Utility of 2-[4-benzo[d]furan-2,1,3-thiazol-2-yl] ethane-nitrile in synthesis of thiazole, coumarin, thiphene, and thiadiazoline derivatives

Article abstract of DOI:10.1080/104265090920949

Coumarine, thiazole, thiophene and 2,3-dihydro-1,3,4-thiadiazole derivatives were synthesized from 2-[4-(4-methyl-2-phenyl-1,3-thiazol.-5-yl)-1, 3-thiazol-2-yl]ethanenitrile and salicylaldehyde, chloroacetone, ethyl chloroacetate, or hydrazonoyl halides, respectively. Copyright Taylor & Francis Inc.

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Utility of 2-[4-
Benzo[d]furan-2,1,3-thiazol-2-
yl)] Ethane-Nitrile in Synthesis
of Thiazole, Coumarin,
Thiphene, and Thiadiazoline
Derivatives
Soad M. Abdel-Gawad a
a Department of Chemistry, Al-Azhar University,
Cairo, Egypt
Published online: 22 Aug 2006.
To cite this article: Soad M. Abdel-Gawad (2005): Utility of 2-[4-Benzo[d]furan-2,1,3-
thiazol-2-yl)] Ethane-Nitrile in Synthesis of Thiazole, Coumarin, Thiphene, and
Thiadiazoline Derivatives, Phosphorus, Sulfur, and Silicon and the Related Elements,
180:10, 2303-2314
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Phosphorus, Sulfur, and Silicon, 180:2303–2314, 2005
Copyright © Taylor & Francis Inc.
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/104265090920949
Utility of 2-[4-Benzo[d]furan-2,1,3-thiazol-2-yl)]
Ethane-Nitrile in Synthesis of Thiazole, Coumarin,
Thiphene, and Thiadiazoline Derivatives
Soad M. Abdel-Gawad
Department of Chemistry, Al-Azhar University, Cairo, Egypt
Coumarine, thiazole, thiophene and 2,3-dihydro-1,3,4-thiadiazole derivatives
were synthesized from 2-[4-(4-methyl-2-phenyl-1,3-thiazol.-5-yl)-1,3-thiazol-2-
yl]ethanenitrile and salicylaldehyde, chloroacetone, ethyl chloroacetate, or hydra-
zonoyl halides, respectively.
Keywords 2,3-Dihydro-1,3,4-thiadiazole; coumarin; hydrazonoyl halides; thiazole;
thiophene
INTRODUCTION
Thiazoles are widely used as accelerators in rubber vulcanization and
as antioxidants.1,2 A large number of dyes are derived from thiazololium
salts. Benzothiazolium salts have been synthesized and many of them
have been used in silver photography, essentially as sensitizing dyes.3
Other derivatives exhibited the phenomenon of photochromism. It this
article, I report the synthesis of some new biologically active thia-
zoles containing different moites such as coumarin, thiophene, and
thiadiazoline.
RESULTS AND DISCUSSION
2-bromoacetylbenzo(d)furanethan-1-one (1) was reacted with cyanoth-
ioacetamide in ethanol to yield the corresponding 2-[4-benzofuryl)-1,3-
thiazol-2-yl] ethanenitrile (3). Structure 3 was confirmed on the basis
1
of elemental analysis and IR, H-NMR, and chemical transformation.
Its 1HNMR spectrum showed signals at δ = 4.17 (s, 2H, CH2CN), 7.34
Received July 29, 2004; accepted October 16, 2004.
Address correspondence to Soad M. Abdel-Gawad, Al-Azhar University. Department
of Chemistry, Faculty of Science (Girl’s Branch), Cairo, Egypt. E-mail: Abdel-Gawad@
yahoo.com
2303

2304
S. M. Abdel-Gawad
(s, 1H, thiazole (CH), and 7.42–7.97 (m, 5H, Ar-H). IR (cm−1) revealed
bands at 2923 (C H) and 2219 (CN).
Compound 3 reacted with both benzaldehyde and salicylaldehyde to
give the corresponding substituted acrylonitrile 4 and the substituted
coumarin 5, respectively (Scheme 1). Structures 4 and 5 were estab-
lished on the basis of elemental analysis and spectral data. The IR
(cm–1) spectrum revealed bands at 3057 (CH arom.), 2924 (CH aliph),
1
2191 (CN), and 1519 (C C). H NMR (δ ppm) spectrum of 4 showed
signals at δ = 7.26–7.99 (m, 10H, ArH’s) and 8.23 (s, 1H, CH ).
1HNMR spectrum of 5 (DMSO-d6) showed signals at δ = 7.22–7.82
(m, 10H, ArH’s) and 9.12 (br., 1H, NH). Its IR (cm−1 ) spectrum revealed
bands at 3309 (NH), 3050 (CH arom), 2921 (CH aliph), and 1658 (C N).
Compound 5 was converted to coumarin derivative 6 by treatment
with hydrochloric acid. IR spectrum of compound 6 revealed bands at
3080 (CH arom.), 2921 (CH aliph), 1720 (CO), and 1604 (C N).
SCHEME 1

2-[4-Benzo[d]furan-2,1,3-thiazol-2-yl)]Ethane-Nitrile
2305
α-substituted cinnamonitrile reacted with 3 in ethanol containing a
catalytic amount of piperidine gave a product identical in all respects
(m.p., mixed m.p., and spectra) with 4. The formation of 4 can be ex-
plained by the addition of cinnamonitrile to 3 via the Micheal addition to
give the adduct intermediate 7 followed by elimination of malononitrile
(or ethyl cyanoacetate), respectively, to give final product 4 (Scheme 1).
Compound 3 reacted with phenyl isothiocyanate in N,N-dimethyl-
formamide containing potassium hydroxide, which acidifies with acetic
acid, to afford thioanilide 8 (Scheme 1). Compound 8 was confirmed on
the basis of elemental analysis, IR, and 1H-NMR, and chemical transfor-
mation. Thus, compound 8 reacted with chloroacetone in the presence
1
of potassium hydroxide to give S-acetonyl derivative 9. H NMR spec-
trum of 9 showed signals at δ = 2.64 (s, 3H, CH3), 3.34 (s, 2H, CH2),
–1
6.86 (s, 1H, CH thiazole) and 7.43–7.94 (m, ArH’s and NH). Its IR (cm
)
spectrum revealed bands at 3433 (NH), 2175 (CN), 1705 (CO), and 1600
(C N).
Compound 9 was conversted to thiazole derivative 10 by heating in
ethanol containing a catalytic amount of piperidine. 1H NMIR showed
signals at δ = 2.79 (s, 3H), 6.49 (s, 1H), 7.02 (s, 1H), and 7.25–7.96 (m,
9H, ArH’s). Its IR (cm–1) spectrum revealed bands at 2167 (CN), 1640
(C N), and 1600 (C C).
Ethyl chloroacetate reacted with thioanilide derivative 9 in N,N-
dimethylformamide containing potassium hydroxide at room tempera-
ture to give 11. Compound 11 was confirmed on the basis of elemental
analysis and spectral data and converted to aminothiophene 12 by boil-
1
ing in ethanol containing a catalytic amount of piperidine. HNMR (δ
ppm) spectrum 11 showed signals at δ = 1.22 (t, 3H, CH3 ester), 2.66,
3.34 (s, 2H, SCH2), 4.11 (q, 2H, CH2CH3), and 7.22–791 (m, 9H, (s, Ar.,
–1
1H, NH). Its IR (cm ) revealed bands at 3440 (NH), 2923 (CH), 2190
1
(CN), 1743 (CO), and 1620 (C N). H-NMR (δ ppm) spectrum of 12
showed signals at δ = 1.35 (t, 3H, CH3 CH2), 4.27 (q, 2H, CH2), 6.10
(s, 2H, NH2), 7.19–7.98 (m, 10H, ArH’s) and 11.51 (s, br., 1H, NH). Its
–1
IR (cm ) revealed bands at 3394, 3301, 3290 (NH2, NH), 1710 (CO),
1645 (C N), and 1600 (C C).
Treatment of the appropriate hydrazonoyl halides 13a–c with
thioanilide 8 in N,N-dimethylformamide containing potassium hydrox-
ide gave a single product (tlc) in each case. IR (cm–1) spectra of the
corresponding products showed bands near 2921 (CN) and 1728 and
1689 (CO’s) 1H NMR spectrum of 14a showed signals at δ = 1.47 (t, 3H,
CH3CH2) 4.49 (q, 2H, CH2 ester), 7.15 (s, 1H, thiazole and 7.26–8.02
1
(m, 9H, Ar H). H NMR spectrum of 14b showed signals at δ = 1.47
(t, 3H, CH2CH3), 2.48 (s, 3H, 4/CH3C6H4), 4.40 (q, 2H, CH2CH3), 7.15
(s, 1H, thiazole C-5), and 7.26–8.02 (m, 9H, ArH). On the above-finding

2306
S. M. Abdel-Gawad
SCHEME 2
structure 15 and 16 were excluded on the results of spectra, elemental
analysis and alternative synthesis methods (Scheme 3).
Unequivocal support on structure 14 was obtained from alterna-
tive method synthesis. Thus, treatment showed evidence that the reac-
tion of the appropriate hydrazonoyl halides with methyl carbodithioate
17, which was prepared by treatment of 3 with carbon disulfide in
presence of potassium carbon hydroxide and iodomethane, in N,N-
dimethylformamide containing triethylamine, gave a product identical
in all respects (m.p., mixed m.p., and spectra) with 14.
Two possible pathways can account for the formation of 14. 1,3-
addition of the thiol tautomer 17 to the nitrilium imide 18a (which
was prepared in situ by treatment of thydrazonoyl chloride 17 with tri-
ethylamine) can give the thiohydrazonate ester 19, which undergoes
nucleophilic cyclization to yield 20, which affords 14 by loss of RSH.
ii) A1ternatively 1,3-cycloaddition of the nitrilium imide 18 to the C S
of 17 can give 20 directly (Scheme 4).
Compound 3 reacted with diazonum chloride and furnished the cor-
responding 22 that also was obtained via reaction of 2-bromoacetyl

2-[4-Benzo[d]furan-2,1,3-thiazol-2-yl)]Ethane-Nitrile
2307
SCHEME 3
benzofuran (1) with phenylazocyanothioacetamide in boiling acetic acid
under reflux. Structure 22 was elucidated by elemental analysis and
spectra and chemical transformation.
Thus, compound 22 reacted with ethyl chloroacetate or chloroace-
tone in N,N dimethylformamide containing potassium carbonate and
triethylamine that gave the pyrazoles 23. 1H NMR (δppm) spectrum of
23a showed at δ =1.35 (t, 3H), 4.27 (q, 2H), 5.3 (br, 2H, NH2), 7.2–7,4
(m, 10 H, Ar, H’s). Its IR (cm–1) reveled band at 329 (NH2), 1710 (CO),
1
and 1600 (C C) HNMR spectrum of 23b showed signals at δ 2.3 (s,
3H, CH3), 5.5 (s, br, 1H, thiazol C-5), and 7.26–8.02 (m, q, ArH’s). Its IR
spectrum revealed bonds at 3290 (NH2), 1710 (CO), 1660 (C N), and
1600 (C C).

2308
S. M. Abdel-Gawad
SCHEME 4
EXPERIMENTAL
All melting points were determined on an electrothermal apparatus and
are uncorrected. IR spectra were recorded (KBr discs) on a Shimadzu
1
FT-IR 8201 PC spectrophotometer. H NMR spectra were recorded in
CDC13 and (DMSO-d6) solutions on a Varian Gemini 300 MHz spec-
trometer and chemical shifts are expressed in δ units using TMS as
an internal reference. Elemental analyses were carried out at the Mi-
croanalytical Center of the Cairo University. Hydrazonoyl halides were
prepared according to reported methods.4−9
Synthesis of 4-Benzo(d) Furan-2-yl Ethanenitrile (3)
A mixture of 2-bromoacetylbenzo(d)furan10 (1) (2.4 g, 0.1 mmol) and
cyanothioacetamide (10.0 g, 0.01 m) in ethanol (25 mL) was refluxed
for 2 h. The reaction mixture was poured onto ice-cold water (50 mL)

2-[4-Benzo[d]furan-2,1,3-thiazol-2-yl)]Ethane-Nitrile
2309
SCHEME 5
and few drop of ammonium hydroxide (25%) were added. The resulting
solid was collected, washed with water, and recrystallized from ethanol
to give thiazolylacetonitrile 3 (Table I).
Synthesis of 2-(4-Benzo(d) Furan(1,3-thiazol-2-yl)-
3-phenylprop-2-eneitrile (3)
Thiazolylacetonitrile 3 (1.2 g, 5 mmol) and benzaldehyde (3 g, 5.0 g
mmol) in ethanol (15 mL) and piperidine (drops) were stirred at room
temperature for 2 h. The stirring was continued for 2 h. The resulting
solid was collected by filtration, washed with ethanol, and recrystallized
from ethanol to give 4 (Table I).
Synthesis of 3-[-4-Benzofuran)-1,3-thiazol-2-yl]-
2H-chromen-2-imin (5)
Thiazolylacetonitrile 3 (1.2 g, 5 mmol) and salicyladehded (0.53 mL, 5
mmol) in ethanol (20) containing a catalytic amount of piperidine were
stirred at room temperature for 2h. The resulting solid was collected
and recrystallized from a mixture of EtOH/DMF to give 5 (Table I).

2310
S. M. Abdel-Gawad
TABLE I Characterization Data of the Newly Synthesized
Compounds
% Analyses, calcd./found
Compound
no.
M.P., ◦
Solvent
C
Yield %
Color
Mol. formula
mol. wt
C
H
N
S
3
4
168–170
EtOH
145–147
EtOH
150
EtOH
170–172
dioxans
180
EtOH
130–32
EtOH
90
Yellow
85
Brown
90
Yellow
90
Yellow
80
Yellow
70
Yellow
40
C13H8N2OS
240.28
C2OH12N2OS
328.39
C2OH12N2O2S
344.39
C2OH11NO3S
345.37
65.00 3.33 11.66 13.33
65.14 3.00 11.28 13.00
73.17 3.65 8.53 9.65
73.05 3.31 8.30 9.40
69.76 3.48 8.13 9.30
69.96 3.11 8.32 9.00
69.56 3.18 4.05 9.27
69.31 3.40 4.22 9.51
69.10 3.66 14.65 8.37
69.38 3.30 14.25 8.00
64.00 3.46 11.20 17.06
63.90 3.21 11.33 17.33
5
6
7
C22OH14N4OS
382.43
C2OH13N3OS2
375.47
8
9
100
C23OH19N3S2O2 63.74 4.38 9.69 14.78
Pet.ether
166–70
EtOH
Yellow
65
Brown
40
Brown
70
433.55
C23H17N3S2O2
431.53
63.50 4.10 9.41 14.51
64.03 3.94 9.74 14.84
64.32 3.60 9.51 14.56
10
11
12
14a
14b
14c
17
22
23a
23b
110◦C
Pet.ether
210-12
C24H19N3O3S2O3 62.47 4.12 9.11 13.88
461.56
C24H19N3O3S2
461.56
24H16N4O3S2
472.54
C25H18N4S2O3
486.47
C23H14N4O2S2
442.52
C15H10N2OS3
330.39
19H12N4OS
344.97
22H17N4O2S
401.38
62.20 4.33 9.00 13.53
62.47 4-12 10.00 13.85
62.25 4.32 9.78 13.61
61.01 3.38 11.86 13.55
61.15 3.18 11.71 13.23
61.72 3.70 11.52 13.16
61.56 3.48 11.35 13.00
62.44 3.16 12.66 14.47
62.21 3.35 12.31 14.19
54.54 3.03 8.48 29.9
54.21 3.30 8.62 29.30
66.27 3.48 16.27 9.30
66.00 3.20 16.00 9.50
65.83 4.23 13.96 7.98
65.55 4.00 13.65 7.73
64.03 4.40 12.99 7.42
64.20 4.12 12.64 7.23
EtOH/DMF Brown
132–34
EtOH
55
Brown
50
Brown
70
Brown
60
Yellow
65
Red
65
Brown
65
Yellow
C
130◦C
EtOH
145–47
EtOH
100–2
Pet. ether
150–52
EtOH
180–182
EtOH
C
C
210–12
EtOH
C
23H19N4O3S
431.49
Synthesis of 3-[Benzofuran)1,3-thiazol-2-yl]-
2H-chromen-2-one (6)
A mixture of 5 (0.5 g 0.01 mmol) and dilute hydrochloric acid (5 mL,
50%) was stirred at room temperature for 1h. The resulting solid was
collected and recrystalized from EtOH/DMF to give coumarin derivative
6 (Table I).

2-[4-Benzo[d]furan-2,1,3-thiazol-2-yl)]Ethane-Nitrile
2311
Synthesis of 2-[4-(4-Benzo(d)furan(1,3-thiazol-yl)]-
3-(phenylamino-sulfanylprop-2-enenitrile (7)
Phenyl isothiocyanate (0.6 mL, 5 mmol) was added to a mixture of thi-
azolylacetonitril 3 (1.2 g, 5 mmol) and potassium hydroxide (0.33 g.
5 mmol) in N,N-dimethylformarmide (15 mL) and was stirred at room
temperature until potassium hydroxide dissolve completely. The reac-
tion mixture was stirred for 1 h. Then the reaction mixture was acidified
with acetic acid. The resulting solid was collected and recrystallized
from ethanol to give thioanilide 7.
Synthesis 9,11,14a and 14b 13a–b
Phenyl isothiocyanate (0.6 mL, 5 mmol) was added to a mixture of
(5 mmol) in thiazolylacetonitrile 3 (1.2 g, 5 mmol) and potassium hy-
droxide in N,N-dimethylformamide (15 mL) while stirring at room
temperature until potassium hydroxide disso1ved completely. The re-
action mixture was stirred for 30 min. Chloroacetone (0.46 g, 0.4 mL,
5 mmol), ethyl chloroacetate (0.65 g, 0.53 mL, 5 mmol), or appro-
priate hydrazonoyl halides 12a,b (5 mmol) was added and the re-
action mixture was stirred for 3h. The resulting solid was collected
and recrystallized from the appropriate solvent to afford 8,9 and
14a,b.
Synthesis of Thiazole 9 and Aminothiophene 11
Each of 8 (1.22 g, 2.5 mmol) and 9 (1.3 g, 2.5 mmol) in ethanol (20 mL)
containing a catalytic amount of piperidine (3 drops) was refluxed for 30
min. The resulting solid was collected and recrystallized from the ap-
propriate solvent to give thiazole 10 or aminothiophene 11, respectively
(Table I).
Preparation of 2-[4-Benzofuryl(1,2-thazol-2-yl)-3-
methyltho-3-thioxo-propenitrile (16)
A mixture of carbon disulfide (0.3 mL, 5 mmol) was added to a mix-
ture of thiazolylacetonitrile 2 (1.2 g, 5 mmol) and potassium hydroxide
(0.33 g, 5 mmol) in N,N-dimethylformamide (15 mL) and was stirred
at room temperature until potassium hydroxide dissolved completely.
The reaction mixture was stirred for 30 min. Iodomethane was then
added (0.72 g, 0.32 mL, 5 mmol) and while sttring continued. The re-
sulting solid was collected and recrystallized from DMF to afford 17
(Table I).

2312
S. M. Abdel-Gawad
(Alternative Method): Synthesis of 2,3-Dihydro-
1,3,4-thiadiazoles Derivatives 14a,b
A mixture of 17 (0.2 g, 5 mmol), the appropriate hydrazonyl chloride
13a,b and triethylamine (0.5 mL, 5 mmol) in N,N-dimethylformamide
(15 mL), while stirring at room temperature for 2h. The resulting solid
was collected and then crystallized from an appropriate solvent to give
a product identical in all respects (m.p., mixed m.p., and spectra) with
14a–b which was obtained before.
Synthesis of 3-Aza-2-(4-benzofuran)1,3-(thizaol
2-yl)-3-phenyl-amino) prop-2-enenitrile (22)
Method A
Benzenediazonium chloride (5 mmol), which was prepared by diazo-
tized aniline (0.45 g, 5 mmol), hydrochloric acid (3 mL, 6 M), and sodium
nitrite (0.35 g, 5 mmol in 5 mL H2O) at 0◦C, was added dropwise to a
solution of 3 (1.2 g, 5 mmol) in pyridine (20 mL) while stirring at 0◦C.
The reaction mixture was stirred for 3h, then the resulting solid was
collected and crystallized from dioxan to affor 22.
Method B
A mixture of an equimolar amount of 2-bromoacetylfuran and 1-
cyano-1-phenylhydrazothioacetamide (5 mmol) in acetic acid (20 mL)
was refluxed for 2 h. The reaction mixture was poured onto ice water,
and the resulting solid was collected and crystallized from dioxan to
give a product identical in all respects (m.p., mixed m.p., and spectra)
with 22, which was obtained in method A.
Synthesis of 3-Thiazol 2-(4-Benzofuran)1,-2-yl)-3-amino
Pyrazole 23a,b
A mixture of compound 22 (1.72 g, 5 mmol) and the appropriate
chloroactone or ethyl chloroacetate (5 mmol) in N,N,-dimethyl for-
mamide (20 mL) containing K2CO3 (2 g) was refluxed for 2 h at 120◦C;
then the reaction mixture was cold and triethylamine (5 mmol) was
added. The reaction mixture was boiled under reflux at 90◦C for 1 h,
was allowed to cool, and was pured onto ice (120 g). The solid product
was collected and recrystallized from ethanol to give 23a,b.
BIOLOGICAL ACTIVITIES OF SYNTHESIZED COMPOUNDS
The tested microorganisms were gram-positive bacteria (Staphylococ-
cus aureus) [ATCC25923] and Streptococcus pyogenes [ATCC19615]

2-[4-Benzo[d]furan-2,1,3-thiazol-2-yl)]Ethane-Nitrile
2313
TABLE II Response of Various Microorganisms to Some Synthesized
Compounds In Vitro (Culture). W: low activity (l–5 mm) (+); M:
moderate activity (6–10 mm) (++); S: high activity (11–15 mm) (+++);
I: Inhibitor
Diameter of the Zone of Inhibition
Staphylococcus Streptococcus Pseudomonas
Compound
no.
aureus
(ATCC25923)
pyogenes
ATCC19615
syringae PV
phasealicola
Aspergillus Fusarium
niger
oxysporum
3
5
6
8
9
11
12
14
17
M
W
M
W
W
W
—
M
M
—
W
M
W
—
M
—
—
W
W
M
W
W
—
W
—
W
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
and gram-negative bacteria (pseudomonas syrinagae PV phasealicola).
In addition, some fungal–plant pathogens (Aspergillus Niger and Fusar-
ium Oxysporum) were tested. Sensitivity of the selected microorgan-
isms to some synthesized compounds were determined in vitro cul-
ture to two concentrations (100, 200 µg/mL) that were dissolved in
CHCl3. The tests were carried out using the filter paper and hole-plate
method.11
Studies on the biological activity of compounds 3, 9, 11, 12, and 14
led to the fact that these compounds have a moderate biological activity
against the tested bacteria but no effect on the Aspergillus niger. It also
has been observed through the results in Table II that the compounds
5, 6, 8, and 17 have a strong effect on bacteria. All the tested compounds
showed no antifungal activities.
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2314
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[9] H. M. Hassaneen, A. S. Shawali, N. E. Elwan, and N. M. Abounada, Sulfur Letters,
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