Synthesis of benzodiazepines catalyzed by chitosan functionalized by triacid imide as a superior catalyst

Article abstract of DOI:10.1007/s11164-020-04281-x

Abstract: Chitosan functionalized by triacid imide has been applied as an effective catalyst for the synthesis of benzodiazepines by one-pot reactions of 1,2-phenylenediamine with dimedone and aryl aldehydes or isocyanides and Meldrum’s acid. Chitosan functionalized by triacid imide was confirmed by FT-IR (infrared spectroscopy), XRD (X-ray diffraction), DSC (differential scanning calorimetry) and TGA (thermogravimetric analysis). To investigate the scope and limitation of this reaction, different aryl aldehydes and isocyanides were used as substrates. Good yields in short reaction times, experimental simplicity, extensive range of products, retrieval of the catalyst and low catalyst loading are some of the substantial aspects of this method. Graphic abstract: [Figure not available: see fulltext.]

Full text of DOI:10.1007/s11164-020-04281-x

Research on Chemical Intermediates
https://doi.org/10.1007/s11164-020-04281-x
Synthesis of benzodiazepines catalyzed by chitosan
functionalized by triacid imide as a superior catalyst
1
2
3
Mozhgan Esfandiari · Ali Kareem Abbas · Mohammad Reza Vakili ·
Hossein Shahbazi‑Alavi4 · Javad Safaei‑Ghomi
5
Received: 31 July 2020 / Accepted: 18 September 2020
©
Springer Nature B.V. 2020
Abstract
Chitosan functionalized by triacid imide has been applied as an eꢀective catalyst
for the synthesis of benzodiazepines by one-pot reactions of 1,2-phenylenediamine
with dimedone and aryl aldehydes or isocyanides and Meldrum’s acid. Chitosan
functionalized by triacid imide was conꢁrmed by FT-IR (infrared spectroscopy),
XRD (X-ray diꢀraction), DSC (diꢀerential scanning calorimetry) and TGA (ther-
mogravimetric analysis). To investigate the scope and limitation of this reaction, dif-
ferent aryl aldehydes and isocyanides were used as substrates. Good yields in short
reaction times, experimental simplicity, extensive range of products, retrieval of the
catalyst and low catalyst loading are some of the substantial aspects of this method.
Graphic abstract
=
chitosan functionalized by triacid imide
O
O
O
O
H
N
O
O
H
R
2
N
C
O
Ar
3
N
O
NH
NH
2
2
O
O
O
3
'
2'
2
NH-R
2
N
H
N
H
CH Cl , rt
2
2
EtOH, rt
Ar
5a-e
1
4a-e
Keywords Benzodiazepines · One-pot · Chitosan · Triacid imide
Electronic supplementary material The online version of this article (https://doi.org/10.1007/s1116
-020-04281-x) contains supplementary material, which is available to authorized users.
4
*
Hossein Shahbazi-Alavi
hosseinshahbazi99@yahoo.com
Extended author information available on the last page of the article
Vol.:(012
1
3456789)
3

M. Esfandiari et al.
Introduction
Benzodiazepines display anti-bacterial [1], anti-tumor [2], anti-anxiety [3], anti-
AIDS [4] and anti-hepatic B virus [5] activities. The discovery of impressive meth-
ods for the preparation of benzodiazepines is a serious challenge. A number of ways
have been improved for the synthesis of diazepines using mercury(II) triꢂuorometh-
anesulfonate [6], organic acid [7], ytterbium(III) triꢂuoromethanesulfonate [8], ceric
ammonium nitrate [9] and scandium(III) triꢂuoromethanesulfonate [10]. Each of
these procedures may have its own advantages but also suꢀer from such apparent
drawbacks as prolonged reaction times, complicated work-up, low-yield or hazard-
ous reaction conditions. The potential of chitosan-based structures to form open
network has provided their use not only as macrochelating ligands, but also as a
direct organocatalyst [11]. The chitosan can be applied as a support for the synthe-
sis of new catalysts in the form of ꢂakes, colloids, ꢁbers, gel or functionalized on
inorganic supports (alumina, titania, silica or other metal oxides) [12, 13]. Chitosan
functionalized with sulfonic acid was utilized as a superior catalyst in the esteriꢁca-
tion of fatty acids with alcohol [14]. Amino and hydroxyl groups in chitosan make
it suitable as an eꢀective catalyst [15, 16]. Chitosan is a biopolymer that can be uti-
lized as green catalyst in many reactions [17, 18]. Ideally, introducing neat processes
and utilizing eco-friendly and green heterogeneous catalysts which can be simply
recycled at the end of reactions have received substantial attention in recent years
[
19, 20]. The catalytic activity of chitosan was increased when chitosan was func-
tionalized by triacid imide. Herein, we report the use of chitosan functionalized by
triacid imide as an eꢀective catalyst for the synthesis of diazepines by one-pot reac-
tions of 1,2-phenylenediamine with dimedone and aryl aldehydes or isocyanides and
Meldrum’s acid at room temperature (Scheme 1). We found that chitosan functional-
ized by triacid imide produces our desired compounds in high yields (83–93%) with
excellent recovery and simple work-up method. In addition, chitosan functionalized
by triacid imide has a good recycling property and this advantage is signiꢁcant from
economic point of view.
=
chitosan functionalized by triacid imide
O
O
O
O
H
N
O
O
H
R
2
N
C
O
Ar
3
N
O
NH
NH
2
2
O
O
O
3
'
2'
2
NH-R
2
N
H
N
H
CH Cl , rt
2
2
EtOH, rt
Ar
5a-e
1
4a-e
Scheme 1 Synthesis of benzodiazepines catalyzed by chitosan functionalized by triacid imide
1
3

Synthesis of benzodiazepines catalyzed by chitosan…
O
O
O
OH
OH
O
AcOH/Py (3:2)
reflux
N
O
O
+
OH
HO
HO
HO
O
O
NH
2
O
O
O
Scheme 2 Preparation of triacid imide
O
O
O
O
2H
H
NH
OH
OH
OH
H
H
N
HO
HO
HO
O
H
+
O
H
OH
O
O
H
H
O
O
H
2
N
H
H
O
O
2H
H
NH
OH
H
O
HO
HO
H
H
H
H
H
OH
O
H
OH
O
H
NH2
H
H
H
O
O
H
3
N
H
O
O
H
HO
HO
H
H
H
O
NH
H
OH
O
OH
H
O
O
O
O
N
O
Heat
N
O
O
O
O
HN
O
O
O
O
H
2
H N
O
H
HO
H
O
2
H N
NH
3
OH
O
H
HO
H
OH
O
O
O
HO
OH
HO
H
HO
Scheme 3 Chitosan functionalized by triacid imide
Results and discussion
We prepared triacid imide according to Scheme 2. Chitosan was functionalized
using triacid imide (Scheme 3).
XRD pattern of chitosan and chitosan functionalized by triacid imide is indicated
in Fig. 1. The XRD pattern of chitosan and chitosan functionalized by triacid imide
displayed two sharp peaks at 20.2 and 11.4 (2 Theta).
1
3

M. Esfandiari et al.
Fig. 1 XRD pattern of (a) chitosan and (b) chitosan functionalized by triacid imide
FT-IR spectra of chitosan and chitosan functionalized by triacid imide are indi-
−1
cated in Fig. 2. The peak at 2600–3400 cm (Fig. 2b) is ascribed to the stretching
−
1
vibrational absorptions of OH (COOH). The peak at 1715 cm is ascribed to the
stretching vibrational absorptions of carbonyl of acidic groups. The peaks at about
−
1
1
615–1640 cm are ascribed to the absorptions of the carbonyl of amide groups
which are formed from the reaction of carboxyl group of the triacid imide with
amino group of chitosan [21–23].
To investigate the degree of substitution of carboxylic acid groups of chitosan
functionalized by triacid imide, a certain amount of the chitosan functionalized by
triacid imide was soaked in 5 mL of 0.1 N NaOH solution. The excess of NaOH
solution was titrated with 0.1 N HCl in the presence of phenolphthalein. Acidic
capacity of this catalyst was estimated 2.1 mmol/gr.
The thermal properties of chitosan and chitosan functionalized by triacid imide
were investigated by TGA/DTG (Fig. 3) and DSC (Fig. 4) at a heating rate of 10 °C/
Fig. 2 FT-IR spectra of (a)
chitosan and (b) chitosan func-
tionalized by triacid imide
1
3

Synthesis of benzodiazepines catalyzed by chitosan…
Fig. 3 TGA/DTG patterns of chitosan (a) and chitosan functionalized by triacid imide (b)
min under N atmosphere. The weight loss at 40–250 °C for chitosan is owing to
2
the moisture vaporization. The weight loss at 250–400 °C is owing to the degrada-
tion of chitosan. The weight loss at 40–250 °C for chitosan functionalized by triacid
imide is owing to the removal of adsorbed solvent and surface hydroxyl groups. The
weight loss at 250–550 °C is due to degradation of chitosan and triacid imide.
DSC of chitosan indicated two peaks, an endothermic broad peak at about
9
3
0–100 °C owing to dehydration of chitosan and another exothermic at about
05–310 °C peak due to exothermic decomposition of chitosan. The DSC of
1
3

M. Esfandiari et al.
Fig. 4 DSC patterns of chitosan (a) and chitosan functionalized by triacid imide (b)
chitosan functionalized by triacid imide displayed a broad endothermic peak at
about 200 °C, a couple of sharp endothermic peaks at about 390 °C and an exo-
thermic peak at 420 °C. These results indicated that heat stability of chitosan
functionalized by triacid imide is satisfactory.
We used the reaction of 1,2-phenylenediamine, 4-chlorobenzaldehyde and dime-
done as a model reaction. Meanwhile, we used the reaction of 1,2-phenylenedi-
amine, tert-butyl isocyanide and Meldrum’s acid as a model reaction. The model
reactions were performed using diꢀerent catalysts including nano-MgO, Et N, p-
3
TSA, chitosan, triacid imide, chitosan functionalized by triacid imide (Table 1). We
found that the reaction gave convincing results in the presence of chitosan function-
alized by triacid imide (7 mg) at room temperature. In further studies on the catalyst
amount, we noticed that yields of compounds 4a and 5a remained almost the same
when 9 mg of chitosan functionalized by triacid imide was used (Table 1). Use of
lower catalyst amount (5 mg) aꢀorded 4a in 85% yield and 5a in 82% yield. The
catalyst showed the best activity for the synthesis of 4a in ethanol and for the syn-
thesis of 5a in CH Cl compared to other solvents such as CH CN, H O, DMF and
2
2
3
2
CHCl . Further to this, we also applied diꢀerent aryl aldehydes and isocyanides as
3
substrates and found uniformly good results (Table 2).
1
3

Synthesis of benzodiazepines catalyzed by chitosan…
Table 1 Optimization of reactions conditions using diꢀerent catalysts
Time (min) 4a/5a Yield (%) 4a /5ab
a
Entry Catalyst
Solvent 4a/5a
1
2
3
4
5
6
7
–
–
500/400
250/300
300/400
200/250
180/250
100/150
40/60
12/trace
33/44
25/30
49/58
53/62
70/63
85/82
MgO NPs (10 mg)
Triethylamine (15 mol%)
p-TSA (10 mol%)
Chitosan (10 mg)
Triacid imide (10 mg)
EtOH/CH Cl
EtOH/CH Cl
EtOH/CH Cl
EtOH/CH Cl
2
2
2
2
2
2
2
2
2
2
EtOH/CH Cl
2
Chitosan functionalized by triacid imide EtOH/CH Cl
2
(
5 mg)
8
9
1
1
Chitosan functionalized by triacid imide H O/DMF
100/120
64/60
70/75
93/90
93/90
2
(
7 mg)
Chitosan functionalized by triacid imide CH CN/ CHCl3 60/90
3
(
7 mg)
0
1
Chitosan functionalized by triacid imide EtOH/CH Cl
40/60
40/60
2
2
2
(
7 mg)
Chitosan functionalized by triacid imide EtOH/CH Cl
2
(
9 mg)
a
Isolated yield (reaction conditions: 1,2-phenylenediamine, dimedone and 4-chlorobenzaldehyde at room
temperature);
Isolated yield (reaction conditions: 1,2-phenylenediamine, Meldrum’s acid and tert-butyl isocyanide at
b
room temperature)
After completion of the reaction, the catalyst was separated from the mixture by
ꢁ
ltration. Then, the catalyst was washed with ethanol and dried in air. The reusabil-
ity of the chitosan functionalized by triacid imide catalyst was tested for the prepara-
tion of 4a and it was found that product yields lessened only to a very small extent
on each reuse (run 1, 93%; run 2, 93%; run 3, 92%; run 4, 92%; run 5, 91%, run 6,
9
1%). This conꢁrms that the catalyst is stable and can be reused multiple times.
To compare the eꢃciency of chitosan functionalized by triacid imide with the
reported catalysts for the synthesis of diazepines, we have tabulated the results in
Table 3. Our study has some advantages in comparison with other mentioned stud-
ies including high yield of synthetic compound, reasonable time reaction and easy
catalyst recovery.
Scheme 4 shows a plausible mechanism for the synthesis of diazepines (4a–e).
At ꢁrst, intermolecular imine formation from dimedone and 1,2-phenylenediamine
promoted by the chitosan functionalized by triacid imide occurs. The amino group
of 1,2-phenylenediamine attacks the C=O of dimedone with elimination of H O
2
to form imine intermediate I. A 1,3-hydrogen shift results in isomeric (tautomer-
ized) to give enamine II. The other amino group of the 1,2-phenylenediamine part
of enamine II attacks the carbonyl group of aldehyde, which is itself activated by
the chitosan functionalized by triacid imide to form intermediate III. The seven-
membered ring products 4a–e are formed via intramolecular cyclization of III [24].
Scheme 5 shows a plausible mechanism for the synthesis of diazepines
(
5a–e). Intermediate II was formed from condensation reaction between
1
3

M. Esfandiari et al.
Table 2 Synthesis of benzodiazepines catalyzed by chitosan functionalized by triacid imide (7 mg)
Entry Product
Time, min Yield (%)a M. p. (°C) M. p. (°C) [references]
1
O
40
93
233–235
237–238 [24]
H
N
N
H
Cl
4
a
2
O
60
83
224–226
229–231 [25]
H
N
N
H
OCH
3
4
b
3
4
O
50
40
87
93
240–242
235–237
246–248 [25]
241–242 [25]
H
N
N
H
4
c
O
H
N
N
H
Br
4
d
5
O
40
91
230–232
232–233 [24]
H
N
Cl
N
H
4
e
6
7
H
N
O
60
70
90
86
>300
>300 [26]
O
NH
N
H
O
5
a
H
N
O
286–288
286–288 [27]
O
NH
N
H
O
5
b
1
3

Synthesis of benzodiazepines catalyzed by chitosan…
Table 2 (continued)
Entry Product
Time, min Yield (%)a M. p. (°C) M. p. (°C) [references]
8
9
1
H
N
O
60
70
60
90
87
90
305–307
306–308 [27]
>300 [26]
–
O
NH
OCH
3
N
H
O
5
c
H
N
O
>300
O
NH
N
H
O
5
d
0
H
N
O
280–282
O
NH
OCH
3
N
H
O
5
e
aIsolated yield
Table 3 Comparison of catalytic activity of chitosan functionalized by triacid imide (7 mg) with other
reported catalysts
a
Entry
Catalyst (condition)
Time (min)
Yield , %
[References]
1
2
3
4
5
Fe O @chitosan (EtOH, 0.03 g)
120
60
180
120
40
84
61
70
88
93
[24]
[28]
[29]
[30]
3
4
Acetic acid (10 mol%, reꢂux, ethanol)
H SO (EtOH, 15 mol%)
2
4
Oxalic acid (H O, reꢂux, 40 mol%)
2
Chitosan functionalized by triacid imide
This work
(
EtOH, 7 mg)
aIsolated yield
1
,2-phenylenediamine and Meldrum’s acid. The acid groups distributed on the
surface of chitosan functionalized by triacid imide activate the carbonyl groups
of the Meldrum’s acid and intermediate I. Afterward, the intermediate II under
a condensation reaction with in situ liberated acetone produces the intermedi-
ate III. Afterward, isocyanides react with α,β-unsaturated carbonyl compound
(
intermediate III) to create intermediate IV (Michael-type addition reaction),
followed by nucleophilic attack of a H O molecule on the nitrilium moiety to
2
produce the diazepines (5a-e) [26]. Here, chitosan functionalized by triacid
+
imide activates the C≡N and C=O groups for better reaction with nucleophiles.
1
3

M. Esfandiari et al.
H OH
N
NH2
O
O
H
O
N
O
N
O
NH2
NH
2
- H O
2
NH2
NH2
I
II
O
H
Ar
H
N
Ar
N
N
Ar
HN
O
NH2
HN
N
N
H
Ar
O
O
O
II
III
chitosan functionalized by triacid imide
=
Scheme 4 Proposed reaction pathway for the synthesis of 4a–e
NH2
product
O
O
NH2
O
O
O
H O
2
O
H
N
R
N
H
N
O
N
H
O
O
IV
NH2 OH
I
O
H
N
R-N
C
H O
2
N
H
H
N
O
O
III
N
H
O
O
II
H
O
O
N
product =
NH-R
=
chitosan functionalized by triacid imide
O
N
H
Scheme 5 Proposed reaction pathway for the synthesis of 5a–e
1
3

Synthesis of benzodiazepines catalyzed by chitosan…
Conclusions
In conclusion, we have reported as an eꢀective method for the synthesis of ben-
zodiazepines by one-pot reactions of 1,2-phenylenediamine with dimedone and
aryl aldehydes or isocyanides and Meldrum’s acid at room temperature. Chitosan
functionalized by triacid imide was conꢁrmed by FT-IR (infrared spectroscopy),
XRD (X-ray diꢀraction), DSC (diꢀerential scanning calorimetry) and TGA (ther-
mogravimetric analysis). The current method provides obvious positive points
containing easy work-up, extensive range of products, retrieval of the catalyst and
low catalyst loading.
Experimental section
Chitosan with average molecular weight of 100,000–300,000 and 70–85% degree
of acetylation was prepared from Sigma–Aldrich. NMR spectra were obtained on
Bruker Avance-400 MHz spectrometer. IR spectra were performed on a Tensor
2
7 instrument. TGA was obtained on a Mettler TA4000 instrument with a heating
−
1
rate of 10 ºC min under N atmosphere. DSC was done on a Shimadzu DSC-
2
5
0 instrument under N atmosphere. Wide-angle X-ray diꢀraction measurements
2
were recorded on a Bruker-D8 X-ray diꢀractometer.
Preparation of triacid imide
Into a 25-mL round-bottom ꢂask, 1.92 g of 1,3-dihydro-1,3-dioxoisobenzofuran-
5
-carboxylic acid, 1.33 g of L-aspartic acid and 10 mL mixture of acetic acid/
pyridine (3:2) were placed. The mixture was stirred at room temperature for 2 h,
and it was reꢂuxed for 6 h. The solvent was evaporated under reduced pressure.
Five milliliters of concentrated HCl was added to mixture. A white precipitate
was formed, ꢁltered oꢀ and dried, to give triacid imide [21, 22].
2
-(1,2-dicarboxyethyl)-1,3-dioxoisoindoline-5-carboxylic acid: m.p. 270–272 °C.
−1
FT-IR (KBr, ν /cm ): 3600–2400 (COOH), 1728–1700 (C=O), 1388, 1299,
max
1
1
200, 1106, 991, 728. H NMR (400 MHz, DMSO-d ): δ 8.62–8.95 (m, 3H), 5.21
6
(
CH, 1H), 4.79 (3 OH, exchanged with water of DMSO-d ), 2.54–2.72 (m, 2H) ppm.
6
Anal. Calcd for C H NO : C, 50.82; H, 2.95; N, 4.56; Found: C, 50.74; H, 2.87; N,
13
9
8
4.48.
Preparation of chitosan functionalized by triacid imide
0
.85 g (2.38 mmol) of chitosan was dissolved in 100 mL of 2.0 wt% acetic acid
solution. 0.365 g (1.19 mmol) of triacid imide was added to solution. The mixture
was stirred at room temperature for 8 h, and it was placed for 10 h at 80 °C under
1
3

M. Esfandiari et al.
stirring. The mixture was washed several times with deionized water and ethanol
and then dried in an oven.
General method for the synthesis of benzodiazepines (4a–e)
A mixture of 1,2-phenylenediamine (1 mmol) dimedone (1 mmol), aryl aldehyde
(
1 mmol) and chitosan functionalized by triacid imide (7 mg) was stirred in etha-
nol (10 mL) at room temperature. After completion of the reaction, (monitored by
TLC), the catalyst was separated from the mixture by ꢁltration. The solvent was
removed under vacuum, and the solid obtained was rinsed with n-hexane and EtOAc
(
7:3) to aꢀord pure benzodiazepine.
General procedure for the preparation of benzodiazepines (5a–e)
Chitosan functionalized by triacid imide (7 mg) was added to a mixture of 1,2-phe-
nylenediamines (1 mmol), isocyanide (1 mmol) and Meldrum’s acid (1 mmol) in
5
mL CH Cl at room temperature. After completion of the reaction, (monitored
2 2
by TLC), the catalyst was separated from the mixture by ꢁltration. The solvent was
evaporated under vacuum, and the solid obtained was washed several times with
water and ethanol to aꢀord pure benzodiazepine.
3
‑Dimethyl‑2,3,4,5,10,11‑hexahydro‑11‑[(4‑chloro)phenyl]‑1H‑dibenzo[b,e][1,4]
diazepin‑1‑one (4a)
Green solid, M. p. 233–235 °C; FT-IR (KBr): ν=3304, 3238, 3056, 2958,
−
1
1
1
582, 1385, 1535, 1328, 1426, 1273 cm ; H NMR (400 MHz, DMSO-d ): δ
6
(
ppm)=1.03 (s, CH , 3H), 1.08 (s, CH , 3H), 2.15 (A.Bq, CH , J=16.0 Hz, 2H),
3
3
2
2
.58 (s, CH C=O, 2H,), 4.97 (s, NH, 1H,), 6.08 (s, 1H, CH), 6.47 (d, J=8.2 Hz,
2
Ar, 1H), 6.55 (m, Ar, 3H), 6.84 (d, J=8.2 Hz, Ar, 1H), 6.98 (d, J=8.4 Hz, Ar, 2H),
1
3
7
.02 (d, J=8.4 Hz, Ar, 1H), 8.63 (s, NH, 1H,); C NMR (100 MHz, DMSO-d ): δ
6
(
ppm)=28.17, 28.68, 32.24, 43.86, 49.92, 56.45, 108.35, 120.63, 120.74, 121.06,
22.12, 124.28, 127.35, 130.44, 137.08, 144.05, 150.03, 152.05, 192.83.—Analysis
for C H ClN O: calcd. C 71.48, H 6.00, N 7.94; found C 71.56, H 6.08, N 7.99.
1
2
1
21
2
N‑tert‑butyl‑2‑(2,3,4,5‑tetrahydro‑2,4‑dioxo‑1H‑benzo[b][1,4]
diazepin‑3‑yl)‑2‑methyl propanamide (5a)
White powder, M. p.>300 °C; FT-IR (KBr): ν=3385, 2965, 2903, 1693, 1645,
−
1 1
1
603, 1528 cm ; H NMR (400 MHz, DMSO-d ): δ (ppm)=1.21(9H, s, C(CH ) ),
3 3
6
1
.37 (s, 2CH ,6H), 3.17 (s, CH,1H), 6.15–7.15 (bs, 4H-Ar and –NH, 5H), 10.37 (bs,
3
1
3
2
NH, 2H); C NMR (100 MHz, DMSO-d ): δ (ppm)=23.14, 27.95, 42.64, 50.45,
6
5
5.12, 121.43, 125.42, 131.34, 168.15, 177.32.—Analysis for C H N O : C 64.33,
1
7
23
3
3
H 7.30, N 13.24, Found: C 64.25, H 7.27, N, 13.15.
1
3

Synthesis of benzodiazepines catalyzed by chitosan…
Supporting information
NMR spectra of products are presented in Supporting Information available online.
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M. Esfandiari et al.
Aꢀliations
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Mozhgan Esfandiari · Ali Kareem Abbas · Mohammad Reza Vakili ·
Hossein Shahbazi‑Alavi4 · Javad Safaei‑Ghomi
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Department of Chemistry, Islamic Azad University, Shiraz Branch, Shiraz,
Islamic Republic of Iran
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College of Applied Medical Sciences, University of Kerbala, Kerbala, Iraq
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Department of Chemistry, Islamic Azad University, Firuzabad Branch, Fars,
Islamic Republic of Iran
4
Young Researchers and Elite Club, Islamic Azad University, Kashan Branch, Kashan,
Islamic Republic of Iran
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Department of Organic Chemistry, Faculty of Chemistry, University of Kashan,
P.O. Box 87317-51167, Kashan, Islamic Republic of Iran
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