A convenient synthesis of thiazol-2(3H)-one skeletons from a reaction involving terminal alkynes, elemental sulfur, and isocyanates

Article abstract of DOI:10.1080/17415993.2019.1703987

An efficient copper-catalysed tandem reaction to synthesize thiazol-2(3H)-one structures from readily available raw materials is described. The protocol provides a cost-effective approach to a decent range of nitrogen and sulfur bearing heterocycles in acceptable yields. The transformation takes place with CuCl as catalyst, N-methylpiperidine as additive, and t-BuOK as base in anhydrous DMF as solvent.

Full text of DOI:10.1080/17415993.2019.1703987

Journal of Sulfur Chemistry
ISSN: 1741-5993 (Print) 1741-6000 (Online) Journal homepage: https://www.tandfonline.com/loi/gsrp20
A convenient synthesis of thiazol-2(3H)-one
skeletons from a reaction involving terminal
alkynes, elemental sulfur, and isocyanates
Fahimeh Heydari-Mokarrar, Reza Heydari, Malek-Taher Maghsoodlou &
Alireza Samzadeh-Kermani
To cite this article: Fahimeh Heydari-Mokarrar, Reza Heydari, Malek-Taher Maghsoodlou &
Alireza Samzadeh-Kermani (2019): A convenient synthesis of thiazol-2(3H)-one skeletons from a
reaction involving terminal alkynes, elemental sulfur, and isocyanates, Journal of Sulfur Chemistry,
DOI: 10.1080/17415993.2019.1703987
To link to this article: https://doi.org/10.1080/17415993.2019.1703987
Published online: 29 Dec 2019.
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JOURNAL OF SULFUR CHEMISTRY
https://doi.org/10.1080/17415993.2019.1703987
A convenient synthesis of thiazol-2(3H)-one skeletons from a
reaction involving terminal alkynes, elemental sulfur, and
isocyanates
Fahimeh Heydari-Mokarrara, Reza Heydaria, Malek-Taher Maghsoodloua and
Alireza Samzadeh-Kermanib
aFaculty of Science, Department of Chemistry, University of Sistan and Baluchestan, Zahedan, Iran; bFaculty
of Science, Department of Chemistry, University of Zabol, Zabol, Iran
ABSTRACT
ARTICLE HISTORY
Received 16 October 2019
Accepted 5 December 2019
An efficient copper-catalysed tandem reaction to synthesize thiazol-
2(3H)-one structures from readily available raw materials is des-
cribed. The protocol provides a cost-effective approach to a decent
range of nitrogen and sulfur bearing heterocycles in accept-
able yields. The transformation takes place with CuCl as catalyst,
N-methylpiperidine as additive, and t-BuOK as base in anhydrous
DMF as solvent.
KEYWORDS
Thiazol-2(3H)-one; elemental
sulfur; copper-acetylide;
isocyanate; cyclization
Introduction
During the last two decades, copper salts have been broadly utilized in catalytic multicom-
ponent reactions to form a wide range of heterocyclic compounds [1–5]. In this regard,
those reactions involving terminal alkynes have attracted considerable attention in prepa-
ration of synthetically important heterocycles [6–8]. The widespread application of copper
salts with alkyne synthons relies on their ability to effectively activate the π-electrons of
triple bonds, providing a partial positive charge on alkyne unit [9].
In this line, the additions of terminal alkynes on various type of electrophiles have been
well documented [10–15]. Pioneered by Gewald [16], the nucleophilic additions of termi-
nal alkynes on elemental sulfur in the presence of appropriate third coupling partners has
emerged to form a diverse range of sulfur heterocycles [17–18].
Owing to their importance in chemical biology and medicinal chemistry, thiazole
possessing molecules have attracted much attention [19–22]. Additionally, some thia-
zole bearing compounds like Plantazolicin exhibited pharmacologically important activity
CONTACT Alireza Samzadeh-Kermani
drsamzadeh@gmail.com
© 2019 Informa UK Limited, trading as Taylor & Francis Group

2
F. HEYDARI-MOKARRAR ET AL.
[23–25]. A number of methods have been developed for the synthesize (US format) of
thiazole building-blocks with condensation reactions being among the most documented
transformations [26–27]. For instance, Ghazanfarpour disclosed an organocatalytic route
to thiazolidine derivatives from a reaction involving aziridines and carbon disulphide [28].
Mehrabi reported a three-component reaction between arylglyoxals with acetylthiourea
and Meldrum’s acid to form thiazole derivatives [29]. Khurana’ laboratory has developed
a novel reaction using acetic acid as mediator to form such important heterocycles [30]. A
domino reaction between alkynes, elemental sulfur, and aziridines has been applied to form
thiazole building blocks [17]. Recently, Domling described an Ugi-type reaction to form
thiazole structures through a cyclodehydration path [31]. The recent efforts on synthesis
of thiazole skeletons are very well recapitulated in a review written by Mahesh [32]. In the
light of previously published methods for the synthesis of sulfur heterocycles [33–39] and
in continuation of our interest on multicomponent reactions involving terminal alkynes
[40–41], we herein report a catalytic multicomponent reaction between terminal alkynes,
elemental sulfur, and isocyanates to form thizaole derivatives.
Results and discussion
To evaluate the suitability of the proposed catalytic multicomponent reaction, an initial
attempt was performed with phenylacetylene (1a), elemental sulfur (2a), and phenyl iso-
cyanate (3a) in the presence of CuI and N-methylpiperidine (NMP) as a sulfur activator
in THF. Stirring at 55 °C for 16 h only afforded the desired compound 4a in low yield
together with S-(phenylethynyl) phenylcarbamothioate (5) in 73% yield. Increasing the
reaction temperature or extending the reaction time did not affect the reaction outcome
in appreciable manners. We thought that the presence of a base source may assist the reac-
tion progress. Accordingly, the reaction with Cs2CO3 afforded the targeted compound 4a
in 26% yield (not shown in Table 1). To further develop the reaction conditions, the reac-
tion was performed with various catalysts, bases, and solvents and the results are shown in
Table 1. Initially, the effect of base source on reaction outcomes was examined. Tetrabuty-
lammonium acetate (TBAAc) as an ionic inorganic base resulted in formation of 4a in low
yield (entry 1). The study also indicated that common organic bases were not effective here
and only DBU afforded 4a in acceptable yield (entries 2–6). Among the inorganic bases,
t-BuOK exhibited much better activity in regards of the formation of 4a (entries 7–11). Of
the copper salts, CuCl was selected as the catalyst of choice based on the cost and efficiency
(entries 12–19). In the cases of Cu(CH3CN)4PF6, a higher catalyst loading was required to
furnish the transformation in a similar yield (entry 15). Copper (II) salts were not suitable
in this transformation (entries 17–19). Finally, the effect of solvent in this transformation
was examined (entries 20–26). By comparison, the reaction in polar aprotic solvents likes
DMSO, DMA, and MeCN exhibited much better productivity (entries 20–22). The reac-
tion in protic solvent like EtOH did not afford 4a (entry 26). The reaction conducted at
lower temperatures and shorter reaction times resulted in diminished yields (not shown in
Table 1).
The substrates scope toward this catalytic multicomponent reaction was then evaluated
using various terminal alkynes and isocyanates (Table 2). The reaction proceeds smoothly
with 1a to afford the targeted the product 4a in 89% yield (entry 1). Alkynes bearing p-
methyl and p-methoxy as motif on aryl ring 1b-1c reacted with acceptable yields (entries

JOURNAL OF SULFUR CHEMISTRY
3
Table 1. Optimization of reaction conditionsa.
Entry
Catalyst
Base
Solvent
Yield of 4 (%)
1
2
3
4
5
6
7
8
CuCl
CuCl
CuCl
CuCl
CuCl
CuCl
CuCl
CuCl
CuCl
TBAAc
Lutidine
Et3N
(i-Pr)2EtN
DBU
DMF
DMF
DMF
DMF
DMF
DMF
DMF
DMF
DMF
DMF
DMF
DMF
DMF
DMF
DMF
DMF
DMF
DMF
DMF
DMSO
DMA
MeCN
THF
25
Traces
27
18
58
DABCO
K3PO4
K2CO3
Cs2CO3
t.BuOLi
t.BuOK
t.BuOK
t.BuOK
t.BuOK
t.BuOK
t.BuOK
t.BuOK
t.BuOK
t.BuOK
t.BuOK
t.BuOK
t.BuOK
t.BuOK
t.BuOK
t.BuOK
t.BuOK
31
NRb
NR
9
56
70
89
68
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
CuCl
CuCl
CuI
CuBr.SMe2
CuOAc
Cu(CH3CN)4PF6
CuOTf
Cu(OTf)2
Cu(BF4)2
Cu(OAc)2
CuCl
37
27
90c
92
Traces
Traces
Traces
71
86
63
CuCl
CuCl
CuCl
CuCl
CuCl
CuCl
30
43
Toluene
DCM
EtOH
16
d
–
Notes: aReaction conditions: 1a (1.2 mmol), 2 (0.2 equiv. based on 3a), 3a (1.0 mmol), catalyst (0.05 mmol), additive
(1.5 mmol), base (1.5 mmol), 250 mg of ground 3 Å molecular sieves, solvent (3.0 mL) at 55 °C for 16 h.
bNo reaction.
cWith 0.10 mmol of catalyst.
dEthyl phenylcarbamate was isolated in 71% yield.
2–3). Electron-deficient alkyne 1d afforded the corresponding product in lower yield how-
ever, a decent increase in the yield occurred by extending the reaction time (entry 4).
Heteroaromatic terminal alkynes 1e-1f were also tolerated, providing the corresponding
thiazol-2(3H)-one skeletons with good success (entries 5–6). Gratefully, alkyl terminal
alkynes 1g-1j were also compatible with this three-component reaction (entries 7–10).
The reaction was also performed with a number of aryl and alkyl isocyanates (entries
11–17). The reactions conducted with isocyanates bearing electron releasing groups such
as Me- and MeO- at para position formed the desired products in acceptable yields (entries
11–12). Chloro group was compatible with this coupling reaction, opening the door for
subsequent cross-coupling reaction (entry 13). The reactions with electron-deficient iso-
cyanates 3e-3f proceeded with moderate yields (entries 14–15). As is typified by substrates
3 g and 3 h, alkyl isocyanates afforded the corresponding products 4p-4q in comparatively
lower yields than that of 3a (entries 16-17), likely due to the either lack of π-electrons of
the phenyl group which could act as an auxiliary coordination site to copper catalyst or

4
F. HEYDARI-MOKARRAR ET AL.
Table 2. Scope of substratesa.
Entry
Alkyne
R1
Isocyanate
R2
Yield (%) of 4
1
2
3
4
5
6
7
8
1a
1b
1c
1d
1e
1f
1g
1h
1i
Ph
3a
3a
3a
3a
3a
3a
3a
3a
3a
3a
3b
3c
3d
3e
3f
Ph
Ph
Ph
Ph
Ph
Ph
Ph
Ph
Ph
Ph
4a, 89
4b, 81
4c, 78
4-Me-C6H4
4-MeO-C6H4
3-CF3-C6H4
3-Pyridyl
2-Furyl
CH3OCH2
t-Bu
n-Bu
TMS
t-Bu
t-Bu
4d, 69 (87)b
4e, 85
4f, 81
4g, 87c
4h, 81
4i, 70
9
10
11
12
13
14
15
16
17
1j
4j, 61
4k, 75
4l, 77
4m, 87
4n, 71
4o, 49
4p, 79d
4q, 75d
1a
1a
1a
1a
1a
1a
1a
4-Me-C6H4
4-MeO-C6H4
4-Cl-C6H4
4-MeOCO-C6H4
4-NO2-C6H4
Cy
t-Bu
t-Bu
t-Bu
t-Bu
3g
3h
t-Bu
i-Pr
Notes: aFor all entries except stated otherwise: 1 (1.2 mmol), 2 (0.2 equiv.), 3 (1.0 mmol), NMP
(1.5 mmol), CuCl (0.05 mmol), t.BuOK (1.5 mmol), 3 Å molecular sieves (250 mg) dry DMF (3.0 mL),
55°C, 16 h under N2.
bThe digit in parentheses refers to the yield for 21 h.
cFor entries 7–17, 0.1 mmol of CuCl was used.
dThe yield at 70°C.
lower electrophilicity. The present transformation was not compatible with the presence of
amine, hydroxyl, nitrile, and aldehyde as motif on alkynes and isocyanates structures.
To get insight on the mechanism of the reaction, the reaction was conducted in stepwise
manner and the results are shown in Scheme 1. The reaction conducted with phenylacety-
lene and elemental sulfur to form phenylethynylthiolate a was unsuccessful and instead the
Glaser coupling product 6 or the dimeric product 7 was obtained (Scheme 1, a). As such,
sodium phenylacetylide 8 was prepared in a separate step using 1a and 2 in the presence
of NaH and was then reacted with isocyanate 3a. The study indicated that the presence
of copper catalyst and base was necessary to form 4a (Scheme 1, b, c). Additionally, the
reaction was conducted in competing mode with isocyanate 3a and isothiocyanate 9 to
explore the effect of electrophilicity of the third coupling partner in reaction outcome.
Control experiment indicated that the reaction proceeded almost entirely through iso-
cyanate 3a which is most likely due to the greater potential of 3a for nucleophilic attack of
phenylethynylthiolate species a (Scheme 1, d).
Based on previous literature [15–17] and our control experiment results, a plausible
mechanism is proposed in Scheme 2. Initially, species 11 was formed from phenylacetylene
using CuCl and t-BuOK. Copper-acetylide 11 reacted with polysulfide 12 to provide alkyne
polysulfide 13. This anionic adduct further reacted with isocyanate 3a to give the corre-
sponding S-(phenylethynyl) phenylcarbamothioate complex 14. Subsequent electrophilic
cyclization of 14 through a 5-endo path afford intermediate 15 which further reacted to
form compound 4a by the action of the conjugated acid of the base.

JOURNAL OF SULFUR CHEMISTRY
5
Scheme 1. Control experiments.
Conclusion
In this report, we have reported a novel catalytic three-component reaction involving ter-
minal alkynes, elemental sulfur, and isocyanates. The reaction scope is wide and the reac-
tions proceeded smoothly to form three covalent bonds in one pot. Control experiments
were performed to explore the reaction intermediates and plausible path. A competing
reaction with isocyanate and isothiocyanate was also conducted to get insight on the effect
of electrophilicity of the third coupling partner on the products outcome.
Experimental
All transformations were performed in pre-dried glass tube (15 mL) under an inert atmo-
sphere. All the substrates, copper catalysts, bases and additives were purchased from com-
mercial sources. All the solvents were purchased from BAHERENERGY Pure Chemical
Industries, and were dried before use. Melting points were recorded with Electrothermal-
9100 apparatus. IR spectra were determined on a Nicolet 6700 spectrometer. 1H and 13
C

6
F. HEYDARI-MOKARRAR ET AL.
Scheme 2. Proposed mechanism.
NMR spectra spectra were taken on a Bruker DRX-500 AVANCE spectrometer. The spec-
tra were obtained in CDCl3 at 500 and 125 MHz, resp; δ in ppm, J in Hz. Mass spectra
were recorded with a EIMS (70 eV): Finnigan-MAT-8430 mass spectrometer, in m/z. Ele-
mental analyses were performed with a Heraeus Rapid analyser. Silica gel 60 (particle size
63–200 μm or 40–100 mesh) was used for column chromatography. TLC analyses were
performed on commercial glass plates of Merck Silica gel 60 (Merck, item number 116835).
General Procedure for the Preparation of Compounds 4
A pre-dried glass vessel (15 mL) was charged with elemental sulfur (0.2 mmol, 51.0 mg),
NMP (1.5 mmol), and anhydrous DMF (2.0 mL). The mixture was then stirred for 40 min
and terminal alkyne (as stated in Table 2), isocyanate (1.0 mmol), CuCl (as stated in
Table 2), t.BuOK (1.5 mmol), 3 Å molecular sieves (250 mg), and anhydrous DMF (2.0 mL)
were then added to the above mixture, respectively. The reaction medium was evacuated
and backfilled with N2 (twice). The mixture was stirred under the conditions described
in Table 2. After the dark greenish mixture being cooled to room temperature, the mix-
ture was passed through an alumina pad and concentrated under reduced pressure. The
residue was purified by flash column chromatography with silica gel (eluent gradient of
EtOAc/hexane, see spectroscopic analysis section) to give the targeted products 4.
3,4-Diphenylthiazol-2(3H)-one (4a)
The crude product was purified by column chromatography (SiO2; Hexane/EtOAc 6/1,
¯
Rf : 0.34) affording 0.22 g (89%) of 4a; Pale yellow oil. IR (KBr): V = 3053, 2976, 1637,
1
1472, 1232, 1123. H NMR (500.1 MHz, CDCl3): δ = 6.79 (1 H, s, CH), 7.37 (2 H, d,
H
3J = 7.1 Hz, 2 CH), 7.49 (2 H, t, J = 7.3 Hz, 2 CH), 7.56-7.63 (4 H, m, 4 CH), 7.76 (2
3
H, d, 3J = 7.3 Hz, 2 CH). 13C NMR (125.7 MHz, CDCl3): δ = 112.8 (CH), 127.6 (CH),
C
127.8 (CH), 128.3 (2 CH), 128.8 (2 CH), 129.7 (2 CH), 130.2 (2 CH), 133.2 (C), 135.8 (C),
149.3 (C), 172.5 (C). EI-MS (70 eV): m/z (%) = 253 (M+, 1), 176 (31), 100 (62), 85 (87),

JOURNAL OF SULFUR CHEMISTRY
7
77 (100). Anal. Calcd (%) for C15H11NOS (252.32): C, 71.12, H, 4.38, N, 5.53, S, 12.66.
Found: C, 71.01, H, 4.55, N, 5.38, S, 12.52.
3-Phenyl-4-(p-tolyl)thiazol-2(3H)-one (4b)
The crude product was purified by column chromatography (SiO2; Hexane/EtOAc 6/1,
¯
Rf : 0.41) affording 0.22 g (81%) 4b. Pale yellow oil. IR (KBr): V = 3017, 2962, 1632, 1231,
1098. 1H NMR (500.1 MHz, CDCl3): δ = 2.35 (3 H, s, Me), 6.64 (1 H, s, CH), 7.18 (2 H,
H
d, 3J = 7.7 Hz, 2 CH), 7.25 (2 H, d, 3J = 7.7 Hz, 2 CH), 7.38 (2 H, d, 3J = 7.2 Hz, 2 CH),
7.53 (2 H, t, J = 7.2 Hz, 2 CH), 7.64 (1 H, t, J = 7.2 Hz, CH). 13C NMR (125.7 MHz,
3
3
CDCl3): δ = 22.5 (Me), 112.3 (CH), 127.5 (CH), 128.2 (C), 128.2 (2 CH), 129.4 (2 CH),
C
129.9 (2 CH), 130.3 (2 CH), 132.7 (C), 138.8 (C), 149.5 (C), 171.3 (C). EI-MS (70 eV): m/z
(%) = 267 (M+, 3), 190 (24), 176 (31), 162 (57), 91 (72), 85 (87), 77 (100). Anal. Calcd (%)
for C16H13NOS (267.35): C, 71.88, H, 4.90, N, 5.24, S, 11.99. Found: C, 71.70, H, 4.78, N,
5.39, S, 12.11.
4-(4-Methoxyphenyl)-3-phenylthiazol-2(3H)-one (4c)
The crude product was purified by column chromatography (SiO2; Hexane/EtOAc 5/1, Rf :
¯
0.29) affording 0.22 g (78%) 4c. Yellow oil. IR (KBr): V = 3031, 2952,1628, 1413, 1232,
1
1065. H NMR (500.1 MHz, CDCl3): δ = 3.76 (3 H, s, OMe), 6.46 (1 H, s, CH), 6.91
H
(2 H, d, 3J = 7.1 Hz, 2 CH), 7.22 (2 H, d, 3J = 7.1 Hz, 2 CH), 7.39 (2 H, d, 3J = 7.8 Hz, 2
CH), 7.52 (2 H, t, 3J = 7.8 Hz, 2 CH), 7.63 (1 H, t, 3J = 7.8 Hz, CH). 13C NMR (125.7 MHz,
CDCl3): δ = 54.2 (OMe), 107.7 (CH), 119.7 (2 CH), 124.2 (C), 127.1 (CH), 128.3 (2 CH),
C
129.2 (2 CH), 129.7 (2 CH), 135.3 (C), 148.6 (C), 160.4 (C), 174.1 (C). EI-MS (70 eV): m/z
(%) = 283 (M+, 1), 206 (9), 191 (32), 107 (100), 85 (81), 77 (83). Anal. Calcd (%) for
C16H13NO2S (283.35): C, 67.82, H, 4.62, N, 4.94, S, 11.31. Found: C, 67.68, H, 4.80, N,
5.10, S, 11.45.
3-Phenyl-4-(3-(trifluoromethyl)phenyl)thiazol-2(3H)-one (4d)
The crude product was purified by column chromatography (SiO2; Hexane/EtOAc 4/1,
¯
Rf : 0.37) affording 0.28 g (87%) 4d. Pale yellow oil. IR (KBr): V = 3015, 2943, 1640,
1
1453, 1231, 1090. H NMR (500.1 MHz, CDCl3): δ = 6.81 (1 H, s, CH), 7.08 (1 H, t,
H
3J = 7.5 Hz, CH), 7.39 (1 H, d, 3J = 7.5 Hz, CH), 7.46 (2 H, d, 3J = 7.1 Hz, 2 CH), 7.50
(1 H, s, CH), 7.55 (2 H, t, 3J = 7.1 Hz, CH), 7.61 (1 H, t, 3J = 7.1 Hz, CH), 7.83 (1 H, d,
3J = 7.5 Hz, CH). 13C NMR (125.7 MHz, CDCl3): 114.2 (CH), 122.9 (CH, q, 3J = 5.2 Hz),
125.1 (CF3, q, 1J = 276.1 Hz), 126.8 (CH, q, 3J = 5.1 Hz), 127.2 (CH), 128.5 (2 CH), 128.9
(2 CH), 130.1 (CH), 132.4 (C, q, 2J = 28.7 Hz), 134.1 (C), 135.9 (C), 149.5 (C), 173.9 (C).
EI-MS (70 eV): m/z (%) = 321 (M+, 1), 244 (37), 146 (25), 100 (73), 85 (81), 77 (100).
Anal. Calcd (%) for C16H10F3NOS (321.32): C, 59.81, H, 3.14, N, 4.36, S, 9.98, F, 17.74.
Found: C, 59.70, H, 3.02, N, 4.51, S, 10.11, F, 17.83.
3-Phenyl-4-(pyridin-3-yl)thiazol-2(3H)-one (4e)
The crude product was purified by column chromatography (SiO2; Hexane/EtOAc 4/1, Rf :
1
¯
0.21) affording 0.22 g (85%) 4e. Yellow oil. IR (KBr): V = 3041, 2977, 1634, 1231, 1143. H
NMR (500.1 MHz, CDCl3): δ = 6.72 (1 H, s, CH), 7.34 (1 H, t, 3J = 7.7 Hz, CH), 7.42 (2
H
H, d, 3J = 7.4 Hz, 2 CH), 7.53 (2 H, t, 3J = 7.4 Hz, 2 CH), 7.64 (1 H, t, 3J = 7.4 Hz, CH),
7.78 (1 H, d, 3J = 7.7 Hz, CH), 8.24 (1 H, d, 3J = 7.7 Hz, CH), 8.53 (1 H, s, CH). 13C NMR
(125.7 MHz, CDCl3): 119.6 (CH), 124.7 (CH), 127.3 (CH), 128.6 (2 CH), 129.15 (2 CH),
132.1 (C), 134.3 (C), 134.9 (CH), 148.7 (C), 149.1 (CH), 149.3 (CH), 174.8 (C). EI-MS

8
F. HEYDARI-MOKARRAR ET AL.
(70 eV): m/z (%) = 254 (M+, 4), 177 (34), 100 (84), 85 (76), 77 (100). Anal. Calcd (%) for
C14H10N2OS (254.31): C, 66.12, H, 3.96, N, 11.02, S, 12.61. Found: C, 66.28, H, 3.82, N,
11.24, S, 12.80.
4-(Furan-2-yl)-3-phenylthiazol-2(3H)-one (4f)
The crude product was purified by column chromatography (SiO2; Hexane/EtOAc 5/1, Rf :
¯
0.33) affording 0.20 g (81%) 4f. Pale yellow oil. IR (KBr): V = 3017, 2957, 1628, 1543, 1241,
1
3
1067. H NMR (500.1 MHz, CDCl3): δ = 6.62 (1 H, s, CH), 6.80 (1 H, t, J = 6.7 Hz,
H
3
3
CH), 7.39 (2 H, d, J = 7.8 Hz, 2 CH), 7.50 (2 H, t, J = 7.8 Hz, 2 CH), 7.63 (1 H, t,
3J = 7.8 Hz, CH), 7.78 (1 H, d, J = 6.7 Hz, CH), 8.31 (1 H, d, J = 6.7 Hz, CH). 13C
NMR (125.7 MHz, CDCl3): 110.2 (CH), 114.9 (CH), 115.7 (CH), 127.3 (CH), 128.5 (2
CH), 129.1 (2 CH), 134.1 (C), 147.4 (CH), 156.2 (C), 158.7 (C), 173.1 (C). EI-MS (70 eV):
m/z (%) = 243 (M+, 1), 176 (45), 166 (24), 100 (83), 85 (67), 77 (100), 67 (53). Anal. Calcd
(%) for C13H9NO2S (243.28): C, 64.18, H, 3.73, N, 5.76, S, 13.18. Found: C, 64.34, H, 3.60,
N, 5.63, S, 13.32.
3
3
4-(Methoxymethyl)-3-phenylthiazol-2(3H)-one (4 g)
The crude product was purified by column chromatography (SiO2; Hexane/EtOAc 6/1,
¯
Rf : 0.45) affording 0.19 g (87%) 4 g. Colorless oil. IR (KBr): V = 3018, 2962, 1636, 1311,
1262, 1106. 1H NMR (500.1 MHz, CDCl3): δ = 3.41 (3 H, s, OMe), 4.27 (2 H, s, CH2),
H
6.41 (1 H, s, CH), 7.39 (2 H, d, 3J = 7.2 Hz, 2 CH), 7.53 (2 H, t, 3J = 7.2 Hz, 2 CH), 7.60
(1 H, t, 3J = 7.2 Hz, CH). 13C NMR (125.7 MHz, CDCl3): δ = 55.7 (OMe), 82.1 (CH2),
C
101.3 (CH), 127.4 (CH), 128.6 (2 CH), 129.2 (2 CH), 134.8 (C), 153.9 (C), 171.7 (C). EI-
MS (70 eV): m/z (%) = 221 (M+, 1), 190 (23), 114 (64), 100 (86), 85 (70), 77 (100). Anal.
Calcd (%) for C11H11NO2S (221.27): C, 59.71, H, 5.01, N, 6.33, S, 14.49. Found: C, 59.88,
H, 5.15, N, 6.24, S, 14.62.
4-(tert-Butyl)-3-phenylthiazol-2(3H)-one (4 h)
The crude product was purified by column chromatography (SiO2; Hexane/EtOAc 1/6, Rf :
¯
0.31) affording 0.19 g (81%) 4 h. Colorless oil. IR (KBr): V = 3415, 3047, 2976, 1726, 1638,
1543, 1346, 1218, 1076. 1H NMR (500.1 MHz, CDCl3): δ = 1.38 (9 H, s, 3 Me), 6.19 (1
H
H, s, CH), 7.38 (2 H, d, 3J = 7.1 Hz, 2 CH), 7.55 (2 H, t, 3J = 7.5 Hz, 2 CH), 7.63 (1 H, t,
3J = 7.5 Hz, CH). 13C NMR (125.7 MHz, CDCl3): δ = 34.9 (3 Me), 42.2 (C), 97.2 (CH),
C
126.9 (CH), 128.8 (2 CH), 129.7 (2 CH), 134.6 (C), 163.4 (C), 173.8 (C). EI-MS (70 eV):
m/z (%) = 233 (M+, 1), 176 (31), 156 (53), 100 (81), 85 (61), 77 (84), 57 (100). Anal. Calcd
(%) for C13H15NOS (233.33): C, 66.92, H, 6.48, N, 6.00, S, 13.74. Found: C, 67.11, H, 6.31,
N, 6.17, S, 13.60.
4-Butyl-3-phenylthiazol-2(3H)-one (4i)
The crude product was purified by column chromatography (SiO2; Hexane/EtOAc 7/1, Rf :
¯
0.21) affording 0.16 g (70%) 4i. Pale yellow oil. IR (KBr): V = 3026, 2965, 1639, 1475, 1237,
1128. 1H NMR (500.1 MHz, CDCl3): δ = 1.02 (3 H, t, 3J = 5.8 Hz, Me), 134-1.42 (4 H,
H
m, 2 CH2), 2.11 (2 H, t, 3J = 5.6 Hz, CH2), 6.19 (1 H, s, CH), 7.35 (2 H, d, 3J = 7.1 Hz, 2
CH), 7.49 (2 H, t, 3J = 7.1 Hz, 2 CH), 7.56 (1 H, t, 3J = 7.1 Hz, CH). 13C NMR (125.7 MHz,
CDCl3): 12.8 (Me), 26.3 (CH2), 31.7 (CH2), 37.7 (CH2), 102.2 (CH), 127.8 (CH), 128.6 (2
CH), 129.4 (2 CH), 133.7 (C), 159.2 (C), 172.8 (C). EI-MS (70 eV): m/z (%) = 233 (M+,
1), 176 (34), 156 (21), 100 (100), 85 (61), 77 (84), 57 (36). Anal. Calcd (%) for C13H15NOS
(233.33): C, 66.92, H, 6.48, N, 6.00, S, 13.74. Found: C, 66.80, H, 6.60, N, 6.17, S, 13.91.

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9
3-Phenyl-4-(trimethylsilyl)thiazol-2(3H)-one (4j)
The crude product was purified by column chromatography (SiO2; Hexane/EtOAc 8/1, Rf :
¯
0.41) affording 0.15 g (61%) 4j. Colorless oil. IR (KBr): V = 3055, 2932, 1630, 1456, 1321,
1207, 640. 1H NMR (500.1 MHz, CDCl3): δ = 0.13 (9 H, s, 3 Me), 6.49 (1 H, s, CH), 7.40
H
(2 H, d, 3J = 7.7 Hz, 2 CH), 7.52 (2 H, t, 3J = 7.7 Hz, 2 CH), 7.61 (1 H, t, 3J = 7.7 Hz, CH).
13C NMR (125.7 MHz, CDCl3): 2.1 (3 Me), 117.3 (CH), 127.6 (CH), 128.9 (2 CH), 129.4
(2 CH), 131.8 (C), 134.5 (C), 173.3 (C). EI-MS (70 eV): m/z (%) = 249 (M+, 3), 176 (19),
173 (24), 157 (83), 100 (69), 85 (81), 77 (100). Anal. Calcd (%) for C12H15NOSSi (249.40):
C, 57.79, H, 6.06, N, 5.62, S, 12.85, Si, 11.26. Found: C, 57.92, H, 6.23, N, 5.45, S, 12.96, Si,
11.35.
4-(tert-Butyl)-3-(p-tolyl)thiazol-2(3H)-one (4k)
The crude product was purified by column chromatography (SiO2; Hexane/EtOAc 5/1, Rf :
¯
0.35) affording 0.18 g (75%) 4k. Colorless oil. IR (KBr): V = 3051, 2937, 1636, 1476, 1236,
1092. 1H NMR (500.1 MHz, CDCl3): δ = 1.35 (9 H, s, 3 Me), 2.42 (3 H, s, Me), 6.15 (1
H
H, s, CH), 7.23 (2 H, d, 3J = 7.1 Hz, 2 CH), 7.29 (2 H, d, 3J = 7.1 Hz, 2 CH). 13C NMR
(125.7 MHz, CDCl3): δ = 23.6 (Me), 35.2 (3 Me), 43.5 (C), 98.5 (CH), 128.3 (2 CH), 129.5
C
(2 CH), 130.2 (C), 138.5 (C), 165.9 (C), 174.1 (C). EI-MS (70 eV): m/z (%) = 247 (M+, 1),
190 (56), 176 (40), 156 (23), 141 (34), 100 (83), 91 (51), 85 (86), 57 (100). Anal. Calcd (%)
for C14H17NOS (247.36): C, 67.98, H, 6.93, N, 5.66, S, 12.96. Found: C, 67.82, H, 6.81, N,
5.80, S, 13.11.
4-(tert-Butyl)-3-(4-methoxyphenyl)thiazol-2(3H)-one (4 l)
The crude product was purified by column chromatography (SiO2; Hexane/EtOAc 4/1,
¯
Rf : 0.40) affording 0.20 g (77%) 4 l. Yellow oil. IR (KBr): V = 3044, 2966, 1641, 1511,
1
1470, 1232, 1176. H NMR (500.1 MHz, CDCl3): δ = 1.37 (9 H, s, 3 Me), 3.90 (3 H,
H
s, OMe), 6.22 (1 H, s, CH), 7.04 (2 H, d, 3J = 7.1 Hz, 2 CH), 7.21 (2 H, d, 3J = 7.1 Hz, 2
CH). 13C NMR (125.7 MHz, CDCl3): δ = 33.8 (3 Me), 41.9 (C), 56.2 (OMe), 96.5 (CH),
C
115.3 (2 CH), 126.2 (C), 129.1 (2 CH), 160.2 (C), 166.3 (C), 173.5 (C). EI-MS (70 eV):
m/z (%) = 263 (M+, 1), 206 (41), 156 (25), 192 (66), 107 (94), 100 (42), 85 (37), 77 (68),
57 (100). Anal. Calcd (%) for C14H17NO2S (263.36): C, 63.85, H, 6.51, N, 5.32, S, 12.17.
Found: C, 63.73, H, 6.68, N, 5.48, S, 12.34.
4-(tert-Butyl)-3-(4-chlorophenyl)thiazol-2(3H)-one (4 m)
The crude product was purified by column chromatography (SiO2; Hexane/EtOAc 5/1, Rf :
¯
0.19) affording 0.23 g (87%) 4 m. Pale yellow oil. IR (KBr): V = 3029, 2953, 1632, 1478,
1234, 1131, 810. 1H NMR (500.1 MHz, CDCl3): δ = 1.40 (9 H, s, 3 Me), 6.19 (1 H, s, CH),
H
7.37 (2 H, d, 3J = 7.6 Hz, 2 CH), 7.46 (2 H, d, 3J = 7.6 Hz, 2 CH). 13C NMR (125.7 MHz,
CDCl3): δ = 35.2 (3 Me), 43.2 (C), 98.2 (CH), 128.7 (2 CH), 129.4 (C), 132.5 (2 CH),
C
135.7 (C), 166.1 (C), 173.9 (C). EI-MS (70 eV): m/z (%) = 267 (M+, 1), 211 (34), 196 (78),
156 (19), 111 (65), 100 (87), 85 (56), 57 (100). Anal. Calcd (%) for C13H14ClNOS (267.77):
C, 58.31, H, 5.27, N, 5.23, S, 11.97, Cl, 13.24. Found: C, 58.44, H, 5.30, N, 5.12, S, 12.08, Cl,
13.30.
Methyl 4-(4-(tert-butyl)-2-oxothiazol-3(2H)-yl)benzoate (4n)
The crude product was purified by column chromatography (SiO2; Hexane/EtOAc 4/1, Rf :
¯
0.38) affording 0.21 g (71%) 4n. Colorless oil. IR (KBr): V = 3055, 2976, 1736, 1646, 1466,
1324, 1255, 1123. 1H NMR (500.1 MHz, CDCl3): δ = 1.41 (9 H, s, 3 Me), 3.95 (3 H, s,
H

10
F. HEYDARI-MOKARRAR ET AL.
OMe), 6.25 (1 H, s, CH), 7.31 (2 H, d, 3J = 7.5 Hz, 2 CH), 7.90 (2 H, d, 3J = 7.5 Hz, 2 CH).
13C NMR (125.7 MHz, CDCl3): δ = 35.2 (3 Me), 42.5 (C), 53.7 (OMe), 99.5 (CH), 126.8
C
(2 CH), 127.9 (C), 132.6 (2 CH), 138.5 (C), 166.1 (C), 167.4 (C), 173.8 (C). EI-MS (70 eV):
m/z (%) = 291 (M+, 1), 260 (11), 156 (38), 105 (91), 100 (73), 85 (53), 57 (100). Anal.
Calcd (%) for C15H17NO3S (291.37): C, 61.83, H, 5.88, N, 4.81, S, 11.00. Found: C, 61.67,
H, 5.72, N, 4.97, S, 11.13.
4-(tert-Butyl)-3-(4-nitrophenyl)thiazol-2(3H)-one (4o)
The crude product was purified by column chromatography (SiO2; Hexane/EtOAc 2/1,
¯
Rf : 0.43) affording 0.14 g (49%) 4o. Yellow solid, m.p = 132-134 °C. IR (KBr): V = 3016,
2942, 1633, 1531, 1340, 1252, 1131. 1H NMR (500.1 MHz, CDCl3): δ = 1.43 (9 H, s, 3
H
Me), 6.22 (1 H, s, CH), 7.86 (2 H, d, 3J = 7.8 Hz, 2 CH), 8.33 (2 H, d, 3J = 7.8 Hz, 2 CH).
13C NMR (125.7 MHz, CDCl3): δ = 35.8 (3 Me), 42.9 (C), 97.2 (CH), 123.6 (2 CH), 131.8
C
(2 CH), 140.2 (C), 145.8 (C), 168.2 (C), 175.2 (C). EI-MS (70 eV): m/z (%) = 278 (M+, 1),
222 (35), 207 (13), 156 (52), 100 (86), 85 (61), 57 (100). Anal. Calcd (%) for C13H14N2O3S
(278.33): C, 56.10, H, 5.07, N, 10.07, S, 11.52. Found: C, 56.24, H, 5.19, N, 10.22, S,
11.44.
4-(tert-Butyl)-3-cyclohexylthiazol-2(3H)-one (4p)
The crude product was purified by column chromatography (SiO2; Hexane/EtOAc 5/1, Rf :
¯
0.21) affording 0.19 g (79%) of 4p; Colorless oil. IR (KBr): V = 3008, 2967, 1632, 1456,
1246, 1132. 1H NMR (500.1 MHz, CDCl3): δ = 1.36 (9 H, s, 3 Me), 1.40-1.95 (10 H, m, 5
H
CH2), 3.72-3.77 (1 H, m, CH), 6.12 (1 H, s, CH). 13C NMR (125.7 MHz, CDCl3): δ = 26.8
C
(CH2), 29.1 (2 CH2), 34.7 (3 Me), 36.3 (2 CH2), 42.1 (C), 70.2 (CH), 101.1 (CH), 160.6 (C),
177.8 (C). EI-MS (70 eV): m/z (%) = 239 (M+, 1), 182 (34), 156 (58), 100 (78), 85 (56),
83 (87), 57 (100). Anal. Calcd (%) for C13H21NOS (239.38): C, 65.23, H, 8.84, N, 5.85, S,
13.39. Found: C, 65.11, H, 8.67, N, 5.73, S, 13.53.
4-(tert-Butyl)-3-isopropylthiazol-2(3H)-one (4q)
The crude product was purified by column chromatography (SiO2; Hexane/EtOAc 5/1,
¯
Rf : 0.32) affording 0.15 g (75%) of 4q; Colorless oil. IR (KBr): V = 3029, 2943, 1639,
1
1435, 1251, 1126. H NMR (500.1 MHz, CDCl3): δ = 1.40 (9 H, s, 3 Me), 1.52 (6 H,
H
d, 3J = 5.6 Hz, 2 Me), 4.55-4.60 (1 H, m, CH), 6.17 (1 H, s, CH). 13C NMR (125.7 MHz,
CDCl3): δ = 23.6 (2 Me), 34.9 (3 Me), 43.1 (C), 66.7 (CH), 103.2 (CH), 159.2 (C), 176.8
C
(C). EI-MS (70 eV): m/z (%) = 199 (M+, 1), 156 (31), 140 (78), 122 (30), 100 (81), 85 (52),
57 (100). Anal. Calcd (%) for C10H17NOS (199.31): C, 60.26, H, 8.60, N, 7.03, S, 16.09.
Found: C, 60.41, H, 8.47, N, 7.19, S, 16.24.
S-(phenylethynyl) phenylcarbamothioate (5)
The crude product was purified by column chromatography (SiO2; Hexane/EtOAc 3/1,
Rf : 0.26) affording 0.23 g (91%) of 5; Colorless solid, m.p = 101-103 °C. IR (KBr):
1
¯
V = 3361, 3046, 2971, 1630, 1252, 1072. H NMR (500.1 MHz, CDCl3): δ = 7.11 (1 H,
H
t, 3J = 7.7 Hz, CH), 7.27 (2 H, t, 3J = 7.7 Hz, 2 CH), 7.36-7.44 (3 H, m, 3 CH), 7.49 (2 H,
d, 3J = 7.1 Hz, 2 CH), 7.65 (2 H, d, 3J = 7.7 Hz, 2 CH), 8.51 (1 H, br s, NH). 13C NMR
(125.7 MHz, CDCl3): δ = 81.1 (C), 94.3 (C), 119.1 (2 CH), 123.5 (C), 127.3 (CH), 127.9
C
(CH), 129.1 (2 CH), 129.7 (2 CH), 133.7 (2 CH), 137.7 (C), 167.4 (C). Anal. Calcd (%) for
C15H11NOS (253.32): C, 71.12, H, 4.38, N, 5.53, S, 12.66. Found: C, 71.24, H, 8.21, N, 5.70,
S, 12.47.

JOURNAL OF SULFUR CHEMISTRY
11
2-Benzylidene-4-phenyl-1,3-dithiole (7)
The crude product was purified by column chromatography (SiO2; Hexane/EtOAc 12/1,
R : 0.31) affording 0.32 g (76%) of 7. 1H NMR (500.1 MHz, CDCl3): δ = 6.47 (1 H, s,
H
f
CH), 6.78 (1 H, s, CH), 7.25 (1 H, t, 3J = 7.7 Hz, CH), 7.30 (1 H, t, 3J = 7.0 Hz, CH), 7.42-
7.50 (6 H, m, 6 CH), 7.67 (2 H, d, J = 7.0 Hz, 2 CH). 13C NMR (125.7 MHz, CDCl3):
3
δ = 116.3 (CH), 121.1 (CH), 126.8 (CH), 127.4 (CH), 128.5 (2 CH), 129.1 (2 CH), 129.6
C
(2 CH), 130.3 (2 CH), 135.9 (C), 137.3 (C), 140.1 (C), 143.8 (C). Anal. Calcd (%) for
C16H12S2 (363.41): C, 71.60, H, 4.51, S, 23.89. Found: C, 71.78, H, 4.63, S, 23.72.
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