O balloon.
2 2
S O
8
4 2 2 8
) S O =
2
2
the use of harsh, impractical, and environmentally hazardous
reaction conditions. Furthermore, tandem reactions are a good
alternative to economize the number of synthetic steps, as
processes such as purification of the intermediates can be
eliminated. As a part of our continued interest in visible-light
photochemistry and medicinally important heterocycles,56-58 we
herein report an unprecedented, green protocol for quinazolinone
synthesis under mild conditions by irradiating styrene and o-
To determine suitable reaction conditions for the visible light-
induced quinazolinone synthesis, we initially chose the reaction of
2
-aminobenzamide (1a) and styrene (2a) as the model system. The
reaction was conducted in DMSO at room temperature in the
aminobenzamide with visible light in the absence of
a
photocatalyst. The reaction proceeded at room-temperature,
utilizing molecular oxygen as a clean oxidant.
Results and Discussion
2
| J. Name., 2012, 00, 1-3
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Table 2. Substrate scope of alkenes and various aminobenzamides
tolerated in this transformation, affording the cor sponding
View ticle Online
reAr
DOI: 10.1039/D0OB02268C
product in good yields (Table 2, 3a-3d). Encouraged by these
results, bulky 4-vinylbiphenyl and 2-vinylnaphthalene were selected
as the substrate. Notably, they were compatible with the reaction
and smoothly afforded the corresponding product (Table 2, 3e, 3f).
Heteroaryl olefins such as 2-vinylpyridine also afforded moderate
yields under the optimized conditions (Table 2, 3g). Interesting
results were obtained when branched chain alkenes (allylbenzene)
were used as the substrate—the C=C bond did not cleave; instead,
it migrated (Table 2, 3h). The reaction was then extended to
substituted o-aminobenzamides. Halogenated aminobenzamides
afforded the corresponding quinazolinones in good yields (Table 2,
3i). The electron-rich 2-amino-4-methoxybenzamide afforded low
yields of the products upon reaction with 4-methylphenylene.
However, the corresponding product could be obtained in a
moderate yield at a prolonged reaction time (Table 2, 3j). Desirable
yields were obtained when N-substituted 2-aminobenzamides were
used (Table 2, 3k, 3l).
O
O
O2
Blue LED
NH
R3
NH2
NH2
R1
R2
R1
DMSO 40 h
N
3
R2
1
2
O
N
O
O
N
O
N
NH
NH
NH
NH
N
O
Cl
3
a, 71% / 36% / 85%
3b, 75%
3c, 76%
3d, 62%
O
O
O
O
NH
N
NH
N
NH
NH
N
N
N
3g, 37%
3h, 42%
3
e, 48%
3
f, 61%
O
O
N
O
O
Cl
N
NH
NH
N
N
O
N
N
3
i, 50%
3j, 34%
3k, 58%
3l, 48%
Interestingly, internal alkenes were also compatible with this
reaction, affording the corresponding quinazolinones. Product 3a
was obtained in up to 85% yield when trans-stilbene was chosen as
the internal alkene substrate. The compatibility of internal alkenes
in this reaction has remarkably expanded the substrate scope of
this reaction as well as the scope of C=C bond cleavage. It is even
more interesting that 1,1-diphenylethylene can be converted into
diphenylmethanone under the optimized conditions, achieving a
transformation from radical trapping agent to an intermediate in
O
NO2
Selected internal alkene substrate
Substrate of 3m
3m, 40%
a
Reaction conditions: 1 (0.20 mmol), 2 (0.6 mmol), DMSO (1.5 mL), and O
balloon irradiated with an 18 W Blue LED at room temperature. 3j (50 h).
2
5
9
organic pigments, pharmaceuticals, fragrances, and pesticides
presence of 5 mol% of photocatalyst upon visible light irradiation (Table 2, 3m).
with an 18-W blue LED (Table 1). Various photocatalysts were
To confirm whether a chain reaction is involved in this process, the
screened (Table 1, entries 1-7), and when 9-fluorenone or
benzophenone (5.0 mol%) was used as the photoredox catalyst, the
desired product 3a was obtained in 12% or 11% yield, respectively
light on/off experiment was performed. It is evident from Fig. 1 that
no product was generated under dark conditions, thus confirming
that light is indispensable during the entire course of the reaction.
(Table 1; Entries 5–6). To our delight, 3a was obtained in 8% yield
when this reaction was conducted in DMSO in the absence of a
photocatalyst (Entry 7).
5
0
4
0
3
0
In the control experiments in DMSO, no desired products were
C
detected in the absence of visible light or O
2
(Table 1, entries 7 and
8
). We next investigated various light sources. It is noteworthy that
the desired product 3a was not formed when the reaction mixture
was irradiated with white LEDs or green LEDs (Table 1, Entry 7 ).
Following this, the influence of oxidant on the formation of 3a was
20
ON
d,e
OFF
1
0
ON
explored. O
for promoting the reaction; the product was obtained in 30% yield
Table 1 Entry 9). Therefore, O was selected as the oxidant in the
2
was found to be the most effective and green oxidant
0
0
5
10
15
20
Time(h)
25
30
35
40
(
2
subsequent experiments. Among the solvents screened (Table 1, Fig. 1. Light on/off experiment with 1a and 2a
entries 9 and 16-19), the best result was obtained when the
reaction was conducted in DMSO (Table 1, entry 9). The 1a:2a ratio Several control experiments were conducted with the aim of
and the reaction time were also optimized, and the results are elucidating the reaction mechanism (Scheme 2). We first reacted 1a
summarized in Table 1 (Entries 9, 20–27).
2 2 2
with 2a in O to afford 3a in 71% isolated yield. Replacing O with N
afforded 3a in a very low yield (Scheme 2a). Under standard
conditions, styrene could be converted to benzaldehyde (Scheme
With the optimized conditions in hand (Table 1, entry 26), we next
examined the substrate scope of this reaction. Table 2 shows the
effect of various substituents on styrene on the overall reaction.
Gratifyingly, styrene derivatives with an electron-donating or
electron-withdrawing group on the aromatic ring were well
2
b). Replacing styrene with benzaldehyde successfully afforded 3a
in a slightly shorter time under an air atmosphere. As expected, no
formation of the target product was observed under dark
conditions or
N
2
atmosphere (Scheme 2c). Although the
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O
O
intermediates were not formed in the dark or under a N
2
O
O
h 
oxidative
cleavage
View Article Online
DOI: 10.1039/D0OB02268C
NH2
atmosphere, the expected intermediate could be successfully
prepared from benzaldehyde and 2-aminobenzamide in the
presence of visible light and air (Scheme 2d). The intermediate
could then be transformed into product 3a in a high yield upon
visible light irradiation under aerobic oxidative conditions (Scheme
Ph
H
O
N
Ph
NH2 intermediate A
trapped
NH2
O
N
O
O
H2O2
NH
NH
Ph
h
O2
intramolecular cyclization
NH
h 
2
e). Since benzaldehyde can be easily converted into benzoic acid,
1O
N
H
2
N
H
O
the latter was chosen to investigate the reaction pathway.
However, the reaction did not proceed under this condition
OH
intermediate B
isolated
(
Scheme 2f). Moreover, 2,2,6,6-tetramethylpiperidine-N-oxide
Scheme 3. Plausible reaction mechanism
(TEMPO), a common radical scavenger, could completely inhibit the
model reaction under the standard conditions, indicating that the
reaction proceeded via a radical pathway (Scheme 2g).
Experimental
Unless otherwise stated, all reagents were purchased from
commercial suppliers and used without further purification.
General experimental procedure for the synthesis of
quinazolinones: A 10 mL glass tube was filled with the required
amounts of 2-aminobenzamide (0.2 mmol) and alkenes (0.7
O
O
Blue LED
NH
Ph
NH2
NH2
(
a)
DMSO, 40 h
N
7
1% with O2
O
Trace with N2
Blue LED
H
2
mmol). An O balloon was used as the oxygen source, and the
(
b)
DMSO, 40 h
mixture was irradiated at room temperature with an 18 W
blue LED for 40 h. After the reaction reached completion
(monitored by TLC), water was added to the reaction solution,
and the mixture was extracted with EtOAc. The combined
4
1% with O2 (detected by HPLC)
Trace in the dark
O
O
O
H
Blue LED
NH
Ph
NH2
(
c)
DMSO, 18 h
N
NH2
89% with air
Trace in the dark
Trace with N2
O
2 4
organic layers were dried over anhydrous Na SO and
concentrated under reduced pressure. The crude product was
purified by silica-gel column chromatography using petroleum
ether/ethyl acetate as the eluent to obtain the desired
product.
O
O
H
Blue LED
DMSO
NH
NH2
NH2
(d)
N
H
Ph
Trace with N2
Trace in the dark
O
O
N
Air: 3h (trace); 7h (94%)
Conclusion
NH
Ph
Blue LED
NH
Ph
(
e)
DMSO, 12 h
In summary, we have developed an unprecedented, green,
efficient, and catalyst-free method for the synthesis of
quinazolinones. Visible light-promoted in situ generation of
aldehydes from alkenes and subsequent reactions with various 2-
aminobenzamides at room temperature, with molecular oxygen as
a clean oxidant, afforded the desired product. A tandem reaction is
involved, and visible light is indispensable during the entire course
of the tandem reaction. This work addresses some of the concerns
associated with the use of bases, metals, and high temperatures
during quinazolinone synthesis. In addition, the direct use of
aldehydes can be avoided. The reaction proceeds under mild
conditions, has a broad substrate scope, does not require a
photocatalyst, and is operationally simple. Most importantly, this
method is significantly greener than the existing methods.
N
H
9
8% in the blue LED
0
% in the dark
O
N
O
O
Blue LED
NH
Ph
NH2
OH
DMSO, 24 h
(
f)
NH2
O
Not detected
O
TEMPO (3 equiv.)
NH
NH2
NH2
(g)
Standard conditions
N
Ph
Not detected
Scheme 2. Control experiments to investigate the reaction mechanism
Based on the above results, we propose a plausible reaction
pathway (Scheme 3). Initially, styrene is oxidized to benzaldehyde
under O
1
8, 60, 61
2
and light.
Following this, 2-aminobenzamide and
benzaldehyde undergo dehydration and condensation to form an
imine intermediate A. Subsequent intramolecular cyclization affords
another intermediate B. Finally, visible light irradiation results in the
generation of singlet oxygen via energy transfer pathways, leading
Conflicts of interest
There are no conflicts to declare.
6
2
2 2
to the release of H O to form the target product.
Acknowledgements
This project was supported by the National Natural Science
Foundation of China (Nos. 11765002, 21966003) and the
4
| J. Name., 2012, 00, 1-3
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ARTICLE
Science and Technology Project of Jiangxi (No. 28.
0192BBH80012).
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F. A. Alasmari, A. K. Rishi and H. AD. OAbI:d1e0l.1-A03z9iz/,DE0uOrB. 0J.2M26e8dC.
Chem., 2015, 92, 191-201.
2
2
3
9.
0.
D. He, M. Wang, S. Zhao, Y. Shu, H. Zeng, C. Xiao, C. Lu
and Y. Liu, Fitoterapia, 2017, 119, 136-149.
M. Mahdavi, K. Pedrood, M. Safavi, M. Saeedi, M. Pordeli,
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Organic & Biomolecular Chemistry
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DOI: 10.1039/D0OB02268C
O
N
O
O2
R3
Blue LED
NH
R1
NH2
NH2
R1
R2
DMSO
R2
Photocatalyst-free
Visible light as eco-friendly energy source
In situ formed acetaldehyde
Oxygen as a clean oxidant
Room temperature
One pot tandem reaction