Aerobic oxidative synthesis of quinazolinones and benzothiazoles in the presence of laccase/DDQ as a bioinspired cooperative catalytic system under mild conditions

Article abstract of DOI:10.1039/c9ra10303a

The current study applied laccase/DDQ as a bioinspired cooperative catalytic system for the synthesis of quinazolinones (80-95% yield) and benzothiazoles (65-98% yield) using air or O₂ as ideal oxidants in aqueous media at ambient temperature. The aerobic oxidative cyclization reactions occur in two steps: (i) chemical cyclization; (ii) chemoenzymatic oxidation. These methods are more environment-friendly, efficient, simple and practical than other reported methods due to the use of O₂ as an oxidant, laccase as an eco-friendly biocatalyst, aqueous media as the solvent and free from any toxic transition metal and halide catalysts. Therefore, these methods can be applied in pharmaceutical and other sensitive synthetic procedures.

Full text of DOI:10.1039/c9ra10303a

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Aerobic oxidative synthesis of quinazolinones and
benzothiazoles in the presence of laccase/DDQ as
a bioinspired cooperative catalytic system under
mild conditions†
Cite this: RSC Adv., 2020, 10, 14254
Nadia Ghorashi,a Zahra Shokri,a Reza Moradi,a Amira Abdelrasoulb
ab
*
and Amin Rostami
The current study applied laccase/DDQ as a bioinspired cooperative catalytic system for the synthesis of
quinazolinones (80–95% yield) and benzothiazoles (65–98% yield) using air or O2 as ideal oxidants in
aqueous media at ambient temperature. The aerobic oxidative cyclization reactions occur in two steps: (i)
chemical cyclization; (ii) chemoenzymatic oxidation. These methods are more environment-friendly, efficient,
simple and practical than other reported methods due to the use of O2 as an oxidant, laccase as an eco-
friendly biocatalyst, aqueous media as the solvent and free from any toxic transition metal and halide
catalysts. Therefore, these methods can be applied in pharmaceutical and other sensitive synthetic procedures.
Received 8th December 2019
Accepted 14th March 2020
DOI: 10.1039/c9ra10303a
rsc.li/rsc-advances
Quinones have been applied as oxidants in organic chem-
istry and hydride acceptors in biological processes.9 Among
1. Introduction
quinones, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) is
well-known as an effective and readily available oxidant for
numerous organic transformations.10–12 In spite of the utility of
DDQ as a stoichiometric oxidant, its high toxicity and cost, the
isolation problem because of the concomitant by-product
DDQH2 are the main issues associated with utilizing DDQ on
a large scale. To overcome these disadvantages, a combination
of the catalytic amount of DDQ and a less expensive co-oxidant
that regenerate DDQ from its reduced hydroquinone form have
been developed.13–15 Recently, the catalytic oxidation systems
using catalytic amounts of DDQ and a co-catalyst in the pres-
ence of molecular oxygen as a terminal oxidant have attracted
more attention.16–18 Although these procedures have been
successfully applied in the eld of aerobic oxidations, the
development of an alternative method which is green and
employing eco-friendly co-catalyst such as biocatalysts in
combination with DDQ for the aerobic oxidation of organic
compounds is in demand.
Laccases, highly attractive biocatalysts in modern organic
synthesis, are easily available multicopper oxidases produced by
numerous organisms, including fungi, plants, and prokaryotes.
Laccase and laccase-mediated system catalyze the oxidation of
various organic compounds in the presence of O2 as an electron
acceptor and produce H2O exclusively as a by-product.19
In continuation of our study in the catalytic applications of
laccase enzyme in the aerobic oxidation of organic
compounds,20 herein, we report the aerobic oxidative synthesis
of quinazolinones and benzothiazoles in the presence of
laccase/DDQ catalyst system.
Quinazolin-4(3H)-ones are important nitrogen-containing
heterocycles which have various biological and medicinal
activities, including antibacterial, anticancer, antimicrobial,
antidiabetic, antifungal, anticonvulsant and antiallergy.1,2 The
cyclization of o-anthranilamides with aldehydes followed by
subsequent oxidation is the most convenient method for the
synthesis of these valuable compounds.3,4
Benzothiazoles are also important members of the family of
fused heterocycles that have attracted much attention because
of their diverse biological activity and medical applications.5
The most popular approach to the synthesis of benzothiazoles
is the condensation of 2-aminothiophenols with aldehydes
under oxidative conditions.6–8
The reported procedures for the synthesis of quinazolinone
and benzothiazole derivatives generally suffer from some
drawbacks including the use of excess amounts of expensive
oxidants, the formation of large amounts of toxic waste, harsh
reaction conditions, and tedious work-up. Therefore, the
development of a simple procedure, which is green and envi-
ronmentally benign, for the synthesis of these valuable
compounds is very important.
aDepartment of Chemistry, Faculty of Science, University of Kurdistan, 66177-15175,
Sanandaj, Iran. E-mail: a_rostami372@yahoo.com; Fax: +988716624004; Tel:
+989183730910
bDepartment of Chemical and Biological Engineering, University of Saskatchewan, 57
Campus Drive, Saskatoon, Saskatchewan, S7N 5A9, Canada
† Electronic supplementary information (ESI) available. See DOI:
10.1039/c9ra10303a
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Scheme 1 Aerobic oxidative cyclization synthesis of quinazolin-4(3H)-ones.
However, the complete conversion of 2,3-dihydroquinazolin-
4(1H)-one to desired product was observed in the presence of
200 U of laccase as co-catalyst, 0.2 mmol of DDQ as catalyst in
NaPBS (0.1 M, pH ¼ 5)/CH3CN (4%) mixture as solvent at 45 ꢀC
(Table 1, entry 4).
2. Results and discussions
The oxidative cyclization synthesis of quinazolinones occurs in
two-step sequence: (i) chemical cyclization of o-anthranilamide
with aldehyde in the presence of sulfamic acid to afford 2,3-
dihydroquinazolin-4(1H)-one (ii) chemoenzymatic aerobic
oxidation of 2,3-dihydroquinazolin-4(1H)-one in the presence of
laccase/DDQ catalyst system (Scheme 1).
Initially, the reaction of o-anthranilamide with benzalde-
hyde was chosen as a model system (Table 1). The formation of
2-phenyl 2,3-dihydroquinazolin-4(1H)-one was accomplished
in the presence of sulfamic acid (0.1 mmol) at room temper-
ature in H2O for 30 minutes. Subsequently, to optimize the
reaction conditions for the aerobic oxidation of 2-phenyl-2,3-
dihydroquinazolin-4(1H)-one to 2-phenyl quinazolin-4(3H)-
one, the effects of the solvents, temperature and the amounts
of laccase and DDQ were investigated (Table 1). Among the
solvents, sodium phosphate buffer solution (NaPBS, 0.1 M, pH
¼ 5)/CH3CN (4%) mixture had the highest isolated yield (Table
1, entry 4). The amounts of laccase and DDQ were also opti-
mized. The results revealed that this transformation needs the
double action of laccase and DDQ (Table 1, entries 1–6).
The scope of this procedure was further examined by
treating a number of substituted benzaldehydes with o-
anthranilamide under optimized reaction conditions (Table
2). The results in Table 2 show that aromatic aldehydes con-
taining electron-donating (methyl and methoxy) and electron-
withdrawing (uoro and bromo) groups were efficiently con-
verted to the respective products in very good to excellent
yields (Table 2, entries 1–9). It was also observed that the
present method was equally applicable to the oxidative cycli-
zation of terephthalaldehyde as a bifunctional aromatic alde-
hyde (Table 2, entry 10). It should be noted that in cases of 4-
uoro benzaldehyde and terephthalaldehyde very small
amounts of starting material were observed together with the
main product.
At this time the exact mechanisms of the reaction and the
precise role of DDQ is not clear and should be further studied in
detail. However, based on previously reported mechanisms for
Table 1 Optimization of aerobic oxidation reaction conditions of 2-phenyl 2,3-dihydroquinazolin-4(1H)-one in the presence of laccase/DDQ
catalyst systema
Temperature
Entry
DDQ (mol%)
Laccase (U)
Solvent
(ꢀC)
Isolated yield%
1
2
3
4
5
6
7
8
-
5
200
200
200
200
100
—
200
200
200
200
200
200
MeCN/NaPBS
MeCN/NaPBS
MeCN/NaPBS
MeCN/NaPBS
MeCN/NaPBS
MeCN/NaPBS
MeOH/NaPBS
NaPBS
45
45
45
45
45
45
45
45
45
45
60
r.t.
30b
50b
70b
90c
60b
35b
70b
45b
10
20
20
20
20
20
20
20
20
20
d
9
MeCN
—
—
d
10
11
12
DMSO/NaPBS
MeCN/NaPBS
MeCN/NaPBS
40
60
a
Reaction conditions unless stated otherwise: 2,3-dihydroquinazolin-4(1H)-one (1 mmol), O2 (balloon), phosphate buffer (0.1 M, pH 4.5, 12.5 mL),
organic solvent (0.5 mL), 24 h. The reaction was not completed. c The reaction was completed (conversion: 100%). d No reaction.
b
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Table 2 Aerobic oxidative synthesis of quinazolin-4(3H)-one derivatives in the presence of laccase/DDQ catalytic systema
Entry
Substrate
Product
Time (h)
Isolated yield%
Mp. (ꢀC) (lit.)
1
24
90
236–238 (ref. 21)
2
20
92
238–240 (ref. 21)
3
4
5
19
20
24
93
95
92
242–247 (ref. 21)
180–182 (ref. 21)
200–202 (ref. 21)
6
7
22
25
92
90
242–243 (ref. 22)
257–260 (ref. 21)
8
24
24
93
85
295–296 (ref. 22)
288–289
9b
10b
24
80
>300
a
Reaction conditions: 2,3-dihydroquinazolin-4(1H)-one (1 mmol), laccase (200 U), DDQ (20 mol%), O2 (balloon), phosphate buffer (0.1 M, pH 4.5,
12.5 mL), MeCN (0.5 mL), 45 ꢀC. b The conversion was not 100%.
the application of DDQ as a hydride acceptor in dehydrogena- a possible reaction pathway for the aerobic oxidation of dihy-
tion reactions9,23 and for oxidative dehydrogenation of N- droquinazolinones to quinazolinones in the presence of
heterocyclic compounds via an anomeric-based oxidation, laccase/DDQ cooperative catalyst system is suggested in Scheme
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Scheme 2 Proposed mechanism for the synthesis of quinazolinones using O2/laccase/DDQ system.
2. It is supposed that oxidation of the substrate occurs by air in NaPBS (0.1 M, pH ¼ 5) at room temperature is the best
hydride transfer from the substrate via anomeric-based oxida- reaction conditions for complete conversion of starting mate-
tion24 to the DDQ, thereby forming an ion-pair adduct.25 rials to the desired product (Table 4, entry 6). It should be
Substrate-cation/DDQH-ion pair may convert to the desired mentioned that the reaction was not completed under other
product and DDQH2. Then, the by-product DDQH2 is oxidized reaction conditions shown in Table 4.
by laccase leading to DDQ and reduced form of laccase.20d
Finally, the reduced laccase is reoxidized by molecular oxygen, hydes under optimized conditions (Table 5). As shown in Table
consequently completing the catalytic cycle (Scheme 2).19c
5, numerous aldehydes such as benzaldehydes with electron-
The scope of the reaction was extended to different alde-
The efficiency of O2/laccase/DDQ catalyst system was donating and electron-withdrawing groups, heterocyclic and
demonstrated by comparison our results on the oxidation of 2- a,b-unsaturated aldehydes, 1-naphthaldehyde, 2-naph-
phenyl 2,3-dihydroquinazolin-4(1H)-one with the previously thaldehyde, 9-anthraldehyde, and terephthaldehyde were
reported methods (Table 3). A case study shows that the successfully applied to prepare the corresponding products via
present protocol is superior than the other systems owing to of the reaction with 2-aminothiophenol. It should be mentioned
free from any toxic transition metal and halide, the use of O2 that in some cases low amounts of starting material were
as a green, inexpensive and abundant oxidant and ambient observed together with the main product (Table 5, entries 5, 7,
temperature.
18, 20–23) and in case of terephthaldehyde the trace amount of
In another effort, we examined the catalytic activity of O2/ 4-(1,3-benzothiazol-2-yl) benzaldehyde was detected.
laccase/DDQ system for the synthesis of 2-arylbenzothiazoles
via oxidative cyclization of Schiff bases derived from the
condensation of 2-aminothiophenol with aldehydes. At the
3. Experimental
beginning, the reaction of 2-aminothiophenol with benzalde-
hyde was chosen as the model reaction. The examination of the
different parameters such as the effects of the solvents,
temperature and the amounts of laccase and DDQ on the model
reaction revealed that 100 U of laccase, 0.1 mmol of DDQ under
3.1. Determination of the activity of laccase from Trametes
versicolor
The activity of commercial enzyme laccase from Trametes ver-
sicolor was determined via UV-Vis spectroscopy by monitoring
the oxidation of 2,20-azino-bis-(3-ethylbenzthiazoline-6-sulfonic
Table 3 Comparison of the synthesis of 2-phenyl quinazolin-4(3H)-one with previously reported methods
Isolated yield
Entry
Reaction conditions
Time (h)
(%)
Ref.
1
2
3
4
5
DMSO, 100 ꢀ
C
36
1.5
6
9
24
98
87
99
90
90
4
26
27
24b
TBAB (1.6 mmol), CuCl2 (1.4 mmol), 100 ꢀ
I2 (0.55 mmol), EtOH, 78 ꢀ
MNPs-DABCO tribromide (50 mg), H2O2 (2.4 eq.), EtOH, 78 ꢀ
Laccase (200 U)/DDQ (20 mol%), NaPBS/CH3CN, O2 or air, 45 ꢀC
C
C
C
Current study
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Table 4 Screening of the reaction conditions for the synthesis of 2-phenylbenzothiazole from oxidative cyclization of 2-aminothiophenol and
benzaldehydea
Temperature
Entry
Laccase (U)
DDQ (mol%)
Solvent
(ꢀC)
pH
Isolated yield%
1
2
3
4
5
6
7
8
50
50
50
50
—
5
NaPBS
NaPBS
NaPBS
NaPBS
NaPBS
NaPBS
MeCN/NaPBS
EtOH/NaPBS
MeOH/NaPBS
THF/NaPBS
NaPBS
r.t.
r.t.
r.t.
r.t.
r.t.
r.t.
r.t.
r.t.
r.t.
r.t.
60
5
5
5
5
5
5
5
5
5
5
5
4
6
30
50
70
70
40
95b
80
60
70
40
60
80
90
10
20
10
10
10
10
10
10
10
10
10
—
100
100
100
100
100
100
100
100
9
10
11
11
13
NaPBS
NaPBS
r.t.
r.t.
a
b
Reaction conditions unless stated otherwise: aldehyde (1 mmol), 2-aminothiopheno (1 mmol), air, solvent (12 mL), 1 h. The reaction was
completed (conversion: 100%).
acid) (ABTS, 3 ¼ 36 000 Mꢁ1 cmꢁ1).36 One unit was dened as
3.4. General procedure for the synthesis of benzothiazole
derivatives
the amount of enzyme that oxidizes 1 mmol of ABTS per minute.
The activity of the laccase enzyme batch applied in this inves-
In an open-air round-bottom ask (25 mL) equipped with
a magnetic stirrer, a mixture of 2-aminothiophenol (1 mmol)
and aldehyde (1 mmol) in phosphate buffer (0.1 M, 12 mL, pH ¼
5) was prepared. Then, DDQ (10 mol%) and laccase (87 mg, 100
U) were added to the reaction mixture and stirred at room
temperature for 1 h. The product was extracted with EtOAc (3 ꢂ
10 mL) and the combined organic phases were dried over
anhydrous Na2SO4. The evaporation of the solvent and puri-
cation by column chromatography (n-hexane/EtOAc) gave the
desired product.
tigation was evaluated at 0.87 U mgꢁ1
.
3.2. General procedure for the synthesis of 2,3-
dihydroquinazolin-4(1H)-one derivatives
A mixture of an aromatic aldehyde (1 mmol) and o-anthranila-
mide (1 mmol) in water (2 mL) was stirred in the presence of
sulfamic acid (0.01 g, 0.1 mmol) for 30 min at room tempera-
ture. The progress was monitored by TLC (n-hexane/EtOAC: 3/
1). Upon completion, the solid product was isolated by ltra-
tion and washed with water. The crude product was recrystal-
lized from ethanol to give the desired product.
4. Conclusions
In summary, laccase/DDQ was applied as a bioinspired coop-
erative catalytic system for the aerobic oxidative synthesis of
quinazolinones and benzothiazoles. The signicant advantages
of these methods are as follows: (i) the use of air or O2 as an
3.3. General procedure for the synthesis of quinazolinone
derivatives
A round-bottomed ask (25 mL) with a magnetic stir bar was environmentally benign, inexpensive and abundant oxidant
charged with 2,3-dihydroquinazolin-4(1H)-one (1 mmol), DDQ and the formation of H2O as the only nontoxic by-product; (ii)
(45.4 mg, 0.2 mmol) and acetonitrile (0.5 mL). Na-Phosphate the synthesis of structurally diverse quinazolinones and ben-
buffer solution (NaPBS) (0.1 M, pH 4.5, 12.5 mL) and laccase zothiazoles in good to high yields in aqueous media at ambient
from Trametes versicolor (200 U, 174 mg) were added and the temperature; (iii) the present methods are superior to other
reaction mixture was stirred under O2 (balloon) at 45 ꢀC for the currently available and attractive for pharmaceutical industry
time given in Table 2. Then, the reaction mixture was extracted owing to free from any toxic and expensive transition metals
with EtOAc (3 ꢂ 10 mL), and the organic layer was dried over and halides catalysts; (iv) these methods conform to several of
anhydrous Na2SO4 and evaporated under reduced pressure. the guiding principles of green chemistry.
Finally, the crude product was puried by column chromatog-
raphy on SiO2 using n-hexane/ethyl acetate (75 : 25).
We believe that the results presented here open up a new
avenue for application of laccase/DDQ catalyst system to
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Table 5 Aerobic oxidative synthesis of benzothiazole derivatives using air/laccase/DDQ systema
Entry
Aldehyde
Product
Isolated yield%
Mp. (ꢀC) (lit.)
1
2
95
90
217–219 (ref. 28)
79–81 (ref. 28)
3
4
98
96
121–122 (ref. 28)
135 (ref. 28)
5b
6
80
97
173–174 (ref. 28)
100–101 (ref. 28)
7
8
87
98
80–82 (ref. 28)
115–117 (ref. 28)
9
92
120–122 (ref. 29)
10
11
12
94
98
96
144 (ref. 30)
133 (ref. 28)
93–95 (ref. 31)
13
95
164 (ref. 28)
14
15
90
90
227–229 (ref. 28)
121–123 (ref. 32)
16
93
95
75
81–83 (ref. 33)
84–85 (ref. 31)
182–184 (ref. 29)
17
18b
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Table 5 (Contd.)
Entry
Aldehyde
Product
Isolated yield%
95
Mp. (ꢀC) (lit.)
19
100–102 (ref. 34)
20b
86
65
129–130 (ref. 31)
218–220 (ref. 28)
21b
22b
23b
85
70
72
129–130 (ref. 28)
111 (ref. 35)
24c,d
259–261 (ref. 28)
a
Reaction conditions: 2-aminothiophenol (1 mmol), aldehyde (1 mmol), DDQ (10 mol%), laccase (87 mg, 100 U), phosphate buffer (0.1 M, 12 mL,
pH ¼ 5), r.t., 1 h. b The conversion was not 100%. c Reaction conditions: 2-aminothiophenol (2 mmol), aldehyde (1 mmol), DDQ (20 mol%), laccase
(174 mg, 200 U), phosphate buffer (0.1 M, 12 mL, pH ¼ 5), r.t., 1 h. d The trace amount of 4-(1,3-benzothiazol-2-yl) benzaldehyde was detected.
accomplish other green and sustainable synthetic
transformations.
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Conflicts of interest
There are no conicts to declare.
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