Efficient, straightforward, catalyst-free synthesis of medicinally important S-alkyl/benzyl dithiocarbamates under green conditions

Article abstract of DOI:10.1007/s11164-017-3167-1

Green synthesis of some novel dithiocarbamate derivatives substituted by aliphatic and aromatic groups as potentially interesting, medicinally important organic compounds via efficient one-pot, catalyst-free reaction is described. In this reaction, dithiocarbamate derivatives are obtained from condensation reaction between primary or secondary amines, carbon disulfide, and alkyl or benzyl halides in one pot and ethanol–aqueous medium. Among aliphatic and aromatic amines, the results generally show that reaction of aliphatic amines with alkyl or benzyl halides led to desired products in highest yields. Also, among aliphatic amines, those which reacted with benzyl halides showed better yields than those that reacted with alkyl halides. Use of environmentally benign solvents is one of the advantages of this procedure. Also, obtaining products in good yield via catalyst-free reaction using a facile, inexpensive, and practical approach can be considered other advantages of this procedure. Target products are very important compounds, because their analogs have been applied in pharmaceutical, chemical, and rubber industries.

Full text of DOI:10.1007/s11164-017-3167-1

Res Chem Intermed
DOI 10.1007/s11164-017-3167-1
Efficient, straightforward, catalyst-free synthesis
of medicinally important S-alkyl/benzyl
dithiocarbamates under green conditions
Ali Asadipour1 Zeynab Shams1
·
·
Khalil Eskandari1
Mohammad-Hassan Moshafi2
·
·
Ehsan Faghih-Mirzaei1 Yaghoub Pourshojaei1,3
·
Received: 19 July 2017 / Accepted: 4 October 2017
© Springer Science+Business Media B.V. 2017
Abstract Green synthesis of some novel dithiocarbamate derivatives substituted by
aliphatic and aromatic groups as potentially interesting, medicinally important
organic compounds via efficient one-pot, catalyst-free reaction is described. In this
reaction, dithiocarbamate derivatives are obtained from condensation reaction
between primary or secondary amines, carbon disulfide, and alkyl or benzyl halides
in one pot and ethanol–aqueous medium. Among aliphatic and aromatic amines, the
results generally show that reaction of aliphatic amines with alkyl or benzyl halides
led to desired products in highest yields. Also, among aliphatic amines, those which
reacted with benzyl halides showed better yields than those that reacted with alkyl
halides. Use of environmentally benign solvents is one of the advantages of this
procedure. Also, obtaining products in good yield via catalyst-free reaction using a
facile, inexpensive, and practical approach can be considered other advantages of
this procedure. Target products are very important compounds, because their ana-
logs have been applied in pharmaceutical, chemical, and rubber industries.
Electronic supplementary material The online version of this article (doi:10.1007/s11164-017-3167-1)
contains supplementary material, which is available to authorized users.
&
&
1
Khalil Eskandari
khalileskandari@yahoo.com
Yaghoub Pourshojaei
y.pourshoja@kmu.ac.ir
Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutics Research Center,
Kerman University of Medical Sciences, Kerman, Iran
2
Department of Pharmaceutical Science, School of Pharmacy, Kerman University of Medical
Science, Kerman, Iran
3
Neuroscience Research Center, Institute of Neuropharmacology, Kerman University of Medical
Sciences, Kerman, Iran
123

A. Asadipour et al.
Keywords Dithiocarbamate · Alkyl halide · Amine · Catalyst-free · Ethanol–
aqueous medium
Introduction
Over the past few decades, synthesis and development of novel, medicinally
important organic compounds with potential applications in medicine and pharma-
ceutical industries have attracted interest in the fields of synthetic chemistry and
pharmacology. Among the broad category of S-containing organic compounds,
dithiocarbamate derivatives have been shown to exhibit a wide range of biological
and pharmacological activities; For instance, numerous investigations have revealed
that dithiocarbamates exhibit various activities, including antiproliferative [1],
antiglaucoma [2], antibacterial [3], antifungal [3], spermicidal [4], breast cancer
treatment [5], and cholinesterase inhibition [6–8] effects, as well as being used as
myocardial imaging agents [9]. In addition, their in vitro antitumor activity against
human myelogenous leukemia K562 cells has been described [10]. They are known
to be HIV-I NCp7 inhibitors, and antivirus agents [11], as well as nonvanilloid
TRPV1 antagonists [12, 13]; For instance, some chemical structures bearing the
dithiocarbamate scaffold that have been recognized as potential therapeutic drugs
are shown in Fig. 1 [14–16]. Furthermore, dithiocarbamates are widely used as
synthetic intermediates [17–21], precursors for synthesis of nanoparticles [22], in
vulcanization of rubbers [23], and as ligands for chelating metals [24].
The importance of this type of compound is clear from the discussion above. To
date, several routes have been proposed and developed by chemists for synthesis of
dithiocarbamates; For instance, reaction of amines with thiophosgene or isothio-
cyanates (costly and toxic reagents) [25], catalytic reaction of amines with carbon
Fig. 1 Selected pharmacologically active organic compounds containing dithiocarbamate framework
123

Efficient, straightforward, catalyst-free synthesis…
disulfide and alkyl halides [26], Michael acceptors [27], organyl thiocyanates [28],
allyl acetate [29], epoxide [30], or tosyl hydrazone [31] can lead to dithiocarbamate
derivatives. However, there are several disadvantages to some of these methods,
including the hazards of handling isothiocyanates, obtaining side-products such as
urethane, poor long-term stability of some precursors, multistep and tedious
procedures, the need for high reaction temperatures, and obtaining low or moderate
yields.
Loading and obtaining organic products in ethanol–aqueous media has attracted
significant attention because of its safety, environmental friendliness, and green
chemistry features [32–35]. Carrying out organic reactions in water-based systems
to successfully obtain products under green conditions is very significant and
notable, especially from the industrial and environmental points of view. Therefore,
use of nontoxic, readily available, inexpensive, and harmless solvents has received
growing attention over the last few decades [32–35].
In continuation of our studies on synthesis of novel derivatives of organic and
heterocyclic compounds [36–41], we report herein a new route for efficient,
catalyst-free, environmentally safe synthesis of some novel and known dithiocar-
bamates via one-pot reaction of primary or secondary amines, carbon disulfide, and
alkyl or benzyl halides in ethanol–aqueous medium (Scheme 1).
Results and discussion
In the first step, and before expanding its scope, the reaction was examined in
presence of various solvents to determine the best solvent(s) for reaction progress.
For this purpose, the reaction to obtain product 4e was selected as a model. The
results of this evaluation on the model reaction are summarized in Table 1.
As seen from Table 1, the product yield obtained when using the mixture of H2O/
EtOH (1:4) was maximum. Furthermore, from the obtained data, it can be
understood that the progress of the reaction was acceptable without need for any
acidic or basic catalyst, which can be considered as one of the advantages of this
procedure. Running the reaction in ethanol–aqueous medium with nontoxic solvents
H2O/EtOH
S
C
S
R'
S
H
N
1:4
R-X
N
r.t., 5-24 h
75-90%
R'
R"
R''
S R
1
2
4
3
R: Me, Et, p-BrbenzylBr(Cl), p-ClbenzylBr(Cl), m-ClbenzylBr(Cl)
3: Benzylamine, p-anisidine, o-toluidine, morpholine, piperidine,
p-benzylpiperidine
Scheme 1 Catalyst-free synthesis of dithiocarbamate derivatives under green conditions
123

A. Asadipour et al.
Yielda (%)
Table 1 Evaluation of reaction
progress in presence of different
solvents
Entry
Solvent
Time (h)
1
Ether
12
12
10
12
8
30
37
65
48
54
10
74
81
80
87
90
92
92
2
Acetone
3
THF
4
Dichloromethane
Chloroform
Toluene
4
5
12
10
10
8
6
H2O
7
EtOH
8
H2O/EtOH (1:1)
H2O/EtOH (1:2)
H2O/EtOH (1:3)
H2O/EtOH (1:4)
H2O/EtOH (1:5)
9
8
10
11
12
7
6
6
a
Isolated yields
makes the procedure environmentally safe and compatible with green chemistry,
while the addition of precursors and synthesis of products in one pot to obtain
products in good to excellent yield represent further advantages of this procedure.
Therefore, we decided to run this reaction in ethanol–aqueous medium, H2O/EtOH
(1:4), without use of any catalysts in one pot. After identifying appropriate solvents
as reaction media, in order to examine the generality and expand the scope of the
reaction, this three-component reaction was carried out with numerous primary or
secondary amines, carbon disulfide, and some different alkyl or benzyl halides in
one pot in presence of the mixture of H2O/EtOH (1:4). The obtained products and
results are summarized in Table 2.
In general, among cyclic or linear alkylamines and arylamines, cyclic alkylami-
nes such as piperidine and morpholine showed higher yields compared with the
others. It is believed that nucleophilicity of cyclic alkylamines is higher than others,
and the nonbonding electron pair on nitrogen is more accessible because they are
rigid and nonflexible. The main role of water as part of the reaction media and its
mechanism are still not clear. In contrast to the low solubility of amines and alkyl
halides in water, this three-component reaction is accelerated in ethanol–aqueous
medium, progressing efficiently at ambient temperature.
The structures of all newly prepared compounds were deduced from their
Fourier-transform infrared (FT-IR), 1H and 13C nuclear magnetic resonance (NMR)
spectroscopy, and elemental analyses. For instance, the FT-IR spectrum of
compound 4k exhibited CH aromatic and aliphatic stretching bands at 2991,
2940, and 2852 cm−1. The band appearing at 1585 cm−1 is related to C–C stretching
of aromatic ring. The bands at 1479 and 1277 cm−1 correspond to C–N and C=S
stretching, respectively. In addition, the peak at 1425 cm−1 corresponds to aromatic
1
C–C bending. In the H NMR spectrum of 4k, four protons of aromatic ring are
represented by two doublets at 7.46 ppm (J = 9 Hz) and 7.31 ppm (J = 9 Hz). A
singlet at 4.56 ppm corresponds to benzylic CH2 group. The four protons of -CH2-
N-CH2 appear at 4.32 and 3.90 ppm as two broad singlets. Also, a broad singlet at
123

Efficient, straightforward, catalyst-free synthesis…
Table 2 Efficient synthesis of medicinally important dithiocarbamate derivatives in ethanol–aqueous
medium
Entry
1
Product
Yielda (%)
75
M.p. (°C)/[Lit.]
S
N
H
S
64–67b
Br
4a
O
H3C
S
S
70–73b
N
S
S
2
3
70
74
H
4b
O
H3C
115–119
N
H
(115) [42]
Br
4c
S
140–143
N
S
H
4
69
92
CH3
(140–141) [43]
4d
S
N
S
89–90
5
6
7
O
Br
(90–91) [44]
4e
S
S
N
N
S
S
81–84
89
90
O
(82–84) [45]
4f
39–42
O
(40) [46]
4g
S
N
S
8
85
48–50b
4h
1.73 corresponds to other six protons of piperidinyl ring. The 13C NMR spectrum of
4k exhibits 10 distinguished peaks, in agreement with the compound’s chemical
structure. Furthermore, the CHN analysis results strongly confirmed the structure of
4k.
123

A. Asadipour et al.
Table 2 continued
Entry
Product
Yielda (%)
M.p. (°C)/[Lit.]
S
N
S
Br
89–91b
9
88
4i
4j
S
S
N
N
S
S
153–156c
10
11
79
82
(155–159) [47]
74–77b
Br
4k
4l
S
N
S
Cl
101–104b
12
86
S
N
S
74–78
13
14
15
84
89
85
O
Cl
Cl
(79–81) [28]
4m
S
N
S
55–58b
O
4n
S
N
S
84–87
Cl
(83–85) [28]
4o
a
Isolated yields
Novel products
b
c
Physical form of isolated product is viscose liquid (oil), therefore its boiling point has been measured
123

Efficient, straightforward, catalyst-free synthesis…
Experimental
All chemicals and starting materials were purchased from Merck and Sigma-Aldrich
chemical companies and were used without further purification. Electrothermal
IA9100 melting point apparatus fixed at 1 °C/min was used for melting point
measurements. Bruker FT-IR Tensor 27 infrared spectrophotometer with KBr as
matrix was used for recording IR spectra. Fourier-transform nuclear magnetic
1
resonance Bruker Avance Ultrashield spectrometer (at 500 MHz for H NMR and
1
125 MHz for 13C NMR, with DMSO-d6 as solvent) was applied for recording H
and 13C NMR spectra. Elemental analyses (C/H/N/S) were carried out on a Heraeus
Rapid analyzer; the results showed good agreement ( 0.3 %) with calculated
values. Reaction progress was monitored on TLC-grade silica gel G/UV (254 nm)
plates.
General procedure for preparation of S-alkyl/benzyl dithiocarbamates
To a stirred round-bottomed flask containing 15 mL solvent (H2O/EtOH, 1:4)
equipped with ice bath, appropriate amine (1 mmol), and carbon disulfide
(1.6 mmol) were added. After 2 h of stirring, appropriate alkyl or benzyl halide
(1 mmol) was added. Then, the temperature of the mixture was allowed to reach
room temperature. Reaction progress was monitored by TLC (n-hexane/EtOAc, 4:1
as eluents). After reaction completion in appropriate time (5–24 h), the product was
precipitated. The synthesized compound was filtrated to obtain crude product. Pure
product was obtained by trituration in boiling ethanol. If the synthesized compound
was not precipitated, the solvent was evaporated by rotary evaporator under reduced
pressure to give crude product. Afterwards, pure product was obtained by column
chromatography using EtOAc/n-hexane 1:6 as eluent.
Representative spectral data
4-Bromobenzyl benzylcarbamodithioate (4a) FT-IR (KBr, ῡ, cm−1): 3310, 3026,
2995, 2903, 1639, 1601, 1506, 1485, 1390, 1235, 1087, 1052, 1009. H NMR
1
(CDCl3, 300 MHz) δ (ppm): 9.54 (1H, d, J = 6 Hz, NH), 7.45 (2H, d, J = 6 Hz,
CHAr), 7.38–7.22 (5H, m, CHAr), 7.13 (2H, d, J = 6 Hz, CHAr), 4.93 (2H, d,
J = 6 Hz, CH2), 4.55 (2H, s, CH2). 13C NMR (CDCl3, 75 MHz) δ (ppm): 197.0,
131.7, 131.6, 131.0, 130.7, 130.5, 129.7, 128.9, 128.8, 128.3, 121.5, 51.4, 42.6.
Anal. Calcd. for C15H14BrNS2 (352.31): C, 51.14; H, 4.01; N, 3.98; S, 18.20.
Found: C, 51.33; H, 4.15; N, 4.01, S, 18.15.
Ethyl (4-methoxyphenyl)carbamodithioate (4b) FT-IR (KBr, ῡ, cm−1): 3119, 3020,
1
2958, 2927, 2834, 1603, 1510, 1250, 1011. H NMR (CDCl3, 300 MHz) δ (ppm):
9.26 (1H, s, NH), 7.31 (2H, d, J = 6 Hz, CHAr), 6.94 (2H, d, J = 6 Hz, CHAr), 3.85
(3H, s, OCH3), 3.29 (2H, q, J = 6 Hz, CH2), 1.36 (3H, t, J = 6 Hz, CH3). 13C NMR
(CDCl3, 75 MHz) δ (ppm): 202.7, 159.0, 130.8, 127.6, 114.4, 55.5, 30.7, 13.7. Anal.
123

A. Asadipour et al.
Calcd. for C10H13NOS2 (227.34): C, 52.83; H, 5.76; N, 6.16; S, 28.20. Found: C,
52.88; H, 5.68; N, 6.20, S, 28.11.
Ethyl 4-benzylpiperidine-1-carbodithioate (4h) FT-IR (KBr, ῡ, cm−1): 3024, 2990,
2930, 1602, 1493, 1473, 1437, 1260, 1186, 1056, 1002, 927, 749, 701. H NMR
1
(CDCl3, 300 MHz) δ (ppm): 7.35–7.16 (5H, m, CHAr), 5.62 (1H, brs, CH), 4.66 (1H,
brs, CH), 3.33 (2H, q, J = 6 Hz, CH2), 3.08 (2H, brs, CH2), 2.60 (2H, d, J = 6 Hz,
CH2), 1.98–1.87 (1H, m, CH), 1.82 (1H, brs, CH), 1.78 (1H, brs, CH), 1.39 (3H, t,
J = 6 Hz, CH3), 1.37 (2H, brs, CH2). 13C NMR (CDCl3, 75 MHz) δ (ppm): 196.1,
139.7, 129.0, 128.3, 126.1, 51.7, 50.3, 42.6, 38.1, 31.8, 31.5, 13.7. Anal. Calcd. for
C15H21NS2 (279.46): C, 64.47; H, 7.57; N, 5.01; S, 22.94. Found: C, 64.55; H, 7.43;
N, 5.12, S, 22.78.
4-Bromobenzyl 4-benzylpiperidine-1-carbodithioate (4i) FT-IR (KBr, ῡ, cm−1):
3059, 3015, 2994, 2934, 1640, 1473, 1451, 1238, 1104, 1002, 933, 745, 703. H
1
NMR (CDCl3, 300 MHz) δ (ppm): 7.47 (2H, d, J = 9 Hz, CHAr), 7.34-7.25 (5H, m,
CHPh), 7.17 (2H, d, J = 9 Hz, CHAr), 5.6 (1H, brs, CH), 4.58 (1H, brs, CH), 4.57
(2H, brs, CH2), 3.11 (2H, brs, CH2), 2.60 (2H, d, J = 3 Hz, CH2Bn), 2.03–1.90 (1H,
m, CH), 1.82 (1H, brs, CH), 1.78 (1H, brs, CH), 1.37 (2H, brs, CH2). 13C NMR
(CDCl3, 75 MHz) δ (ppm): 194.8, 139.6, 135.6, 131.7, 131.1, 129.1, 128.4, 126.2,
121.4, 52.2, 50.6, 42.6, 41.3, 38.1, 31.9. Anal. Calcd. for C20H22BrNS2 (420.43): C,
57.14; H, 5.27; N, 3.33; S, 15.25. Found: C, 57.29; H, 5.31; N, 3.36, S, 15.29.
4-Bromobenzyl piperidine-1-carbodithioate (4k) FT-IR (KBr, ῡ, cm−1): 3052,
2991, 2940, 1585, 1479, 1425, 1221, 1131, 1007, 974, 830, 741, 500. H NMR
1
(CDCl3, 300 MHz) δ (ppm): 7.46 (2H, d, J = 9 Hz, CHAr), 7.31 (2H, d, J = 9 Hz,
CHAr), 4.56 (2H, s, CH2), 4.32 (2H, brs, CH2), 3.90 (2H, brs, CH2), 1.73 (6H, brs,
3CH2). 13C NMR (CDCl3, 75 MHz) δ (ppm): 194.8, 135.8, 131.6, 131.0, 121.3,
53.1, 51.5, 41.2, 26.0, 24.2. Anal. Calcd. for C13H16BrNS2 (330.30): C, 47.27; H,
4.88; N, 4.24; S, 19.41. Found: C, 47.31; H, 4.75; N, 4.29, S, 19.50.
4-Chlorobenzyl 4-benzylpiperidine-1-carbodithioate (4l) FT-IR (KBr, ῡ, cm−1):
3062, 3015, 2995, 2934, 1594, 1491, 1471, 1451, 1238, 1093, 1028, 1003, 746, 703.
1H NMR (CDCl3, 300 MHz) δ (ppm): 7.37 (2H, d, J = 9 Hz, CHAr), 7.35-7.23 (5H,
m, CHPh), 7.17 (2H, d, J = 9 Hz, CHAr), 5.59 (1H, brs, CH), 4.59 (1H, bs, CH), 4.58
(2H, brs, CH2), 3.10 (2H, brs, CH2), 2.60 (2H, d, J = 9 Hz, CH2), 2.00–1.87 (1H, m,
CH), 1.83 (1H, brs, CH), 1.78 (1H, brs, CH), 1.38 (2H, brs, CH2). 13C NMR (CDCl3,
75 MHz) δ (ppm): 194.9, 139.7, 135.0, 133.3, 130.7, 129.1, 128.7, 128.4, 126.2,
52.2, 50.4, 42.6, 41.3, 33.1, 31.8. Anal. Calcd. for C20H22ClNS2 (375.97): C, 63.89;
H, 5.90; N, 3.73; S, 17.05. Found: C, 63.91; H, 5.67; N, 3.81, S, 17.11.
3-Chlorobenzyl morpholine-4-carbodithioate (4n) FT-IR (KBr, ῡ, cm−1): 3050,
2976, 2919, 1596, 1449, 1422, 1267, 1244, 1114, 1031, 996, 866, 776, 713, 539. 1H
NMR (CDCl3, 300 MHz) δ (ppm): 7.42 (12H, s, CHAr), 7.32–7.26 (3H, m, CHAr),
4.60 (2H, s, CH2), 4.30 (2H, brs, CH2), 4.04 (2H, brs, CH2), 3.79 (4H, s, 2CH2). 13
C
NMR (CDCl3, 75 MHz) δ (ppm): 196.5, 138.2, 134.3, 129.8, 129.3, 127.7, 127.5,
66.2, 50.8, 41.0. Anal. Calcd. for C12H14ClNOS2 (287.82): C, 50.08; H, 4.90; N,
4.87; S, 22.28. Found: C, 50.19; H, 4.88; N, 4.81, S, 22.17.
123

Efficient, straightforward, catalyst-free synthesis…
Conclusions
We developed a simple and highly efficient catalyst-free protocol for synthesis of
some novel dithiocarbamate derivatives by one-pot three-component reaction
between different alkyl and aryl amines, carbon disulfide, and numerous alkyl and
benzyl halides in ethanol–aqueous medium. High to excellent product yield, atom
economy, obtaining some novel, potentially interesting, medicinally important
molecules, and use of readily available starting materials are some of the remarkable
advantages of this procedure.
Acknowledgements The authors gratefully thank the Pharmaceutics Research Center, Institute of
Neuropharmacology, Kerman University of Medical Sciences for supporting this work.
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