Synthesis of a series of novel 2,3-dihydrofuranonaphthoquinone derivatives

Article abstract of DOI:10.3184/174751917X14999542807785

A green and highly efficient synthesis of 12 novel trans-2-(4-chlorobenzoyl)-3-aryl-2,3-dihydronaphtho[2,3-b]furan-4,9-diones has been achieved via a three-component, one-pot condensation of 2-[2-(4-chlorophenyl)-2-oxoethyl)]isoquinolinium bromide with 2-hydroxy-1,4-naphthoquinone and an aromatic aldehyde in the presence of catalytic amounts of choline hydroxide in water under reflux conditions. The advantages of this method are a short reaction time, high yields and the avoidance of any hazardous organic solvent. Therefore, this procedure can be classified as green chemistry.

Full text of DOI:10.3184/174751917X14999542807785

4
48 RESEARCH PAPER
VOL. 41 AUGUST, 448–451
JOURNAL OF CHEMICAL RESEARCH 2017
Synthesis of a series of novel 2,3-dihydrofuranonaphthoquinone derivatives
a
a
b
Maryam Salari , Mohammad H. Mosslemin *and Alireza Hassanabadi
a
Department of Chemistry, Yazd Branch, Islamic Azad University, Yazd, Iran
Department of Chemistry, Zahedan Branch, Islamic Azad University, Zahedan, Iran
b
A green and highly efficient synthesis of 12 novel trans-2-(4-chlorobenzoyl)-3-aryl-2,3-dihydronaphtho[2,3-b]furan-4,9-diones has been
achieved via a three-component, one-pot condensation of 2-[2-(4-chlorophenyl)-2-oxoethyl)]isoquinolinium bromide with 2-hydroxy-1,4-
naphthoquinone and an aromatic aldehyde in the presence of catalytic amounts of choline hydroxide in water under reflux conditions.
The advantages of this method are a short reaction time, high yields and the avoidance of any hazardous organic solvent. Therefore, this
procedure can be classified as green chemistry.
Keywords: 2-hydroxy-1,4-naphthoquinone, green chemistry, 2,3-dihydrofuranonaphthoquinone derivatives, aromatic aldehydes, 4-chlorophenacyl
bromide, choline hydroxide
Multi-component reactions (MCRs), by virtue of their convergence,
productivity, facile execution and generally high yields, have
excellent yields of 2,3-dihydrofuranonaphthoquinones. We have
previously reported the synthesis of 2,3-dihydrofuranocoumarins
using choline hydroxide as catalyst.
1–3
20
attracted much attention in the area of combinatorial chemistry.
Many important heterocyclic syntheses are MCRs.
Dihydrofurans are important heterocycles commonly found in a
Recently,organicreactionsinaqueousmediahaveattractedagreat
21
deal of attention as a result of increasing interest in the concepts of
4,5
22
large variety of naturally occurring substances. The development
of new and efficient methods for their synthesis remains an area
of current interest and a whole series of new synthetic methods
sustainability and green chemistry. In continuation of our previous
20,23,24
work on the synthesis of heterocyclic compounds,
we decided
to investigate the reaction of 2-[2-(4-chlorophenyl)-2-oxoethyl)]
isoquinolinium bromide 2 with 2-hydroxy-1,4-naphthoquinone
3 and an aromatic aldehyde 4 in presence of catalytic amounts of
choline hydroxide in water under reflux conditions (Scheme 1).
6
–19
have appeared in the literature. Among synthetic methodologies
towards dihydrofurans, non-ionic as well as ionic procedures
2
10–12
have been exploited. Radical or carbenoid
additions to olefins
have been utilised as non-ionic procedures. Among ionic reaction
Results and discussion
conditions, dihydrofuran syntheses via tandem nucleophilic
13–15
16–19
25
reaction of 1,3-dicarbonyl compounds
or ylides
with
Using a previously reported method, we prepared in nearly
enones have been reported. The methods reported previously for
the synthesis of dihydrofurans suffer from severe disadvantages,
such as hazardous solvents, long reaction times, inadequate yields
and use of expensive non-recoverable surfactants. Based on the
above information and due to our interest in developing synthetic
strategies for the construction of heterocyclic compounds, in the
present work, we used choline hydroxide as an efficient catalyst
to overcome these limitations in a new, rapid method affording
quantitative yield one of the starting materials, 2-[2-(4-chloro-
phenyl)-2-oxoethyl)]isoquinolinium bromide 2, by treatment of
isoquinoline with 4-chlorophenacyl bromide 1 in acetonitrile
(Scheme 2).
As a test run, a three-component reaction of 2-[2-(4-chloro-
phenyl)-2-oxoethyl)]isoquinolinium bromide 2 with 2-hydroxy-
1,4-naphthoquinone 3 and benzaldehyde 4 (Ar = Ph) in the
presence of catalytic amounts of choline hydroxide in refluxing
O
Cl
OH
O
-
_
Br
+
N
OH
O
OH
H
+
3
O
N
O
O
+
Ar
O
H O , Reflux , 5 h
2
2
H
Cl
Ar
H
O
4
5
Scheme 1
O
Br CH CN, rt, 20 min
_
Br
3
O
+
+
N
N
Cl
2
1
Cl
Scheme 2
*
Correspondent. E-mail: mhmosslemin@iauyazd.ac.ir

JOURNAL OF CHEMICAL RESEARCH 2017 449
O
Cl
OH
O
_
Br
+
N
OH
-
O
OH
H
+
3
O
N
O
O
+
Ar
O
H O , Reflux , 5 h
2
2
H
Cl
Ar
H
O
4
5
*
*
5
a
Ar
C H
%Yield
94
M.p.(°C)
57–259
5
Ar
%Yield
M.p.(°C)
197–199
g
2
4-CH O
C H
91
95
92
6
5
3
6
4
b
c
2-O N
204–206
201–203
265–267
269–271
244–246
h
i
4-F
C H
6
239–241
232–234
C H
93
96
92
2
6
4
4
4
-O N
C H
4-Cl-3-O N
2
C H
6 3
2
6
4
d
e
f
2-ClC H4
j
C H
4
91
90
93
212–214
184–186
6
4-NC
4-CH C H
4
6
4-ClC H4
9
3
k
l
3
6
6
2
-FC H4
94
4
-Br
C H
6 4
209–211
6
*
Yields refer to the pure isolated prodoucts
Scheme 3
H O
2
+
N
OH
+
-
_
Br
Br
O
O
+
-
OH
N
+
N
OH
+
2
Cl
N
_
6
O
O
Cl
OH
O
-
O
Ar
O
OH
+
Ar
H
3
4
O
+
7
_
O
+
O
N
_
N
6
_
Cl
O
N
5
O
O
Ar
Ar
O
O
O
Cl
8
7
Scheme 4
water gave the expected product 5a (Ar = Ph) in an excellent yield
of 94% (Scheme 3). Then, 11 other araldehydes 4 (Ar = various)
were then employed to prepare the corresponding analogues
5b–l (Ar = various) (Scheme 3). Yields were uniformly high
(90–96%) for both electron-donating and electron-withdrawing
groups. The structures of compounds 5a–l were deduced from

450 JOURNAL OF CHEMICAL RESEARCH 2017
1
13
13
their elemental analyses and their IR, H NMR and C NMR
spectra.
J = 4.8 Hz CH, 1H), 7.60–8.02 (m, 12H, arom); C NMR (100 Hz,
CDCl ): δ 36.9, 83.7, 118.2, 124.8, 126.6, 126.8, 128.3, 128.6, 128.7,
30.2, 131.8, 132.5, 134.2, 135.1, 138.9, 148.6, 160.2, 179.6, 183.1,
191.1; MS m/z (%): 459 (4). Anal. calcd for C H ClNO : C, 65.30; H,
3
1
The mass spectra of compounds 5a–l are fairly similar and
display molecular ion peaks. In the H NMR spectra, the two
1
25 14
6
3
.07; N, 3.05; found: C, 65.46; H, 3.20; N, 3.17%.
-(4-Chlorobenzoyl)-3-(4-nitrophenyl)-2,3-dihydronaphtho[2,3-b]
furan-4,9-dione (5c): Brown powder; m.p. 201–203 °C; IR (KBr)
protons at the 2,3-position of the dihydrofuran ring display
two doublets at 4.34 and 6.08 ppm with a vicinal coupling
constant of 4.8 Hz. It has been documented that in cis-2,3-
dihydrofurans, the vicinal coupling constant of the two
methine protons is 7–10 Hz, while in trans-2,3-dihydrofurans
the vicinal coupling constant is 2.8–6.0 Hz. Therefore, we
concluded that the thermodynamically stable trans isomers of
2
−1
(
νmax cm ): 2934, 2853, 1646, 1532, 1455, 1415, 1252, 118, 747, 575;
1
H NMR (400 Hz, CDCl ): δ 4.45 (d, J = 4.8 Hz, CH, 1H), 6.05 (d,
3
13
J = 4.8 Hz, CH, 1H), 7.61–8.04 (m, 12H, arom); C NMR (100 Hz,
CDCl ): δ 37.2, 84.7, 118.2, 123.3, 126.6, 128.4, 128.7, 129.9, 130.5,
31.8, 132.3, 135.1, 138.7, 145.4, 146.7, 159.8, 179.8, 183.2, 192.4; MS
m/z (%): 459 (7). Anal. calcd for C H ClNO : C, 65.30; H, 3.07; N,
.05; found: C, 65.43; H, 3.18; N, 3.19%.
- ( 4 - C h l o r o b e n z o y l ) - 3 - ( 2 - c h l o r o p h e n y l ) - 2 , 3 -
dihydronaphtho[2,3-b]furan-4,9-dione (5d): Brown powder; m.p.
65–267 °C; IR (KBr) (ν cm ): 2926, 2853, 1646, 1454, 1412, 1255,
124, 755, 574; H NMR (400 Hz, CDCl ): δ 4.89 (d, J = 5.2 Hz, CH,
H), 5.98 (d, J = 5.2 Hz, CH, 1H), 7.18–8.02 (m, 12H, arom); C NMR
100 Hz, CDCl ): δ 32.5, 84.2, 118.8, 126.7, 126.8, 127.4, 128.7, 129.8,
129.3, 130.2, 130.8, 131.7, 132.3, 133.6, 135.7, 138.4, 138.6, 160.1, 179.8,
3
1
2
6
the 2,3-dihydrofuran derivatives were formed.
2
5
14
6
A proposed mechanism for this reaction is shown in Scheme
. The formation of the product can be explained as follows. The
-[2-(4-chlorophenyl)-2-oxoethyl)]isoquinolinium bromide 2
undergoes deprotonation in the presence of aqueous choline
hydroxide to give the reactive isoquinolinium ylide 6. The
-hydroxy-1,4-naphthoquinone 3 reacts with aromatic aldehyde
in the presence of choline hydroxide to give the Knoevenagel
product 7. This reacts instantly with the isoquinolinium ylide
to form the zwitterionic intermediate 8, which undergoes
3
4
2
2
−1
2
1
max
1
3
2
4
13
1
(
3
6
183, 190.9; MS m/z (%): 448 (9). Anal. calcd for C H Cl O : C, 66.83;
2
5
14
2
4
cyclisation with the elimination of isoquinoline to give the
H, 3.14; found: C, 67.00; H, 3.26%.
desired product 5.
2 - ( 4 - C h l o r o b e n z o y l ) - 3 - ( 4 - c h l o r o p h e n y l ) - 2 , 3 -
In summary, here we report a simple and efficient, one-
pot condensation of 2-[2-(4-chlorophenyl)-2-oxoethyl)]
isoquinolinium bromide with 2-hydroxy-1,4-naphthoquinone
and an aromatic aldehyde in presence of catalytic amounts
of choline hydroxide in water under reflux conditions to
dihydronaphtho[2,3-b]furan-4,9-dione (5e): Brown powder; m.p.
−1
269–271 °C; IR (KBr) (ν cm ): 2924, 2824, 1647, 1412, 1257, 1024,
max
1
754, 535; H NMR (400 Hz, CDCl
): δ 4.99 (d, J = 5.0 Hz, CH, 1H),
3
13
6
.04 (d, J = 5.0 Hz, CH, 1H), 7.42–8.01 (m, 12H, arom); C NMR (100
Hz, CDCl ): δ 37.2, 84.7, 118.2, 126.6, 126.8, 128.7, 129.2, 130.2, 130.8,
3
131.3, 131.5, 132.6, 135.9, 138.9, 160.2, 179.6, 183.1, 191.1; MS m/z
give
a series of trans-2-(4-chlorobenzoyl)-3-aryl-2,3-di-
(
%): 448 (7). Anal. calcd for C H Cl O : C, 66.83; H, 3.14; found: C,
hydronaphtho[2,3-b]furan-4,9-diones. The advantages of this
method are readily available starting materials, short reaction
times, easy and clean work-up, and excellent yields.
25 14
2
4
6
6.96; H, 3.24%.
- ( 4 - C h l o r o b e n z o y l ) - 3 - ( 2 - f l u o r o p h e n y l ) - 2 , 3 -
dihydronaphtho[2,3-b]furan-4,9-dione (5f): Brown powder; m.p.
2
−1
2
44–246 °C; IR (KBr) (ν cm ): 2922, 2853, 1646, 1452, 1402, 1254,
Experimental
max
1
1
126, 755, 574; H NMR (400 Hz, CDCl ): δ 4.35 (d, J = 5.2 Hz, CH,
3
Melting points were determined with an Electrothermal 9100
apparatus. Elemental analyses were performed using a Heraeus CHN-
O-Rapid analyser. Mass spectra were recorded on a FINNIGAN-
MAT 8430 mass spectrometer operating at an ionisation potential of
13
1H), 6.04 (d, J = 5.2 Hz, CH, 1H), 7.07–8.02 (m, 12H, arom); C NMR
(
1
100 Hz, CDCl ): δ 30.7, 84.7, 115.8, 118.2, 124.4, 126.2, 127.3, 127.5,
3
28.7, 129.3, 130.3, 130.8, 131.8, 132.6, 135.2, 138.5, 160.2, 179.4,
1
83.6, 190.3; MS m/z (%): 432 (5). Anal. calcd for C H ClFO : C,
2
5
14
4
70 eV. IR spectra were recorded on a Shimadzu IR-470 spectrometer.
6
9.37; H, 3.26; found: C, 66.54; H, 3.39%.
- ( 4 - C h l o r o b e n z o y l ) - 3 - ( 4 - m e t h o x y p h e n y l ) - 2 , 3 -
dihydronaphtho[2,3-b]furan-4,9-dione (5g): Brown powder; m.p.
NMR spectra were obtained on a Bruker DRX 400 MHz spectrometer
2
1
13
(
H NMR at 400 Hz, C NMR at 100 Hz) in CDCl using TMS as an
3
internal standard. Chemical shifts (δ) are given in ppm and coupling
constants (J) are given in Hz. 2-[2-(4-Chlorophenyl)-2-oxoethyl)]
−1
1
97–199 °C; IR (KBr) (ν cm ): 1694, 1649, 1607, 1512, 1410, 1254,
max
1
1202, 1238, 1175; H NMR (400 Hz, CDCl ): δ 3.82 (s, OCH , 3H),
2
5
3
3
isoquinolinium bromide 2 was prepared by a literature method.
4.36 (d, J = 4.8 Hz, 1H), 5.98 (d, J = 4.8 Hz, 1H), 6.80–8.03 (m, 8H,
Others chemicals used in this work were purchased from Fluka (Buchs,
Switzerland) and were used without further purification.
13
arom); C NMR (100 Hz, CDCl ): δ 37.3, 55.6, 84.7, 101.6, 114.2,
3
118.8, 126.8, 127.8, 130.2, 130.8, 131.8, 132.3, 132.9, 135.5, 138.7,
Synthesis of trans-2-(4-chlorobenzoyl)-3-aryl-2,3-dihydro-naphtho-
157.6, 160.3, 179.7, 183.4, 191.4; MS m/z (%): 444 (11). Anal. calcd for
[
2,3-b]furan-4,9-diones (5); general procedure
C H ClO : C, 70.20; H, 3.85; found: C, 70.23; H, 3.71%.
2
6
17
5
Choline hydroxide (0/0121 g, 0.1 mmol) in H O (4 mL) was added to
2 - ( 4 - C h l o r o b e n z o y l ) - 3 - ( 4 - f l u o r o p h e n y l ) - 2 , 3 -
2
a magnetically stirred solution of 2-[2-(4-chlorophenyl)-2-oxoethyl)]
isoquinolinium bromide (1 mmol), 2-hydroxy-1,4-naphthoquinone (1
dihydronaphtho[2,3-b]furan-4,9-dione (5h): Brown powder; m.p.
−1
239–241 °C; IR (KBr) (ν cm ): 2924, 2824, 1643, 1410, 1272, 1116,
max
1
mmol) and an araldehyde (1 mmol) in H O (10 mL). The mixture was
754, 534; H NMR (400 Hz, CDCl ): δ 4.37 (d, J = 5.0 Hz, CH, 1H),
5.93 (d, J = 5.0 Hz, CH, 1H,), 7.16–8.05 (m, 12H, arom); C NMR (100
2
3
13
then refluxed for 5 h. The solid product was filtered and recrystallised
from ethanol to afford the pure products 5a–l.
Hz, CDCl ): δ 37.1, 85.5, 115.4, 118.8, 126.8, 128.7, 129.3, 130.4, 130.8,
3
2-(4-Chlorobenzoyl)-3-phenyl-2,3-dihydronaphtho[2,3-b]furan-4,9-
131.8, 132.4, 134.9, 136.2, 138.7, 160.1, 160.5, 179.6, 183.2, 191.5;
−1
dione (5a): Brown powder; m.p. 257–259 °C; IR (KBr) (ν cm ): 2934,
MS m/z (%): 432 (4). Anal. calcd for C H ClFO : C, 69.37; H, 3.26;
max
25 14
4
1
2862, 1645, 1455, 1406, 1255, 1120, 1024, 753, 576; H NMR (400 Hz,
found: C, 66.50; H, 3.41%.
CDCl ): δ 4.34 (d, J = 4.8 Hz, CH, 1H), 6.08 (d, J = 4.8 Hz, CH, 1H),
3- (4- Chloro-3-nitrophenyl) -2- (4-chlorobenzoyl) -2, 3-
3
13
7
.35–8.01 (m, 13H, arom); C NMR (100 Hz, CDCl ):δ 37.2, 84.7, 118.5,
dihydronaphtho[2,3-b]furan-4,9-dione (5i): Brown powder; m.p.
3
−1
120.4, 125.9, 126.8, 127.7, 128.6, 128.7, 130.2, 130.8, 131.8, 132.3, 138.7,
232–234 °C; IR (KBr) (ν cm ): 2931, 2852, 1646, 1524, 1410, 1245,
max
1
140.9, 146.6, 160.3, 179.1, 183.1, 191.1; MS m/z (%): 414 (6). Anal. calcd
1123, 748, 575; H NMR (400 Hz, CDCl ): δ 4.34 (d, J = 4.8 Hz, CH,
3
13
for C H ClO : C, 72.38; H, 3.64; found: C, 72.53; H, 3.77%.
1H), 6.08 (d, J = 4.8 Hz CH, 1H), 7.16–8.05 (m, 12H, arom); C NMR
2
5
15
4
2
-(4-Chlorobenzoyl)-3-(2-nitrophenyl)-2,3-dihydronaphtho[2,3-b]
(100 Hz, CDCl ): δ 36.2, 84.7, 118.2, 125.2, 125.7, 126.8, 128.9, 130.2,
3
furan-4,9-dione (5b): Brown powder; m.p. 204–206 °C; IR (KBr)
130.8, 131.8, 132.3, 135.1, 135.3, 138.7, 139.6, 147.5, 160.2, 179.6, 183.1,
−1
(
νmax cm ): 2925, 2855, 1645, 1512, 1406, 1254, 1120, 1028, 745, 576;
191.8; MS m/z (%): 493 (5). Anal. calcd for C H Cl NO : C, 60.75; H,
25
13
2
6
1
H NMR (400 Hz, CDCl ): δ 4.44 (d, J = 4.8 Hz, CH, 1H,), 6.02 (d,
2.65; N, 2.83; found: C, 60.90; H, 2.53; N, 2.97%.
3

JOURNAL OF CHEMICAL RESEARCH 2017 451
References
4
- (2- (4-Chlorobenzoyl) - 4,9-dioxo-2,3,4,9-tetrahydro-
naphtho[2,3-b]furan-3-yl)benzonitrile (5j): Brown powder; m.p.
12–214 °C; IR (KBr) (ν cm ): 2934, 2855, 1647, 1522, 1415, 1244,
1
2
3
4
I. Ugi, Angew. Chem. Int. Ed. Engl., 1982, 21, 810.
A. Dömling and I. Ugi, Angew. Chem. Int. Ed., 2000, 39, 3169.
A. Dömling, Chem. Rev., 2006, 106, 17.
F.M. Dean and M .V . Sargent, Comprehensive heterocyclic chemistry, eds C.W.
Bird and G.W.H. Cheeseman. Pergamon, New York, 1984, 4, 531.
B.H. Lipshutz, Chem. Rev., 1986, 86, 795.
V. Nair, J. Mathew, and L.G. Nair, Synth. Commun., 1996, 26, 4531.
S.C. Roy and P.K. Mandal, Tetrahedron, 1996, 52, 2193.
S.C. Roy and P.K. Mandal, Tetrahedron, 1996, 52, 12495.
Y.R. Lee, N.S. Kim and B.S. Kim, Tetrahedron Lett., 1997, 38, 5671.
−1
2
7
6
max
1
47, 575; H NMR (400 Hz, CDCl ): δ 4.36 (d, J = 4.8 Hz, CH, 1H),
3
13
.07 (d, J = 4.8 Hz, CH, 1H), 7.58–8.32 (m, 12H, arom); C NMR (100
Hz, CDCl ): δ 37.2, 84.7, 109.8, 118.2, 126.8, 128.4, 130.8, 131.8, 132.1,
32.2, 132.2, 135.1, 138.7, 144.9, 160.2, 179.8, 183.1, 191.8; MS m/z
%): 439 (6). Anal. calcd for C H ClNO : C, 71.00; H, 3.21; N, 3.18;
3
5
6
7
8
9
1
(
2
6
14
4
found: C, 71.15; H, 3.10; N, 3.28%.
-(4-Chlorobenzoyl)-3-(p-tolyl)-2,3-dihydronaphtho[2,3-b]
furan-4,9-dione (5k): Brown powder; m.p. 184–186 °C; IR (KBr) (ν
2
10 M.C. Pirrung, J. Zhang and A.T. McPhail, J. Org. Chem., 1991, 56, 6269.
11 H.M.L. Davies, G. Ahmed, R.L. Calvo, M.R. Churchill and D.G. Churchill, J.
Org. Chem., 1998, 63, 2641.
max
−1
1
cm ): 2932, 2864, 1646, 1458, 1404, 1245, 1125, 756; H NMR (400
Hz, CDCl ): δ 2.19 (s, CH , 3H), 4.34 (d, J = 5.4 Hz, CH, 1H), 5.99
d, J = 5.4 Hz, CH, 1H), 6.93–8.06 (m, 12H, arom); C NMR (100
Hz, CDCl ): δ 21.3, 37.2, 84.7, 118.3, 126.9, 127.6, 128.7, 128.9, 130.2,
3
3
12
M.C. Pirrung and F. Blume, J. Org. Chem., 1999, 64, 3642.
13
(
13
A.A. Jaxa-Chamiec and P.G. Sammes, J. Chem. Soc. Perkin Trans. 1, 1980, 170.
3
14 H. Hagiwara, K. Sato, T. Suzuki and M. Ando, Tetrahedron Lett., 1997, 38,
103.
1
30.8, 131.7, 132.3, 135.2, 135.8, 137.6, 138.7, 160.2, 179.6, 183.2, 191.7;
2
MS m/z (%): 428 (7). Anal. calcd for C H ClO : C, 72.82; H, 4.00;
15 S. Arai, K. Nakayama, Y. Suzuki, K. Hatano and T. Shioiri, Tetrahedron Lett.,
1998, 39, 9739.
16 Y. Jiang and D. Ma, Tetrahedron Asymmetry, 2002, 13, 1033.
2
6
17
4
found: C, 72.96; H, 4.17%.
- (4-Bromophenyl) -2- (4-chlorobenzoyl) -2, 3-dihydro-
naphtho[2,3-b]furan-4,9-dione (5l): Brown powder; m.p. 209–211 °C;
3
17
W. Cao, W. Ding, J. Chen, Y. Chen, Q. Zang and G. Chen, Synth. Commun.,
2004, 34, 1599.
−1
IR (KBr) (ν cm ): 2919, 2821, 1645, 1402, 1265, 1024, 751, 535;
max
18
Z. Yang, M. Fan, R. Mu, W. Liu and Y. Liang, Tetrahedron, 2005, 61, 9140.
1
H NMR (400 Hz, CDCl ): δ 4.42 (J = 5.2 Hz, CH, 1H), 6.07 (J = 5.2 Hz,
3
19 C.P. Chuang and A.I. Tsai, Synthesis, 2006, 4, 675.
13
CH, 1H), 7.33–8.06 (m, 12H, arom); C NMR (100 Hz, CDCl ): δ 37.2,
3
20 M. Salari, M.H. Mosslemin and A. Hassanabadi, J. Chem. Res., 2016, 40, 655.
8
1
4.7, 118.2, 120.1, 126.8, 128.7, 129.9, 130.3, 130.8, 131.5, 131.8, 132.4,
35.1, 138.7, 139.6, 160.2, 179.6, 183.2, 192.4; MS m/z (%): 493 (8). Anal.
calcd for C H BrClO : C, 60.82; H, 2.86; found: C, 60.69; H, 2.70%.
21
C.-J. Li and T.-H. Chan, Organic reactions in aqueous media. Wiley, New York,
1997.
22 C. Jiménez-González and D.J.C. Constable, Green chemistry and engineering:
a practical design approach. Wiley, Hoboken, 2011.
2
5
14
4
2
2
2
3
4
5
M. Salari, M.H. Mosslemin and A. Hassanabadi, J. Chem. Res., 2017, 41, 60.
M. Salari, A. Hassanabadi and M.H. Mosslemin, J. Chem. Res., 2017, 41, 139.
M. Anary-Abbasinejad, K. Charkhati and A. Hassanabadi, J. Chem. Res., 2009,
Received 28 April 2017; accepted 10 June 2017
Paper 1704730
https://doi.org/10.3184/174751917X14999542807785
Published online: 31 July 2017
2, 95.
26 A.T. Khan, M.S. Lal and R. Basha, Synthesis, 2013, 45, 406.