Sulfated polyborate: mild, efficient and eco-friendly catalyst for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones

Article abstract of DOI:10.1007/s13738-017-1109-x

Abstract: An efficient, inexpensive and recyclable sulfated polyborate catalyst was applied in a three-component, one-pot cyclocondensation of isatoic anhydride, aldehydes and ammonium acetate/amines to afford the corresponding 2,3-dihydroquinazolin-4(1H)-ones. The key advantages of the present method are high yields, short reaction time, easy workup, recyclability of catalyst and ability to tolerate a variety of functional groups which gives economical as well as ecological rewards. Graphical Abstract: [Figure not available: see fulltext.].

Full text of DOI:10.1007/s13738-017-1109-x

J IRAN CHEM SOC
DOI 10.1007/s13738-017-1109-x
ORIGINAL PAPER
Sulfated polyborate: mild, efficient and eco‑friendly catalyst
for the synthesis of 2,3‑dihydroquinazolin‑4(1H)‑ones
Chetan K. Khatri1 · Manisha S. Patil1 · Ganesh U. Chaturbhuj1
Received: 17 December 2016 / Accepted: 24 March 2017
© Iranian Chemical Society 2017
Abstract An efficient, inexpensive and recyclable sulfated
polyborate catalyst was applied in a three-component, one-
pot cyclocondensation of isatoic anhydride, aldehydes and
ammonium acetate/amines to afford the corresponding
2,3-dihydroquinazolin-4(1H)-ones. The key advantages
of the present method are high yields, short reaction time,
easy workup, recyclability of catalyst and ability to tolerate
a variety of functional groups which gives economical as
well as ecological rewards.
Quinazoline and its derivatives are gaining importance
in organic and medicinal chemistry. Quinazolines are an
important class of fused heterocycles with a wide range
of pharmacological and biological activities such as anti-
cancer [2], antitumor [3], antitremor [4], antiatheroscle-
rotic [5], antimicrobial [6], antitubercular [7], antifungal
[8], antimalarial [9], antiinflammatory and analgesic [10],
choleretic and antifibrillatory [11], angiotensin-II recep-
tor antagonists [12], monoamine oxidase inhibitors [13],
potent and selective ALK5 inhibitors [14]. These com-
pounds also have antihypertensive [15], sedative and tran-
quilizer properties [16]. In particular, there are several
drugs containing 2,3-dihydroquinazolin-4(1H)-one scaffold
commercially available such as quinethazone and fenqui-
zone; diuretics [17, 18]; and evodiamine, a novel anticancer
agent [19] (Fig. 1).
Graphical Abstract
In the synthesis of quinazolinone compounds, widely
used reagents are 2-aminobenzoic acid or its derivatives,
2-aminobenzamide, 2-aminobenzonitrile, isatoic anhy-
dride, 2-carbomethoxyphenylisocyanate, N-arylnitrilium
salts and 3,1-benzoxazinones [20–22]. Other methods
involve the reaction of anthranilic acid and the substituted
imidate, cycloaddition of anthranilic acid iminoketene to
methylbutyrolactam via sulfonamide anhydride. However,
use of isatoic anhydride is common due to its rapid reaction
with low side product formation [7, 21, 23].
Keywords Sulfated polyborate · 2,3-Dihydroquinazolin-
4(1H)-ones · Isatoic anhydride · Recyclable catalyst
Introduction
It has been more than a century since the initial studies on
synthesis of quinazoline derivatives were published [1].
There are many reports on the synthesis of 2,3-dihy-
droquinazolin-4(1H)-one using various catalysts such as
sulfuric acid–silica gel [24], potassium alum [25], Mont-
morillonite K-10 [26], p-TSA [27], 1-n-butyl-3-methyl-
imidazolium tetrafluoroborate [28], iodine [29], gallium
trifluoromethanesulfonate [30], aluminum tris (dihydrogen
phosphate) [31], SrCl2·6H2O [32], 2,2,2-trifluoro etha-
nol [33], sodium lauryl sulfate/tartaric acid [34], l-pro-
line [35], copper(II) benzene-sulfonate hexahydrate [36],
Electronic supplementary material The online version of this
article (doi:10.1007/s13738-017-1109-x) contains supplementary
material, which is available to authorized users.
* Ganesh U. Chaturbhuj
gu.chaturbhuj@gmail.com
1
Department of Pharmaceutical Sciences and Technology,
Institute of Chemical Technology, Mumbai, Maharashtra
400019, India
1 3

J IRAN CHEM SOC
Fig. 1 Pharmacologically
active drug molecules
C3H9AlO6S3·4H2O [37], thiamine chloride hydrochloride
[38], tetrabutylammonium bromide [39], indium sesquiox-
ide [40], 2-pyrrolidon-1-ium hydrogen sulfate [41], H3PO4/
Al2O3 [42], PFPAT [43], Fe3O4/SBA-15 [44], hydroxyapa-
tite nanoparticles [45], lactic acid [46], etc. However, many
of the methods suffer from various disadvantages such as
unsatisfactory yields, longer reaction time, extractive prod-
uct isolation with toxic organic solvents, use of expensive,
metal-based, toxic/corrosive catalysts, which limits their
use due to environmental issues. Thus, the development
of a safe, environmentally benign, mild, efficient and high
yielding rapid reaction procedure using cost effective and
recyclable catalyst would be valuable.
used were of LR grade and purchased from SD fine, Avra
Synthesis and Spectrochem and used without purification.
The purity determination of the starting materials and reac-
tion monitoring was accomplished by thin-layer chroma-
tography (TLC) on Merck silica gel G F254 plates.
Preparation of sulfated polyborate
The sulfated polyborate catalyst was prepared following
procedure reported in the literature [47].
Pursuit of green, convenient and practical catalytic meth-
ods for the current interest of organic synthesis and commer-
cial process; recently we have introduced sulfated polybo-
rate catalyst and demonstrated its efficiency for catalyzing
various organic transformations [47, 55–59]. Its mild acid-
ity, easy preparation, eco-friendliness and reusability have
encouraged us to investigate its potential to catalyze many
other useful reactions. Therefore, in continuation of our pre-
vious study, in this paper, we explored the application of sul-
fated polyborate as a highly effective catalyst for the prepa-
ration of 2,3-dihydroquinazolin-4(1H)-ones (Scheme 1).
General procedure for the synthesis
of 2,3‑dihydroquinazolin‑4(1H)‑ones
To a DMSO solution of isatoic anhydride (2 mmol), alde-
hydes (2 mmol) and ammonium acetate (2.4 mmol))/amines
(2 mmol) was added sulfated polyborate (10 wt%). The
mixture was heated at 100 °C in an oil bath. The reaction
was monitored by thin layer chromatography. After comple-
tion of the reaction, the mixture was cooled to room temper-
ature and quenched by water. Solid was filtered at vacuum
pump, washed with water (3 × 5 mL), dried under vacuum
and recrystallized from ethanol to afford the pure products.
The products obtained were known compounds and were
1
Experimental
identified by melting point, FTIR and H NMR spectros-
copy. The spectral data were compared with those in the
literature.
Melting points of all the compounds were recorded by
Analab ThermoCal melting point apparatus in the open
capillary tube and are uncorrected. The FTIR spectra (KBr)
were recorded on Shimadzu FTIRAffinity-1 Fourier Trans-
Representative spectral data
1
form Infrared spectrophotometer. H NMR spectra were
recorded on MR400 Agilent Technology NMR spectrom-
eter using tetramethylsilane (TMS) as an internal standard
and DMSO-d6/CDCl3 as solvent. Chemicals and solvents
2‑phenyl‑2,3‑dihydroquinazolin‑4(1H)‑one (4a) (Table 3,
entry 1) 1H NMR (400 MHz, CDCl3) δ 7.92 (d,
J = 7.6 Hz, 1H), 7.57 (d, J = 3.2 Hz, 2H), 7.46–7.38 (m,
Scheme 1 Sulfated polyborate
catalyzed synthesis of 2,3-dihy-
droquinazoline-4(1H)-ones
1 3

J IRAN CHEM SOC
3H), 7.32 (t, J = 7.6 Hz, 1H), 6.88 (t, J = 7.6 Hz, 1H), 6.65
(d, J = 8.1 Hz, 1H), 5.88 (s, 1H), 5.85 (s, 1H), 4.38 (s, 1H).
7.41–7.33 (m, 2H), 7.23 (t, J = 7.6 Hz, 1H), 6.99 (s, 1H),
6.73 (d, J = 8.2 Hz, 1H), 6.69 (t, J = 7.5 Hz, 1H), 6.11 (s,
1H).
2‑(4‑methoxyphenyl)‑2,3‑dihydroquinazolin‑4(1H)‑one
(4b) (Table 3, entry 2) 1H NMR (400 MHz, DMSO-
d6) δ 8.16 (s, 1H), 7.58 (d, J = 7.4 Hz, 1H), 7.39 (d,
J = 8.0 Hz, 2H), 7.21 (t, J = 7.4 Hz, 1H), 6.99 (s, 1H),
6.92 (d, J = 7.8 Hz, 2H), 6.71 (d, J = 8.0 Hz, 1H), 6.64 (t,
J = 7.4 Hz, 1H), 5.68 (s, 1H), 3.72 (s, 3H).
2‑(2‑hydroxyphenyl)‑2,3‑dihydroquinazolin‑4(1H)‑one
(4i) (Table 3, entry 9) 1H NMR (400 MHz, DMSO-
d6) δ 9.82 (s, 1H), 7.91 (s, 1H), 7.59 (d, J = 7.8 Hz, 1H),
7.31 (d, J = 7.6 Hz, 1H), 7.19 (t, J = 7.6 Hz, 1H), 7.12 (t,
J = 7.7 Hz, 1H), 6.83 (d, J = 8.1 Hz, 1H), 6.79–6.72 (m,
3H), 6.63 (t, J = 7.5 Hz, 1H), 5.97 (s, 1H).
2‑(4‑bromophenyl)‑2,3‑dihydroquinazolin‑4(1H)‑one (4c)
(Table 3, entry 3) 1H NMR (400 MHz, DMSO-d6) δ 8.31
(s, 1H), 7.57 (d, J = 7.2 Hz, 3H), 7.41 (d, J = 8.1 Hz, 2H),
7.22 (t, J = 7.6 Hz, 1H), 7.12 (s, 1H), 6.71 (d, J = 8.0 Hz,
1H), 6.65 (t, J = 7.3 Hz, 1H), 5.72 (s, 1H).
2‑cyclohexyl‑2,3‑dihydroquinazolin‑4(1H)‑one
(4j)
(Table 3, entry 10) 1H NMR (400 MHz, DMSO-d6) δ 7.85
(s, 1H), 7.52 (d, J = 7.7 Hz, 1H), 7.17 (t, J = 7.6 Hz, 1H),
6.71 (d, J = 8.1 Hz, 1H), 6.58 (t, J = 7.3 Hz, 1H), 6.53 (s,
1H), 4.42 (s, 1H), 1.69–1.52 (m, 6H), 1.10–1.09 (m, 5H).
2‑(4‑chlorophenyl)‑2,3‑dihydroquinazolin‑4(1H)‑one (4d)
(Table 3, entry 4) 1H NMR (400 MHz, DMSO-d6) δ 8.31
(s, 1H), 7.58 (d, J = 7.6 Hz, 1H), 7.48 (d, J = 8.3 Hz, 2H),
7.43 (d, J = 8.3 Hz, 2H), 7.22 (t, J = 7.6 Hz, 1H), 7.12 (s,
1H), 6.71 (d, J = 7.8 Hz, 1H), 6.65 (t, J = 7.4 Hz, 1H),
5.74 (s, 1H).
1′H‑spiro[cyclohexane‑1,2′‑quinazolin]‑4′(3′H)‑one (4k)
(Table 3, entry 11) 1H NMR (400 MHz, DMSO-d6) δ 7.87
(s, 1H), 7.52 (d, J = 7.4 Hz, 1H), 7.17 (t, J = 7.3 Hz, 1H),
6.77 (d, J = 8.0 Hz, 1H), 6.63–6.50 (m, 2H), 1. 75–1.65
(m, 2H), 1.63–1.42 m, 6H), 1.43–1.34 (m, 1H), 1.28–1.17
(m, 1H).
2‑(4‑fluorophenyl)‑2,3‑dihydroquinazolin‑4(1H)‑one (4e)
(Table 3, entry 5) 1H NMR (400 MHz, DMSO-d6) δ 8.23
(s, 1H), 7.56 (d, J = 7.4 Hz, 1H), 7.49 (dd, J = 8.2, 5.7 Hz,
2H), 7.22–7.15 (m, 3H), 7.05 (s, 1H), 6.70 (d, J = 8.1 Hz,
1H), 6.63 (t, J = 7.4 Hz, 1H), 5.72 (s, 1H).
2,3‑diphenyl‑2,3‑dihydroquinazolin‑4(1H)‑one
(4l)
(Table 3, entry 12) 1H NMR (400 MHz, DMSO-d6) δ
7.69 (d, J = 7.8 Hz, 1H), 7.63 (s, 1H), 7.35 (d, J = 7.9 Hz,
2H), 7.34–7.18 (m, 8H), 7.16 (t, J = 6.7 Hz, 1H), 6.73 (d,
J = 8.1 Hz, 1H), 6.69 (t, J = 7.5 Hz, 1H), 6.26 (s, 1H).
2‑(p‑tolyl)‑2,3‑dihydroquinazolin‑4(1H)‑one (4f) (Table 3,
entry 6) 1H NMR (400 MHz, DMSO-d6) δ 8.20 (s, 1H),
7.57 (d, J = 7.7 Hz, 1H), 7.34 (d, J = 7.6 Hz, 2H), 7.24–
7.12 (m, 3H), 7.03 (s, 1H), 6.71 (d, J = 8.1 Hz, 1H), 6.64
(t, J = 7.5 Hz, 1H), 5.68 (s, 1H), 2.27 (s, 3H).
3‑(4‑bromophenyl)‑2‑phenyl‑2,3‑dihydroquinazo-
lin‑4(1H)‑one (4m) (Table 3, entry 13) 1H NMR
(400 MHz, DMSO-d6) δ 7.67 (d, J = 7.6 Hz, 1H), 7.61 (s,
1H), 7.46 (d, J = 8.7 Hz, 2H), 7.32 (d, J = 7.0 Hz, 2H),
7.29–7.20 (m, 4H), 7.17 (d, J = 8.7 Hz, 2H), 6.75–6.64 (m,
2H), 6.26 (s, 1H).
2‑(4‑(dimethylamino)phenyl)‑2,3‑dihydroquinazo-
lin‑4(1H)‑one (4g) (Table 3, entry 7) 1H NMR (400 MHz,
DMSO-d6) δ 8.05 (s, 1H), 7.57 (d, J = 7.7 Hz, 1H), 7.27 (d,
J = 8.4 Hz, 2H), 7.20 (t, J = 7.6 Hz, 1H), 6.89 (s, 1H), 6.69
(d, J = 6.5 Hz, 3H), 6.63 (t, J = 7.4 Hz, 1H), 5.60 (s, 1H),
2.85 (s, 6H).
3‑(4‑chlorophenyl)‑2‑phenyl‑2,3‑dihydroquinazo-
lin‑4(1H)‑one (4n) (Table 3, entry 14) 1H NMR
(400 MHz, DMSO-d6) δ 7.85–6.89 (m, 12H), 6.66 (d,
J = 14.5 Hz, 2H), 6.24 (s, 1H).
2‑(2‑chlorophenyl)‑2,3‑dihydroquinazolin‑4(1H)‑one (4h)
(Table 3, entry 8) 1H NMR (400 MHz, DMSO-d6) δ
8.19 (s, 1H), 7.63 (d, J = 6.1 Hz, 2H), 7.53–7.44 (m, 1H),
2‑phenyl‑3‑(p‑tolyl)‑2,3‑dihydroquinazolin‑4(1H)‑one (4o)
(Table 3, entry 15) 1H NMR (400 MHz, DMSO-d6) δ
7.66 (d, J = 7.6 Hz, 1H), 7.53 (s, 1H), 7.31 (d, J = 7.2 Hz,
1 3

J IRAN CHEM SOC
Table 1 Results of optimization studies
2H), 7.28–7.15 (m, 4H), 7.12–7.04 (m, 4H), 6.73–6.59 (m,
2H), 6.18 (s, 1H), 2.20 (s, 3H).
Entry Catalyst
(wt%)
Solvent
Tempera- Time
ture (°C)
Yielda (%)
(min)
1.
2.
3.
4.
5.
6.
7.
0
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
100 °C
100 °C
100 °C
100 °C
100 °C
100 °C
100 °C
180
30
15
15
15
15
30
69
80
85
91
97
97
88
3‑benzyl‑2‑phenyl‑2,3‑dihydroquinazolin‑4(1H)‑one (4p)
(Table 3, entry 16) 1H NMR (400 MHz, DMSO-d6) δ
7.66 (d, J = 7.5 Hz, 1H), 7.37–7.10 (m, 12H), 6.68–6.56
(m, 2H), 5.70 (d, J = 2.3 Hz, 1H), 5.28 (d, J = 15.4 Hz,
1H), 3.78 (d, J = 15.4 Hz, 1H).
1
2.5
5
10
15
10
Solvent
free
3‑phenethyl‑2‑phenyl‑2,3‑dihydroquinazolin‑4(1H)‑one
(4q) (Table 3, entry 17) 1H NMR (400 MHz, DMSO-d6)
δ 7.61 (d, J = 7.6 Hz, 1H), 7.32–7.28 (m, 6H), 7.24–7.20
(m, 2H), 7.17–7.11 (m, 4H), 6.63–6.57 (m, 2H), 5.80 (s,
1H), 4.00–3.89 (m, 1H), 2.95–2.81 (m, 2H), 2.71–2.61 (m,
1H).
8.
10
10
10
10
10
10
10
10
EtOH
ACN
Reflux
Reflux
Reflux
Reflux
Reflux
Rt
30
30
30
30
30
30
30
30
82
9.
90
10.
11.
12.
13.
14.
15.
THF
88
Water
Toluene
DMSO
DMSO
DMSO
Traces
91
79
50 °C
80 °C
86
95
a
Isolated yield
Results and discussion
For initial screening, the study was structured to investigate
the suitability of sulfated polyborate as a catalyst at differ-
ent reaction conditions. For the preliminary experiment,
a mixture of benzaldehyde—a representative substrate,
isatoic anhydride and ammonium acetate was used. The
results are summarized in Table 1.
The effect of the catalyst loading on time and yields of
the reaction was assessed. In absence of a catalyst, the reac-
tion proceeded at 100 °C but took longer reaction time with
a lower yield (Table 1, entry 1). An increase in the catalyst
loading increased the product yield with significate reduction
in the reaction time (Table 1, entries 2–5). The catalyst load-
ing beyond 10 wt % was not advantageous (Table 1, entries
5 and 6). Hence, a 10 wt% catalyst loading was chosen for
further study.
The effect of various solvents on time and yield of the
reaction was ascertained (Table 1, entries 5 and 7–12).
None of the solvents have shown advantage over DMSO.
Hence, DMSO was regarded as a best solvent to carry out
the further reactions.
Temperature played an important role in the synthesis of
2,3-dihydroquinazolin-4(1H)-one. The temperature effect was
examined at ambient, 50, 80 and 100 °C using sulfated polyb-
orate (Table 1, entries 5 and 13–15). The reaction proceeded
at room temperature but took longer reaction time with a
lower yield (Table 1, entry 13). An increase in the temperature
to 100 °C resulted in significantly increased product yield in
shorter reaction time (Table 1, entries 5, 14 and 15). Therefore,
100 °C was chosen as optimum temperature for the reaction.
Various catalysts are reported for the synthesis of
2,3-dihydroquinazolin-4(1H)-one. Herein, in compari-
son with other acid catalysts, sulfated polyborate cata-
lyst showed an advantage with respect to reaction condi-
tions, workup procedure, time and yields (Table 2, entries
1–10).
To study the generality and scope, optimized reaction
conditions were applied to various aromatic/aliphatic
aldehydes and amines. All the substrate variants reacted
well and afforded higher yields of 2,3-dihydroquina-
zolin-4(1H)-ones in shorter reaction time (Tables 3,
4). Various electron donating or electron withdrawing
substituents at the ortho and para position of aromatic
aldehydes have been examined. The nature of substitu-
tions on aromatic aldehydes has no significant effect on
the reaction time and yields (Table 3, entries 2–9). The
protocol is also extended to an aliphatic aldehyde/ketone
variants cyclohexane carboxaldehyde and cyclohexanone
to get corresponding 2,3-dihydroquinazolin-4(1H)-ones
in shorter reaction time in good yield (Table 3, entry 10
and 11).
On the other side, the applicability of this protocol on
aromatic and aliphatic amines was also examined using
substituted aniline, benzylamine and phenylethylamine
variants. All the amine variants were reacted well and
afforded higher yields of the corresponding 2,3-dihydro-
quinazolin-4(1H)-ones in shorter reaction time (Table 4,
entries 12–17).
1 3

J IRAN CHEM SOC
Table 2 Efficiency of sulfated polyborate in comparison with literature-reported catalyst for the 2-phenyl-2,3-dihydroquinazolin-4(1H)-one
Entry
Catalyst
Conditions
Time (min)
Yielda (%)
References
1.
2.
3.
4.
5.
6.
7.
8.
9.
10.
Sulfated polyborate
DMSO/100 °C
EtOH/water/reflux
EtOH/reflux
15
30
97
93
92
92
91
90
89
87
85
84
This work
[36]
Copper(II) benzene-sulfonate hexahydrate
Sulfuric acid–silica gel
180
90
[24]
1-n-Butyl-3-methyl imidazolium tetrafluoro borate
C3H9AlO6S3·4H2O
Solvent free/70 °C
EtOH/water/reflux
Solvent free/70 °C
Solvent free/80 °C
EtOH/70 °C
[28]
60
[37]
Lactic acid
30
[46]
2-Pyrrolidon-1-ium hydrogen sulfate
Gallium trifluoro methanesulfonate
Montmorillonite K-10
11
[41]
55
[30]
EtOH/reflux
240
60
[26]
p-TSA
Water/reflux
[27]
a
Isolated yield
Table 3 Synthesis of 2,3-dihydroquinazolin-4(1H)-ones using a variety of aldehydes
Entry
Aldehydes (R1)
Products
Time (min)
Yielda (%)
Melting point (°C)
Obtained
Literature
1.
C6H5
4a
4b
4c
4d
4e
4f
15
15
15
15
15
15
15
15
20
15
20
97
95
93
94
94
93
89
90
88
92
93
215–216
190–191
195–196
201–202
195–196
227–228
222–223
206–208
209–210
174–175
227–228
216–218 [48]
189–191 [49]
196–198 [49]
202–204 [49]
194–196 [49]
230–232 [49]
220–222 [50]
206–208 [51]
210–211 [50]
–
2.
4-CH3O-C6H4
4-Br-C6H4
4-Cl-C6H4
4-F-C6H4
3.
4.
5.
6.
4-CH3-C6H4
4-(CH3)2N-C6H4
2-Cl-C6H4
2-HO-C6H4
c-C6H11
7.
4g
4h
4i
8.
9.
10.
11.
4j
c-C5H10
4k
228–230 [52]
a
Isolated yields
The reusability of the catalyst for the model reaction
of isatoic anhydride, benzaldehyde and ammonium ace-
tate in DMSO at 100 °C was evaluated. After completion
of each cycle, the reaction was quenched with water and
the product was filtered off. The water was evaporated
from the filtrate in vacuum rotary evaporator to recover
the catalyst quantitatively in DMSO. The recovered cata-
lyst in DMSO was recycled for four times with no sig-
nificant loss in the catalytic activity (Fig. 2).
Conclusion
In conclusion, the present procedure is a rapid, efficient
and eco-friendly protocol for the synthesis of 2,3-dihy-
droquinazolin-4(1H)-ones using various aldehydes,
ammonium acetate/amines and isatoic anhydride under
optimized conditions. Mild reaction conditions, easy of
workup procedure, shorter reaction time, high yields and
recyclability of the catalyst are the key features of this
1 3

J IRAN CHEM SOC
Table 4 Synthesis of 2,3-dihydroquinazolin-4(1H)-ones using various amines
Entry
Amines (R2)
Products
Time (min)
Yielda (%)
Melting point (°C)
Obtained
Literature
1.
2.
3.
4.
5.
6.
C6H5
4k
4l
20
20
20
20
15
15
94
90
91
93
90
94
203–204
125–127
214–215
197–198
128–129
146–147
203–204 [40]
228–229 [45]
216–217 [45]
198–199 [45]
128–130 [53]
145–147 [54]
4-Br-C6H4
4-Cl-C6H4
4-CH3-C6H4
C6H5CH2
C6H5CH2CH2
4m
4n
4o
4p
a
Isolated yields
References
1. A. Widdege, Prakt. Chem. 36, 141 (1887)
2. C. Párkányi, D.S. Schmidt, J. Heterocycl. Chem. 37, 725 (2000)
3. E. Hamel, C.M. Lin, J. Plowman, H.K. Wang, K.H. Lee, K.D.
Paull, Biochem. Pharmacol. 51, 53 (1996)
4. H. Lee, S.Y. Jung, H.A. Park, H.B. Kang, J. Kim, D.J. Choo, A.
Handforth, J.Y. Lee, Bull. Korean Chem. Soc. 31, 2451 (2010)
5. N. Li, X. Wang, J. Zhang, C. Liu, Y. Li, T. Feng, Y. Xu, S. Si,
Biochem. Pharmacol. 92, 438 (2014)
6. A.M. Farghaly, R. Soliman, M.A. Khalil, A.A. Bekhit, A. El-
Din, A. Bekhit, Boll. Chim. Farm. 141, 372 (2001)
7. M. Adib, S. Ansari, A. Mohammadi, H.R. Bijanzadeh, Tetrahe-
dron Lett. 51, 30 (2010)
8. J. Bartroli, E. Turmo, M. Algueró, E. Boncompte, M.L. Veri-
cat, L. Conte, J. Ramis, M. Merlos, J. García-Rafanell, J. Forn,
J. Med. Chem. 41, 1869 (1998)
Fig. 2 Reusability of the catalyst
9. H. Kikuchi, H. Tasaka, S. Hirai, Y. Takaya, Y. Iwabuchi, H.
Ooi, S. Hatakeyama, H.S. Kim, Y. Wataya, Y. Oshima, J. Med.
Chem. 45, 2563 (2002)
procedure. Moreover, this protocol has the ability to tol-
erate a wide variety of substituents along with enhanced
product purity which promises economical as well as
ecological rewards.
10. Y.S. Sadanandam, K.R.M. Reddy, A.B. Rao, Eur. J. Med.
Chem. 22, 169 (1987)
11. G. Bonola, P. Da Re, M.J. Magistretti, E. Massarani, I. Setni-
kar, J. Med. Chem. 11, 1136 (1968)
12. J.I. Levin, P.S. Chan, T. Bailey, A.S. Katocs, A.M. Venkatesan,
Bioorg. Med. Chem. Lett. 4, 1141 (1994)
13. N. Mulakayala, B. Kandagatla, R.K. Rapolu, P. Rao, C. Mula-
kayala, C.S. Kumar, J. Iqbal, S. Oruganti, Bioorg. Med. Chem.
Lett. 22, 5063 (2012)
Supplementary information
14. F. Gellibert, M.H. Fouchet, V.L. Nguyen, R. Wang, G. Krysa,
A.C. de Gouville, S. Huet, N. Dodic, Bioorg. Med. Chem.
Lett. 19, 2277 (2009)
15. M. Amir, I. Ali, M.Z. Hassan, Arch. Pharm. Res. 36, 61 (2013)
16. V. Jatav, P. Mishra, S. Kashaw, J.P. Stables, Eur. J. Med. Chem.
43, 135 (2008)
Full experimental details and 1H NMR spectra can be
found in Electronic Supplementary Information section of
this article’s webpage.
Acknowledgements The authors are grateful to University Grants
17. E. Cohen, B. Klarberg, J.R. Vaughan Jr., J. Am. Chem. Soc.
Commission (UGC) for their financial support.
82, 2731 (1960)
1 3

J IRAN CHEM SOC
40. S. Santra, M. Rahman, A. Roy, A. Majee, A. Hajra, Catal. Com-
mun. 49, 52 (2014)
18. C. Ferrando, J.M. Foy, C. Pratt, J.R. Purvis, J. Pharm. Pharma-
col. 33, 219 (1981)
41. H.R. Shaterian, M. Aghakhanizadeh, Res. Chem. Intermed. 40,
1655 (2014)
42. H.R. Shaterian, N. Fahimi, K. Azizi, Res. Chem. Intermed. 40,
1879 (2014)
19. J. Jiang, C. Hu, Molecules 14, 1852 (2009)
20. S. Boyapati, U. Kulandaivelu, S. Sangu, M.R. Vanga, Arch.
Pharm. 343, 570 (2010)
21. A. Davoodnia, S. Allameh, A.R. Fakhari, N. Tavakoli-Hoseini,
43. M.T. Maghsoodlou, N. Khorshidi, M.R. Mousavi, N. Hazeri,
S.M. Habibi-Khorassani, Res. Chem. Intermed. 41, 7497 (2015)
44. A. Maleki, M. Rabbani, S. Shahrokh, Appl. Organomet. Chem.
29, 809 (2015)
45. N. Razavi, B. Akhlaghinia, New J. Chem. 40, 447 (2016)
46. S. Zhaleh, N. Hazeri, M.T. Maghsoodlou, Res. Chem. Intermed.
42, 6381 (2016)
Chin. Chem. Lett. 21, 550 (2010)
22. F. Tamaddon, F. Pouramini, Synlett 25, 1127 (2014)
23. S.B. Mhaske, N.P. Argade, Tetrahedron 62, 9787 (2006)
24. M. Dabiri, M. Baghbanzadeh, A.S. Delbari, J. Comb. Chem.
10, 700 (2008)
25. M. Dabiri, P. Salehi, S. Otokesh, M. Baghbanzadeh, G. Koze-
hgary, A.A. Mohammadi, Tetrahedron Lett. 46, 6123 (2005)
26. P. Salehi, M. Dabiri, M. Baghbanzadeh, M. Bahramnejad, Synth.
Commun. 36, 2287 (2006)
47. C.K. Khatri, D.S. Rekunge, G.U. Chaturbhuj, New J. Chem. 40,
10412 (2016)
48. M. Singh, N. Raghav, Bioorg. Chem. 59, 12 (2015)
49. A. Ghorbani-Choghamarani, B. Tahmasbi, New J. Chem. 40,
1205 (2016)
50. S.P. Bahekar, N.D. Dahake, P.B. Sarode, H.S. Chandak, Synlett
26, 2575 (2015)
27. M. Baghbanzadeh, P. Salehi, M. Dabiri, G. Kozehgary, Synthesis
2006, 344 (2006)
28. M. Dabiri, P. Salehi, M. Baghbanzadeh, Monatshefte Für Chem.-
Chem. Mon. 138, 1191 (2007)
29. S. Rostamizadeh, A.M. Amani, R. Aryan, H.R. Ghaieni, N.
51. A.V.D. Rao, B.P. Vykunteswararao, T. Bhaskarkumar, N.R. Jog-
dand, D. Kalita, J.K.D. Lilakar, V. Siddaiah, P.D. Sanasi, A. Rag-
hunadh, Tetrahedron Lett. 56, 4714 (2015)
Shadjou, Synth. Commun. 38, 3567 (2008)
30. J. Chen, D. Wu, F. He, M. Liu, H. Wu, J. Ding, W. Su, Tetrahe-
dron Lett. 49, 3814 (2008)
52. M. Abdollahi-Alibeik, E. Shabani, J. Iran. Chem. Soc. 11, 351
(2014)
31. H.R. Shaterian, A.R. Oveisi, M. Honarmand, Synth. Commun.
40, 1231 (2010)
53. M. Heidary, M. Khoobi, S. Ghasemi, Z. Habibi, M.A. Faramarzi,
32. M. Wang, T.T. Zhang, Y. Liang, J.J. Gao, Chin. Chem. Lett. 22,
1423 (2011)
Adv. Synth. Catal. 356, 1789 (2014)
54. M. Sharma, S. Pandey, K. Chauhan, D. Sharma, B. Kumar,
P.M.S. Chauhan, J. Org. Chem. 77, 929 (2012)
55. C.K. Khatri, V.B. Satalkar, G.U. Chaturbhuj, Tetrahedron Lett.
58, 694 (2017)
33. S. Khaksar, S.M. Talesh, C. R. Chim. 15, 779 (2012)
34. R. Sharma, A.K. Pandey, P.M.S. Chauhan, Synlett 23, 2209
(2012)
35. K. Kumari, D.S. Raghuvanshi, K.N. Singh, Indian J. Chem. Sect.
56. D.S. Rekunge, C.K. Khatri, G.U. Chaturbhuj, Tetrahedron Lett.
B 51, 860 (2012)
58, 1240 (2017)
36. M. Wang, T.T. Zhang, Y. Liang, J.J. Gao, Monatshefte Für
Chem.-Chem. Mon. 143, 835 (2012)
37. Z. Song, L. Liu, Y. Wang, X. Sun, Res. Chem. Intermed. 38,
1091 (2012)
38. Y. Chen, W. Shan, M. Lei, L. Hu, Tetrahedron Lett. 53, 5923
(2012)
39. M.A.B. Fard, A. Mobinikhaledi, M. Hamidinasab, Synth. React.
Inorg. Met. Nano-Metal Chem. 44, 567 (2014)
57. K.S. Indalkar, C.K. Khatri, G.U. Chaturbhuj, J. Chem. Sci. 129,
141 (2017)
58. K.S. Indalkar, C.K. Khatri, G.U. Chaturbhuj, J. Chem. Sci.
(2017). doi:10.1007/s12039-017-1257-7
59. C.K. Khatri, A.S. Mali, G.U. Chaturbhuj, Monatsh. Chem.
(2017). doi:10.1007/s00706-017-1944-6
1 3