Synthesis, characterization and thermal behavior study of new 1,2,3-triazole derivatives containing 1,3,4-oxadiazole ring

Article abstract of DOI:10.13005/ojc/350153

In this present work, a series of new 1-(substituted-phenyl)-1H-1,2,3-triazolyl-4-carboxylic acid derivatives was synthesized via copper (I) catalyzed azide-alkyne cycloaddition reaction. Since these synthesized 1,2,3-triazole compounds containing a carbo

Full text of DOI:10.13005/ojc/350153

ISSN: 0970-020 X
CODEN: OJCHEG
019, Vol. 35, No.(1):
Pg. 416-422
ORIENTAL JOURNAL OF CHEMISTRY
An International Open Access, Peer Reviewed Research Journal
2
www.orientjchem.org
Synthesis, Characterization andThermal Behavior Study of New
1,2,3-Triazole Derivatives Containing 1,3,4-Oxadiazole Ring
RIYADH J. NAHI* and ZAINAB I. KUꢀAIT
Department of Chemistry, College of Science, Al-Muthanna University, Iraq.
*
Corresponding author E-mail: riyadhnahi@yahoo.com
http://dx.doi.org/10.13005/ojc/350153
(Received: December 07, 2018; Accepted: January 28, 2019)
ABSTRACT
In this present work, a series of new 1-(substituted-phenyl)-1H-1,2,3-triazolyl-4-carboxylic acid
derivatives was synthesized via copper (I) catalyzed azide-alkyne cycloaddition reaction. Since these
synthesized 1,2,3-triazole compounds containing a carboxyl functional group, it was exploited for the
combinationof1,2,3-triazoleringwith1,3,4-oxadiazoleringsysteminonemolecule.Thus, thesynthesized
1,2,3-triazoles were the key starting materials to synthesize the target compounds via a condensation
reaction with semicarbazide hydrochloride in the presence of POCl .Furthermore, the thermal behavior
3
of all newly heterocyclic compounds was also studied by TGA and DTG techniques.
Keywords: Heterocyclic, 1,2,3-Triazole, 1,3,4-Oxadiazole, Click reaction,
1,3-Dipolarcycloaddition, Thermal study.
INTRODUCTION
The knowledge of chemistry of heterocyclic
compounds represents a basic point for the
developmentofnewheterocyclescompoundsthathave
an important role in agrochemical, pharmaceuticals
1-3
and materials science .Interestingly, azolestructures
being the most common among different classes of
4
heterocyclic compounds . Structurally, azoles are
Fig. 1. Different structures of azole
composedoffive-memberedringscontainingnitrogen
atom and at least one other non-carbon atom of either
nitrogen, oxygen or sulphur as heteroatoms as shown
Currently,1,2,3-triazoleand1,3,4-oxadiazole
derivatives have a special attention due to their
remarkable biological, chemical and physical
5
,6
in Figure 1 .
This is an
Open Access article licensed under a Creative Commons license: Attribution 4.0 International (CC- BY).
Published by Oriental Scientific Publishing Company © 2018

NAHI et al., Orient. J. Chem., Vol. 35(1), 416-422 (2019)
417
7
-9
properties . In general, 1,2,3-triazole ring system
is one of two aromatic isomeric structures of the
CuSO .5H O (0.25 g, 1.03 mmol) and sodium
4
2
ascorbate (0.38 g, 1.93 mmol), a mixture of
tert-butanol:water (30.0 ml 2:1) was added. To the
resultedsolution, propiolicacid(1.2ml, 20.0mmol)and
a substituted-phenyl azide (20.0 mmol) were added,
sequentially. The reaction mixture was then stirred
10
general formula C N OH . Currently, click reaction
is a method choice for the synthesis of 1,2,3-triazole
ring .This click reaction is described as a copper
I) catalyzed azide-alkyne 1,3-dipolarcycloaddition
CuAAC) and a simple synthetic route in relatively
2
2
2
1
1-13
(
(
o
at 50 C for overnight. The reaction mixture was then
high yields with high regioselectivity to produce 1,4-
allowed to cool into room temperature before addition of
water(100ml).Theformedprecipitatewasthencollected
by filtration under vacuum, washed with ether and dried
to give the titled compounds as solid products.
1
4-16
disubstituted-1,2,3-triazole derivatives
,3,4-oxadiazole ring system can be described as
one of four isomers that have the molecular formula
. While,
1
1
2
7,18
C N OH
. Depending on the starting materials
2
2
that are used, several synthetic routes have been
followed in the literatures for the synthesis of 1,3,4-
Synthesis of 1-(3-methoxyꢂhenyl)-1H-1,2,3-
triazolyl-4-carboxylic acid (6)
1
9,20
oxadiadole derivatives . However, the common
synthetic approach is a cyclization reaction of the
intermediate acylsemicarbazides in the presence of a
variety of dehydrating agents such as thionyl chloride
and polyphosphoric acid to introduce 2-amino-1,3,4-
It was prepared by using 1-azido-3-methoxy-
benzene 1 (2.98 g, 20.0 mmol):Yield (3.3 g, 77%) as a
-1
graysolid.FT-IR(KBrdisc,cm ),3576-2400(OH,COOH),
3136 (Ar-H), 2947 (C-H, aliphatic), 1706 (C=O), 1647
1
(C=C-triazole),1612(Ar,C=C)and1422(-N=N-). H-NMR
2
1,22
oxadiazole derivatives . As the combination of
two or more pharmacophores in one molecule is
a strategy for development of new compounds, we
are interested in synthesizing a new heterocyclic
compounds containing 1,2,3-triazole and 1,3,4-
oxadiazole rings combined in one molecule.
(500 MHz, DMSO-d ): δ= 3.4 (s, 3H, OCH ), 7.49-7.57
6
3
+
(m, 4H, Ar-H) and 9.4 (s, 1H, C=CH-triazolyl).HPMS-EI
(m/z): Calc. for C H N O = 219.06, found= 219.1.
10
9
3
3
Synthesis of 1-(3-methylꢂhenyl)-1H-1,2,3-
triazolyl-4-carboxylic acid (7)
It was prepared by using 1-azido-3-methyl-
benzene 2 (2.66 g, 20.0 mmol):Yield (2.03 g, 50%)
EꢁpERIMENTAL
-
1
as a gray solid. FT-IR (KBr disc, cm ), 3525-2400
OH, COOH), 3063 (Ar-H), 2922 (C-H aliphatic),
Chemicals and Instruments
(
All solvents and starting materials were
purchased from commercially available sources and
they were directly used without further purification.
FT-IR spectra were recorded on an FT-IR–8400S plus
spectrometer operating from 4000–500 cm as KBr
disc. H-NMR spectra were recorded at 500 MHz on a
1
708 (C=O), 1654 (C=C-triazole), 1619 (Ar, C=C)
1
and 1383 (-N=N-). H-NMR (500 MHz, DMSO-d ):
6
δ= 2.1 (s, 3H, CH ), 6.6-7.8(m, 4H, Ar-H) and 8.89
3
+
(
s, 1H, C=CH-triazolyl). HPMS-EI (m/z): Calc. for
-1
C H N O = 203.07, found= 203.1.
10
9
3
2
1
BrukerAC400spectrometer.Massdataweremeasured
on Agilent Technology (HP). TG-DTG analysis was
performed by using a Perkin Elmer TG 4000 at the
Synthesis of 1-(3-nitroꢂhenyl)-1H-1,2,3-triazolyl-
4-carboxylic acid (8)
It was prepared by using 1-azido-3-nitro-
benzene 3 (3.8 g, 20.0 mmol):Yield (3.9 g, 84%) as
o
temperature ranged 39-900 C, with flow rate 20 ml/min
o
-1
and heating rate 40 C/min under nitrogen current.
light green solid.FT-IR (KBr disc, cm ),3500-2500(OH,
COOH), 3113 (Ar-H), 1695 (C=O, COOH), 1631 (C=C-
triazole), 1594 (Ar, C=C), 1390 (-N=N-) and 1315,
procedures
1
Synthesis of substituted ꢂhenyl azides (1-5)
All phenyl azides that were used in the
present work were synthesized according to the
modified procedure that was described in the
1257 (asymmetric, symmetric NO ). H-NMR (500
2
MHz, DMSO-d ): δ= 13.3 (s, 1H, COOH), 7.9-8.9 (m,
6
+
4H, Ar-H) and 9.05 (s, 1H, C=CH-triazolyl). HPMS-EI
(m/z): Calc. for C H N O = 234.04, found= 234.01.
9
6
4
4
2
3
literature .
Synthesis of 1-(2-nitroꢂhenyl)-1H-1,2,3-triazolyl-
4-carboxylic acid (9)
It was prepared by using 1-azido-2-nitro-
benzene 4 (3.8 g, 20.0 mmol): Yield (3.4 g, 70%)
Generalꢂrocedureforthesynthesisof1,2,3-triazole
derivatives (6-10)
To a stirred aqueous solution containing

NAHI et al., Orient. J. Chem., Vol. 35(1), 416-422 (2019)
418
-
1
as a gray solid. FT-IR (KBr disc, cm ), 3500-2700
OH, COOH), 3115 (Ar-H), 1720 (C=O), 1608 (C=C-
1626 (C=N), 1595 (C=C-triazole), 1558 (Ar, C=C)
1
(
and 1363 (-N=N-). H-NMR (500 MHz, DMSO-d ):
6
triazole), 1589 (Ar, C=C), 1404 (-N=N-), 1356 and
δ= 2.0 (s, 3H, CH ), 7.3-7.9 (m, 4H, Ar-H) and 8.7
3
1
1
313 (asymmetric, symmetric NO ). H-NMR (500
(s, 1H, C=CH-triazolyl). HPMS-EI+ (m/z): Calc. for
C H N O= 242.09, found= 242.01.
2
MHz, DMSO-d ): δ= 7.3-8.4(m, 4H, Ar-H) and 8.7
6
11 10
6
+
(
s, 1H, C=CH-triazolyl). HPMS-EI (m/z): Calc. for
C H N O = 234.04, found= 234.0.
Synthesis of 2-amino-5-[1-(3-nitroꢂhenyl)-1H-
9
6
4
4
1,2,3-triazol-4-yl]-1,3,4-oxadiazole (13)
Synthesis of 1-(4-bromoꢂhenyl)-1H-1,2,3-triazole-
-carboxylic acid (10)
It was prepared by using 1-azido-4-bromo-
benzene 5 (3.96 g, 20.0 mmol): Yield (4.7 g, 88%)
It was prepared by using compound 8
4
(2.34 g, 10.0 mmol): Yield (2.0 g, 74%) as a green
-
1
solid. FT-IR (KBr disc, cm ), 3113 (Ar-H), 1664
(C=N), 1632 (C=C-triazole), 1593 (Ar, C=C) and
-
1
1
as a white solid. FT-IR (KBr disc, cm ), 3500-2400
OH, COOH), 3128 (Ar-H), 1705 (C=O), 1656 (C=C-
1352 (-N=N). H-NMR (500 MHz, DMSO-d ): δ=
6
(
4.36 (s, 2H, NH ), 7.4-8.02 (m, 4H, Ar-H) and 8.8
2
+
triazole), 1591 (Ar, C=C), 1413 (-N=N-) and 825
(s, 1H, C=CH-triazolyl). HPMS-EI (m/z): Calc. for
1
(
C-Br). H-NMR (500 MHz, DMSO-d ): δ= 13.2 (s, 1H,
C H N O = 273.06, found= 273.0.
6
10
7
7
3
COOH), 7.6-8.8(m, 4H, Ar-H) and 9.1 (s, 1H, C=CH-
+
triazolyl). HPMS-EI (m/z): Calc. for C H BrN O =
2
Synthesis of 2-amino-5-[1-(2-nitroꢂhenyl)-1H-
1,2,3-triazol-4-yl]-1,3,4-oxadiazole (14)
9
6
3
2
66.96, found= 266.07.
It was prepared using compound 9 (2.34
General ꢂrocedure for synthesis of 1,3,4-
oxadiazoles derivatives (11-15)
g, 10.0 mmol):Yield (1.99 g, 73%) as a brown solid.
-
1
FT-IR (KBr disc, cm ), 3119 (Ar-H), 1653 (C=N),
1608(C=C-triazole), 1590 (Ar, C=C) and 1348
An appropriate 1,2,3-triazole derivative
1
(6-10) (10.0 mmol) and semicarbazide hydrochloride
(1.11 g, 10.0 mmol) were dissolved in POCl3
(25 ml).The resulting reaction mixture was refluxed
(-N=N-). H-NMR (500 MHz, DMSO-d ): δ= 4.9 (s,
6
2H, NH ), 7.3-8.2 (m, 4H, Ar-H) and 8.72 (s, 1H,
2
+
C=CH-triazolyl).HPMS-EI (m/z):Calc.for C H N O
10
7
7
3
for overnight. The reaction mixture was then
allowed to cool into room temperature before being
slowly poured onto crush-ice (200 g). The formed
precipitate was stirred in the same solution for
= 273.06, found= 273.1.
Synthesis of 2-amino-5-[1-(4-bromoꢂhenyl)-1H-
1,2,3-triazol-4-yl]-1,3,4-oxadiazole(15)
1
5 min before being treated carefully with an
It was prepared by using compound 10
(2.68 g, 10.0 mmol):Yield (2.42 g, 79%), as a green
solid. FT-IR (KBr disc, cm ), 3126 (Ar-H), 1654
aqueous solution of sodium hydroxide 50%. The
precipitate was then collected by filtration under
vacuum, washed with water and dried.
-
1
(C=N), 1595 (C=C-triazole), 1560 (Ar, C=C) and
1
1
435 (-N=N-). H-NMR (500 MHz, DMSO-d ): δ=
6
Synthesis of 2-amino-5-[1-(3-methoxyꢂhenyl)-
4.37 (s, 2H, NH ), 7.4-7.99 (m, 4H, Ar-H) and 8.86
(s, 1H, C=CH-triazolyl). HPMS-EI (m/z): Calc. for
2
+
1H-1,2,3-triazol-4-yl]-1,3,4-oxadiazole (11)
It was prepared by using compound 6
C H BrN O= 307.98, found= 308.1.
10
7
6
(
2.19 g, 10.0 mmol): Yield (2.1 g, 85%) as a light
-
1
RESULTS AND DISCUSSION
green solid. FT-IR (KBr disc, cm ), 3136 (Ar-H),
1
653 (C=N), 1610 (C=C-triazole), 1595 (Ar, C=C)
1
Chemistry
For the synthesis of the target 1,3,4-triazole
derivatives 6-10, a series of electron-rich and poor
p-, o- and m-substituted phenyl azido compounds
and 1440 (N=N). H-NMR (500 MHz, DMSO-d ): δ=
6
3.7 (s, 3H, OCH ), 4.3 (s, 2H, NH ), 7.0-7.9 (m, 4H,
3
2
+
Ar-H) and 8.8 (s, 1H, C=CH-triazolyl). HPMS-EI
m/z): Calc. for C H N O = 258.09, found= 258.01.
(
9
7
3
3
1-5 was designed as azido components for CuAAC
Synthesis of 2-amino-5-[1-(3-methylꢂhenyl)-1H-
reaction. These intermediates were synthesized
via reaction of diazonium salts with sodium azide
(Scheme 1) according to the procedure that was
described in the literature . Choosing of these
different azides is to investigate the effect of the
1,2,3-triazol-4-yl]-1,3,4-oxadiazole (12)
It was prepared by using compound 7
2
3
(
2.03 g, 10.0 mmol): Yield (2.17 g, 90%) as a dark
-
1
green solid. FT-IR (KBr disc, cm ), 3059 (Ar-H),

NAHI et al., Orient. J. Chem., Vol. 35(1), 416-422 (2019)
419
nature and position of the substituent group on the
reactivity of their corresponding azides towards click
reaction and on the thermal stability of the synthesized
compounds 6-15. Thus, following our previous
investigations, the synthetic route involved addition of
propiolicacidandanappropriateazide1-5toasolution
of tert-butanol:water (2:1) containing CuSO .5H Oand
titled compounds 6-10 in a relatively high yield. Our
synthetic pathway highlighted a simple work up and
thetargetproducts6-10wereseparatedasprecipitates
from the reaction mixture as pure compounds with no
need to purification by column chromatography. All
newly synthesized compounds were characterized by
1
FT-IR, H-NMR and Mass spectra.
4
2
sodium ascorbate as described in Scheme 1.
As the synthesized 1,2,3-triazole derivatives
6-10 containing a carboxyl function group, so it can be
used to extend their structure. In the current work, it
was aimed to combine the synthesized 1,2,3-triazole
ring system with 1,3,4-oxadiazole ring system in one
molecule to obtain new heterocyclic compounds such
as 11-15 as described in Scheme 3. To achieve this
aim, the synthesized 1,2,3-triazole derivatives 6-10
and semicarbazide hydrochloride were condensed
O
C
OH
NH2
N3
o
COOH .
N
N
i) HCl, NaNO
ii) NaN
2
(0 - 5) C
.
N
3
CuSO4, Na-ascorbate
x
X
x
t-BuOH:H
2
O (2:1)
.
0
5
0
C, 24 h
X= m-OCH
X= m-CH
X= m-NO2
X= o-NO2
X= p-Br
3
1
X= m-OCH
X= m-CH
X= m-NO
X= o-NO
X= p-Br
3
6
7
8
3
2
3
4
5
3
2
in the presence of POCl . The latter is a chlorinating
3
2
9
10
reagent for carboxyl function, which either used as
such or in combination with a solvent.
Scheme 1. Synthesis of 1,2,3-triazole derivatives
N
N
.
Sodium ascorbate was used as a reducing
COOH
agent to produce in situ Cu (I) that is required
to perform a copper (I) catalyzed azide-alkyne
cycloaddition reaction and this reaction is proceeded
according to the general suggested mechanism that
is describe in Scheme 2.
O
NH2
N
N
NH NHCONH .HCl
N
N
2
2
N
N
POCl3
X
X
X= m-OCH3
X= m-CH
X= m-NO2
X= o-NO
X= p-Br
6
7
8
9
10
3
X= m-OCH 11
X= m-CH
X= m-NO
3
12
13
14
15
3
R
1
H
H
2
+
]
[CuL
n
R
1
CuLn-1
2
.
X= o-NO
X= p-Br
2
N
R
2
N
N
R
2
N
N
N
Scheme 3. Synthesis of 1,3,4-oxadiazole derivatives
R
1
H
H
N
R
2
N
N
R
2
N
N
The synthetic route that was devised for the
N
R
1
CuLn-2
synthesis of the target compounds 11-15 followed the
R
1
CuLn-1
25,26
procedures that were described in the litertures
.
The key step in this synthetic route is formation
in situ the intermediate acylsemicarbazides, followed
by a dehydro-cyclization reaction according to a
general mechanism that is shown in Scheme 4. In
general, this reaction was preceded smoothly without
a problem seen to obtain the target compounds 11-15
in a simple work up and pure enough.The structure of
the synthesized compounds 6-15 were characterized
N
R
2
N
N
CuLn-2
R
1
Scheme 2. A general mechanism for the synthesis of
,2,3-triazole derivatives24
1
o
The reaction mixture was heated up to 50 C
and left to stir for overnight. By the first attempt, all
synthesized m-, p- and o-substituted phenyl azides
displayed a reactivity towards click reaction to give the
1
by FT-IR, H-NMR and Mass spectra.
O
O
-
O
O
H
+
N
H
H
N
O
C
HN NH
POCl
3
H
N
- HCl
R
OH
R
Cl
+
H
2
N
R
C
NH
2
R
NH
2
NH
2
O
O
H
3
PO
4
Cl
Tautomerizm
H
H
N
N
N
N
N
N
HN
N
..
-
2
H O
R
NH
2
R
+
NH
2
R
NH
2
O
NH
O
O
-
O
R
2
HO
O
O
H
H
Scheme 4. A general mechanism for the synthesis of 1,3,4-oxadiazoles derivatives27,28

NAHI et al., Orient. J. Chem., Vol. 35(1), 416-422 (2019)
420
Thermal behavior study
Thermal analysis is an important technique
used to investigate the thermal behavior of
compounds such as a presence of intermediates,
degradation process, melting and final known
2
9-31
composition
. In the current study, the thermal
analysis of the target compounds 6-15 was achieved
by using TGA combine DTG techniques. Thermo
gravimetry (TG) is a useful analytical technique
used for thermal analysis that is used for recording
weight losing of a tested sample as a function of
32
temperature .While, DTG curves help to permit the
direct application of the rate function of the change
in the weight of the target sample to the study of
phenomena occurring during thermo gravimetric
analysis. Where, the area of the peak (Tinitial, Tfinal) is
directly proportional to the mass loss over the same
temperature range and the DTG peak high at any
temperature gives the rate of mass loss (dm/dT in mg/
min unit) .Practically, depending on the nature of the
m-, p-, o-rich or poor-electron substituted phenyl that
is attached to N1-position of 1,2,3-triazole ring,
TG-DTG curves of compounds 6-10 are depicted in
Fig.2 and 3.It is evident from these figures andTable
Fig. 2. TG curves of comꢂounds 6-10
Fig. 3. DTG curves of comꢂounds 6-10
Fig. 4. TG curves of comꢂounds 11-15
33
1
that compounds 6,7,8,9 and 10 are thermally stable
o
up to 205, 223, 182, 135 and 222 C, respectively,
followed a single decomposition stage. In addition,
as expected compounds 8 and 9 displayed a
less thermal stability due to their structures
contain nitro group which can be described as
thermally unstable group. Since, 1,3,4-oxadiazole
ring system is considered a thermally stable
species, TG-DTG measurements indicated that the
synthesized compounds 11-15 have a higher thermal
o
stability than their precursors 6-10 up to 205 C
then decomposed in a single stage as shown in
Fig. 4 and 5 and Table 1.
Table 1:TG-DTG data of comꢂounds 6-15
o
Comp. No TG decomposition Losing weight (%) DTGmix ( C)
temperature
o
Range ( C)
6
7
8
9
205-302
223-243
182-232
135-195
222-283
250-378
206-403
248-363
215-382
238-402
49
51
42
97
29
30
23
31
24
38
258
234
220
188
235
342
326
327
285
343
1
0
1
2
3
4
5
1
1
1
1
1

NAHI et al., Orient. J. Chem., Vol. 35(1), 416-422 (2019)
CONCLUSION
421
In conclusion, a series of electron-rich and
poor phenyl azide compounds displayed a reactivity to
react with propiolic acid via click reaction (CuAAC).Since
the synthesised 1,2,3-triazole derivatives containing
a carboxyl functional group, it used to extend their
structure with 2-amino-1,3,4-oxadiazole ring system
via reaction with semicarbazide hydrochloride in the
presence of POCl . Furthermore, all synthesized
3
heterocyclic compounds displayed a relatively good
thermal stability.
ACKNOꢀLEDGMENT
Theauthorswouldliketothankthedepartment
ofchemistry/CollegeofScience/Al-MuthannaUniversity
for the facilities during doing this work.
Fig. 5. DTG curves of comꢂounds 11-15
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