Dodecanoyl thiosemicarbazide derivatives as useful synthons in the synthesis of 1,2,4-triazole, 1,3,4-thiadiazole, and 1,3-benzothiazole derivatives

Article abstract of DOI:10.1080/00397911.2016.1164865

A convenient synthesis of the dodecanoyl thiosemicarbazide derivatives 3a, b has been achieved from the reaction of 2-benzamido-3-arylacryloylhydrazides 1a, b and lauroyl isothiocyanate (2). The thiosemicarbazide derivative 3a is used as precursor for syn

Full text of DOI:10.1080/00397911.2016.1164865

Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic
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Dodecanoyl Thiosemicarbazide Derivatives
as Useful Synthons in the Synthesis of 1,2, 4-
triazole, 1, 3, 4-thiadiazole and 1, 3-benzothiazole
Derivatives
Magdy M. Hemdan, Wael S. I. Abou Elmagd, Sandy S. Samy & Ahmed S. A.
Youssef
To cite this article: Magdy M. Hemdan, Wael S. I. Abou Elmagd, Sandy S. Samy & Ahmed
S. A. Youssef (2016): Dodecanoyl Thiosemicarbazide Derivatives as Useful Synthons in the
Synthesis of 1,2, 4-triazole, 1, 3, 4-thiadiazole and 1, 3-benzothiazole Derivatives, Synthetic
Communications, DOI: 10.1080/00397911.2016.1164865
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Date: 06 April 2016, At: 21:46

Dodecanoyl thiosemicarbazide derivatives as useful synthons in the synthesis of 1,2,
-triazole, 1, 3, 4-thiadiazole and 1, 3-benzothiazole derivatives
4
1
1
1
1
Magdy M. Hemdan , wael S. I. Abou Elmagd , Sandy S. Samy , Ahmed S. A. Youssef
1
Chemistry Department, Faculty of Science, Ain Shams University, Abassia, Cairo,
Egypt
Corresponding author wael S. I. Abou Elmagd E-mail: waelmagd97@yahoo.com
Abstract
A convenient synthesis of the dodecanoyl thiosemicarbazide derivatives 3a, b has been
achieved from the reaction of 2-benzamido-3-arylacryloylhydrazides 1a, b and lauroyl
isothiocyanate (2). The thiosemicarbazide derivative 3a is used as precursor for synthesis
of 1, 2, 4-triazole, 1, 3, 4-thiadiazole and 1, 3-benzothiazole derivatives. The
antimicrobial activity of some of the synthesized compounds was tested.
KEYWORDS: lauroyl isothiocyanate, hydrazide; 1,2,4-triazole; 1,3,4-thiadiazole; 1,3-
benzothiazole derivatives
INTRODUCTION
Derivatives of thiosemicarbazide are class of organic compounds that were found to be
[1-4]
[5]
associated with various biological activities.
They are known to exhibit antifungal,
[
6]
[7]
anti-inflammatory, anti HIV and herbicidal activities. Moreover, they are used as
[
8]
[9]
corrosion inhibitors of steal and semiconductors, in addition to their uses in the metal
[10, 11]
complexes.
Thiosemicarbazides are versatile compounds, that have been extensively
1

[
12-14]
used in the synthesis of different heterocyclic ring systems.
The synthesis of
compounds that involve 1, 2, 4-triazole, 1, 3, 4-thiadiazole and 1, 3-benzothiazole rings
in their structures has attracted widespread attention, mainly in connection with their
wide range of pharmacological properties. Several synthetic protocols have been reported
[
15-20]
in the literature for this aspect.
In view of the above-mentioned finding and in
[
21-22]
continuation of our research in the domain of heterocyclic synthesis,
herein, the
synthesis of acyl thiosemicarbazides and their cyclization with different reagent under
different media are described.
RESULTS AND DISCUSSIONS
Dodecanoyl thiosemicarbazide derivatives 3a, b were prepared by reaction of a solution
of lauroyl isothiocyanate (2) in dry acetonitrile with hydrazide derivatives 1a and 1b,
respectively (Scheme 1). The spectral properties of the new products agree with their
proposed structures. Thus, their multiple NH groups give rise to bands in the range 3382-
-1
-
3
128 cm in their infrared (IR) spectra. Intense broad bands in the region 1547-1540 cm
1
,
indicative of C-N-H vibration that is regarded as combination bands due to NH-
-1
deformation and C-N stretching. They show stretching C-H bands at 2954 and 2850 cm .
-1. T
1
Their carbonyl groups produced absorption bands at 1693-1644 cm he H NMR
spectra of compounds 3a, b are presented in the experimental section and are in accord
with their proposed structures. They are revealed aliphatic and aromatic protons in
addition to NH protons in the downfield region that were exchanged with D O shake.
2
Their Mass spectra showed important fragments peaks consistence with the proposed
structures.
2

The idea behind the uses of the thiosemicarbazide derivatives 3a, b as useful building
blocks for synthesis of many target heterocyclic systems depends on the fact that they are
open chain multifunctional compounds. Their behaviors toward different reagents are
interesting and sometimes are unexpected. Thus, the reaction of a solution of compound
3
a with hydrazine hydrate in ethanol afforded a mixture of 1, 2, 4-triazol derivative 4 and
hydrazide derivative 1a. However, its treating with phenylhydrazine gave the adduct 5 in
a good yield. On the other hand, refluxing of 3a with 2-aminothiophenol in n-butanol
gave a mixture of 1, 3-benzothiazole derivative 7 and hydrazide derivative 1a (Scheme
2
).
The infrared spectra of the synthesized compounds showed absorption frequencies
correlated with NH group, as well as, C=N group for compound 7 in addition to C=O
group for compounds 1a, 4, and 5. Further support for the assigned structures of
1
compounds 4, 5 and 7 was gained from their HNMR spectra that displayed signals
corresponding to aliphatic and aromatic protons lauryl group as well as exchangeable
signals in the down field region correlated with NH protons and in addition to aromatic
protons for compounds 5 and 7 (see Experimental). The appearance of two broad singlet
1
signals in the down field region of HNMR spectrum of compound 7 suggests its
existence as an equilibrium mixture of two tautomeric forms 7a and 7b in the ratio 3:2.
The higher ratio of tautomer 7a as compared with tautomer 7b may be attributed to its
higher stability as the thiazole ring is fully aromatic. In addition, the higher δ value for
the signal of NH proton of tautomer 7b suggests its existence as its chelated form shown
3

1
3
(
Scheme 2). Further evidence for structures 4, 5 and 7 was gained from their CNMR
spectrum (cf. experimental). Their mass spectra revealed the correct molecular ion peaks,
in addition to some important fragments peaks consistence with their proposed structures.
The formation of compound 4 can be explained on the basis of nucleophilic attack of a
hydrazine molecule on the thiocarbonyl group of 3a to give the hydrazide 1a and the
lauoryl thiosemicabazide (not isolated) that underwent cyclization followed by reaction
with another molecule of hydrazine to afford the 1, 2, 4-triazol derivative 4 as shown in
Scheme 2. Compound 7 is formed by cyclocondensation of 2-aminothiophenol with
compound 3a, followed by expulsion of the hydrazide 1a. In case of the reaction of 3a
with phenylhydrazine, β-addition to the α-enone system is favored to give compound 5.
A further aspect of reactivity of compound 3a was exemplified by its heating with
phosphoryl trichloride to produce 1, 3, 4-thiadiazole derivative 8. Treating an alcholic
solution of 3a with a mixture of hydrogen peroxide and hydrochloric acid gave 1, 2, 4-
triazine derivative 10. On the other hand, its refluxing with a mixture of hydrochloric acid
and acetic acid furnished 1,2,4-triazole derivative 11 and oxazolone derivative 12.
Compounds 11and 12 were rigidly confirmed by TLC and mp comparison with authentic
[
22,23]
samples as reported.
Furthermore, it afforded 1, 2, 4-triazole derivative 13 on its refluxing with ethanolic
sodium hydroxide solution as shown in Scheme 3.
4

The infrared spectra of the synthesized compounds 8, 9-13 showed absorption bands
correlated with their functional groups (see Experimental part). Further support for the
1
assigned structures was gained from their H NMR spectra, which exhibit signals
characteristic for aliphatic and aromatic protons in addition to NH protons in the
1
downfield region which were exchanged with D O shake. Inspection of the HNMR
2
spectrum of compound 13 revealed the existence of eight exchangeable broad singlet
signals in the down field region; this suggests its existence in deuterated dimethyl
sulfoxide solution as an equilibrium mixture of tautomers 13a-c (cf.scheme 3). Moreover,
the mass spectral data are in accord with their proposed structures as they showed the
molecular ion peaks as well as some of the important fragment peaks. The most plausible
explanation for the formation of compound 8 is explained by elimination of a molecule of
water from 3a by the action of POCl . The formation of compound 10 can be rationalized
3
on the basis of hydrolysis of 3a to the corresponding hydrazide followed by cyclization
via removel of a water molecule to give the non-isolable intermediate 9. As shown in
Scheme 4, compound 3a undergoes hydrolysis in acidic medium to give compounds 11
and 12. The formation of compound 13 can be explained on the basis of hydrolysis of
compound 3a to afford the non-isolable thiosemicarbazide derivative [A] that underwent
cyclocondensation.
BIOLOGICAL ACTIVITY
The antimicrobial screening of some of the synthesized compounds was done using
.
[24]
Kirby-Bauer disc diffusion method
Briefly, 100 μl of the tested bacteria/fungi were
grown in 10 μl of fresh media until they reached a count of approximately 108 cells/ml
5

.
[25]
for bacteria or 105 cells/ml for fungi 100 μl of microbial suspension was spread onto
agar plates corresponding to the broth in which they were maintained. The possible
antimicrobial activities of the synthesized compounds 3a, 5 and 8 were investigated to
four standard organisms including the Gram-positive bacteria, Staphylococcus aureus and
the Gram-negative bacteria, Escherichia coli, in addition to Candida albicans (fungus)
and Aspergillus flauvs (fungus). The obtained results in (Table 1) emphasized the fact
that the chemical agent symbolized Compounds 3a and 5 exhibited high activity against
the examined microorganisms. While 8 showed moderate activity against the Gram-
positive bacteria, Staphylococcus aureus, the Gram-negative Escherichia coli and
Candida albicans (fungus) and didn't show activity against Aspergillus flauvs (fungus).
CONCLUSION
The dodecanoyl thiosemicarbazides could serve as a useful building block for synthesis
of many target heterocyclic systems. It depends on the fact that it is an open chain
multifunctional compound. Its behavior towards different reagents is interesting. The
introduction of lauryl group (a hydrocarbon part) to compound 3a, 5 and 9 affected their
antimicrobial activity. The lipophilic property of the hydrocarbon moiety, favors the
permeation of the compounds through lipoid barriers in the microorganisms cells
[
26]
membrane.
EXPERIMENTAL
Melting points of the reaction products were measured in open capillary tubes on an
electrothermal melting point apparatus and were uncorrected. The elemental analyses
6

were performed on a Perkin-Elemer 2400 CHN elemental analyzer. The infrared spectra
were recorded on Perkin-Elemer Modle 297 Infrared spectrometer using the KBr wafer
1
13
technique. The H- and C-NMR spectra were measured on Varian Gemini 300 and 75
MHz spectrometer, with chemical shift (δ) expressed in ppm downfield with
tetramethylsilane (TMS) as internal standard, in DMSO-d6 and coupling constants J in
Hz. Mass spectra were determined on Shimadzu GC-MSQP 1000 EX instrument
operating at 70 eV. Thin layer chromatography (TLC) was run using TLC aluminum
sheets silica gel F254 (Merck). It was carried out the monitoring of the progress of all
reactions and homogeneity of the synthesized compounds. The antimicrobial activity was
done at Micro Analytical Center at Cairo University.
SYNTHESIS OF THE THIOSEMICARBAZIDE DERIVATIVES 3A AND 3B
General Method
A solution of lauroyl isothiocyanate 3 mmol and hydrazide derivatives 1a or 1b
3
mmol in 30 ml dry acetonitrile was stirred at room temperature for 2h. The resulting
yellow solid product was collected by filtration and recrystallized from benzene to give
the corresponding compounds 3a or 3b, respectively.
1
-(2-BENZAMIDO-3-PHENYLACRYLOYL)-4-
DODECANOYLTHIOSEMICARBAZIDE (3A):
-1
Yellow crystals (86%), m.p 164-166 °C (benzene); FTIR (KBr) cm : 3382, 3243, 3191
(NH), 3051, 3022 (aryl-H), 2954, 2919, 2850 (alkyl-H), 1689, 1661, 1643 (CO), 1287
1
(
CS), 689, 762 δ . HNMR (DMSO-d6): δ 0.85 (t, J = 6.9, 6.3 Hz, 3H,
5
H
7

CH (CH ) CH CH CO), 1.25 (m, 16H, CH (CH ) CH CH CO), 1.55 (m, 2H,
3
2 8
2
2
3
2 8
2
2
CH (CH ) CH CH CO), 2.42(t, J = 7.5, 7.2 Hz, 2H, CH (CH ) CH CH CO), 7.34-7.41
3
2 8
2
2
3
2 8
2
2
(
m, 4H, (3PhH+1CH=)), 7.50-7.62 (m, 5H, Ph-H), 7.99 (d, J = 7.2 Hz, 2H), 10.11 (br. s,
H, CSNHNHCO, exchangeable), 10.76 (br.s, 1H, CSNHNHCO, exchangeable), 11.56
br. s, 1H, NHCOPh, exchangeable), 12.51 (br. s, 1H, CONHCS, exchangeable). MS
1
(
(
+
.
70eV) m/z (%): 522 (M , 1), 504 (27), 445 (90), 262 (100), 183 (97), 145 (45). Anal.
Calcd. for C H N O S (522.70): C, 66.64; H, 7.33; N, 10.72. Found C, 66.32; H, 7.11;
2
9
38
4
3
N, 10.56%.
1
-(2-Benzamido-3-(1, 3-diphenyl-1H-pyrazol-4-yl)acryloyl)-4-dodecanoylthio-
-1
semicarbazide (3b): Yellow crystals (81%), m.p 170-172 °C (EtOH);FT IR (KBr) cm :
3
6
1
=
284, 3196 (NH), 3059 (aryl-H), 2923, 2851 (alkyl-H), 1693, 1644 (CO), 1243 (CS),
1
92, 750 δ . HNMR (DMSO-d6): δ 0.85 (t, J = 6.6 Hz, 3H, CH (CH ) CH CH CO),
5
H
3
2 8
2
2
.24 (m, 16H, CH (CH ) CH CH CO), 1.54 (m, 2H, CH (CH ) CH CH CO), 2.42 (t, J
3
2 8
2
2
3
2 8
2
2
7.5, 7.2 Hz, 2H, CH (CH ) CH CH CO), 7.35 (t, J = 7.5 Hz, 2H, Ar-H), 7.44-7.60 (m.
3
2 8
2
2
9
, (7Ph-H+ 1CH=, pyrazolo-H)), 7.73 (t, J = 9.0 Hz, 4H), 8.03 (d, J = 7.2 Hz, 2H), 8.66
br.s, 1H, CSNHNHCO, exchangeable), 9.91 (br.s, 1H, CSNHNHCO, exchangeable),
0.77 (br.s, 1H, NHCOPh, exchangeable), 11.54 (br. s, 1H, CONHCS, exchangeable).
(
1
+
.
MS (70eV) m/z (%): 664 (M , 0), 392 (0.5), 391 (8),298 (10), 244 (7), 242 (2), 197 (9),
05 (39), 80 (100).
Anal. Calcd. for C H N O S (664.86): C, 68.65; H, 6.67; N, 12.64. Found C, 68.49; H,
1
3
8
44
6
3
6
.53; N, 12.37%.
8

MEASUREMENT OF ANTIMICROBIAL ACTIVITY USING KIRBY-BAUER
METHOD
o
Plates inoculated with filamentous fungi as Aspergillus fluvs at 25 C for 48 hours; Gram-
positive bacteria, as Staphylococcus aureus; Gram-negative bacteria as Escherichia coli
o
they were incubated at 35-37 C for 24-48 hours and yeast as Candida albicans incubated
o
at 30 C for 24-48 hours and then the diameters of the inhibition zones were measured in
millimeters. Standard discs of Tetracycline (antibacterial agent) and Amphotericin
(antifungal agent) were served as positive controls for antimicrobial activity, but filter
discs impregnated with 10 μl of DMSO were used as a negative control. The agar used is
Meuller-Hinton agar. Blank paper disks (Schleicher & Schull, Spain) with a diameter 8.0
mm were impregnated 10 μl of tested concentration of the stock solutions. When a filter
paper disc impregnated with a tested chemical is placed on agar the chemical will diffuse
from the disc into the agar. This diffusion will place the chemical in the agar only around
the disc. The solubility of the chemical and its molecular size will determine the size of
the area of chemical infiltration around the disc. If an organism is placed on the agar it
will not grow in the area around the disc if it is susceptible to the chemical, this area of no
growth around the disc is known as "zone of inhibition" of "clear zone".
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1
3

Table 1 Antimicrobial Activity of Selected Compounds
No Inhibition zone diameter (mm/mg sample)
Staphylococcus
Escherichia
Candida albicans Aspergillus flauvs
+
-
aureus G
coli G
(fungus)
18
(fungus)
21
3
5
8
a
20
19
14
16
18
14
18
15
13
15
0.0
Am 22
Am
B
17
19
Am =Ampicillin (antibacterial agent), AmB= Amphotericin B (antifungal agent). The
concentration of all synthesized compounds and the reference was (5 mg / 1 mL of
DMSO). Zone of inhibition: 0-11 mm (low); 11-15 mm (moderate); > 15 mm (high); 0.0
=
no inhibition.
1
4

Scheme 1.
1
5

Scheme 2.
1
6

Scheme 3.
1
7

Scheme 4.
1
8