Application of SBA-Pr-SO3H in the synthesis of 2,3-dihydroquinazoline-4(1H)-ones: characterization, UV–Vis investigations and DFT studies

Article abstract of DOI:10.1007/s13738-016-1006-8

An efficient one-pot synthesis of 2,3-dihydroquinazoline-4(1H)-one derivatives 4a–l is described using SBA-Pr-SO₃H as a heterogeneous acid catalyst. The present methodology resulted in various derivatives of 2,3-dihydroquinazoline-4(1H)-one in

Full text of DOI:10.1007/s13738-016-1006-8

J IRAN CHEM SOC
DOI 10.1007/s13738-016-1006-8
ORIGINAL PAPER
Application of SBA‑Pr‑SO3H in the synthesis
of 2,3‑dihydroquinazoline‑4(1H)‑ones: characterization,
UV–Vis investigations and DFT studies
Seyedeh Yasaman Afsar1 · Ghodsi Mohammadi Ziarani1 · Hoda Mollabagher1 ·
Parisa Gholamzadeh1 · Alireza Badiei2 · Ali Abolhasani Soorki3
Received: 28 June 2016 / Accepted: 2 November 2016
© Iranian Chemical Society 2016
Abstract An efficient one-pot synthesis of 2,3-dihyd-
roquinazoline-4(1H)-one derivatives 4a–l is described
using SBA-Pr-SO3H as a heterogeneous acid catalyst.
The present methodology resulted in various derivatives
of 2,3-dihydroquinazoline-4(1H)-one in good yield via a
three-component reaction of isatoic anhydride, aldehydes
and ammonium acetate. SBA-Pr-SO3H played a significant
role as an efficient mesoporous catalyst due to its pore size
of 6 nm. Additionally, UV–Vis spectrum of the products
was studied in order to investigate their application as UV
absorbers.
alkaloid with antimalarial properties extracted from
Dichroa febrifuga, was firstly synthesized by McLaughlin
and coworkers (Fig. 1) [3]. In the view of their importance
and useful properties, several procedures for preparing of
2,3-dihydroquinazolin-4(1H)-ones have been reported in
the past few years, such as: (1) the reaction of aldehydes
or ketones with anthranilamide using Lewis or Brønsted
acids as the catalyst [5, 6]; (2) the reductive cyclization
of 2-nitrobenzamide with different aldehydes or ketones
by the use of SnCl2 as the catalyst [7]; (3) the reaction of
primary amine (or ammonium salts) and isatoic anhydride,
with aldehydes or ketones using Lewis or Brønsted acids as
the catalyst [8–10].
Natural or artificial ultraviolet (UV) light is responsi-
ble for the destruction and decomposition of organic com-
pounds, the dyes discoloration and the loss of mechanical
properties in polymeric compounds and plastics [11]. Many
efforts have been made to improve the durability of these
materials upon exposure to UV light. The use of organic
UV absorbers in the matrices of the mentioned materials is
one of the most convenient and effective methods to avoid
their photoaging [12]. The organic UV absorbers must, of
necessity, be colorless compounds and absorb UV light in
the range of 280 and 400 nm [13].
Keywords SBA-Pr-SO3H · 2,3-Dihydroquinazoline-
4(1H)-one · Multicomponent reaction · Isatoic anhydride ·
UV absorbers
Introduction
2,3-Dihydroquinazoline-4(1H)-ones are important het-
erocyclic compounds with a broad range of biological and
pharmacological properties including antitumor, antihista-
mine, analgesic, anticancer, vasodilating and diuretic activ-
ities [1–4]. For example, febrifugine, as a quinazolinone
SBA-15, as a mesoporous silica, was synthesized by
Zhao and coworkers for the first time in 1998 [14]. The
internal surface of SBA-15 can be functionalized with dif-
ferent organic functional groups [15–18] to produce an
effective and active catalyst. It has exceptional advantages
such as high surface area, large pore size and high thermal
stability; in conclusion, it shows excellent catalytic activ-
ity in organic transformations [19–21]. In this paper, sul-
fonic acid functionalized silica (SBA-Pr-SO3H) was used
as a heterogeneous Brønsted acid catalyst in the synthesis
of 2,3-dihydroquinazolin-4(1H)-one derivatives. Then, in
* Ghodsi Mohammadi Ziarani
gmziarani@hotmail.com; gmohammadi@alzahra.ac.ir
1
Department of Chemistry, Alzahra University, Vanak Square,
Tehran, Iran
2
School of Chemistry, College of Science, University
of Tehran, Tehran, Iran
3
Research Institute of Petroleum, Academic Center
of Education, Culture and Research, Shahid Beheshti
University, Tehran, Iran
1 3

J IRAN CHEM SOC
Fig. 1 Febrifugine structure
order to investigate their application as UV absorbers, the
UV–Vis spectrum of the products was studied.
anhydride 1 (1 mmol, 0.163 g), aromatic aldehyde 2a–l
(1 mmol) and ammonium acetate 3 (1.2 mmol) were added
to it. The mixture was heated under solvent-free condition
at 115 °C for an appropriate time. Completion of the reac-
tion was monitored through thin layer chromatography
technique (TLC). The resulting solid product was dissolved
in hot EtOH and filtered to remove the unsolvable catalyst,
and then the filtrate was cooled to give the pure product.
The spectroscopic and analytical data for the new products
are presented in the following part.
Experimental
Materials and techniques
Fourier transform infrared (FT-IR) spectra were recorded
on KBr disks using a FT-IR Bruker Tensor 27 instrument.
Melting points were measured by the capillary tube method
1
using an electro thermal 9200 apparatus. The H NMR
Spectral data for some compounds
(250 MHz) and 13C NMR (62.5 MHz) spectra were run on
a Bruker DPX using tetramethylsilane (TMS) as an internal
standard in CDCl3 and/or DMSO-d6 solution. Mass spec-
trometry (MS) analysis was performed on a model 5973
mass-selective detector (Agilent). UV–Vis spectrum was
run on an Analytik Jena Specord® S600 spectrophotometer.
2‑(2,6‑dichlorophenyl)quinazolin‑4(3H)‑one (4j) FT-IR
(KBr): υ (cm−1) = 3433, 3189 (NH), 3062 (C–H Aro-
matic), 1650 (C=O), 1517, 1436 (C–C Aromatic). 1H
NMR (250 MHz, DMSO-d6): δH = 6.61 (t, J = 7.5 Hz,
1H, Ar–H), 6.75 (s, 1H, Ar–H), 7 (s, 1H, Ar–H), 7.9 (t,
J = 6.25, 1H, Ar–H), 7.3–7.7 (m, 3H, Ar–H), 8.3 (s, 1H,
NH) ppm. 13C NMR (62.5 MHz, DMSO-d6): δC = 64.9,
113.79, 114, 116.9, 127.6, 130.1, 131.4, 133.7, 133.9,
135.8, 148.2, 163.2 ppm. MS (m/e): 292 (M+, 18%), 120
(68%), 92 (38%), 65 (17%).
Quantum chemical calculations
All of the quantum chemical calculations were accom-
plished using DFT method at B3LYP/6-31g(d) level by
Gaussian 98 program package. The optimized structures
4a–l were subjected to some quantum chemical param-
eters such as the energy of the highest occupied molecu-
lar orbital (EHOMO), the energy of the lowest unoccupied
molecular orbital (ELUMO) and the energy gap between
these orbitals (ΔE = EHOMO − ELUMO).
2,3‑dihydro‑2‑(3‑methoxyphenyl)quinazolin‑4(1H)‑one
(4k) FT-IR (KBr): υ (cm−1) = 3291, 3190 (NH), 3051
(C–H Aromatic), 1518, 1490 (C–C Aromatic), 1647
(C=O), 1149 (C–O). 1H NMR (250 MHz, CDCl3):
δH = 3.82 (s, 3H, CH), 5.86 (s, 1H, NH), 6 (s, 1H, C–H),
6.68 (d, J = 8, 1H, Ar–H), 6.92 (m, 2H, Ar–H), 7.12 (t,
J = 7.5, 2H, Ar–H), 7.33 (m, 2H, Ar–H), 7.91 (d, J = 25,
1H, Ar–H), 7.94 (s, 1H. NH) ppm. 13C NMR (62.5 MHz,
CDCl3): δC = 55.3, 68.9, 112.3, 114.5, 115.9, 119.6, 126.3,
128.6, 130.1, 134.7 ppm. MS (m/e): 254 (M+, 65%), 147
(100%), 120 (70%), 92 (43%), 77 (13%), 65 (20%).
Production and functionalization of SBA‑15
The nanoporous compound SBA-15 was synthesized and
functionalized according to our previous report [22, 23],
and the modified SBA-Pr-SO3H was used as a mesoporous
solid acid catalyst in the following reaction.
General procedure for the preparation of quinazolinone
compounds 4a–l
2,3‑dihydro 2‑(5‑methylfuran‑2‑yl)‑ quinazolin‑4(1H)‑
The SBA-Pr-SO3H (0.02 g) was firstly activated under
vacuum and then after cooling to room temperature, isatoic
one (4l) FT-IR (KBr):
(NH), 3067 (C–H Aromatic), 2921 (C–H Aliphatic),
υ
(cm−1
)
=
3267, 3187
1 3

J IRAN CHEM SOC
Scheme 1 Synthesis of 2,3-dihydroquinazolin-4(1H)-one 4a–l
Table 1 The optimization of reaction conditions for the synthesis of
2,3-dihydroquinazolin-4(1H)-one 4a
Table 2 The effect of catalyst amount on the synthesis of 2,3-dihyd-
roquinazolin-4(1H)-one 4a
Entry Solvent
Catalyst
Tempera- Time (h) Yield (%)
ture (°C)
Entry
Catalyst (g)
Time (min)
Yield (%)
1
2
3
4
0.01
0.02
0.03
0.04
5
4
4
4
66
90
87
88
1
2
3
4
5
CH3CH2OH SBA-Pr-
SO3H
Reflux
Reflux
Reflux
120 °C
120 °C
7 h
12 h
3 h
70
36
50
H2O
SBA-Pr-
SO3H
CH3CN
Neat
SBA-Pr-
SO3H
SBA-Pr-
SO3H
4 min 90
5 h 40
reaction yield does not change significantly. Therefore,
0.02 g of catalyst was selected as modified amount for the
further reactions.
Neat
–
Therefore, this reaction was developed with different
aldehydes under solvent-free condition and the results have
been summarized in Table 3. After completion of the reac-
tion (monitored by TLC), the crude product was dissolved
in hot EtOH, and the catalyst was easily filtrated from the
reaction mixture. The acid catalyst can be reactivated by
washing with hot EtOH and subsequently with a dilute
acid solution, water and acetone to reuse for several times
without significant loss of activity. The new products were
characterized by melting point, FT-IR, GC–MS and NMR
spectral data. Melting points of the known products were
compared with the reported values in literature as displayed
in Table 3.
1645.73 (C=O). 1H NMR (250 MHz, DMSO-d6):
δH = 2.2 (s, 3H, CH Aliphatic), 5.66 (s, 1H, NH), 5.9 (s,
1H, Ar–H), 6.0 (s, 1H, Ar–H), 6.7 (td, 2H, J = 3), 7.1 (s,
2H, Ar–H), 7.4–7.8 (m, 1H, Ar–H), 8.3 (s, 1H, NH) ppm.
13C NMR (62.5 MHz, DMSO-d6): δC = 13.7, 60.7, 106.7,
108.5, 114.9, 117.6, 126.6, 127.7, 133.6, 147.6, 151.8,
152.9, 163.7 ppm. MS (m/e): 226 (M+, 100%), 211(42%),
147 (15%), 120 (46%), 92 (21%).
Results and discussion
In order to study the effect of physical characteristics of
SBA-Pr-SO3H as catalyst in this reaction, the model reac-
tion was tested in the presence of sulfonic acid modified
amorphous silica (SiO2-Pr-SO3H). As illustrated in Table 3,
Entries 1–2, the reaction time and the product yield were
significantly increased and decreased, respectively, in the
presence of SiO2-Pr-SO3H compared to SBA-Pr-SO3H.
Since the substrate constituent of both these catalysts is
same, it can be, therefore, concluded that the mesoporous
structure of SBA-Pr-SO3H provides appropriate space for
treating the reactants to gain the product. Additionally,
the conditions of present methodology were compared
with some other published methods and are summarized
in Table 4 (Entries 3–5). As it is clear, the safe and green
SBA-Pr-SO3H catalyzed and accelerated the reaction more
efficiently to give the higher yield of product within shorter
reaction time.
Synthesis of 2,3-dihydroquinazoline-4(1H)-ones was per-
formed through the one-pot three-component condensa-
tion of isatoic anhydride 1, aromatic aldehydes 2a–l and
ammonium acetate 3 in the presence of SBA-Pr-SO3H
(Scheme 1). To optimize the reaction conditions for com-
pound 4a (Ar=Ph), different solvents were studied includ-
ing H2O, EtOH, CH3CN as well as solvent-free systems
(Table 1). Among the tested conditions, the use of SBA-Pr-
SO3H (0.02 g) under solvent-free system showed the best
results with excellent product yield and shortest reaction
time (4 min).
Additionally, the amount of SBA-Pr-SO3H was modi-
fied for the synthesis of 2,3-dihydroquinazolin-4(1H)-
one 4a as shown in Table 2. The results confirmed that
by increasing the catalyst amount from 0.02 to 0.04, the
1 3

J IRAN CHEM SOC
Table 3 Synthesis of
Entry No. Ar
Time (min) Yield (%) Crystal colors m.p. (°C) m.p. (Lit)
2,3-dihydroquinazoline-4(1H)-
ones 4a–l in the presence of
SBA-Pr-SO3H as catalyst
1
4a
4b 4-Me-C6H4
4c 4-OH-C6H4
4d 2,3-Cl2C6H3
4-OMe-C6H4
4
7
90
87
93
90
97
78
88
87
92
90
99
65
White
190–192 192–193 [24]
229–231 229–231 [25]
285–287 285–287 [26]
232–233 233–235 [25, 26]
206–208 207–208 [25, 26]
173–175 173–175 [25, 26]
204–206 205–207 [27]
186–188 186–187 [27]
190–193 190–193 [27]
167–170 New
2
White
3
5
White
4
5
Cream
White
5
4e
4f
4-Cl-C6H4
2-OMe-C6H4
4-F-C6H4
5
6
25
10
8
White
7
4g
White
8
4h 2,4-(OCH3)2C6H3
White
9
4i
4j
2-NO2-C6H4
2,6-Cl2C6H3
30
40
10
30
Light orange
Cream
White
10
11
12
4k 3-OMe-C6H4
148–150 New
4l
Brown
173–175 New
Table 4 Comparing
the reaction conditions
in the synthesis of
2,3-dihydroquinazolin-4(1H)-
one 4a
Entry
Solvent Catalyst
Conditions
Time (min) Yield (%) Year [ref.]
1
2
3
4
5
Neat
Neat
EtOH
EtOH
Neat
SBA-Pr-SO3H
SiO2-Pr-SO3H
120 °C
120 °C
Reflux
Reflux
4
7
90
77
83
89
80
This work
This work
2008
Ga(OTf)3
I2
40
70
8
2009
Al/Al2O3 nanoparticles 120 °C
2010
Scheme 2 A proposed mechanism for the formation of 4a–l
The reaction mechanism of quinazolinone compounds is
similar to that of Friedländer reaction [28]. Previously, Javan-
shir and coworkers investigated the effect of p-toluenesul-
fonic acid as catalyst in the reaction mechanism of quinoline
compounds through DFT computational method [29]. Cor-
respondingly, the proposed mechanism for the formation of
compounds 4a–l can be explained as shown in Scheme 2. The
carbonyl group of isatoic anhydride 1 is firstly protonated
1 3

J IRAN CHEM SOC
Investigation of UV–Vis spectrum
The UV spectra of 2,3-dihydroquinazolin-4(1H)-one
derivatives 4a–l were obtained in ethanol at 5 × 10−5
M
concentration (Fig. 4). The results showed that a num-
ber of 2,3-dihydroquinazolin-4(1H)-one derivatives may
have potential as UV absorbers. While all compounds
displayed very strong absorptions in the UV-A region
(239–275 nm), the most interesting are those compounds
which can absorb in the range of 280 and 400 nm (UV-B
and UV-A regions). Compound 4c showed an excellent
absorption at UV-B, while the absorptions of 4a, 4b, 4e
and 4j were in a range of UV-A. Among the compounds,
4d, 4f, 4g, 4l and 4k have a broad range absorption
from 260 to 400 nm; the absorption of 4k was so strong.
Therefore, these compounds are good candidates as UV
absorbers, although compounds 4h and 4i showed a weak
absorption.
Fig. 2 Synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives
using SBA-Pr-SO3H as a nanoreactor
In order to have a better insight on the electronic prop-
erties, the quantum chemical calculations of the com-
pounds 4a–l were performed by density functional theory
(DFT) to determine the HOMO and LUMO. We choose
a B3LYP/6-31G(d) level for DFT calculations. The den-
sity distributions of HOMO and LUMO orbitals for the
product 4a with optimized geometry are presented in
Fig. 3a and b, respectively. According to Fig. 3a–b, it is
obvious that the HOMO electron density is distributed on
the whole atoms of quinazoline ring; however, in LUMO
structure, the density is diffused on the ring part. There-
fore, the quinazoline ring (in the ground state of the mol-
ecules) is the active cite for the absorption of the photons
from the UV irradiation.
Herein, the quantum chemical parameters such as the
energy of the HOMO and LUMO orbitals and the band gap
energy of 4a–l were calculated by DFT and then compared
to the calculated band gap energy and ΔE from the λmax
(Table 5). The λmax was obtained from the UV–Vis spec-
tra of each compounds in EtOH (Fig. 4). The data obtained
by DFT are in agreement with the experimental data (UV–
Vis) except compound 4e. Since the transition energies
of HOMO → LUMO (S1 ← S0) are in the range of UV
absorber compounds, it means that the synthesized com-
pounds 4a–l may be used as UV absorbers.
by the solid acid catalyst to give intermediate 5. Then, this
intermediate can be easily attacked by ammonia from the
ammonium acetate 3, followed by decarboxylation to pro-
duce 2-aminobenzamide 6. Condensation of the protonated
aromatic aldehyde with 2-aminobenzamide 6, followed by
the loss of a water molecule gives imine 8, which then under-
goes an intramolecular cyclization to afford the desired prod-
uct 4a–l (Scheme 2). SBA-Pr-SO3H can act as a nanoreactor
where the reaction takes place easily in its nanopores (Fig. 2).
The catalyst recyclability was also examined under opti-
mized conditions for the synthesis of compound 4a. In this
regard, the reaction was performed in the first cycle for four
times to recover about 0.06 gr of SBA-Pr-SO3H. Subse-
quently, it was washed with hot EtOH and reactivated using
diluted H2SO4 and then reused. Then, the recycling process
was repeated for four times and the product yields were
90, 84, 83 and 81%. It was found that the catalytic activity
drops slightly from the first cycle to the second cycle due
to leaching of some sulfonic acid groups which were not
grafted well on the surface of SBA-15. Additionally, no sig-
nificant drop of catalytic activity was detected for the third
and fourth cycles which means the catalyst is stable after
leaching the week grafted organic groups. In fact, this cata-
lyst is completely recoverable.
Fig. 3 Frontier molecular
orbital density distributions of
compound 4a
1 3

J IRAN CHEM SOC
Table 5 The quantum chemical parameters derived from compounds 4a–l using DFT method and obtained by UV–Vis spectrum
Entry Compound no. Calculated data using DFT method Obtained data via UV–Vis spectrum
λmax (nm) Oscillator strength (f) Predicted HOMO–LUMO gap (ev) λmax (nm) HOMO–LUMO gap (ev) from
E = hc/λmax
1
4a
4b
4c
4d
4e
4f
313
312
314
336
317
325
315
353
325
587
313
355
0.0417
0.0436
0.0415
0.0026
0.0319
0.0357
0.037
3.96
3.98
3.95
3.69
3.92
3.82
3.94
3.52
3.82
2.11
3.96
3.50
340
345
300
270
345
318
320
350
345
350
345
330
3.6
3.6
4.1
4.5
3.6
3.9
3.8
3.5
3.6
3.5
3.6
3.7
2
3
4
5
6
7
4g
4h
4i
8
0.004
9
0.0412
0.0141
0.0394
0.2374
10
11
12
4j
4k
4l
Fig. 4 UV–Vis spectrum of 2,3-dihydroquinazolin-4(1H)-one derivatives 4a–l in EtOH
Antimicrobial and antifungal tests
microorganisms used in this study were Escherichia coli
and Pseudomonas aeruginusa as gram negative bacteria,
Bacillus subtilis and Staphylococcus aureus as gram posi-
tive bacteria and Candida albicans as a fungus. Products
All products 4a–l were investigated for antimicrobial and
antifungal activities using disk diffusion method. The
1 3

J IRAN CHEM SOC
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Conclusion
In summary, SBA-Pr-SO3H has employed as an efficient
catalyst for the one-pot three-component synthesis of
2,3-dihydroquinazolin-4(1H)-ones. Some advantages of
this method are environmentally friendly conditions, short
reaction times, excellent yields and simple work-up proce-
dures without using any chromatographic method for puri-
fication of products. Additionally, according to the compu-
tational and UV–Vis studies, it was found that some of the
products are good candidates as UV absorbers due to their
colorless crystal as well as broad and strong absorption in
the range of UVB and UVA.
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Acknowledgements We gratefully acknowledge the financial sup-
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