A new strategy for the synthesis of 2-mercaptobenzazole derivatives by green chemistry metrics

Article abstract of DOI:10.1080/10426507.2019.1571494

A green and efficient method has been developed for the synthesis of 2-mercaptobenzazole derivatives via the reaction of commercially available aniline derivatives with low-cost and nontoxic potassium thiocyanate in water. The reactions proceeded smoothly under catalyst- and ligand-free conditions to give the corresponding products in good to excellent yields. The versatility, low cost, and environmental friendliness, in combination with high yields and easy work-up makes the procedure noteworthy.

Full text of DOI:10.1080/10426507.2019.1571494

Phosphorus, Sulfur, and Silicon and the Related Elements
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A new strategy for the synthesis of 2-
mercaptobenzazole derivatives by green chemistry
metrics
Esmail Vessally, Aazam Monfared, Zahra Eskandari, Morteza Abdoli & Akram
Hosseinian
To cite this article: Esmail Vessally, Aazam Monfared, Zahra Eskandari, Morteza Abdoli &
Akram Hosseinian (2020): A new strategy for the synthesis of 2-mercaptobenzazole derivatives
by green chemistry metrics, Phosphorus, Sulfur, and Silicon and the Related Elements, DOI:
10.1080/10426507.2019.1571494
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PHOSPHORUS, SULFUR, AND SILICON AND THE RELATED ELEMENTS
https://doi.org/10.1080/10426507.2019.1571494
SHORT COMMUNICATION
A new strategy for the synthesis of 2-mercaptobenzazole derivatives by green
chemistry metrics
Esmail Vessallya, Aazam Monfareda, Zahra Eskandaria, Morteza Abdolia, and Akram Hosseinianb
Ã
b
aDepartment of Chemistry, Payame Noor University, Tehran, Iran; School of Engineering Science, College of Engineering, University of
Tehran, Tehran, Iran
ABSTRACT
ARTICLE HISTORY
Received 7 December 2018
Accepted 6 January 2019
A green and efficient method has been developed for the synthesis of 2-mercaptobenzazole deriv-
atives via the reaction of commercially available aniline derivatives with low-cost and nontoxic
potassium thiocyanate in water. The reactions proceeded smoothly under catalyst- and ligand-free
conditions to give the corresponding products in good to excellent yields. The versatility, low
cost, and environmental friendliness, in combination with high yields and easy work-up makes the
procedure noteworthy.
KEYWORDS
2-Mercaptobenzazoles;
potassium thiocyanate;
aqueous medium; catalyst-
free; ligand-free
GRAPHICAL ABSTRACT
Introduction
synthesis of 2-mercaptobenzazoles by "Green Chemistry" meth-
ods is still a significant issue.
The preparation of 2-thio-substituted benzazoles (benzimida-
zoles, benzothiazoles, benzoxazoles) has developed into an inter-
esting topic for synthetic organic chemists, as these molecules
show an impressive variety of biological properties such as anti-
cancer, anti-convulsion, anti-inflammatory, antifungal, and anti-
oxidant properties.[1–5] Several commercially available drugs are
derived from 2-thio-substituted benzazo-core entities (Figure 1)
and many researchers have been working to explore these
motifs to their maximum potential against several diseases or
disorders.[6–10] Traditionally, 2-mercaptobenzazoles are prepared
through the reactions of the corresponding anilines (1,2-phenyl-
enediamines, 2-aminophenols, 2-aminothiophenols) with carbon
disulfide (Scheme 1, route a).[11] However, carbon disulfide is a
toxic reagent and may cause serious environmental pollution,
health, and safety problems. Alternatively, the cyclization of anil-
ine derivatives with potassium O-ethyl dithiocarbonate/phenyl
chlorothionocarbonate for the synthesis of titled compounds were
developed by Deligeorgiev[12] and Sun,[13] respectively (Scheme 1,
routes a, b). Nevertheless, the instability, toxicity and/or unpleas-
ant odor of these reagents impede their application. Very recently,
Dong reported an efficient synthesis of 2-mercaptobenzazoles by
cyclization of anilines with tetramethylthiuram disulfide using
water as solvent (Scheme 1, route c).[14] However, tetramethylth-
iuram disulfide is a highly allergenic compound.[15] Thus, the
Recently, the development of eco-friendly reaction sys-
tems using water as a reaction medium has been the subject
of considerable degree of attention because water is safe,
cheap, widely available, and environmentally-benign as com-
pared with organic solvents.[16] In recent years, significant
efforts have been devoted to the synthesis of valuable sulfur-
containing compounds employing thiocyanate salts (e.g.
KSCN, NaSCN, NH4SCN) as inexpensive, nontoxic, and ver-
satile synthetic intermediates.[17] In connection with our
interest in green chemistry[18] and following our research on
the synthesis of sulfur-containing compounds,[19] herein we
propose a novel and environment friendly synthesis of 2-
mercaptobenzazole derivatives through the reaction of the
corresponding anilines with potassium thiocyanate under
catalyst- and ligand-free conditions in aqueous medium.
Results and discussion
To test our hypothesis, we chose benzene-1,2-diamine 1a as
the model substrate to optimize the reaction conditions, and
a variety of solvents were screened, as show in Table 1.
Firstly, the reaction was carried out in methanol at ambient
temperature under air conditions. However, the reaction did
development of an efficient and economical protocol for the not initiate at all after 24 h (Table 1, entry 1). Performing
CONTACT Akram Hosseinian
hoseinian@ut.ac.ir
Color versions of one or more of the figures in the article can be found online at www.tandfonline.com/gpss.
Supplemental data for this article can be accessed on the publisher’s website at http://dx.doi.org/10.1080/10426507.2019.1571494
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2
A. MONFARED ET AL.
MeO
S
OMe
OMe
Me
OMe
Me
EtO
O
S
MeO
N
N
O
N
N
NH2
S
N
S
O
O
Anti-breast cancer agent
Omeprazole
Ethoxzolamide
Figure 1. Selected examples of drugs containing 2-mercaptobenzazole scaffold.
CS2
a
KSC(S)OEt
b
XH
X
SH
N
NH2
PhOC(S)Cl
c
X= NH, O, S
d
NMe2C(S)S-SC(S)NMe2
Scheme 1. Main synthetic routes to 2-mercaptobenzazoles.
2a increased and the expected product was isolated in 82%
yield (Table 1, entry 8). When the reaction was carried out
in HCl (2 M), the yield slightly increased to 87% (Table 1,
entry 9). It is noteworthy that increasing of the concentra-
tion of the solution to 3 M did not improve the outcome of
the reaction and 2a was isolated in 79% yield (Table 1, entry
10). Thus, the optimal reaction conditions were determined
to be aqueous hydrochloric acid (2.0 M) as the solvent at
80 ꢀC for 24 hours.
With the optimized reaction conditions in hand, we pro-
ceeded to explore the scope of the reaction with various 1,2-
diaminobenzenes, as summarized in Table 2. Interestingly,
both electron-rich and electron-deficient 1,2-diaminoben-
zenes 1 reacted efficiently under the optimized conditions
and provided the expected benzimidazole-2-thiones 2 in
good to excellent yields. Pleasingly, the reaction was success-
fully performed on a gram scale to give isolated yields com-
parable to those obtained from small-scale reactions.
Inspired by these results, we applied this procedure for
the synthesis of 2-mercaptobenzothiazole 4 from the corre-
sponding 2-aminothiophenol 3. As shown in Scheme 2, the
protocol worked well for this reaction and afforded the
expected product in excellent yield (92%).
Next, we turned our attention to extend this protocol to
the synthesis of 2-mercaptobenzoxazole derivatives. Thus the
reaction of 2-aminophenol 5a with KSCN was carried out
under standard conditions. Surprisingly, the synthesis of 2-
mercaptobenzoxazole 6 under these conditions was ham-
pered due to the unexpected formation of 4-hydroxy-1H-
benzo[d]imidazole-2(3H)-thione 7 in 71% yield as the sole
product (Scheme 3a). Interestingly, the reaction of 3-amino-
phenol 5 b with KSCN under the same conditions resulted
Table 1. Screening of the reaction conditions for the cyclization of benzene-
1,2-diamine 1a with KSCN.a
H
NH2
N
Solvent
24 h
C
S
]
+ KSCN
[
N
H
NH2
1a
2a
Entry
Solvent
Temperature (ꢀC)
Yield (%)b
1
2
3
4
MeOH
MeOH
EtOH
25
reflux
25
reflux
25
25
25
80
80
80
NRc
NR
NR
NR
trace
26
53
82
87
79
EtOH
5
EtOH/H2O
EtOH/H2O
HCl (1 M)
HCl (1 M)
HCl (2 M)
HCl (3 M)
6d
7
8
9
10
aReaction conditions: aniline (0.2 g, 1.0 equiv.), KSCN (1.0 equiv.), solv-
ent (4 mL).
bIsolated yields.
cNo reaction.
dOne drop of HCl were added to the reaction mixture.
the reaction under reflux conditions gave identical results
(Table 1, entry 2). Likewise, no product was detected when
the reaction was performed in ethanol (Table 1, entries 3, 4)
but in the presence of an ethanol–water solvent, a very low
yield was noticed (Table 1, entry 5). It was pleasing to
observe that adding a single drop of concentrated hydro-
chloric acid to the reaction mixture afforded a 26% yield of
the desired product 2a (Table 1, entry 6). The results
encouraged us to further explore and optimize the condi-
tions. Interestingly, the yield of benzo[d]imidazole-2(3H)-
thione 2a increased from 26% to 53% when the reaction was in the formation of the same product 7 in slightly higher
carried out in 1.0 M HCl solution as the solvent at ambient yield (Scheme 3b). However, 4-aminophenol failed to par-
temperature (Table 1, entry 7). At 80 ꢀC, the formation of ticipate in the reaction (Scheme 3c).

PHOSPHORUS, SULFUR, AND SILICON AND THE RELATED ELEMENTS
3
Table 2. Formation of benzimidazole-2-thiones 2 by reaction of benzene-1,2-diamine 1 with KSCN in water.
H
N
H
N
H
N
MeO
Me
S
S
S
N
H
N
H
N
H
2a, (87%)
2b, (83%)
2c, (80%)
H
H
H
N
Me
Cl
Br
N
N
S
S
S
N
H
N
H
N
H
Me
2d, (81%)
2e, (79%)
2f, (75%)
HS
SH
S
HCl (2 M)
80 oC, 24 h
C
SH
+ KSCN
H
N
N
H
N
NH2
XH
S
N
NH2
+ NH3
S
NH2
3
4, (92%)
X
XH
X= NH, S
A
Scheme 2. Cyclization of 2-aminothiophenol with KSCN in water.
KSCN + HCl
HSCN + KCl
Scheme 5. Postulated reaction pathway.
O
(a)
SH
N
OH
A mechanism for the cyclization of 1,2-diaminobenzenes
and 2-aminophenols with KSCN is proposed in Scheme 5.
The reaction proceeds via generation of a thiourea inter-
mediate A by nucleophilic addition of the amino group of
the starting aniline to the carbon atom of in situ generated
mercaptoformonitrile (from potassium thiocyanate and
hydrochloric acid). Next, the intermediate A undergoes
intramolecular nucleophilic addition to give the expected
product and one molecule of ammonia. The mechanistic
studies for the cyclization of aminophenoles and KSCN are
currently under investigation in our laboratory.
6
HCl (2 M)
+ KSCN
80 oC, 24 h
OH
NH2
H
N
5a
S
N
H
7, (71%)
OH
(b)
(c)
H
N
OH
HCl (2 M)
80 oC, 24 h
S
+ KSCN
OH
N
H
NH2
7, (83%)
5b
Conclusions
HCl (2 M)
80 oC, 24 h
NR
+ KSCN
In conclusion, we developed a novel, environmentally
friendly and efficient protocol for the synthesis of 2-mercap-
tobenzazole derivatives through the reaction of low-cost
commercially available potassium thiocyanate with anilines
in aqueous medium. Without metal catalyst and ligand, the
reaction tolerates a range of functional groups, obtaining the
desired products in good to excellent yields. Furthermore,
the products could be easily isolated from the reaction mix-
ture by a simple filtration. Further investigations of the reac-
tion mechanism and the extension of the substrate scope are
currently underway in our laboratory.
H2N
5c
Scheme 3. Reaction of aminophenols with KSCN in aqueous medium.
S
HCl (2 M)
80 oC, 24 h
XH
HN
X
+ KSCN
H2N
X= NH, OH, SH
Scheme 4. Reaction of aliphatic amine derivatives with KSCN.
Finally, we used analogous conditions for the cyclization
of aliphatic amine derivatives (ethylenediamine, ethanol-
amine, and cysteamine) with KSCN. Unfortunately, these
substrates did not give the desired azolidin-2-thions under
the optimized reaction conditions (Scheme 4).
Experimental
Experimental details and spectroscopic data of the products
are compiled in the supplemental materials file.

4
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Advantages in the Metal (Bulk and Nano)-Catalyzed S-
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Perfect Synergy for Eco-compatible Preparation of Aromatic
Thioethers. J. Sulfur Chem. 2018, 39, 332–349. DOI: 10.1080/
17415993.2018.1436711.
Disclosure statement
No potential conflict of interest was reported by the authors.
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