An efficient method for synthesis of some heterocyclic compounds containing 3-iminoisatin and 1,2,4-triazole using Fe3O4 magnetic nanoparticles

Article abstract of DOI:10.1080/17415993.2017.1278761

1,2,4-triazole derivatives were prepared by reaction of thiocarbohydrazide and some esters in 60% ethanol. Condensation of 1,2,4-triazole derivatives with isatin gave Schiff bases of 3-iminoisatin derivatives. Reaction of malonic or succinic acid dihydraz

Full text of DOI:10.1080/17415993.2017.1278761

Journal of Sulfur Chemistry
ISSN: 1741-5993 (Print) 1741-6000 (Online) Journal homepage: http://www.tandfonline.com/loi/gsrp20
An efficient method for synthesis of some
heterocyclic compounds containing 3-iminoisatin
and 1,2,4-triazole using Fe3O4 magnetic
nanoparticles
Navabeh Nami, Daryoush Zareyee, Maryam Ghasemi, Ameneh
Asgharzadeh, Mehdi Forouzani, Somayeh Mirzad & S. Milad Hashemi
To cite this article: Navabeh Nami, Daryoush Zareyee, Maryam Ghasemi, Ameneh
Asgharzadeh, Mehdi Forouzani, Somayeh Mirzad & S. Milad Hashemi (2017): An efficient
method for synthesis of some heterocyclic compounds containing 3-iminoisatin and
1,2,4-triazole using Fe3O4 magnetic nanoparticles, Journal of Sulfur Chemistry, DOI:
10.1080/17415993.2017.1278761
To link to this article: http://dx.doi.org/10.1080/17415993.2017.1278761
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Date: 31 January 2017, At: 00:31

JOURNAL OF SULFUR CHEMISTRY, 2017
http://dx.doi.org/10.1080/17415993.2017.1278761
An efficient method for synthesis of some heterocyclic
compounds containing 3-iminoisatin and 1,2,4-triazole using
Fe3O4 magnetic nanoparticles
Navabeh Namia, Daryoush Zareyeea, Maryam Ghasemia, Ameneh Asgharzadeha,
Mehdi Forouzanib, Somayeh Mirzadb and S. Milad Hashemic
aDepartment of Chemistry, Qaemshahr Branch, Islamic Azad University, Qaemshahr, Iran; bDepartment of
Chemistry, Payam Noor University, Sari Branch, Sari, Iran; cDepartment of Chemistry, Guilan University,
Guilan, Iran
ABSTRACT
ARTICLE HISTORY
Received 12 June 2015
Accepted 28 December 2016
1,2,4-triazole derivatives were prepared by reaction of thiocarbo-
hydrazide and some esters in 60% ethanol. Condensation of 1,2,4-
triazole derivatives with isatin gave Schiff bases of 3-iminoisatin
derivatives. Reaction of malonic or succinic acid dihydrazide with
isatin lead to formation of N,N’-bis-(3-imino-1,3-dihydro-indolyl-
2-one)-malonamide 8a and N,N’-bis-(3-imino-1,3-dihydro-indolyl-2-
one)succinamide 8b in good yields under mild reaction conditions.
These reactions are catalyzed by Fe3O4 MNPs. The chemical struc-
tures were confirmed by Fourier transform-infrared, 1H-NMR, 13C-
NMR, gas chromatography-mass spectrometry spectroscopy, and
elemental analysis.
KEYWORDS
Fe3O4 magnetic
nanoparticles; therphthalic
acid ethyl ester; malonic
dihydrazide; succinic
dihydrazide;
thiocarbohydrazide;
3-iminoisatin; 1,2,4-triazole
1. Introduction
Magnetic nanoparticles are excellent catalysts for synthesis of organic reactions [1–3].
The magnetic properties make the recovery of the catalyst facile by mean of an external
magnetic field [4–7]. In comparison to bulk Fe3O4 and known magnetic nanoparticles,
Fe3O4 nanoparticles have attracted a great attention as heterogeneous catalysts because of
their interesting structure, large surface area, eco-friendly nature, their relatively non-toxic
CONTACT Navabeh Nami
navabehnami@yahoo.com
© 2017 Informa UK Limited, trading as Taylor & Francis Group

2
N. NAMI ET AL.
properties, high coercively, low Curie temperature, ability to be recycled, and high catalytic
activities in synthesis of organic compounds [8–10].
A large number of heterocyclic compounds containing 1,2,4-triazoles are well known
as drugs [11–16] and have attracted the interest of chemists for a wide variety of chemical
properties, synthetic versatility [17–20], and pharmacological antifungal [21, 22], anti-
convulsant [23], anticancer [24–26], antibacterial [27], and anti-inflammatory activities
[28, 29].
Isatin (1H-indole-2,3-dione) has also been known for several years as a raw material
for synthesis of large variety of heterocyclic compounds [30–32]. Isatin derivatives exhibit
a wide range of biological and pharmacological activities [33–36]. Because of the above
reasons, we have focused on the application of Fe3O4 magnetic nanoparticles for synthesis
of some 1,2,4-triazole and 3-imino isatin derivatives in good yields and under mild reaction
conditions.
2. Results and discussion
We report that nano Fe3O4 is a highly efficient and eco-friendly catalyst for synthesis of
iminoisatin and 1,2,4-triazole derivatives. A reaction mixture of thiocarbohydrazide and a
carboxylic acid ethyl ester was stirred under reflux condition in 60% ethanol in the presence
of Fe3O4 MNPs and monitored by thin layer chromatography (TLC) in n-hexane: ethy-
lacetate/4 : 1. Using these conditions 1,2,4-triazoles were obtained after 1 h. The products
were identified by gas chromatography-mass spectrometry (GS-MS), nuclear magnetic
resonance (NMR), Fourier transform-infrared (FT-IR) spectra, and physical data and by
comparison to authentic samples.
Fe3O4 MNPs were prepared according to previously published procedures [37, 38]. The
IR spectra of prepared Fe3O4 nanoparticles are shown in Figure 1 and are the same as
Figure 1. FT-IR spectra of Fe3O4 magnetic nanoparticles.

JOURNAL OF SULFUR CHEMISTRY
3
reported in literature [35, 36]. A strong peak at around 590 cm−1 is corresponds to the
Fe–O stretching frequency. The broad band at around 3500–3000 cm–1 is attributed to
adsorbed water.
The morphology and particle size distribution of Fe3O4 MNPs were studied using trans-
mission electron microscopy (TEM) and scanning electron microscope (SEM). The SEM
image (Figure 2) shows that Fe3O4 particles composed of small spherical shape particles,
and the TEM image(Figure 3) shows the average particle size is about 10–30 nm.
X-ray diffraction (XRD) can be used to characterize the crystallinity of nanoparticles,
as well as the average nanoparticle diameter. XRD patterns (Figure 4) of Fe3O4 nanopar-
ticles prepared under standard conditions [39, 40] reveal diffraction peaks, which are the
characteristic peaks of the Fe3O4 crystal [41]. Particle size of Fe3O4 is quite small from the
relatively wide half-peak breadth. With the XRD pattern, the average diameter which can
be evaluated from Scherrer equation [42, 43] (D= Kλ/βcosθ, where K is constant, λ is
X-ray wavelength and β is the peak width of half-maximum) is obtained as 12.7 nm.
Figure 2. SEM image of Fe3O4 MNPs.
Figure 3. TEM image of Fe3O4 MNPs.

4
N. NAMI ET AL.
Figure 4. XRD image of Fe3O4 MNPs.
In the preliminary stage of investigation, the model reaction of thiocarbohydrazide and
benzoic acid ethyl ester was carried out using various amounts of Fe3O4 and Fe3O4@SiO2
MNPs with different solvents and under solvent-free conditions. According to Table 1 the
best solvent for preparation of triazole is 60% ethanol. In the absence of catalyst, the desired
product was obtained in 67% yield after 4 h of reaction (Table 1, Entry 17), but in the pres-
ence of Fe3O4MNPs the reaction gave the desired product in 60% ethanol after 1 h with
good yields. According to Table 1 (Entry 18–21), the yield of the product does not improve
with increasing amount of catalyst, whereas it decreased with decreasing the amount of
catalyst. The best results were obtained with (5 mol%) Fe3O4 magnetic nanoparticles.
The catalyst was simply recovered by an external magnet, washed with ethanol, and
air-dried. Reaction of thiocarbohydrazide with terephthalic acid, benzoic acid, and acetic
Table 1. Reaction of thiocarbohydrazide(1 mmol) and benzoic acid ethyl ester
(1 mmol) under different conditions.
Entry
Solvent
Catalyst
Catalyst (mol%)
Time (h)
Yielda (%)
1
2
3
4
5
6
7
8
THF
THF
THF
THF
THF
CH3CN
CH3CN
n-Hexane
n-Hexane
EtOEt
EtOEt
EtOH
EtOH
EtOH
EtOH
EtOH
–
–
3
4
5
7
–
5
–
5
–
5
–
3
4
5
7
–
3
4
5
7
7
7
5
7
7
7
4
4
4
2
2
4
4
4
4
4
4
4
4
4
2
2
4
4
3
1
1
2
2
4
4
4
4
52
60
63
79
78
42
69
trace
48
34
64
62
68
75
83
83
67
80
83
92
91
73
85
73
75
67
56
Fe3O4 MNPs
Fe3O4 MNPs
Fe3O4 MNPs
Fe3O4 MNPs
–
Fe3O4 MNPs
–
Fe3O4 MNPs
–
Fe3O4 MNPs
Fe3O4 MNPs
Fe3O4 MNPs
Fe3O4 MNPs
Fe3O4 MNPs
Fe3O4 MNPs
Fe3O4 MNPs
Fe3O4 MNPs
Fe3O4 MNPs
Fe3O4 MNPs
Fe3O4 MNPs
Fe3O4 MNPs
Fe3O4 MNPs
Fe3O4@SiO2 MNPs
Fe3O4@SiO2 MNPs
Fe3O4 MNPs
Fe3O4@SiO2 MNPs
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
EtOH 60%
EtOH 60%
EtOH 60%
EtOH 60%
EtOH 60%
EtOH 60% (RT)
EtOH 60% (50°C)
EtOH 60%
EtOH 60%
Solvent-free
Solvent-free
aIsolated yield.

JOURNAL OF SULFUR CHEMISTRY
5
acid ethyl esters in the presence of Fe3O4 MNPs gave 3,3ꢀ-(1,4-phenylene)bis(4-amino-1H-
1,2,4-triazole-5(4H)-thione) 6, 4-amino-3-phenyl-1H-1,2,4-triazole-5(4H)-thione 3a and
4-amino-3-methyl-1H-1,2,4-triazole-5(4H)-thione 3b, respectively, in good yields. The
structures of these compounds were determined by IR, NMR, mass spectrometry, and
microanalysis. The IR spectra of compound 6 exhibited absorption bands at 1670 cm−1
(C S), 3270 cm−1 (NH2), 3400 cm−1 (NH). The 1H-NMR spectra of compound 6 showed
=
sharp signal at δ 5.27 ppm arising from NH2, and a broad signal at δ 12.77 ppm from NH.
The mass spectra of 6 revealed a molecular ion peak at m/z 306. The fragments at m/z 192
and 116 can be attributed to the loss of C2H2N4S and C8H6N4S from the molecular ion,
respectively.
Compounds 3a–b, and 6, along with malonic or succinic dihydrazide was added to
isatin and Fe3O4 MNPs, the mixture was refluxed in ethanol to form Schiff bases 3-
(3-substituted-2,4-dihydro-1,2,4-triazol-5-mercapto-4-yl]iminoisatin 4a–b, (3E,3E’)-3,3ꢀ-
(3,3ꢀ-(1,4-phenylene)bis(5-thioxo-1H-1,2,4-triazole-4,3(5H)-diyl))bis(azan-1-yl-ylidene)
diindolin-2-one 7, N,N’-Bis-(3-imino-1,3-dihydro-indolyl-2-one)-malonamide 8a and
N,N’-Bis-(3-imino-1,3-dihydro-indolyl-2-one)-succinamide 8b, respectively (Scheme 1).
The structures were deduced from elemental analyses, IR, NMR and mass spectrome-
try. The IR spectra of 7 exhibited an absorption band for (NH) vibrations at 3250 cm−1
,
and (C O) vibrations at 1670 cm−1. The 1H-NMR spectra of compound 7 showed broad
signal at δ 12.44 and 11.17 ppm arising from the indole and triazole NH group. Signals
around δ7.08–7.66 ppm are assigned to CHAromatic protons. The mass spectra of 7 revealed
a molecular ion peak at m/z 564. The IR spectra of compound 8a showed absorption for
=
(NH) stretching vibrations at 3250 cm−1, (C O) vibrations at 1730 cm−1. The 1H-NMR
=
spectra of 8a exhibited a broad signals at δ 10.80 and 11.16 ppm for protons of (NH).
Scheme 1. Synthesis of isatin-3-imine, catalyzed by Fe3O4 magnetic Nanoparticles.

6
N. NAMI ET AL.
Scheme 2. Plausible mechanism for synthesis of 1,2,4-triazoles and iminoisatin derivatives using Fe3O4
MNPs.
Table 2. Comparison of the efficacy of Fe3O4 MNPs with some of those reported in the literature.
Compound
Catalyst
Time
Yeild
Ref.
4b
4b
8a
8a
8b
8b
HCl
Fe3O4 MNPs
EtOH
Fe3O4 MNPs
AcOH
Fe3O4 MNPs
6 h
30 min
1 h
30 min
1 h
76
94
94
94
80
94
[44]
This work
[45]
This work
[46]
30 min
This work
A plausible mechanism for reaction of thiocarbohydrazide with carboxylic acid ester
and 1,2,4-triazole with isatin is envisaged in Scheme 2. The carbonyl group is activated
by MNPs (Fe3+) to provide a more electrophilic center for intermolecular cyclization
and production of 4-amino-3-phenyl-1H-1,2,4-triazole-5(4H)-thione. Reaction of 1,2,4-
triazole and isatin is catalyzed by MNPs (Fe3+). The carbonyl group of isatin is activated
by Fe3O4 MNPs, then the nitrogen of 1,2,4-triazole attacks at the electrophilic center to
afford (E)-3-(3-phenyl-5-thioxo-1H-1,2,4-triazole-4(5H)-ylimino)indolin-2-one 4a.
A comparison of the efficacy of Fe3O4MNPs catalyst with other catalysts reported in the
literature is presented in Table 2. In addition to having the general advantages attributed
to the inherent magnetic property of nanocatalysts, Fe3O4MNPs exhibited exceptionally
high catalytic activity compared to other catalysts, to yield the desired products in shorter
reaction times and under milder reaction conditions.
3. Conclusions
In summary, an efficient and environmentally friendly method for synthesis of 1,2,4-
triazole derivatives was described. The reactions were performed under reflux condition
and the corresponding products were afforded in good to excellent yields. Also, the
magnetically recoverable iron oxide nanoparticles are found to be more efficient for the
synthesis of triazole and 3-iminoisatin derivatives. The advantages of this method are short
reaction time, simple work-up procedure, ease of separation, high conversion, easier and
less expensive than the other methods. The magnetic Fe3O4 nanoparticles are effective in

JOURNAL OF SULFUR CHEMISTRY
7
green chemistry and increases reaction speed without air pollution, these nanoparticles
could be successfully recovered and reused.
4. Experimental
The chemical materials and solvents were purchased from Merck and Aldrich Chemical
Company. The melting points were obtained using an Electrothermal IA 9100 Digitalmelt-
ing point apparatus. The IR spectra were recorded on a Bruker IFS-88 instrument (the
samples as KBr disks for the range 4000–400 cm−1). The1H-NMR and13C-NMR spec-
tra were recorded on a Bruker AC-300 spectrometer (1H, 400 MHz; 13C, 75.469 MHz)
using trimethylsilyl as an internal standard. Mass spectrometric measurements were made
on an Agilent Technologies 6890 N Network GC system. The C, H, and N analyses were
performed by the micro analytical service of the NIOC Research Institute of Petroleum
Industry.
4.1. Preparation of thiocarbohydrazide
Thiocarbohydrazide was synthesized according to previously published procedures [47].
4.2. Preparation of catalyst
MNPs (Fe3O4andFe3O4@SiO2) were synthesized according to previously published pro-
cedures [37, 38].
4.3. General procedure for synthesis of 1,2,4-triazole derivatives (3a–b, 6)
Thiocarbohydrazide (1 mmol for 3a-b, 2 mmol for 6) was added to esters (1 mmol) and
Fe3O4MNs (5mol%). The mixture was stirred in 60% ethanol (10 ml) under reflux con-
ditions. The progress of the reaction was monitored using TLC (n-hexane–ethyl acetate,
1 : 2) and detected by UV lamp (254 and 366 nm). At the end of the reaction (after 30 min-
1 h), the catalyst was recovered by an external magnet, washed with EtOH, dried at 60°C
for 1 h, and reused seven times for the same reaction. The residue of the reaction mixture
was filtered. The filtrate was rotary evaporated, the solvent recovered by distillation and the
crude product was purified by usual a crystallization procedure in hot water/ethanol (2:1).
The pure triazole derivatives were obtained after drying under vacuum. In most cases, the
products were white powders.
4.3.1. 4-amino-3-phenyl-1H-1,2,4-triazole-5(4H)-thione [48] (3a)
Yield 92%, m.p. 236°C; white powder.
cm−1): 3150 (NH2), 1650 (C S), 1520 (C C), 1500 (C N), 1320
=
=
=
IR (KBr) (υ
max
1
(C–N). H-NMR:(400 MHz, d6-DMSO) δ ppm, 5.78 (S, 2H, NH2), 7.53 (s, 3H, Ar-H),
8.01 (s, 2H, Ar-H), 13.91 (S, 1H, NH).

8
N. NAMI ET AL.
4.3.2. 4-amino-3-methyl-1H-1,2,4-triazole-5(4H)-thione [49, 50] (3b)
Yield 97%, m.p. 202°C; white powder. IR (KBr) (υ
Cm−1): 3272 (NH), 3154 (NH2),
max
1
=
=
2800 (C–H), 1660 (C S), 1600 (C N), 1340 (C–N). H-NMR:(400 MHz, d6-DMSO) δ
ppm, 2.24 (s, 3H, CH3), 5.72 (s, 2H, NH2), 13.40 (s, 1H, NH).
4.3.3. 3,3ꢀ-(1,4-phenylene)bis(4-amino-1H-1,2,4-triazole-5(4H)-thione) (6)
Terphthalic acid ethyl ester and thiocarbohydrazid, yield 92%, m.p. 216°C; white powder.
IR (KBr) (υmax Cm−1): 3400 (NH), 3270 (NH2), 1670 (C S), 1550 (C C), 1500 (C N),
1300 (C–N), 1150 (C–C). 1H-NMR:(400 MHz, d6-DMSO) δ ppm, 5.27 (s, 2H, NH2), 9.15
(s, 2H, Ar-H), 12.77 (br, 1H, NH).MS: m/z 306 (M+). Anal. Calcd For C10H10N8S2: C,
39.20; H, 3.29; N, 36.57. Found: C, 39.22; H, 3.27; N, 36.60.
=
=
=
4.4. General procedure for synthesis of iminoisatin derivatives (4a–b, 8a–b)
1,2,4-triazole or dihydrazide derivative(1 mmol) and isatin (1 mmol) were added in ethanol
(10 mL) to Fe3O4MNPs (5 mol%). The mixture was stirred under reflux conditions. The
progress of the reaction was monitored using TLC (n-hexane: ethyl acetate 1:2). When
the reaction finished (after 30 min), the catalyst was recovered by an external magnetic
field, washed with ethanol, air-dried, and could be used for additional reactions. The
remaining mixture was cooled and the precipitant was filtered, washed, recrystallized with
ethanol, and dried. The products were identified using NMR, IR, mass spectrometry, and
microanalysis.
4.4.1. 3-(3-phenyl-2,4-dihydro-1,2,4-triazol-5-mercapto-4-yl]iminoisatin [51] (4a)
Yield 88%, m.p. 221°C; orange powder. IR (KBr) (υ
Cm−1): 3200 (isatin NH), 3185
max
=
=
=
=
(triazole NH), 1727 (C O), 1616 (C N), 1511 (C N), 1474 (C C), 1200 (C–N), 1125
(C–C).1H-NMR:(400 MHz, d6-DMSO) δ ppm, 6.95 (d, J = 7.6 Hz, 3H, Ar-H), 7.10 (t,
J = 7.6 Hz, 2H, Ar-H), 7.36 (t, J = 7.6 Hz, 2H, Ar-H), 7.62 (d, J = 7.6 Hz, 2H,Ar-H),
10.98 (s, 1H, NH triazole), 11.97 (br, 1H, NH indole). MS: m/z 321 (M+). Anal. Calcd
For C16H11N5OS: C, 59.80; H, 3.45; N, 21.79. Found: C, 59.83; H, 3.47; N, 21.83.

JOURNAL OF SULFUR CHEMISTRY
9
4.4.2. 3-(3-methyl-2,4-dihydro-1,2,4-triazol-5-mercapto-4-yl]iminoisatin [44] (4b)
Yield 90%, m.p. 192°C; orange powder. IR (KBr) (υ
Cm−1): 3250 (NH), 2800 (CH3),
max
1
=
=
1650 (C O), 1500(C N), 1320 (C–N). H-NMR:(400 MHz, d6-DMSO) δ ppm,2.23 (s,
1H, CH3), 6.89 (d, J = 8 Hz, 1H, Ar-H), 7.03 (t, J = 7.2 Hz, 1H, Ar-H), 7.47 (d, J = 7.2 Hz,
1H, Ar-H), 7.56 (t, J = 7.6 HZ, 1H, Ar-H), 11.08 (s, 1H, triazole NH), 13.97 (br, 1H,indole
NH).MS: m/z 321 (M+). Anal. Calcd For C11H9N5OS: C, 50.95; H, 3.50; N, 27.01. Found:
C, 50.92; H, 3.53; N, 26.98.
4.4.3. (3E,3E’)-3,3ꢀ-(3,3ꢀ-(1,4-phenylene)bis(5-thioxo-1H-1,2,4-triazole-4,3(5H)-diyl))
bis(azan-1-yl-ylidene)diindolin-2-one (7)
Yield 87%, m.p. decompose 242°C; orange powder. IR (KBr) (υ
Cm−1): 3250 (NH),
max
1
=
=
=
1670 (C O), 1500 (C C), 1450 (C N), 1350 (C–N), 1200 (C–C), 1100 (C–O). H-
NMR:(400 MHz, d6-DMSO) δ ppm, 7.08 (t, J =7.2 Hz, 2H, Ar-H), 7.17 (d, J =15.2 Hz,
1H, Ar-H), 7.33 (t, J =7.6 Hz, 2H, Ar-H), 7.41 (t, J =7.6 Hz, 2H, Ar-H), 7.53 (d, J =7.6 Hz,
1H, Ar-H), 7.59 (d, J =7.2 Hz, 2H, Ar-H), 7.66 (d, J =7.2 Hz, 2H, Ar-H), 11.17 (br, 2H,
NH), 12.44 (br, 2H, indole NH).13C-NMR:(100 MHz, d6-DMSO) δ ppm, 111.8, 120.1,
121.7, 123.1, 131.1, 132.6, 134.2, 139.5, 140.6, 143.4, 163.2, 175.7.MS: m/z 564 (M+).
Anal. Calcd For C26H16N10O2S2: C, 55.31; H, 2.86; N, 24.81 Found: C, 55.39; H, 2.90;
N, 24.79.
4.4.4. N,Nꢀ-Bis-(3-imino-1,3-dihydro-indolyl-2-one)-malonamide [45] 8a
Malonic dihydrazide and isatin, yield 92%, M.p. 183°C; yellow crystals. IR (KBr) (υ
max
Cm−1): 3250 (NH), 1730 (C O), 1630 (C N), 1500 (C C), 1480 (CH2), 1350 (C–N).
1H-NMR:(400 MHz, d6-DMSO) δ ppm, 3.15 (s, 2H, CH2), 6.90 (d, J = 7.6 Hz, 1H, Ar-
H), 7.04 (t, J = 7.2 Hz, 2H, Ar-H), 7.09 (d, J = 7.6 Hz, 1H, Ar-H), 7.37 (t, J = 7.6 Hz, 1H,
=
=
=

10
N. NAMI ET AL.
Ar-H), 7.55 (d, J = 7.0 Hz, 1H, Ar-H), 8.12 (d, J = 7.6 Hz, 2H, Ar-H), 10.80 (s, 2H, amidic
NH), 11.16 (s, 2H, indole NH).
4.4.5. N,N’-Bis-(3-imino-1,3-dihydro-indolyl-2-one)-succinamide [46] 8b
Cm−1): 3280 (NH), 1700 (C O),
=
Yield 94%, m.p. 242°C; yellow crystals. IR (KBr) (υ
max
1
=
=
1600 (C N), 1450 (C C), 1350 (C–N). H-NMR:(400 MHz, d6-DMSO) δ ppm, 3.15
(s, 2H, CH2), 6.95 (d, J = 8.0 Hz, 1H, Ar-H), 7.09 (t, J = 7.6 Hz, 1H, Ar-H), 7.37(t,
J = 7.0 Hz, 1H, Ar-H), 7.56 (d, J = 7.2 Hz, 1H, Ar-H), 11.26 (s, 1H, amidic NH), 12.56
(s,1H, indole NH). 13C-NMR:(100 MHz, d6-DMSO) δ ppm, 36.25, 111.0, 120.27, 122.12,
131.89, 132.86, 134.51, 144.07, 162.98, 165.11.
Acknowledgement
The authors wish to thanks Islamic Azad University in Qaemshahr Branch and Payame Noor
University in Sari Branch for the institutional support.
Disclosure statement
No potential conflict of interest was reported by the authors.
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