2-(4-naphtho[1,2-d]furan-2-yl-1,3-thiazol-2-yl)-ethanenitrile in heterocyclic synthesis

Article abstract of DOI:10.1080/10426500590885066

Coumarin, thiazole, and 2,3-dihydro-1,3,4-thiadiazole derivatives were synthesized from 2-(4-naphtho[1,2-d]furan-2-yl-1,3-thiazol-2-yl)ethanenitrile and different reagents. Structures of the new compounds were elucidated on the basis of elemental analysis, spectral data, and alternative methods of synthesis whenever possible. Copyright Taylor & Francis Inc.

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2-(4-Naphtho[1,2-d]furan-2-
yl-1,3-thiazol-2-yl)-
ethanenitrile in Heterocyclic
Synthesis
Abdou O. Abdelhamid a & Mohamed A. M. Alkhodshi
a
a Department of Chemistry, Cairo University , Giza,
Egypt
Published online: 01 Feb 2007.
To cite this article: Abdou O. Abdelhamid & Mohamed A. M. Alkhodshi (2005) 2-(4-
Naphtho[1,2-d]furan-2-yl-1,3-thiazol-2-yl)-ethanenitrile in Heterocyclic Synthesis,
Phosphorus, Sulfur, and Silicon and the Related Elements, 180:7, 1647-1656, DOI:
10.1080/10426500590885066
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Phosphorus, Sulfur, and Silicon, 180:1647–1656, 2005
Copyright © Taylor & Francis Inc.
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426500590885066
2-(4-Naphtho[1,2-d ]furan-2-yl-1,3-thiazol-2-yl)-
ethanenitrile in Heterocyclic Synthesis
Abdou O. Abdelhamid
Mohamed A. M. Alkhodshi
Department of Chemistry, Cairo University, Giza, Egypt
Coumarin, thiazole, and 2,3-dihydro-1,3,4-thiadiazole derivatives were synthe-
sized from 2-(4-naphtho[1,2-d]furan-2-yl-1,3-thiazol-2-yl)ethanenitrile and differ-
ent reagents. Structures of the new compounds were elucidated on the basis of el-
emental analysis, spectral data, and alternative methods of synthesis whenever
possible.
Keywords 2,3-Dihydro-1,3,4-thiadiazole; coumarin; hydrazonoyl halides; thiazole
INTRODUCTION
Recently, a large number of thiazole derivatives have been found
to exhibit pharmacological activity.1,2 They also were used as an
anthelmintic,3 fungicidal,4 and antifungal activity, inhibiting in vivo
the growth of Xanthomonas oryzae,5 an ingredient of herbicides.6 As
an extension of our study7−11, we report herein the synthesis of differ-
ent thiadiazoles, coumarines, and pyrazolo[1,5-a]pyrimidines contain-
ing thiazole moiety.
RESULTS AND DISCUSSION
2-Bromo-1-naphtho[1,2-d]furan-2-ylethan-1-one (1) reacted with cyan-
othioacetamide in boiling ethanol under reflux and afforded 2-(4-
naphtho[1,2-d]furan-2-yl-1,3-thiazol-2-yl)ethanenitrile (2). Structure 2
was confirmed on the basis of elemental analysis, spectral data, and
chemical transformation. 1H NMR (δ ppm) spectrum showed signals at
δ = 4.12 (s, 2H, CH2CN), 7.51–8.19 (m, 8H, thiazole C-5, and ArH’s). Its
IR (cm−1) revealed bands at 3101 (C H), 2252 (CN) and 1620 (C C).
Received June 17, 2004; accepted August 12, 2004.
Address correspondence to Abdou O. Abdelhamid, Department of Chemistry, Faculty
of Science, Cairo University, Giza 12316, Egypt. E-mail: Abdou abdelhamid@yahoo.com
1647

1648
A. O. Abdelhamid and M. A. M. Alkhodshi
Compound 2 reacted with each of salicylaldehyde and benzalde-
hyde to give 3-(4-naphtho[1,2-d]furan-2-yl-1,3-hiazol-2yl)-2H-chromen-
2-imine (3) and (2E)-2-(4-naphtho[1,2-d]furan-2-yl(1,3-thiazol-2-yl))-3-
phenylprop-2-enenitrile (5), respectively (Scheme 1).
SCHEME 1
Structures of 3 and 5 were established on the basis of elemental anal-
ysis, spectral data, and chemical transformation (or alternative route
synthesis). 1H NMR (δ ppm) spectrum of 3 showed signals at δ = 6.68–
7.41 (m, 13H, ArH’s) and 8.42 (s, 1H). Its IR (cm−1) spectrum revealed
bands at 3124 (NH), 3057 (CH), and 1599 (C C). More evidence on
structure 3 came from its conversion to 3-(4-naphtho[1,2-d]furan-2-yl-
1,3-thiazole-2-yl)-2H-chromen-2-one (4) by hydrochloric acid. IR spec-
trum of 4 revealed bands at 3055 (CH), 1712 (CO), and no bands be-
tween 3150–3500 due the absence of NH group. 1H NMR (δ ppm) spec-
trum of 5 showed one signal at δ = 7.00–7.41 (m, ArH’s). Its IR (cm−1
)
spectrum revealed bands at 3057 (CH), 2214 (CN), and 1604 (C C).
Thus, compound 2-(aminothioxomethyl)-3-phenylprop-2-enenitrile (6)
reacted with naphtho[1,2-d]furan-2-ylethan-1-one (1) in boiling ethanol

Naphthofuranyl Thiazolyl Ethanenitrile
1649
to give a product identical in all respects (mp., mixed mp., and spectra)
with 5.
Treatment of 2 with arenediazonium chloride in ethanolic sodium ac-
etate solution at 0◦C afforded (2E)-3-aza-3-(arylamino)-2-naphtho[1,2-
d]furan-2-yl(1,3-thiazol-2-yl))-2-enenitrile 7a–c, respectively. Structure
7 was confirmed on the basis of elemental analysis, spectral data, and
1
chemical transformation. Thus, H NMR spectrum of 7b showed sig-
nals at δ = 2.37 (s, 3H), 7.26–8.20 (m, 12H), and 14.05 (s, br., 1H). Its
IR revealed bands at 3349 (NH) and 2221 (CN). Its 13C NMR showed
signals at 24, 102, 111, 115, 116, 119, 121, 124, 127, 128, 129, 130,
140, 143, 153, 155 ppm. Also, treatment of the appropriate (2E)-2-
aminothioxomethyl)-3aza)-3-(arylamino)prop-2-enenitrile 8a–c with 2-
Bromo-1-naphtho[1,2-d]furan-2-ylethan-1-one (1) in boiling acetic acid
under reflux afford products identical in all respects (mp., mixed mp.,
and spectra) with 7a–c.
Compound
2
reacted with phenyl isothiocyanate in N,N-
dimethylformamide containing potassium hydroxide to give non-
isolable product which converted to a product by hydrochloric acid.
The resulting product seems to be one of the four isomers 9a–d (cf.
Scheme 2). According to M.O. calculation, using Hyper Chem. AM1
semi-empirical Method, the total energy proved that the most stable
isomer formulated was 2-(4-naphtho[1,2-d]furan-2-yl(1,3-thiazol-
2yl))-3-(phenylamino)-3-thioxopropanenitrile (9B). Also, structure
9 was elucidated by microanalytical, spectral data, and chemical
transformation. Thus, treatment of 9 with iodomethane afforded
(2E)-3-methylthio-2-(4-naphtho[1,2-d]furan-2-yl(1,3-thiazol-2-yl))-3-
(phenylamino)prop-2-enenitrile (10) (cf. Scheme 3).
IR spectrum of 10 revealed characteristic bands at 3386 (NH) and
1
2198 (CN). Its H NMR showed signals at δ = 2.27 (s, 3H), 7.31–8.10
(m, 13H), and 12,53 (s, br., 1H). 13C NMR showed signals at δ = 16,
71, 102, 111, 115, 116, 118, 122, 127, 129, 130, 143, 144, 150, 153, 155,
and 167 ppm. Also, compound 10 reacted with hydrazine hydrate in
boiling ethanol under reflux gave [5-Amino-4-(4-naphtho[1,2-d]furan-
2-yl)(1,3-thiazol-2-y))pyrazol-3-yl]phenyl amine (11). Structure 11 was
elucidated by elemental analysis and spectral data (cf. Experimental).
On the other hand, the appropriate hydrazonoyl halides 12a–h re-
acted with 9 in ethanolic triethylamine at room temperature to give 2,3-
dihydro-1,3,4-thiadiazole derivatives 15a–h, respectively (Scheme 3).
IR spectra of 15a–h revealed bands near 2190 (CN) and 1720–1680
(CO). 1H NMR spectrum of 15a showed signals at δ = 4.15 (s, 3H)
and 7.52–8.31 (m, 13H) ppm. Its 13C NMR spectrum showed signals
at δ = 14, 61, 89, 115, 119, 118, 121, 122, 127, 128, 129, 130, 146, 149,
150, 153, 154, 155, 162, and 163 ppm.

1650
A. O. Abdelhamid and M. A. M. Alkhodshi
SCHEME 2
Also, C-methoxy-N-phenylhydrazonoyl chloride 12a reacted with
3-methylthio-2-(4-naphtho[1,2-d]furan-2-yl(1,3-thiazol-2-yl)-3-thioxo-
propanenitrile (17) in ethanolic triethylamine to give product identical
in all respects (mp., mixed mp., and spectra) with 15a .
In the light of the forgoing results, the mechanism outlined in
Scheme 3 seems to be the most plausible pathway for the formation of
15 from the reaction of the 9 with 12 (or nirile imine 16, which prepared
in situ by treatment of 12 with triethylamine). The reaction involves
initial formation of thiohydrazonate 13, which undergoes intermolec-
ular cyclization as soon as it is formed to yield the intermediate 14 or
via 1,3-dipolar cycloaddition of nitrilimine 16 to C S double bond of 9
to give the final product 15 via elimination of aniline.
EXPERIMENTAL
All melting points were determined on an electrothermal apparatus and
are uncorrected. IR spectra were recorded (KBr discs) on a Shimadzu

Naphthofuranyl Thiazolyl Ethanenitrile
1651
SCHEME 3
1
FT-IR 8201 PC spectrophotometer. H NMR spectra were recorded in
CDCl3 and (CD3)2 SO solutions on a Varian Gemini 300 MHz spec-
trometer and chemical shifts are expressed in δ units using TMS as an
internal reference. Mass spectra were recorded on a GC-MS QP1000 EX
Shimadzu. Elemental analysis were carried out at the Microanalytical
Center of the Cairo University. Hydrazonoyl halides were obtained as
previously reported.12−18
SYNTHESIS OF 2-(4-NAPHTHO[1,2-d ]FURAN-2-yl-1,3-
THIAZOL-2-yl)ETHANENITRILE (2)
A mixture of 2-Bromo-1–naphtho[1,2-d]furan-2-ylethan-1-one (1),19
(2.9 g, 0.01 mmol) and cyanothioacetamide (1.0 g, 0.01 mmol) in ethanol
(25 mL) was refluxed for 2 h. The reaction mixture was poured onto

1652
A. O. Abdelhamid and M. A. M. Alkhodshi
ice-cold water (50 mL) and drops of conc. ammonium hydroxide (25%)
were added. The resulting solid was collected and washed with wa-
ter, and recrystallized from ethanol to give thiazolylacetonitrile 2
(Table I).
TABLE I Characterization Data of the Newly Synthesized
Compounds
Calcd./found%
Corp. Mp., ◦
C
Color
yield%
Mol. formula
mol. wt.
no.
solvent
C
H
N
S
2
175–78
EtOH
228–30
DMF
268–70
AcOH
209–210
DMF
232–34
Dioxane
230–32
DMF
265–67
Dioxane
220–22
Dioxane
207–209
DMF
Pale Brown
69
Yellow
C17H10N2OS
290.35
70.33
70.45
3.47
3.30
3.58
3.80
3.54
3.40
3.73
3.65
3.58
3.68
3.95
4.15
3.06
2.90
3.55
3.70
3.90
3.80
4.05
4.10
3.17
3.10
3.47
3.32
3.36
3.25
3.27
3.35
3.27
3.00
2.88
2.60
3.33
3.50
3.13
3.10
3.18
3.00
9.69 11.04
9.80 11.15
3
C
24H14N2O2S 73.08
7.10
7.00
12.14
12.00
7.40
8.13
8.25
8.11
7.95
8.47
8.65
8.13
8.25
7.85
7.71
7.48
7.70
64
394.46
24H13NO3S
395.44
72.85
72.90
73.10
76.17
76.25
70.03
69.80
70.57
70.70
4
Yellowish gray
C
61
Yellow
52
Brown
40
Brown
41
Brown
39
5
C
24H14N2OS
378.46
7.20
7a
7b
7c
9
C23H14N4OS
394.46
14.20
13.95
13.72
13.94
13.06
12.90
C
24H16N4OS
408.49
C23H13ClN4OS 64.41
428.90
24H15N3OS2
425.53
64.50
67.74
67.50
68.31
68.20
68.07
67.90
Brown
67
C
9.87 15.07
9.70 14.80
9.56 14.59
9.72 14.82
10
Yellowish gray
58
C
25H17N3OS2
439.56
11
244–46
AcOH
275–77
DMF
Brown
72
Yellow
60
C
24H17N5OS
423.50
16.54
16.45
7.57
7.40
15a
15b
15c
15d
14e
15f
15g
15h
17
C27H16N4O3S2 63.77
508.58 63.92
11.02 12.61
10.97 12.42
10.72 12.27
10.90 12.40
12.29 11.26
12.10 11.40
11.37 13.02
11.50 12.90
10.10 11.56
9.95 11.65
9.99 17.16
10.10 17.00
9.27 10.60
9.40 10.70
302–304 Yellowish brown C28H18N4O3S2 64.35
DMF 66 522.61 64.10
274–76 Yellowish brown 32H19N5O2S2 67.47
DMF 63 569.67 67.29
198–200 Yellowish brown 27H16N4O2S2 65.84
492.58 65.900
C32H18N4O2S2 69.30
554.65 69.40
30H16N4O2S3 64.27
560.68 64.00
C36H20N4O2S2 71.51
604.71 71.30
C38H20N4O3S2 70.79
C
C
DMF
243–45
DMF
59
Brown
69
Brown
64
Brown
67
Brown
61
265–67
DMF
265–268
DMF
C
>320
DMF
272–75
DMF
8.69
9.95
644.74
C19H12N2OS3
380.51
70.90
59.97
59.70
8.50 10.20
7.36 25.28
7.50 25.40
Brown
62

Naphthofuranyl Thiazolyl Ethanenitrile
1653
SYNTHESIS OF 3-(4-NAPHTHO[1,2-d]FURAN-2-yl-1,3-HIAZOL-
2yl)-2H-CHROMEN-2-IMINE (3) AND (2E)-2-(4-NAPHTHO-
[1,2-d ]FURAN-2-yl(1,3-THIAZOL-2-yl))-3-PHENYLPROP-2-
ENENITRILE (5)
Method A: Thiazolylacetonitrile 2 (1.45 g, 5 mmol) and salicylaldehyde
or benzaldehyde (5 mmol) in ethanol (20) containing a catalytic amount
of piperidine were stirred at room temperature for 2 h. The resulting
solid was collected and recrystallized to give 3 and 5, respectively
(Table I).
Method B: Equimolar amounts of 2-(aminothioxomethyl)-3-phenyl-
prop-2-enenitrile20 (6) and naphtho[1,2-d]furan-2-ylethan-1-one (1) (5
mmol) in acetic acid (15 mL) was boiled under reflux for 2 h. The re-
sulting solid was collected and crystallized to give a product identical
(mp., mixed mp, and spectra) with 5
SYNTHESIS OF 3-(4-NAPHTHO[1,2-d ]FURAN-2-yl-1,3-
THIAZOLE-2-yl)-2H-CHROMEN-2-ONE (4)
A mixture of 3 (0.5 g) and hydrochloric acid (5 mL, 6 M) was stirred at
room temperature for 1 h. The resulting solid was collected and recrys-
tallized from acetic acid to give substituted coumarin 4 (Table I).
SYNTHESIS OF (2E)-3-AZA-3-(ARYLAMINO)-2-NAPHTHO[1,2-
d ]FURAN-2-yl(1,3-THIAZOL-2-yl))-2-ENENITRILE 7a–c
Method A: The appropriate arenediazonium chlorides (5 mmol) was
added dropwise to a cold ethanol solution, containing thiazolyacetoni-
trile 2 (1.45 g, 5 mmol) and sodium acetate (1 g), (50 mL) at 0–5◦C
while stirring. The mixture was stirred for 3 h at 0–5◦C. The resulting
solid was collected and crystallized from dioxane to give 7a–c (Tables I
and II).
Method B: A mixture of the appropriate (2E)-2-aminothioxomethyl)-
3aza)-3-(arylamino)prop-2-enenitrile21 8a–c and 2-Bromo-1-naphtho-
[1,2-d]furan-2-ylethan-1-one (1) (5 mmol each) in ethanol (30 mL) was
boiled under reflux for 2 h. The resulting solid, which formed after cool-
ing, was collected and crystallized from acetic acid to afford a product
identical in all respects (mp., mixed mp., and spectra) with products
obtained in method A.
SYNTHESIS OF THIOANILID 9
Phenyl isothiocyanate (0.65 g (0.6 mL), 5 mmol) was added to a mix-
ture of thiazolylacetonitrile (1.45 g, 5 mmol) 2 and potassium hydroxide

1654
A. O. Abdelhamid and M. A. M. Alkhodshi
TABLE II 1H NMR Spectra of Some Newly Synthesized Compounds
Comp. no.
Spectral data
2
1H NMR: 4.22 (s, 3H), 7.51–8.19 (m, 8H)
IR: 2252 (CN)
4
IR: 1660 (C N), 1604 (C C)
5
7a
IR: 1712 (CO), 1604 (C C)
1H NMR: 7.5–8.12 (m, 13H), 8.21 (s, 1H)
IR: 3342 (NH), 2214 (CN)
Mass: 378 (100%), 223 (4.2%), 195 (42%), 152 (48.8%).
IR: 3349 (NH), 221 (CN)
7b
7c
1H NMR: 2.37 (s, 3H), 7.26–8.20 (m, 12H) and 14.05 (s, br., 1H).
IR: 3349 (NH) and 2221 (CN).
9
10
11
IR: 3350 (NH), 2214 (CN), 1651 (C N), 1569 (C C)
IR: 3323 (NH), 2177 (CN), 1623 (C N)
1H NMR: 4.10 (s, br., 2H), 6.70–7.67 (m, 14H), 9.32 (s, br., 1H).
IR: 3350, 3280, 3150 (NH2, NH), 3050 (CH), 1620 (C N), 1596 (C C).
1H NMR: 2.27 (s, 3H), 7.31–8.10 (m, 13H) and 12,53 (s, br., 1H).
IR: 2191 (CN), 1720 (CO), 1666 (C N)
1H NMR: 1.56 (t, 3H), 4.55 (s, 2H), 7.60–8.29 (m, 13H) and 12,53 (s, br.,
1H).
15a
15b
IR: 2191 (CN), 1743 (CO), 1624 (C N)
1H NMR: 2.20 (s, 3H), 6.46 (d, 4H), 6.72 (s, 1H), 7.01–7.67 (m, 10H), 8.21
(s, 1H).
15d
13C NMR: 23, 89, 102, 111, 115, 118, 121, 124, 127, 128, 129, 143, 146,
149, 150, 153, 154, 155, 194.
IR: 2198 (CN), 1685 (CO), 1596 (C C)
1H NMR: 2.40 (s, 3H), 7.50–8.32 (m, 13)
IR: 2191 (CN), 1674 (CO)
15f
15g
17
IR: 2191 (CN), 1680 (CO), 1635 (C N)
1H NMJR: 1.51 (s, 1H), 2.25 (s, 3H), 6.71–7.76 (m, 8H).
(0.28 g, 5 mmol) in N,N-dimethylformamide (15 mL) while stirring
at room temperature until potassium hydroxide dissolve completely,
and the reaction mixture was continued stirring for 1 h. The reaction
mixture was poured onto water (30 mL) and acidifies with acetic acid.
The resulting solid was collected and recrystallized from dioxin to give
thioanilide 9 (Table I).
SYNTHESIS OF (2E)-3-METHYLTHIO-2-(4-NAPHTHO[1,2-d ]-
FURAN-2-yl(1,3-THIAZOL-2-yl))-3-(PHENYLAMINO)PROP-2-
ENENITRILE (10)
Phenyl isothiocyanate (0.65 g, (0.6 mL), 5 mmol) was added to a mix-
ture of thiazolylacetonitrile (1.45 g, 5 mmol) 2 and potassium hydroxide

Naphthofuranyl Thiazolyl Ethanenitrile
1655
(0.28 g, 5 mmol) in N,N-dimethylformamide (15 mL) while stirring at
room temperature until potassium hydroxide dissolve completely, and
the reaction mixture was stirred for 1 h, then Iodomethane (0.71 g,
5 mmol) was added dropwise while stirring. The reaction mixture was
stirred for 2 h and the resulting solid was collected and recrystallized
from N,N-dimethylformamide to give 10 (Table I).
SYNTHESIS OF [5-AMINO-4-(4-NAPHTHO[1,2-d ]FURAN-2-
yl)(1,3-THIAZOL-2-y)PYRAZOL-3-yl]-PHENYLAMINE (11)
A mixture of 10 (2.18 g, 5 mmol) and hydrazine hydrate (1 m, 99%)
in ethanol (20 mL) was boiled under reflux for 4 h. The resulting solid
was collected and crystallized from N,N-dimethylformamide to give 11
(Table I).
SYNTHESIS OF 2,3-DIHYDRO-1,3,4-THIADIAZOLES 15a–h
Method A: Phenyl isothiocyanate (0.65 g (0.6 mL), 5 mmol) was added
to a mixture of thiazolylacetonitrile (1.45 g, 5 mmol) 2 and potassium
hydroxide (0.28 g, 5 mmol) in N,N-dimethylformamide (15 mL) while
stirring at room temperature until potassium hydroxide dissolved com-
pletely and the reaction mixture was stirred for 30 min. The appropri-
ate hydrazonoyl halides 12a–h (5 mmol) were added and stirred for 3 h.
The resulting solid was collected and recrystallized from the appropri-
ate solvent to afford 15a–h (Table I).
Method B: Triethylamine (0.5 g, (0.75 mL), 5 mmol) was added drop-
wise to a mixture of the appropriate hydrazonoyl halides 12a–h and 17
(1.9 g, 5 mmol) in ethanol (20 mL) while stirring. Stirred was continued
for 1 h and the resulting solid was collected and crystallized to give
products identical in all respects (mp., mixed mp., and spectra) with
those obtained in method A.
SYNTHESIS OF 3-METHYLTHIO-2-(4)-NAPHTHO[1,2-d]FURAN-
2-yl(1,3-THIAZOL-2-yl)-3-THIOXOPROPANENITRILE (17)
A mixture of thiazolylacetonitrile 2 (1.45 g, 5 mmol), potassium hy-
droxide (0.28 g (5 mmol) and carbon disulfide (0.47 g, 5 mmol) in N,N-
dimethylformamide (15 mL) was stirred for 6 h at room temperature.
Iodometane (0.71 g, 5 mmol) was added dropwise to the above mixture
and stirred for 1 h. The resulting solid was collected and crystallized
from acetic acid to give 17 (Tables I and II)

1656
A. O. Abdelhamid and M. A. M. Alkhodshi
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