FeCl3-DMF complex as efficient catalyst for the synthesis of 6-acyl-2(3H)-benzoxazolones and 6-acyl-2(3H)-benzothiazolones

Article abstract of DOI:10.4314/bcse.v33i3.18

FeCl3-DMF complex has been tested on Friedel-Crafts reaction of 2(3H)-benzoxazolone and 2(3H)-benzothiazolone with acid chlorides and anhydrides as acylating agents. In these conditions, the 6-acyl-2(3H)-benzoxazolones and 6-acyl-2(3H)-benzothiazolones were obtained in yields ranging from 52 to 89%. Among the various commonly catalysts; AlCl3-DMF, ZnCl2-DMF and PPA, explored in this study, the best conditions using FeCl3-DMF were found the most convenient one

Full text of DOI:10.4314/bcse.v33i3.18

Bull. Chem. Soc. Ethiop. 2019, 33(3), 579-585.
2019 Chemical Society of Ethiopia and The Authors
ISSN 1011-3924
Printed in Ethiopia

DOI: https://dx.doi.org/10.4314/bcse.v33i3.18
SHORT COMMUNICATION
FeCl -DMF COMPLEX AS EFFICIENT CATALYST FOR THE SYNTHESIS OF
3
6-ACYL-2(3H)-BENZOXAZOLONES AND 6-ACYL-2(3H)-BENZOTHIAZOLONES
*
Faouzi Guenadil
Laboratory of Organic and Medicinal Chemistry, Department of Chemistry, University of
Chadli Bendjedid El Tarf-36000, Algeria
(
Received November 12, 2018; Revised April 20, 2019; Accepted June 5, 2019)
ABSTRACT. FeCl
3
-DMF complex has been tested on Friedel-Crafts reaction of 2(3H)-benzoxazolone and
(3H)-benzothiazolone with acid chlorides and anhydrides as acylating agents. In these conditions, the 6-acyl-
(3H)-benzoxazolones and 6-acyl-2(3H)-benzothiazolones were obtained in yields ranging from 52 to 89%.
-DMF, ZnCl -DMF and PPA, explored in this study, the best
-DMF were found the most convenient one
2
2
Among the various commonly catalysts; AlCl
conditions using FeCl
3
2
3
3 3 2
KEY WORDS: FeCl -DMF, AlCl -DMF, ZnCl -DMF, PPA, 6-Acyl-2(3H)-benzothiazolones, 6-Acyl-2(3H)-
benzothiazolones
INTRODUCTION
The 6-acyl-2(3H)-benzoxazolones and 6-acyl-2(3H)-benzothiazolones derivatives, in particular
are interesting, with anti-inflammatory, analgesic, antiepiliptic and antiviral properties. They are
important building block in organic synthesis and in the design of new pharmacophores [1-15].
Due to their wide range of application, the syntheses of these derivatives by Friedel-Crafts
acylation reaction have received great deal of attention [16-23]. In the literature, the most
straight forward protocols using polyphosphoric acid (PPA), and Lewis acids such as aluminium
chloride (AlCl ) and zinc chloride (ZnCl ) in N,N-dimethylformamide (DMF) as solvent, with
3 2
carboxylic acids, acid chlorides or anhydrides have been reported [24-29].
Moreover, the Friedel-Crafts acylation using these conditions, generally involve the use of a
large excess of catalysts and after aqueous work-up a large of amount of toxic waste is
generated [24-29]. During recent years, the ferric chloride (FeCl ) catalyst has been used as a
3
catalyst in several organic transformations with excellent yields and great regioselectivity due to
its low cost, ease of use, and environmental friendly properties [30-38]. On the other hand, it has
been known that ferric chloride forms a complex with N,N-dimethylformamide by interaction
with the carbonyl oxygen [39]. Previously, we reported the I
as useful catalyst in the Friedel-Crafts acylation of aromatic substrates [40]. In the work
reported here, we use the ferric chloride-N,N-dimethylformamide complex (FeCl -DMF) as a
2
-N,N-dimethylformamide complex
3
potential catalyst in the Friedel-Crafts acylation of 2(3H)-benzoxazolone and 2(3H)-
benzothiazolone substrates with acid chlorides and anhydrides as acylatings agents for the first
time.
EXPERIMENTAL
All reactions were monitored by thin layer chromatography using Merck TLC silica gel 60 F254
.
Melting points were measured in open capillary tubes on an Electro thermal-apparatus. The IR
1
13
spectra were obtained on a Perkin-Elmer 457 spectrometer using KBr pellets. H and C NMR
spectra were recorded on a Brucker 400 spectrometer using DMSO-D or CDCl as solvent and
TMS) as an internal standard.
6
3
(
_
_________
*
Corresponding author. E-mail: guendouda@yahoo.fr
This work is licensed under the Creative Commons Attribution 4.0 International License

580
Faouzi Guenadil
General procedure using FeCl
3
-DMF complex for the acylation of 2(3H)-benzoxazolone and 3-
methyl-2(3H)-benzoxazolone. A mixture of FeCl (38.92 g, 0.24 mol) and DMF (4.7 mL, 0.066
3
mol) were placed in a three neck round bottom flash (250 mL). The flask was then equipped
with a reflux condenser with a CaCl tube, and a mechanical stirrer. The flash was then placed in
2
a oil bath thermostated at 90 °C. (0.04 mol) of 2(3H)-benzoxazolone or 3-methyl-2(3H)-
benzoxazolone was added in portions. When the mixture was uniformly mixed, (0.06 mol) of
acid chloride or acid anhydride was then added dropwise, and the temperature was subsequently
raised to 170 °C under stirring for 3 hours. The products were isolated by addition of ice water.
The precipitate was stirred for 1 h, collected by filtration, dried and crystallized.
General procedure using FeCl
3
-DMF complex for the acylation of 2(3H)-benzothiazolone and
3
-methyl-2(3H)-benzothiazolone. A mixture of FeCl (38.92 g, 0.24 mol) and DMF (4.7 mL,
3
0
.066 mol) were placed in a three neck round bottom flash (250 mL). The flask was then
tube, and a mechanical stirrer. The flash was
equipped with a reflux condenser with a CaCl
2
then placed in a oil bath thermostated at 90 °C. (0.04 mol) of 2(3H)-benzothiazolone or 3-
methyl-2(3H)-benzothiazolone was added in portions. When the mixture was uniformly mixed,
(
0.06 mol) of acid chloride or acid anhydride was then added dropwise, and the temperature was
subsequently raised to 170 °C under stirring for 3 hours. The products were isolated by addition
of ice water. The precipitate was stirred for 1 h, collected by filtration, dried and crystallized.
The present products demonstrate the procedure.
-
1
6
(
4
4
-Benzoyl-2(3H)-benzoxazolone (3). Yield: 72%; m.p. 169-170 °C; IR (KBr, cm ) ν: 3140
1
NH), 1780 (CO), 1640 (CO); 1610 (C=C). H-NMR (DMSO-d , 400 MHz) δ: 7.22 (d, 1H, H-
H ), 12.07 (s, 1H, NH); C-NMR (DMSO-d ,
6 5 6
00 MHz): 107.75, 108.81, 125.74, 126.95, 127.84, 129.31, 130.76, 133.22, 135.89, 141.67
6
13
, J = 7.99 Hz), 7.54-7.72 (m, 7H, H-5, H-7, C
(
aromatic carbons), 152.82 (CO), 192.82 (CO).
-
1
6
(
4
(
-Benzoyl-2(3H)-benzothiazolone (13). Yield: 74%; m.p. 216-217°C; IR (KBr, cm ) ν: 3240
11
NH), 1667 (CO), 1638 (CO), 1618 (C=C). H-NMR (DMSO-d
, J = 7.88 Hz, C ), 7.70-7.95 (m, 7H, H-5, H-7, C ), 12.19 (s, 1H, NH); C-NMR
DMSO-d , 400 MHz): 111.35, 123.61, 124.84, 128.61, 128.96, 129.41, 131.38, 132.32, 137.37,
40.22 (aromatic carbons), 170.34 (CO), 198.71 (CO).
6
, 400 MHz) δ: 7.24 (d, 1H, H-
13
6
H
3
6 5
H
6
1
RESULTS AND DISCUSSION
In order to optimize the experimental conditions, the activity of FeCl
explored in the acylation of 2(3H)-benzoxazolone and 2(3H)-benzothiazolone, with benzoyl
chloride. Using the FeCl -DMF complex, after various attempts, 6-benzoyl-derivatives were
obtained with 68 and 69% yields at 170 °C after 3 hours. It is also mentioning that, the best
yields were obtained when the amount of FeCl was in the range of 6 equivalents with respect to
.1 mol equivalent of 2(3H)-benzoxazolone and 2(3H)-benzothiazolone and 0.15 equivalent of
benzoyl chloride as acylating agent.
It is clear that the FeCl cannot be considered, in such conditions, as a catalyst. It is
previously reported that in the Friedel-Crafts acylation using AlCl -DMF catalyst, the formation
of a complex between AlCl , N,N-dimethylformamide involving the π and the n electrons of the
heterocycles [25-27]. In these conditions, 2(3H)-benzoxazolone and 2(3H)-benzothiazolone can
be acylated only when the amount of AlCl was in the range of 7-11 equivalents [25-27]. As
illustrated in Scheme 1, we propose a mechanism which is a complex formation of FeCl -DMF.
When dissolved in DMF, FeCl has the possibility to interact with the oxygen atom to generate
3
-DMF catalyst was first
3
3
0
3
3
3
3
3
3
equilibration between the free species and the Lewis salt stabilized by mesomery.
Bull. Chem. Soc. Ethiop. 2019, 33(3)

Short Communication
581
Cl
Fe Cl
Cl
H
O
H
O
H
O
Cl
Fe
Cl
O
Cl
CH
Cl
+
N
N
Fe
N
CH3
CH3 Cl
Cl
H
CH
3
3
CH3
N
CH3
CH3
CH3
3
Scheme 1. Proposed mechanism of FeCl -DMF complex formation.
Table 1. 6-Acyl-2(3H)-benzoxazolones and 6-acyl-2(3H)-benzothiazolones derivatives under optimized
conditions.
a
b
Compound
X
O
O
O
O
O
O
O
O
O
O
S
S
S
S
S
S
S
S
S
R
1
R
CH
CH
2
M.p. (°C)
227-228
167-168
169-170
147-148
233-234
140-141
218-219
179-180
243-244
210-211
190-191
145-146
216-217
147-148
223-224
124-125
241-242
226-227
236-237
221-222
Yield
68
73
72
86
63
77
52
63
53
58
69
75
74
89
62
69
56
68
55
60
1
2
3
4
5
6
7
8
9
H
CH
H
CH
H
CH
H
CH
H
CH
H
CH
H
CH
H
CH
H
3
3
3
3
3
3
3
3
3
3
3
3
C
C
6
H
H
5
6
5
2-C
2-C
4
H
H
3
O
O
4
3
CH
CH
2
CH
CH
2
COOH
2
COOH
2
2-COOH-C
2-COOH-C
6
H
H
5
1
1
1
1
1
1
1
1
1
1
2
0
1
2
3
4
5
6
7
8
9
0
6
5
CH
CH
3
3
C
C
6
H
H
5
6
5
2-C
2-C
4
H
H
3
S
S
4
3
CH
CH
2
CH
CH
2
COOH
2
COOH
CH
H
CH
2
2-COOH-C
2-COOH-C
6
H
H
5
S
6
5
a
b
Melting point. Isolated yield after crystallization.
R1
N
R
1
N
FeCl
3
-DMF, 170°C
O
O
acid chlodes or anhydrides
R
2
X
X
X= O, S
X= O, S
R = H, CH3
O
R1
= H, CH
3
1
CH
3
, CH CH , CH CH COOH
2
3
2
2
R
2
=
HOOC
,
,
,
O
S
3
Scheme 2. Acylation of 2(3H)-benzoxazolone, 2(3H)-benzothiazolone using FeCl -DMF
catalyst.
Bull. Chem. Soc. Ethiop. 2019, 33(3)

582
Faouzi Guenadil
As shown in Table 1, we have exemplified the versality of our catalyst for different cases.
Good to excellent yields were observed. It should also be noted that the yields of N-methyl-
derivatives are higher than for 2(3H)-benzothiazolone and 2(3H)-benzoxazolone. This may be
probably due to the hydrogen mobility of the heterocycles [23]. Using these conditions, we have
produced a number of 6-acyl-2(3H)-benzoxazolones and 6-acyl-2(3H)-benzothiazolones using
acid chlorides and anhydrides (Scheme 2).
The efficiency and applicability of these conditions were compared with reported methods
commonly used for the preparation of 6-acyl-derivatives (Table 2) [24-27, 29]. As Table 2
demonstrates, the behavior of 2(3H)-benzoxazolone and 2(3H)-benzothiazolone in the presence
3 3
of FeCl -DMF catalyst appears to be parallel to that in the case of AlCl -DMF catalyst and in
our method which afforded the best results [24-29]. We have exemplified the versality of our
catalyst for different cases. Good to excellent yields were observed for aliphatic and aromatic
acid chlorides or anhydrides.
3
These results can probably due to the rate of formation of the complex FeCl -DMF in the
initial stage was greater for FeCl due to its high melting point and its simple decomposition
3
complex witch permit the reactive intermediate to be formed under the reaction conditions
compared with other Lewis acids used.
Table 2. The comparative yields of 6-acyl-derivatives using the present method versus the reported
methods.
Comparative yields (%)
Compound
X
R
1
R
2
a
b
c
PPA
AlCl
3
-DMF
ZnCl
2
-DMF
3
FeCl -DMF
1
2
3
4
5
6
7
8
9
O
O
O
O
O
O
O
O
O
O
S
S
S
S
S
S
S
S
S
H
CH
H
CH
H
CH
H
CH
H
CH
H
CH
H
CH
H
CH
H
CH
CH
3
62
63
58
69
-
-
-
-
-
65
70
67
76
61
71
48
61
49
53
66
73
69
79
58
62
52
58
51
55
59
67
65
73
58
58
23
32
24
33
60
69
63
75
49
58
29
39
47
44
68
73
72
86
63
77
52
63
53
58
69
75
74
89
62
69
56
68
55
60
3
3
3
3
3
3
3
3
3
3
3
C
C
6
H
H
5
6
5
2-C
2-C
4
H
H
3
O
O
4
3
CH
CH
2
CH
CH
2
COOH
COOH
2
2
2-COOH-C
2-COOH-C
6
H
H
5
5
1
1
1
1
1
1
1
1
1
1
2
0
1
2
3
4
5
6
7
8
9
0
6
-
CH
CH
3
61
65
65
72
-
-
-
-
-
3
C
C
6
H
H
5
6
5
2-C
2-C
4
H
H
3
S
S
4
3
CH
CH
2
CH
CH
2
COOH
COOH
CH
H
CH
2
2
2-COOH-C
2-COOH-C
6
H
5
H
5
S
6
-
Methods: (a) PPA (120 g), carboxylic acids (0.06 mol), 3 h, 100 °C. (b) AlCl
3
(0.36 mol) in 7.1 mL of DMF, acid
chlorides or anhydrides (0.06 mol), 3 h, 85 °C ; (c) ZnCl
anhydrides (0.06 mol), 3 h, 135 °C.
2
(0.32 mol) in 6.25 mL of DMF, acid chlorides or
CONCLUSION
We developed an efficient method using FeCl
3
-DMF complex for the acylation of 2(3H)-
benzoxazolone and 2(3H)-benzothiazolone. This reaction take place at 170°C with a variety of
acid chlorides or anhydrides to yield 6-acyl-2(3H)-benzoxazolones and 6-acyl-2(3H)-
benzothiazolones in excellent yields rangring from 52 to 89%.
Bull. Chem. Soc. Ethiop. 2019, 33(3)

Short Communication
583
REFERENCES
1
2
3
4
5
6
7
8
. Poupaert, J.H.; Carato, P.; Colacino, E.; Yous, S. 2(3H)-Benzoxazolone and bioisosters as
Privileged Scaffold” in the design of pharmacological probes. Curr. Med. Chem. 2005, 12,
77-885.
. Yous, S.; Poupaert, J.H.; Chavatte, Ph.; Bi, J.G.; Caignard, Espiard, D.H.; Lesieur, D.
Synthesis and pharmacological evaluation of analgesic 6-substituted 2(3H)-benzothiazo-
lones. Drug. Desig. Disc. 2001, 17, 331-336.
. Yous, S.; Lebegue, N.; Poupaert, J.H.; Chavatte, Ph.; Berthelot, P. Lipid-lowering properties
of 6-benzoyl-2(3H)-benzothiazolone and structurally related compounds. J. Enzyme Inhib.
Med. Chem. 2005, 20, 525-532.
. Renard, P.; Lesieur, D.; Lespagnol, Ch.; Cazin, M.; Brunet, C.; Cazin, J.C. Acyl-6-
benzoxazolinones et acides (acyl-6-oxo-2-benzoxazolinyl-3)alcanoiqines Eur. J. Med.
Chem. 1980, 15, 453-456.
. Van derpoorten, K.; Ucar, H.; Andrei, G.; Snoeck, R.; Balzarini, J.; De Clercq, E.; Poupaert,
J.H. Synthesis and antiviral activity of 6-benzoyl-benzoxazolin-2-one and 6-benzoyl-
benzothiazolin-2-one derivatives. Antivirus Chem. Chemother. 1999, 10, 87-97.
. Doğruer, D.S.; Unlü, S.; Sahin, M.F.; Yeşilada, E. Anti-nociceptive and antiinflammatory
activity of some (2-benzoxazolinone-3-yl and 2-benzothiazolone-3-yl)acetic acid
derivatives. Il Farmaco 1998, 53, 80-84.
. Safak, C.; Erdogan, H.; Palaska, E.; Sunal, R.; Duru, S. Synthesis of 3-(2-
pyridylethyl)benzoxazolinone derivatives: potent analgesic and antiinflammatory
compounds inhibiting prostaglandin E2. J. Med. Chem. 1992, 35, 1296-1299.
. Ferreira, S.H.; Lorenzetti, B.B.; Devissaguet, M.; Lesieur, D.; Tsouderos, Y. S14080, a
peripheral analgesic acting by release of an endogenous circulating opioid-like substance.
Br. J. Pharmacol. 1995, 114, 2, 303-308.
“
8
9
1
. Moussavi, Z.; Lesieur, D.; Lespagnol, C.; Sauzieres, J.; Olivier, P. Acyl-7- dihydro-2,3
benzoxazin-1,4 ones-3 et propriétés normolipémiantes. Eur. J. Med. Chem.1989, 24, 55-60.
0. Blanc, D.E.; Lebegue, N.; Wallez, V.; Leclerc, V.; Yous, S.; Carato, P.; Farce, A.;
Bennejean, C.; Renard, P.; Caignard, D.H.; Audinot Bouchez, V.; Chomarat, P.; Boutin, J.;
Hennuyer, N.; Louche, K.; Carmona, M.C.; Staels, B.; Penicaud, L.; Casteilla, L.;
Lonchampt, M.; Dacquet, C.; Chavatte, P.; Berthelot, P.; Lesieur, D. Novel 1,3-dicarbonyl
compounds having 2(3H)-benzazolonic heterocycles as PPARγ agonists. Bioorg. Med.
Chem. 2006, 14, 7377-7391.
1
1
1. Lespagnol, C.; Cazin, M.; Cazin, J.C.; Lesieur, D.; Dupont, C. Recherches sur lactivite
analgesique de derives de la benzoxazolinone. Chim. Ther. 1967, 2, 347-348.
2. Mesangeau, C.; Narayanan, S.; Green, A.M.; Shaikh, J.; Kaushal, N.; Viard, E.; Yan, T.X.;
Fishback, J.A.; Poupaert, J.H.; Matsumoto.Rae, R.; McCurdy, C.R. Conversion of a highly
selective sigma-1 receptor–ligand to sigma-2 receptor preferring ligands with anticocaine
activity. J. Med. Chem. 2008, 51, 1482-1486.
1
1
3. Aïda; R.: Nadji, B.; Omar, K.; Thierry, T.; Messaoud, Liacha.; Patrice, V. TDAE strategy in
the benzoxazolone series: synthesis and reactivity of a new benzoxazolinonic anion.
Molecules 2015, 20, 1262-1276.
4. Guenadil, F.; Aichaoui, H.; Kapanda Nankwa, C.; Lambert, D.; McCurdy, C.R.; Poupaert,
J.H. Design and synthesis of 3-acyl-2(3H)-benzoxazolone and 3-acyl-2(3H)-benzo-
thiazolone derivatives. Monatsh Chem. 2011, 142, 67-80.
1
5. Aichaoui, H.; Guenadil, F.; Kapanda Nankwa, C.; Lambert, D.; McCurdy, C.R. ; Poupaert,
J.H. Synthesis and pharmacological evaluation of antioxidant chalcone derivatives of 2(3H)-
benzoxazolones. Med. Chem. Res. 2009, 18, 467-476.
Bull. Chem. Soc. Ethiop. 2019, 33(3)

584
Faouzi Guenadil
1
1
1
6. Diouf, O.; Carato, P.; Depreux, P.; Bonte, J.P.; Caignard, D.H.; Guardiola-Lemaitre, B.;
Rettori, M.C.; Belzung, C.; Lesieur, D. 5-HT1A and 5-HT2A ligands with anxiolytic and
antipanic-like properties. Bioorg. Med. Chem. Lett. 1997, 7, 2579-2584.
7. Diouf, O.; Carato, P.; Lesieur, I.; Rettori, M.C.; Caignard, D.H. Synthesis and
pharmacological evaluation of novel 4-(4-fluorobenzoyl)piperidine derivatives as mixed 5-
HT /5-HT /D receptor ligands. Eur. J. Med. Chem. 1999, 34, 69-73.
1
A
2A
2
8. Lesieur, D.; Carato, P.; Bonte, J.P.; Depreux, P.; Caignard, D.H.; Millan, M.; Newman-
Tancredi, A.; Renard, P.; Rettori, M.C. Preparation of piperazinylmethylbenzothiazo-
linones, -benzoxazolinones, -benzoxazinones, and related compounds as central nervous
system agents. Eur. Patent 1998, EP 841330.
1
2
9. Carato, P.; Depreux, P.; Lesieur, D.; Millan, M.; Newman-Tancredi, A.; Rettori, M.C.;
Caignard, D.H. Synthesis and binding studies on a new series of arylpiperazino benzazol-2-
one and benzoxazin-3-one derivatives as selective D4 ligands. Drug. Design. Disc. 2000, 17,
1
73-181.
0. Lesieur, D.; Delmas, E.: Yous, S.; Depreux, P.; Guillaumet, G.; Dacquet, C.; Levens, N.;
Boutin, J.; Bennejean, C.; Renard, P. Preparation of novel heterocyclic derivatives and
pharmaceutical composition containing them as hypoglycemic agents. French Patent 2001,
FR 2804431.
2
2
2
1. Lesieur, D.; Blanc-Delmas, E.; Bennejean, C.; Chavatte, P.; Guillaumet, G.; Dacquet, C.;
Levens, N.; Boutin, J.; Renard, P. Preparation of azolylalkylphenylalkylindolinones as
hypoglycemic andhypolipidemic agents. French Patent 2003, FR 2830012.
2. Urbain, C.K.; Fernand, A.G.; Pascal, C.; Christopher, R, McCurdy; Poupaert, J.H. Synthesis
and antiepileptic activity assessment of 5-benzoyloxindole, a novel phenytoinergic template.
Org. Chem. Curr. Res. 2015, 4, 1-4.
3. Carato, P.; Yous, S.; Sellier, D.; Poupaert, J.H.; Lebeguea, N.; B erthelot, P. Efficient and
selective deprotection method for N-protected 2(3H)-benzoxazolones and 2(3H)-
benzothiazolones. Tetrahedron 2004, 60, 10321-10324.
2
2
2
2
4. Bonte, J.P.; Lesieur, D.; Lespagnol, C.; Plat, M.; Cazin, M. 6-Acyl-benzoxazolinones. Eur.
J. Med, Chem. 1974, 9, 491-496.
5. Aichaoui, H.; Poupaert, J.H.; Lesieur, D.; Henichart, J.P. Regioselectivity in the C-acylation
of 2(3H)-benzoxazolones. Tetrahedron 1991, 47, 6649-6654.
6. Aichaoui, H.; Lesieur, D.; Henichart, J.P. A convenient and efficient method for the
preparation of 6‐acyl‐2(3H)‐benzoxazolones. J. Heterocyclic. Chem. 1992, 29, 171-175.
7. Yous, S.; Poupaert, J.H.; Lesieur, I.; Depreux, P.; Lesieur, D. AlCl -DMF reagent in the
3
Friedel-Crafts reaction. Application to the acylation reaction of 2(3H)-benzothiazolones. J.
Org. Chem. 1994, 59, 1574-1576.
2
8. Guenadil, F.; Liacha, M.; Aichaoui, H. Benzoylation of 2(3H)-benzothiazolones in the
presence of 8 equivalents of zinc chloride in N,N-dimethylformamide. Phosphorus Sulfur
Silicon 2002, 177, 2633-2638.
2
3
9. Guenadil, F.; Aichaoui, H. Study of the acylation reaction of 2(3h)-benzothiazolones in the
mixture of ZnCl
2
-DMF Phosphorus Sulfur Silicon 2003, 178, 1703-1708.
0. Gay, R.M.; Manarin, F.; Schneider, C.C.; Barancelli, D.A.; Costa, M.D.; Zeni, G. FeCl
3
-
diorganyl dichalcogenides promoted cyclization of 2-alkynylanisoles to 3-chalcogen
benzo[b]furans. J. Org. Chem. 2010, 75, 5701-5706.
3
3
3
1. Zhiyong, W.; Xiaoyu, S.; Jie, W. FeCl : An efficient catalyst for reaction of electron-rich
arenes with imines or aziridines. Tetrahedron 2008, 64, 5013-5018.
3
2. Glaucia, H.; Prado, C.; Arno, D.K. Alkylation of asphaltenes using FeCl catalyst. Energy
3
Fuels 2015, 29, 4947-4955.
3. Majid, M.; Heravi, M.E.; Hossein, A.; Oskooie, B.B. FeCl : Highly efficient catalyst for
3
synthesis of α‐amino nitriles. Chin. J. Chem. 2010, 28, 480-482.
Bull. Chem. Soc. Ethiop. 2019, 33(3)

Short Communication
585
3
3
4. Komura, K.; Ozaki, A.; Ieda, N.; Sugi, Y. FeCl
3
-6H
2
O as versatile catalyst for the
esterification of steroid alcohols with fatty acids. Synthesis 2008, 21, 3407-3410.
5. Mohammad, A.T.; Changiz, K.; Mehdi, Sh. A.; Hossein, A.; Yasaman, K. Efficient
FeCl /SiO as heterogeneous nanocatalysis for the synthesis of benzimidazoles under mild
3
2
conditions. Int. Nano. Lett. 2016, 6, 85-90.
3
3
3
3
6. Ritmaleni, P.; Lestari, Y. Iron (III) chloride, aluminium chloride and zinc chloride as
catalysts in the synthesis of tetrahydropentagamavunon-0. Chem. Mat. Res. 2013, 3, 32-39.
7. Jette, K.; Irina, J.; Kristin, M.; Alexander, Z.; Matthias, B. A convenient FeCl -catalyzed
3
hydroarylation of styrenes. Org. Lett. 2006, 8, 19-22.
8. Ingmar, B.; Hans-Joachim, K. Iron catalysis in organic synthesis. Chem. Rev. 2015, 115,
170-3387.
3
9. Young, J.K.; Chong, R.P. Analysis of problematic complexing behavior of ferric chloride
with N,N-dimethylformamide using combined techniques of FT-IR, XPS, and TGA/DTG.
Kor. Inorg. Chem. 2002, 41, 6211-6216.
4
0. Guenadil, F.; Aichaoui, H.; Lambert, D.M.; McCurdy, C.R.; Poupaert, J.H. Highly selective
2
catalytic Friedel–Crafts acylation of activated aromatic compounds using the I .DMF
complex as catalyst. Lett. Org. Chem. 2008, 5, 665-668.
Bull. Chem. Soc. Ethiop. 2019, 33(3)