An Efficient One-Pot Synthesis of 2,3-dihydroquinazolin-4(1H)-ones in Green Media

Article abstract of DOI:10.1080/15533174.2013.776605

A series of mono- and disubstituted 2,3-dihydroquinazoline-4(1H)-ones have been synthesized in good yields by one-pot reaction using isatoic anhydride, ammonium acetate or amines and aldehydes in green and mild reaction conditions. The effects of various

Full text of DOI:10.1080/15533174.2013.776605

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An Efficient One-Pot Synthesis of 2,3-
dihydroquinazolin-4(1H)-ones in Green Media
Mohammad Ali Bodaghi Fard a , Akbar Mobinikhaledi a & Mahdia Hamidinasab a
a Department of Chemistry, Faculty of Sciences , Arak University , Arak , I. R. Iran
Accepted author version posted online: 22 Oct 2013.Published online: 21 Nov 2013.
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To cite this article: Mohammad Ali Bodaghi Fard , Akbar Mobinikhaledi & Mahdia Hamidinasab (2014) An Efficient One-Pot
Synthesis of 2,3-dihydroquinazolin-4(1H)-ones in Green Media, Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-
Metal Chemistry, 44:4, 567-571, DOI: 10.1080/15533174.2013.776605
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Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 44:567–571, 2014
Copyright ꢀ Taylor & Francis Group, LLC
C
ISSN: 1553-3174 print / 1553-3182 online
DOI: 10.1080/15533174.2013.776605
An Efficient One-Pot Synthesis of
2,3-dihydroquinazolin-4(1H)-ones in Green Media
Mohammad Ali Bodaghi Fard, Akbar Mobinikhaledi, and Mahdia Hamidinasab
Department of Chemistry, Faculty of Sciences, Arak University, Arak, I. R. Iran
conductivity; and dissolve in vast range of organic and inorganic
materials.[6] Recently TBAB has been used as an extremely use-
ful catalyst in various organic transformations.[3,7] TBAB is also
inexpensive, readily available and has inherent properties such
as environmental compatibility, greater selectivity, operational
simplicity, noncorrosive nature, and ease of reusability.
Mono- and disubstituted 2,3-dihydroquinazoline-4(1H)-
ones have a wide range of biological and pharmacological activ-
ities such as analgesic, antitumor, anticancer, diuretic and herbi-
cide activities.[8–10] In addition, these compounds can be easily
oxidized to their quinazolin-4(3H)-one analogues,[11] which also
include important pharmacologically active compounds.[12]
Several methods have been reported for the synthesis of
2,3-dihydroquinazolinones.[13–16] However, these methods suf-
fer fromlengthyprocedures and/or low yields, useof volatileand
harmful solvents, and vigorous reaction conditions.[13–16] Salehi
and coworkers reported a new one-pot synthesis of these com-
pounds using p-toluenesolfonic acid, silica sulfuric acid, alum,
and montmorillonite K-10.[17] Very recently, Su and cowork-
ers reported efficient methods for the preparation of quinazoli-
nones.[18] However, the development of simpler and high yield
approaches and milder reaction conditions toward this valuable
nucleus is very desirable.
A series of mono- and disubstituted 2,3-dihydroquinazoline-
4(1H)-ones have been synthesized in good yields by one-pot re-
action using isatoic anhydride, ammonium acetate or amines and
aldehydes in green and mild reaction conditions. The effects of var-
ious parameters such as the solvent, catalyst amount, reaction time,
and temperature were examined. The protocol is simple, efficient,
and environmentally benign and the catalyst can be recovered and
reused without evident loss of reactivity.
Keywords dihydroquinazoline, green synthesis, ionic liquid, TBAB
1. INTRODUCTION
As a consequence of serious pollution problems, the adop-
tion of “cleaner production” methods is an urgent priority.[1]
Organic solvents are volatile, most of them flammable, toxic,
and harmful for environment. Thus, removing organic solvents
in synthesis is very important in the drive towards environmen-
tally friendly technologies.[2,3] The potential of water or other
nonclassical solvents such as ionic liquids has become highly
relevant when designing organic syntheses. The use of these al-
ternative reactions solvents can have inherent advantages such
as enhanced rates of reaction or fewer or more readily iso-
lated side products as well as facilitating product recovery.[2,4]
The use of ionic liquids as solvent and catalyst has attracted
much attention in the context of green synthesis.[5] However,
the high cost of the most of the conventional room temperature
ionic liquids and apprehension regarding the toxicity of some
of them have led to the use of more benign salts in the molten
state as practical alternatives. Tetra-n-butyl ammonium bromide
(TBAB) and related ionic liquids have considerable interests as
potential eco-friendly reagents due to their lack of measurable
vapor pressure. These liquids are nonvolatile, nonflammable;
possess high thermal and chemical stability; possess high ionic
In continuation of our efforts to develop more versatile
methodologies for the synthesis of heterocyclic compounds,[19]
herein we report a simple and efficient method for the se-
lective one-pot preparation of mono- and disubstituted 2,3-
dihydroquinazolin-4(1H)-ones.
EXPERIMENTAL
General
All products are known and characterized by comparison
of their physical and spectroscopic data with those reported in
literature. Melting points were obtained in open capillaries on
an electrothermal 5000 digital apparatus and are not corrected.
IR spectra were recorded on a galaxy series FT-IR 5000 spec-
trometer. NMR spectra were recorded on a Bruker 300 MHz
spectrometer in DMSO-d6 with TMS as an internal standard.
Elemental analyses were measured by Vario EL equipment by
Arak University. Progresses of the reactions were followed by
Received 22 January 2013; accepted 10 February 2013.
The authors gratefully acknowledge the financial support (Grant
no. 91/13689) from the Research Council of Arak University.
Address correspondence to Mohammad Ali Bodaghi Fard, De-
partment of Chemistry, Faculty of Sciences, Arak University, Arak
38156–879, I. R. Iran. E-mail: mbodaghi2007@yahoo.com
567

568
M. A. B. FARD ET AL.
O
O
R2
R1
N
NH4OAc
O
A or B
R1CHO
+
+
or
R2NH2
N
H
N
H
O
1
3
2
4
SCH. 1. A: Solvent-free, 105◦C (oil bath), 40 mol% TBAB (0/128 g). B: Water, 70◦C, 10 mol% TBAB (0/032 g).
dissolving a sample in ethyl acetate and monitoring by TLC (1 mmol) in water (5 mL), TBAB (0.1 mmol) was added.
using n-Hexane/EtOAc (2:1 v/v) as an eluent.
The reaction mixture was stirred at 70◦C for the appropriate
time. After completion of the reaction, as indicated by TLC,
the reaction mixture was cooled to room temperature and fil-
tered to afford the crude products. The further purified products
were obtained by recrystalization from ethanol-water (4:1). In
addition, the filtrate could be also reused for the next batch
reaction.
General Procedure for One-pot Synthesis of
2,3-dihydroquinazolin-4(1H)-ones (Method A)
A well powdered mixture of isatoic anhydride (1 mmol),
ammonium acetate (2 mmol) or primary amine (1.2 mmol),
aldehyde (1 mmol), and TBAB (0.4 mmol) was added to a
screw-capped vial containing magnetic stirring bar and heated
at 105◦C in a preheated oil bath for appropriate time. After
completion of reaction, as indicated by TLC, the mixture was
cooled to room temperature and washed with cold water. The
solid residue was extracted with ethanol or acetone (2 × 10 mL).
The further purified products were obtained by recrystalization
from ethanol-water (4:1). .
Selected Characterization Data for Products
4b: Mp: 232–234◦C. IR (KBr): 3314, 3195 (NH), 1659
1
(C O) cm–1. H NMR (300 MHz, DMSO-d6): δ = 8.23 (s,
1 H), 7.60 (d, J = 7.7 Hz, 1 H), 7.37 (d, J = 8.1 Hz, 2 H),
7.17 – 7.25 (m, 3 H), 7.05 (s, 1 H), 6.14 (d, J = 8.1 Hz, 1 H),
6.66 (t, J = 7.7 Hz, 1 H), 5.70 (s, 1 H), 2.28 (s, 3 H). 13C NMR
(75 MHz, DMSO-d6): δ = 163.7, 147.6, 138.9, 137.7, 133.2,
128.8, 127.5, 126.8, 117.3, 115.2, 114.6, 66.7, 21.8. Anal. Calcd.
for C15H14N2O: C 75.61, H 5.92, N 11.76; Found: C, 75.49; H,
5.99; N, 11.68.
General Procedure for One-pot Synthesis of
2,3-dihydroquinazolin-4(1H)-ones (Method B)
To a mixture of isatoic anhydrides (1 mmol), ammonium
acetate (2 mmol) or primary amine (1.2 mmol) and aldehyde
4c: Mp: 198–200◦C, IR(KBr): 3310, 3191(NH), 1655(C O).
1H NMR (300 MHz, DMSO-d6): δ = 8.35 (s, 1 H), 7.60 (d, J =
7.8 Hz, 1 H), 7.27 (t, J = 7.8 Hz, 1 H), 7.15 (s, 1 H), 6.74 (d, J
= 8.2 Hz, 1 H), 6.68(t, J = 7.8 Hz, 1 H), 5.76 (s, 1 H). 13C NMR
(75 MHz, DMSO-d6): δ = 163.5, 147.7, 140.2, 133.4, 131.2,
128.8, 128.3, 127.4, 117.3, 115.0, 114.5, 66.3. Anal. Calcd. for
C14H11BrN2O: C, 55.47; H, 3.66; N, 9.24; Found: C, 55.53; H,
3.71; N, 9.30.
TABLE 1
Optimization of reaction condition
Temperature
(◦C)
Yield
(%)a
Entry
Solvent
Catalyst
1
2
Solvent-free
Solvent-free
None
None
25
105
0
10
81
90
10
25
15
15
4k: Mp: 227–229◦C. IR (KBr): 3291, 3191 (NH), 1655
1
(C O) cm–1. H NMR (300 MHz, DMSO-d6): δ = 8.09 (s,
3
4
Solvent-free TBAB (20%)
Solvent-free TBAB (40%)
105
105
1 H), 7.59 (d, J = 7.5 Hz, 1 H), 7.21–7.30 (m, 3 H), 6.93 (s, 1
H), 6.63–6.71 (m, 4 H), 5.62 (s, 1 H), 2.86 (s, 6 H). 13C NMR
(75 MHz, DMSO-d6): δ = 162.8, 147.9, 133.1, 131.8, 128.7,
127.6, 117.3, 115.1, 114.3, 113.8, 67.1, 41.7 Anal. Calcd. for
C16H17N3O: C, 71.89; H, 6.41; N, 15.72; Found: C, 71.81; H,
6.47; N, 15.67.
5
6
7
8
CHCl3
CH3CN
DMF
Toluene
C2H5OH TBAB (10%)
H2O
H2O
H2O
TBAB (10%)
TBAB (10%)
TBAB (10%)
TBAB (10%)
Reflux
Reflux
Reflux
Reflux
Reflux
25
9
57
48
4i: Mp: 191–193◦C. IR (KBr): 3299, 3184 (NH), 1659
10
11
12
TBAB (10%)
TBAB (10%)
None
1
(C O) cm–1. H NMR (300 MHz, DMSO-d6): δ = 8.20 (s,
70
Reflux
89, 87, 89b
18
1 H), 7.61 (d, J = 7.7 Hz, 1 H), 7.42 (d, J = 8.6 Hz, 2 H), 7.24
(t, J = 7.2 Hz, 1 H), 7.02 (s, 1 H), 6.95 (d, J = 8.6 Hz, 2 H),
6.74 (d, J = 8.1 Hz, 1 H), 6.67 (t, J = 7.2 Hz, 1 H), 5.70 (s, 1
H), 3.75 (s, 3 H). 13C NMR (75 MHz, DMSO-d6): δ = 164.1,
aIsolated yields.
bCatalyst reused for three consecutive reactions.

EFFICIENT ONE-POT SYNTHESIS
569
TABLE 2
One-pot synthesis of 2,3-dihydroquinazolin-4(1H)-ones promoted by TBAB
Method A
Method B
NH4OAc or
R2NH2
Time Yield
(min) (%)a
Time Yield
(min) (%)a
Entry
R1
Product
Mp (◦C)
Ref
1
2
3
4
5
6
7
8
C6H5
4-MeC6H4
4-BrC6H4
NH4OAc
NH4OAc
NH4OAc
NH4OAc
NH4OAc
NH4OAc
NH4OAc
NH4OAc
NH4OAc
NH4OAc
NH4OAc
NH4OAc
NH4OAc
NH4OAc
PhNH2
4a
4b
4c
4d
4e
4f
4g
4h
4i
4j
4k
4l
4m
4n
4o
4p
4q
4r
30
90
91
88
87
81
79
71
89
91
86
92
91
82
85
88
83
85
90
91
89
50
89
87
89
87
78
79
67
83
90
87
90
89
73
77
87
86
82
89
90
87
217–219
232–234
198–200
206–208
214–216
261–218
190–193
277–279
191–193
200–202
227–229
212–214
165–167
184–186
205–207
196–197
187–189
216–218
173–174
121–123
17c
17c
—
30
35
35
40
40
40
30
30
35
25
25
35
35
35
40
40
35
35
40
50
60
60
75
75
75
45
45
50
40
40
55
55
60
60
60
55
60
60
4-ClC6H4
18a
18a
18a
18a
18a
18a
18a
18a
17c
18a
18a
17c
17c
17c
17c
—
4-NO2C6H4
3-NO2C6H4
2-NO2C6H4
4-OHC6H4
4-OMeC6H4
4-FC6H4
4-N(Me)2C6H4
3,4-(OMe)2C6H3
2-Furyl
9
10
11
12
13
14
15
16
17
18
19
20
2-Pyridyl
C6H5
4-NO2C6H4
3-NO2C6H4
4-ClC6H4
PhNH2
PhNH2
PhNH2
PrNH2
4-ClC6H4
4-NO2C6H4
4s
4t
PrNH2
18a
aIsolated yield.
147.1, 139.8, 133.1, 130.9, 128.6, 127.9, 127.1, 117.2, 115.3, or primary amines, and different aldehydes in molten TBAB or
114.7, 66.7, 56.3. Anal. Calcd. for C15H14N2O2: C, 70.86; H, in aqueous media with the use of catalytic amount of TBAB
5.51; N, 11.02; Found: C, 70.92; H, 5.55; N, 10.98.
(Scheme 1). We optimized the reactions condition using isatoic
4o: Mp: 205–207◦C. IR (KBr): 3307 (NH), 1657 (C O) anhydride, ammonium acetate and benzaldehyde in the pres-
cm–1. 1H NMR (300 MHz, DMSO-d6): δ = 7.73 (d, J = 7.5 Hz, ence of TBAB (Table 1). Results showed the efficient cat-
1 H), 7.67 (s, 1 H), 7.27–7.47 (m, 11 H), 6.75 (m, 2 H), 6.29 (s, alytic activity (Table 1, entries 2, 4, 11, and 12) and reusability
1 H). Anal. Calcd. For C20H16N2O: C, 79.98; H, 5.37; N, 9.33; (Table 1, entry 11) of TBAB. After optimization we studied the
Found: C, 79.91; H, 5.46; N, 9.38.
scope of this reaction. Generally, the cyclocondensation reac-
4s: MP: 173–174◦C. IR (KBr): 3303 (NH), 1662 (C O) tions proceeded well and afforded the desired products in good
1
cm–1. H NMR (300 MHz, DMSO-d6): δ = 7.20–7.33 (m, 5 to excellent yields. The reaction was compatible with a variety
H), 7.18 (s, 1 H), 7.58–7.61 (m, 1 H), 6.68 (t, J = 7.5 Hz, 1 of aryl aldehydes and heterocyclic aldehydes (Table 2).
H), 6.64 (d, J = 7.2 Hz, 1 H), 5.86 (s, 1 H), 3.80–3.85 (m, 1
On the other hand, we investigated the synthesis of 2,3-
H), 2.70–2.75 (m, 1 H), 1.42–1.55 (m, 1 H), 0.82 (t, J = 6 Hz, disubstituted 2,3-dihydroquinazolin-4(1H)-ones from isatoic
3H). 13C NMR (75 MHz, DMSO-d6): δ = 162.6, 146.5, 140.7, anhydride, primary amines and aryl aldehydes under optimized
133.6, 133.3, 128.9, 128.4, 127.9, 117.7, 115.5, 114.8, 69.7, reaction condition and the disubstituted products of 4o-4t were
46.6, 21.3, 11.6. Anal. Calcd. for C17H17ClN2O: C, 67.88; H, obtained in high yields. (Table 1, entries 15–20). The method A
5.70; N, 9.31; Found: C, 67.77; H, 5.79; N, 9.43.
has often better yields and shorter reaction times but the method
B has a very simple workup procedure.
A tentative mechanism for the formation of 2,3-dihydro-
quinazolin-4(1H)-ones was proposed (Scheme 2). At the first
step the condensation of isatoic anhydride with ammonia fol-
lowed by decarboxylation could be produced antranilamide 5.
The intermediate imine 6, could be obtained by the addition
RESULTS AND DISCUSSION
After many examinations, we found that the TBAB promoted
efficiently synthesis of 2,3-dihydroquinazolin-4(1H)-ones in
green and mild condition. This one-pot method involves three
component reactions of isatoic anhydride, ammonium acetate

570
M. A. B. FARD ET AL.
N(n-Bu)4
O
O
NH2
O
NH4OAc
-CO2
N(n-Bu)4
NH2
N
H
O
H
O
5
R
1
-H2O
O
O
NH
NH2
H
N
H
R
N
R
6
4
N(n-Bu)4
SCH. 2.
of 5 with aldehydes promoted by TBAB. Imine 6 can un-
dergo a cyclization to afford the dihydroquinazolinone product
4 (Scheme 2).
7. (a) Ranu, B.C.; Dey, S.S. An efficient synthesis of pyrroles by a one-
pot, three-component condensation of a carbonyl compound, an amine
and a nitroalkene in a molten ammonium salt. Tetrahedron Lett. 2003, 44,
2865–2868. (b) Ranu, B.C.; Dey, S.S.; Hajra, A. Catalysis by an ionic
liquid: efficient conjugate addition of thiols to electron deficient alkenes
catalyzed by molten tetrabutylammonium bromide under solvent-free con-
ditions. Tetrahedron 2003, 59, 2417–2421. (c) Mallakpour, S.; Rafiee,
Z. Tetrabutylammonium bromide: an efficient, green and novel media
for polycondensation of 4-(4-dimethylaminophenyl)-1,2,4-triazolidine-3,5-
dione with diisocyanates. Eur. Pol. J. 2007, 43, 1510–1515. (d) Khodaei,
M.M.; Khosropour, A.R.; Chozati, K. A powerful, practical and chemose-
lective synthesis of 2-anilinoalkanols catalyzed by Bi(TFA)3 or Bi(OTf)3
in the presence of molten TBAB. Tetrahedron Lett. 2004, 45, 3525–3529.
(e) Chary, M.V.; Keerthysri, N.Ch.; Vupallati, S.V. N.; Lingaiah, N.; Kan-
tevari, S. Tetrabutylammonium bromide (TBAB) in isopropanol: An ef-
ficient, novel, neutral and recyclable catalytic system for the synthesis
of 2,4,5-trisubstituted imidazoles. Catal. Commun. 2008, 9, 2013–2017.
(f) Kantevari, S.; Chary, M.V.; Das, A.P. R.; Vupallati, S.V. N.; Lingaiah,
N. Catalysis by an ionic liquid: highly efficient solvent-free synthesis of
aryl-14H-dibenzo[a.j]xanthenes by molten tetrabutylammonium bromide
under conventional and microwave heating. Catal. Commun. 2008, 9, 1575–
1578.
CONCLUSION
In conclusion, we described an efficient selective synthesis
of 2,3-dihydroquinazolin-4(1H)-ones by the condensation reac-
tion of isatoic anhydride, ammonium acetate or primary amine
and an aldehyde using TBAB as a solvent and catalyst in good to
excellent yields. Simple operations, short reaction time, environ-
mental compatibility, availability and reusability of catalyst, and
mild reaction conditions are key features of this new protocol.
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