Reactions with hydrazonoyl halides 341: Synthesis of some new 2,3-dihydro-1,3,4-thiadiazoles

Article abstract of DOI:10.1080/714040950

Hydrazonoyl halides 4a-h have been caused to react with each of alkyl carbodithioates (3, 13-17)a,b in the presence of triethylamine to give 2,3-dihydro-1,3,4-thiadiazoles in good yields. Structures of the new compounds were elucidated on the basis of ele

Full text of DOI:10.1080/714040950

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Phosphorus, Sulfur, and Silicon and the Related
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Reactions with Hydrazonoyl Halides 341: Synthesis of
Some New 2,3-Dihydro-1,3,4-thiadiazoles
Omer S. Abu-Team a , Nora M. Rateb a & Abdou O. Abdelhamid a
a Cairo University, Giza, Egypt
Published online: 18 Jun 2010.
To cite this article: Omer S. Abu-Team , Nora M. Rateb & Abdou O. Abdelhamid (2003) Reactions with Hydrazonoyl Halides
341: Synthesis of Some New 2,3-Dihydro-1,3,4-thiadiazoles, Phosphorus, Sulfur, and Silicon and the Related Elements, 178:11,
2363-2371, DOI: 10.1080/714040950
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Phosphorus, Sulfur, and Silicon, 178:2363–2371, 2003
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Copyright Taylor & Francis Inc.
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426500390234867
REACTIONS WITH HYDRAZONOYL HALIDES 341:
SYNTHESIS OF SOME NEW
2,3-DIHYDRO-1,3,4-THIADIAZOLES
Omer S. Abu-Team, Nora M. Rateb, and Abdou O. Abdelhamid
Cairo University, Giza, Egypt
(Received April 5, 2003; accepted May 21, 2003)
Hydrazonoyl halides 4a–h have been caused to react with each of alkyl
carbodithioates (3, 13–17)a,b in the presence of triethylamine to give
2,3-dihydro-1,3,4-thiadiazoles in good yields. Structures of the new
compounds were elucidated on the basis of elemental analyses, spec-
tral data, and alternative methods of synthesis whenever possible.
Keywords: 1,3-dipolar cycloaddition; 1,3,4-thiadiazoles; carbodithio-
ates; hydrazonoyl halides; unsymmetrical azines
1,3,4-Thiadiazole and its derivatives have become very useful com-
pound in medicine, agriculture and in many fields of technology.2 Al-
though few patented compounds become marketed products, patents
do give a rough indication of utility. Some of the technological uses in-
volve dyes, lubricant compositions, optically active liquid crystals, pho-
tographic materials, epoxy resins and miner others. A large number of
thiadiazoles have been patented in the agricultural filed as herbicides,
insecticides, fungicides, bactericides, and anthelmintics. In the medical
field they have been patents for almost every disease known to man, and
quite a few of them have become commercial products. As an extension
of our study3−5 and as a part of our program aiming at the synthesis of
different 1,3,4-thiadiazoles, here we report on the reactivity of α-keto
hydrazonoyl halides toward some alkyl carbodithioates.
RESULTS AND DISCUSSION
The reaction of equimolar amounts of C-ethoxycarbonyl-N-
phenylhydrazonoyl chloride (4a) with [((1E,3E)-1-aza-4-phenylbuta-
1,3-dienyl)amino]methylthiomethane-1-thione (3a) in ethanolic
Address correspondence to Abdou O. Abdelhamid, Department of Chemistry, Faculty
of Science, Cairo University, Giza 12316, Egypt. E-mail: Abdou@main-scc.cairo.eun.eg
2363

2364
O. S. Abu-Team et al.
triethylamine solution furnished exclusively one product (as evi-
denced by TLC) and its structure is seemed to be 5–8. Elemental
analyses, spectral data, and alternative synthesis are in agreement
with the formation of ethyl 2-((2E,4E)-1,2-diaza-5-phenylpenta-2,4-
dienylidene)-3-phenyl-1,3,4-thiadiazoline-5-carboxylate (8a). Thus,
the IR (cm−1) spectrum of the product revealed bands at 1710 (CO),
1
1618 (C N) and 1583 (C C). Its H NMR (δ ppm) showed signals at
δ = 1.42 (t, 3H, CH2CH3), 4.47 (q, 2H, CH2CH3), 6.95–7.51 (m, 10H,
ArH’s), 7.96–8.00 (d, 2H), and 8.19–8.23 (d, 1H). Unequivocal support
of the structure of 8 obtained by reaction of 2-hydrazino-2,3-dihydro–
1,3,4–thiadiazole6 (9) with cinnamaldehyde gave identical product in
all respects (m.p., mixed m.p., and spectra) with 8a (cf. Scheme 1). Also,
4a reacted with 3b in ethanolic triethylamine gave product identical
in all respects (m.p., mixed m.p., and spectra) with 8a. Structures 5–7
were excluded on the basis of the previous data.
SCHEME 1
Two possible pathways can account for the formation of 8: 1) 1,3-
Addition of the thiol tautomer 3 to the nitrilium imide 10a, (which
prepared in situ by treatment of hydrazonoyl chloride 4a with triethy-
lamine), can give the thiohydrazonate ester 11a, which undergoes nu-
cleophilic cyclization to yield 12a, which affords 8a by loss of RSH; and
2) 1,3-cycloaddition of the nitrilium imide 10a to the C S of 3a (or 3b)
can give 12a directly (cf. Scheme 2).

Dihydrothiadiazoles
2365
SCHEME 2
Similarly, the appropriate hydrazonoyl halides 4b–h react with each
of alkyl carbodithioate 3a (or 3b), to afford 2,3-dihydro-1,3,4-thiadiazole
derivatives 8b–h respectively.
Hydrazonoyl chloride 4a reacts with the appropriate ({(1E)-1-
aza-2-[4-(methylethyl)phenyl]vinyl}amino)methylthiomethane-1-thione
(13a) or (methane{(1E)-1-aza-2-[4-(methylethyl)phenyl]vinyl}amino)-
phenylmethylthio-1-thione (13b) in ethanolic triethylamine afforded,
in each case, the same isolable product (m.p., mixed m.p., and spectra).
Structure 18a was assigned to the isolated products on the bases of
their elemental analyses and spectral data. For example, IR spectra of
18a revealed absorption band at 1710 cm−1 due to the carbonyl group.
1
Its H NMR spectrum showed signals at δH 1.25 (d, 6H, 2CH3), 1.40
(t, 3H, CH3CH2), 2.94 (hept., 1H, CH(CH3)2), 4.45 (q, 2H, CH2CH3),
7.25–8.02 (m, 9H, ArH’s) and 8.38 (s, 1H, CH).
By similar route, the appropriate alkyl carbodithioates 13 (a, b) react
with the appropriate hydrazonoyl halides 4b–h to afford unsymmetrical
azines 18b–h, respectively (cf. Scheme 3).
Hydrazonoyl chloride 4a reacts with each of the appropriate
[((1E)-2-(2H-benzo[3,4-d]1,3-dioxolan-5-yl)-1-azavinyl)amino]methy-
lthiomethane-1-thione (14a), [((1E)-2-(2H-benzo[3,4-d]1,3-dioxolan-
5-yl)-1-azavinyl)amino](phenylmethylthio)methane-1-thione
[((1E)-1-aza-2-pyrol-2-ylvinyl)amino]methylthiomethane-1-thione
(15a), [((1E)-1-aza-2-pyrrol-2-ylvinyl)amino]phenylmethylthio)me-
(14b),
thane-1-thione (15b), [((1E)-1-aza-2-indol-3-ylvinyl)amino]methylthio-
methane-1-thione (16a), [((1E)-1-aza-2-indol-3-ylvinyl)amino]phenyl-
methylthio)methane-1-thione (16b), 4-{(1E)-2-aza-2-[(methylthiothio-
xomethyl)-amino]vinyl}benzene-1,2-diol (17a), 4-{(1E)-2-aza-2-[(phe-
nylmethylthio)thioxomethyl)-amino]vinyl}benzene-1,2-diol (17b), to
give 2,3-dihydro-1,3,4-thiadiazoles (19–22)a respectively. Structures

2366
O. S. Abu-Team et al.
SCHEME 3
19–22 were confirmed on the basis of elemental analyses, spectral
data, and alternative synthesis (cf. Scheme 3 and Experimental).
Analogously, the appropriate hydrazonoyl halides 4b–h, react with
the appropriate (14–17)a,b in ethanol containing triethylamine at room
temperature to give unsymmetrical azines (18–22)b–h, respectively, in
a good yields.
Moreover, C-phenyl-N-phenylhydrazonoyl chloride (23) reacts with
the appropriate methyl carbodithioates (3, 13–17)a, in ethanolic
trietyhlamine to give the corresponding 2,3-dihydro-1,3,4-thiadiazoles
24a–e, respectively (cf. Scheme 4).
SCHEME 4

Dihydrothiadiazoles
2367
TABLE I Characterization Data of the Newly Synthesized Compounds
% Analyses, calcd./found
Compd.
no.
m.p., ◦
solvent
C
Yield
(%)
Mol. formula
(mol. wt.)
C
H
N
S
3a
3b
160–162
EtOH
187–189
EtOH
118–120
EtOH
89
87
85
87
87
90
80
78
75
78
80
55
90
95
95
90
95
91
86
85
85
75
87
C11H12N2S2
(236.36)
C17H16N2S2
(312.46)
55.90
56.20
65.35
65.50
63.47
63.60
62.62
62.40
65.50
65.30
70.22
70.40
65.99
66.00
63.45
63.20
73.02
73.00
67.75
67.50
57.10
57.30
65.81
66.00
47.00
47.20
58.16
58.30
42.19
42.40
56.70
56.90
52.99
53.10
62.74
62.50
44.61
44.80
56.58
56.80
63.94
64.00
63.14
63.30
65.91
65.70
5.12
5.30
5.16
5.30
4.79
4.90
4.43
4.40
4.63
4.40
4.42
4.60
4.03
4.20
3.87
3.60
4.38
4.30
4.50
4.30
6.39
6.50
6.14
6.30
3.92
4.10
4.27
4.40
4.55
4.80
4.76
4.90
4.45
4.60
4.65
4.40
4.16
4.30
4.43
4.30
5.62
5.80
5.30
5.50
5.53
5.30
11.85
12.00
8.97
27.13
27.30
20.52
20.70
8.47
8.60
8.80
8.60
9.20
9.00
7.81
8.00
8.01
9.00
8a
C
20H18N4O2S
(378.46)
14.80
15.00
15.37
15.10
16.08
15.90
13.65
13.80
13.99
14.00
13.45
13.20
12.16
12.10
16.46
16.20
11.10
11.30
8.53
8b
135–138
ACOH
160–162
ACOH
175–176
ACOH
190–191
ACOH
198–200
ACOH
168–170
ACOH
200–202
ACOH
106–108
EtOH
C19H16N4O2S
(364.43)
8c
C
19H16N4OS
(348.43)
8d
C
24H18N4OS
(410.50)
8e
C
22H16N4O2S
(400.46)
8.20
8f
C22H16N4OS2
(416.46)
C28H20N4OS
(460.56)
15.40
15.10
6.96
6.90
7.54
8g
8h
C
24H19N5OS
(425.49)
7.20
13a
13b
14a
14b
15a
15b
16a
16b
17a
17b
18a
18b
18c
C
12H16N2S2
(252.40)
25.41
25.60
19.52
19.70
25.21
25.40
19.41
19.60
32.18
32.30
23.29
23.40
25.72
25.90
19.70
19.50
26.46
26.60
20.14
19.80
8.13
65–67
EtOH
C
18H20N2S2
(328.50)
8.70
199–200
EtOH
180–182
ACOH
124–124
EtOH
130–133
EtOH
193–196
EtOH
188–190
EtOH
207–210
EtOH
175–177
EtOH
85–86
C10H10N2O2S2
(254.33)
11.01
11.20
8.48
C16H14N2O2S2
(330.43)
C7H9N3S2
(199.30)
C13H13N3S2
(275.40)
8.60
21.08
21.30
15.26
15.40
16.85
17.00
12.91
12.70
11.56
11.70
8.80
C
11H11N3S2
(249.36)
C
17H15N3S2
(325.46)
C9H10N2O2S2
(242.32)
C15H14N2O2S2
(318.42)
8.90
C
21H22N4O2S
(394.50)
14.20
14.40
14.73
14.90
15.37
15.10
EtOH
98–100
EtOH
134–135
ACOH
8.30
8.43
8.60
8.80
C20H20N4O2S
(380.47)
C20H20N4OS
(364.47)
8.60
(Continued on next page)

2368
O. S. Abu-Team et al.
TABLE I Characterization Data of the Newly Synthesized Compounds
(Continued)
% Analyses, calcd./found
Compd.
no.
m.p., ◦
Solvent
C
Yield
(%)
Mol. formula
(mol. wt.)
C
H
N
S
18d
18e
18f
145–147
ACOH
163–165
ACOH
183–184
ACOH
138–140
ACOH
133–135
ACOH
180–182
EtOH
173–175
ACOH
162–163
ACOH
166–168
ACOH
243–245
ACOH
169–170
ACOH
208–210
ACOH
170–172
ACOH
122–124
EtOH
159–160
EtOH
173
EtOH
149–150
EtOH
160
EtOH
148–150
EtOH
218–220
EtOH
89
85
79
81
83
80
93
83
86
80
85
89
90
90
84
93
95
93
85
93
98
95
C25H22N4OS
(426.54)
C23H20N4O2S
(416.51)
C23H20N4OS2
(432.56)
C29H24N4OS
(476.60)
70.40
70.60
66.33
66.10
63.86
63.80
73.08
73.30
68.00
68.20
57.57
57.80
56.54
56.70
59.01
59.30
64.47
64.40
60.25
60.40
58.05
58.30
67.77
67.70
62.29
62.40
56.29
56.10
55.04
55.10
57.86
57.80
64.33
64.30
56.98
67.00
61.84
61.60
61.37
61.50
60.46
60.40
63.14
63.00
5.20
5.50
4.84
4.60
4.66
4.60
5.08
5.20
5.25
5.40
4.07
4.00
3.69
3.90
3.85
4.00
3.76
3.70
3.37
3.50
3.25
3.40
3.79
3.70
3.86
4.00
4.43
4.40
4.00
4.10
4.21
4.20
4.05
4.20
3.45
3.40
4.15
4.00
4.38
4.50
4.01
4.00
4.18
4.00
13.14
13.30
13.45
13.10
12.95
12.90
11.76
11.80
15.86
16.00
14.13
14.30
14.65
14.90
15.29
15.40
13.08
13.00
13.39
13.50
12.98
13.00
11.71
11.60
15.79
16.00
20.51
20.40
21.39
21.50
22.49
22.40
18.75
18.90
18.46
18.40
21.63
21.40
17.89
17.90
18.56
18.50
19.38
19.10
7.52
7.70
7.60
7.40
14.82
14.80
6.73
6.90
7.26
7.40
8.09
8.30
8.34
8.50
8.75
8.90
7.48
7.40
7.66
7.80
14.76
15.00
6.70
6.50
7.23
7.50
9.39
9.30
9.79
10.00
10.30
10.30
8.59
8.70
16.90
16.90
8.25
8.00
8.19
8.30
8.49
8.50
8.87
8.60
18g
18h
19a
19b
19c
19d
19e
19f
C
25H23N5OS
(441.56)
C
C
C
19H16N4O4S
(396.43)
18H14N4O4S
(382.40)
18H14N4O3S
(366.40)
C23H16N4O3S
(428.47)
C
21H14N4O4S
(418.43)
C21H14N4O3S2
(434.50)
C27H18N4O3S
(478.53)
C23H17N5O3S
(443.49)
19g
19h
20a
20b
20c
20d
20f
C
16H15N5O2S
(341.40)
C
15H13N5O2S
(327.37)
C
15H13N5OS
(311.37)
C20H15N5OS
(373.44)
C
18H13N5OS2
(379.47)
20h
21a
21b
21c
C20H16N6OS
(388.45)
C
20H17N5O2S
(391.45)
236–236
EtOH
218–229
EtOH
C
19H15N5O2S
(377.43)
C
19H15N5OS
(361.43)
(Continued on next page)

Dihydrothiadiazoles
2369
TABLE I Characterization Data of the Newly Synthesized Compounds
(Continued)
% Analyses, calcd./found
Compd.
no.
m.p., ◦
Solvent
C
Yield
(%)
Mol. formula
(mol. wt.)
C
H
N
S
21d
21f
248
91
92
85
87
86
90
89
92
85
81
90
85
87
C24H17N5OS
(423.50)
C22H15N5OS2
(429.53)
C24H18N6OS
(438.51)
C18H16N4O4S
(384.42)
68.07
68.20
61.52
61.50
65.74
65.70
56.24
56.20
55.13
55.10
57.62
57.40
63.45
63.60
56.86
56.80
72.23
72.00
72.33
72.30
65.99
66.00
69.84
69.90
64.93
64.90
4.05
4.00
3.52
3.50
4.14
4.10
4.16
4.20
3.81
3.90
3.98
3.70
3.87
4.00
3.34
3.30
4.74
4.50
5.56
5.50
4.03
4.00
4.33
4.50
4.15
4.10
16.54
16.70
16.30
16.30
19.16
19.10
14.57
14.50
15.13
15.30
15.81
15.60
13.45
13.60
13.26
13.20
14.65
14.40
14.06
14.00
13.99
14.00
17.71
17.90
14.42
14.40
7.57
8.00
14.93
15.00
7.31
7.30
8.34
8.30
8.66
8.60
9.05
9.00
7.70
7.90
15.18
15.10
8.38
8.10
8.05
8.00
8.01
8.00
8.11
8.30
8.25
8.20
ACOH
305–307
ACOH
277–280
ACOH
200–203
EtOH
195–198
EtOH
217
EtOH
218–220
EtOH
239–241
EtOH
138–140
EtOH
113–115
EtOH
195–197
EtOH
210–212
EtOH
235–238
EtOH
21h
22a
22b
22c
22d
22f
C
C
C
17H14N4O4S
(370.39)
17H14N4O3S
(354.39)
22H16N4O3S
(416.46)
C
20H14N4O3S2
(422.49)
24a
24b
24c
24d
24e
C23H18N4S
(382.49)
C24H22N4S
(398.53)
C
22H16N4O2S
(400.46)
C
23H17N5S
(395.49)
C21H16N4O2S
(388.45)
Structure 24 was confirmed on the basis of elemental analyses, spec-
tral data, and alternative route synthesis. Thus, 23 reacted with the ap-
propriate benzyl carbodithioates (3, 13–17)b in ethanolic triethylamine
at room temperature gave identical product (m.p., mixed m.p., and spec-
tra) with the corresponding 24a–e which obtained before.
EXPERIMENTAL
All melting points were determined on an Electrothermal appara-
tus and are uncorrected. IR spectra were recorded (KBr discs) on a
1
Shimadzu FT-IR 8201 PC spectrophotometer. H NMR spectra were
recorded in CDCl3 and (CD3)2SO on a Varian Gemini 200 MHz spe-
ctrometer and chemical shifts were expressed in δ units using TMS
as internal reference. Elemental analyses were carried out at the

2370
O. S. Abu-Team et al.
TABLE II 1H NMR Spectra of Some Selected Synthesized Compounds
Compd. no.
1H NMR (δ ppm)
3a
3b
8b
8c
8d
8f
2.66 (s, 3H), 6.94–7.79 (m, 8H) and 10.91 (s, br., 1H).
4.47 (s, 2H), 6.88–8.10 (m, 13H) and 13.2 (s, 1H).
3.92 (s, 3H), 7.95–8.2 (m, 13H).
2.62 (s, 3H), 7.95–7.55 (m, 10H), 7.98–8.02 (d, 2H) and 8.19–8.24 (t, 1H).
6.96–8.41 (m, aromatic protons).
6.96–7.57 (m, 11H), 7.81 (d, 1H), 8.09 (d, 2H), 8.22 (d, 1H) and 8.38
(t, 1H).
13a
13b
14a
14b
18a
1.28 (d, 6H), 2.66 (s, 3H), 2.97–2.97 (sep., 1H), 7.26–7.30 (d, 2H),
7.64–7.68 (d, 2H), 7.90 (s, 1H) and 10.7 (s, br., 1H).
1.27 (d, 6H), 2.90–2.99 (sept., 1H), 4.47 (s, 2H), 7.26–7.72 (m, 9H), 8.10
(s, 1H) and 13.26 (s, br., 1H).
2.7 (s, 3H), 6.11 (s, 2H), 6.99–7.26 (m, 3H), 8.16 (s, 1H) and 13.25
(s, br., 1H).
4.46 (s, 2H), 6.12 (s, 2H), 7.26–7.85 (m, 8H), 8.17 (s, 1H) and 13.26
(s, br. 1H).
1.25 (d, 6H), 1.40 (t, 3H), 2.90–2.97 (sept., 1H), 4.45 (q, 2H), 7.25–7.71
(m, 5H), 7.91 (d, 2H), 7.97 (d, 2H) and 8.38 (s, 1H).
1.25 (d, 6H), 2.94 (sep., 1H), 7.22–8.12 (m, 12H) and 8.41 (s, 1H).
1.43 (t, 3H), 4.45 (q, 2H), 6.02 (s, 2H), 6.86-8.00 (m, 8H) and 8.30 (s, 1H).
6.02 (s, 2H), 6.80–8.40 (m, 12H).
7.11–7.51 (m, 15H), 7.96–8.00 (d, 2H) and 8.19 (t, 1H).
1.28 (d, 6H), 2.94 (sep., 1H), 7.22–8.12 (m, 14H) and 8.31 (s, 1H).
6.01 (s, 2H), 7.22–8.12 (m, 13H) and 8.35 (s, 1H).
18f
19a
19f
24a
24b
24c
Microanalytical Center of the University of Cairo, Giza, Egypt.
Hydrazonoyl halides 4a–h and 23 were prepared according to the
literature.7−14
Synthesis of Alkyl Carbodithioates 3a,b, and (13–17)a,b
An appropriate cinnamaldehyde, cumenaldehyde, piperenal, pyrrole-
2-carboxaldehyde, 3-formylindole, or 2,4-dihydroxybenzaldehyde
(0.01 mol) was added to solution of the appropriate alkyl hydra-
zinecarboditioates15,16 (0.01 mol) in 2-propanol (50 ml) while stirring
at room temperature. The reaction mixture was stirred for 2 h. The
solid so formed was collected and crystallized from ethanol to give 3a,b
and (13–17)a,b, yields (87–83%) respectively (cf. Tables I and II).
Synthesis of 2,3-Dihydro-1,3,4-thiadiazole Derivatives
8a–g, (18–22)a–h, and 24a–e
Method A
A mixture of the appropriate alkyl carbodithioates 3a,b or (13–17)a,b
(0.005 mol) and the appropriate hydrazonoyl halides 4a–h or 23 and

Dihydrothiadiazoles
2371
triethylamine (0.75 ml, 0.005 mol) in ethanol (20 ml) was stirred for
30 min. The resulting product was collected and crystallized from the
proper solvent to give 2,3-dihydro-1,3,4-thiadiazoles (8, 18–22)a–h and
24a–e, respectively, in good yield (cf. Tables I and II).
Method B
A mixture of 5-hydrazono-4-phenyl-4,5-dihydro-1,3,4-thiadiazole-2-
carboxylic acid ethyl ester (9) (1.3 g, 0.005 mol) and the appropriate
of aldehydes (cinnamaldehyde, piperenal, cumenaldehyde, pyrrole-
2-carboxaldehyde, 3-formylindole, or 2,4-dihydroxybenzaldehyde)
(0.005 mmol) in ethanol (30 ml) was stirred for 2 h. The solid was
collected and crystallized from the proper solvent to give in all respects
(m.p., nixed m.p., and spectra) with the corresponding prepared in
method A.
REFERENCES
[1] Part 33: A. O. Abdelhamid, S. A. Abdelgawad, and S. F. El-Sharnoby, Phosphorus,
Sulfur, Silicon. Relet. Elem., 177, 2699 (2002).
[2] D. I. Kornis, Comperhensive Heterocyclic Chemistry, edited by A. R. Katritzky, C. W.
Ress, and E. F. V. Scriven (Pergamon, Oxford, 1996), Vol. 4.
[3] A. O. Abdelhamid, M. M. M. Sallam, and S. A. Amer, Heteroatom Chem., 12, 486
(2001).
[4] A. O. Abdelhamid, H. F. Zohdi, and N. A. Ali, Molecules, 5, 961 (2001).
[5] A. O. Abdelhamid, N. M. Rateb, and K. M. Dawood, Phosphorus, Sulfur, Silicon
Relet. Elem., 167, 251 (2000).
[6] H. F. Zohdi, N. M. Rateb, M. M. M. Sallam, and A. O. Abdelhamid, J. Chem. Res.,
(S) 742; (M) 3329 (1998).
[7] G. Fravel, Bull. Soc. Chim. Fr., 31, 150 (1904).
[8] N. E. Eweiss and A. Osman, Tetrahedron Lett., 1169 (1979).
[9] A. S. Shawali and A. Osman, Tetrahedron, 27, 2571 (1971).
[10] A. S. Shawali and A. O. Abdelhamid, Bull. Chem. Soc. Jpn., 49, 321 (1976).
[11] A. O. Abdelhamid and F. H. H. El-Shiatey, Phosphorus, Sulfur, Silicon and Relat.
Elem., 39, 45 (1988).
[12] A. O. Abdelhamid, F. A. Attaby, F. A. Khalifa, and S. S. Ghabrial, Arch. Pharm. Res.,
15, 14 (1992).
[13] H. M. Hassaneen, A. S. Shawali, N. E. Elwan, and N. M. Abounada, Sulfur Lett.,
14, 41 (1992).
[14] P. Wolkoff, Can. J. Chem., 53, 1333 (1975).
[15] D. L. Klayman, J. F. Bartosevichm, T. S. Griffin, C. J. Mason, and J. P. Scovill,
J. Med. Chem., 22, 855 (1979).
[16] J. Korosi, Ger. Offen. 1, 934, 899 29 Jan. (1970); Chem. Abstr., 72, 100334s (1970).