Synthesis of new heterocycles containing more than one 1,2,3-thia or selenadiazole rings

Article abstract of DOI:10.1002/jhet.5570440427

(Chemical Equation Presented) The diketones 2a-d with different alkyl chain length are used for the synthesis of di-1,2,3-thia or selenadiazole derivatives 4a-d and 5a-d. The diketones 2a-d where prepared by a unique method through the reaction between the corresponding dibromoalkanes 1a-d and ethyl acetoacetate, which are transformed into the corresponding semicarbazone derivatives 3a-d. The di-1,2,3-thia or selenadiazole derivatives 4a-d and 5a-d were prepared from the semicarbazones derivatives 3a-d on oxidative cyclization with thionyl chloride and selenium dioxide respectively in high yield.

Full text of DOI:10.1002/jhet.5570440427

Jul-Aug 2007
915
Synthesis of New Heterocycles containing more than one 1,2,3-
Thia or Selenadiazole Rings
Mousa Al-Smadi
Department of Applied Chemical Sciences, Jordan University of Science and Technology
P.O.Box 3030, Irbid 22110, Jordan
Mariam10@just.edu.jo
Received June 28, 2006
The diketones 2a-d with different alkyl chain length are used for the synthesis of di-1,2,3-thia or
selenadiazole derivatives 4a-d and 5a-d. The diketones 2a-d where prepared by a unique method through
the reaction between the corresponding dibromoalkanes 1a-d and ethyl acetoacetate, which are
transformed into the corresponding semicarbazone derivatives 3a-d. The di-1,2,3-thia or selenadiazole
derivatives 4a-d and 5a-d were prepared from the semicarbazones derivatives 3a-d on oxidative
cyclization with thionyl chloride and selenium dioxide respectively in high yield.
J. Heterocyclic Chem., 44, 915 (2007).
INTRODUCTION
selenadiazoles, the analogous target compounds are
prepared.
Sulfur or selenium containing heterocyclic systems are
of increasing interest because of their chemical properties
[1] especially their wide application in synthesizing other
heterocyclic compounds [2-7] and biological activities as
antibacterial and antifangi [8-11]. Both sulfur and selen-
ium compounds show wide similarities according to their
applications in the syntheses of pharmaceuticals, dyes,
and fine chemicals. However, remarkable differences
between S- and Se-compounds are found. Due to the
larger size of the Se-atom, selenium compounds show an
increased polarizability, which leads to less stability
compared to the S-analogues. Also, the characteristic
physical properties of selena-heterocycles make them
attractive materials in the development of organo-electric
or organo-optic materials.
Multi-arm 1,2,3-thia and selenadiazole aromatic deriv-
atives were recently prepared from the corresponding
multi-arm ketones using both of the Hurd and Mori and
the Lalezari and Shafiee methods respectively by Al-
Smadi and Meier et. al [12-14], however heterocyclic
systems containing two 1,2,3-selenadiazole rings were
also recently prepared through reacting the corresponding
multiple diazoketones with Lawesson reagent by Reddy
et. al [15-16]. But di-1,2,3-selenadiazole derivatives with
different alkyl spacers are still unknown. Therefore
depending on a previous knowledge of the principal
investigator in synthesizing multi-arm 1,2,3-thia and
The preparation was carried out following the methods
that are first reported by Lalezari et. al. [17-19] and Hurd
and Mori [20], through reacting the corresponding semi-
carbazones or hydrazones of ꢀ-ketomethylene function-
ality, which contain aminocarbonyl or ethoxycarbonyl
groups as good leaving groups with selenium dioxide in
the presence of acetic acid or with thionyl chloride.
Scheme 1: Synthesis of compounds 4a-d and 5a-d
O
O
O
O
Br CH2 Br
n
2 NaOEt
1a-d
2
2
O
O
O
O
O
O
O
O
NaOH
Reflux
2 H2NHN
EtOH
NH2
CH2
n
O
n
2a-d
O
O
S
S
SOCl
O
2
N
O
N
N
H2NCNHN
N
NNHCNH2
n
4a-d
n
Se
N
Se
SeO2
N
3a-d
N
HOAc
N
n
5a-d
Where n = 4, 6, 8, 10

916
M. Al-Smadi
Vol 44
Our synthetic procedure of the heterocyclic compounds
synthesis of new dendrimers. Since the compounds 4a-d
and 5a-d are solid, it was found that the mp of the
compound increases as the number of carbon atoms in the
molecule increases. Also, it was found that the mp of the
1,2,3-thiadiazole derivatives is higher than that for the
corresponding 1,2,3-selenadiazole derivatives. Due to
structural similarities, the compounds 4a-d all showed
similar modes of stretching in their ir-spectra with small
differences in the position and shape of the peaks. The
same behavior was observed in case of compounds 5a-d.
4a-d and 5a-d started from the dibromoalkanes 1a-d. The
diketones 2a-d were prepared by reacting the ethyl
acetoacetate with equivalent amount of sodium ethanoate
to generate the corresponding thermodynamically stable
enolate derivatives which react with the dibromoalkanes
1a-d, then hydrolysis with sodium hydroxide under reflux
lead to the formation of the diketones 2a-d. Condensation
of 2a-d with semicarbazide in absolute ethanol forms the
corresponding semicarbazones 3a-d. Treatment of 3a-d
with Thionyl chloride using the Hurd and Mori procedure
provided compounds 4a-d, whereas with selenium
dioxide in acetic acid using Lalezari procedure provided
the compounds 5a-d in high chemical yield.
EXPERIMENTAL
Melting points (mp) were determined on an electrothermal
digital melting point apparatus. Infrared (ir) spectra were
recorded using a NICOLET 410 FT-IR spectrometer (ꢀ in cm-1).
The ir spectra of pure substances were measured as KBr-pellets.
Table 1
Chemical percentage yield of the compounds 1-, 2-, 3-, 4- and 5a-d.
1
The H and 13C nmr spectra were recorded on Bruker AM400
R
R
and AC200 spectrometers in deuteriochloroform or DMSO-d6
with TMS as internal standard. The spectral data were reported
in delta (ꢁ) units relative to TMS reference line. The mass
spectra were carried out by using the instrument MAT95 of the
Finnigan Company (FD: 5 kV Ionizing energy, field desorption).
Elemental analyses were performed in the analytical laboratory
of the institute of organic chemistry of university of Mainz,
Germany. Dibromoalkanes, semicarbazide hydrochloride and
ethyl acetoacetate were obtained from Aldrich.
General Procedure for the Preparation of Di-Ketones (2a-d).
Sodium (6.10 g, 265.10 mmol) were added in small portions to
150 mL absolute ethanol, then the whole mixture was refluxed
to dissolve the remaining sodium pieces. Then an equivalent
amount of ethyl acetoacetate (34.50 g, 265.10 mmol) was added
drop wise over a 15 min. period untill a clear solution formed.
After that (132.50 mmol) of the dibromoalkanes 1a-d were
added to the reaction mixture and left refluxing over night. A
saturated sodium hydroxide solution was added to the reaction
mixture and left refluxing such that a white solid was formed.
The reaction was monitored using TLC in chloroform until
completion. After cooling, the reaction mixture was diluted with
water (50 mL) and extracted with diethyl ether (3 ꢂ 50 mL). The
combined organic layers were dried over magnesium sulphate.
The solvent was evaporated under vacuum and the residual solid
was washed with diethyl ether. When necessary, a recrystal-
ization from acetone or chloroform was performed.
n
4
a
6
b
8 10
c
d
Cpd
n
Cpd* Yield[%] Cpd Yield[%]
Cpd Yield[%]
1c
Yield[%]
Cpd
1d
R
Br
O
1a
1b
93
2a
99
95
2b
97
98
2c
3c
4c
5c
2d
3d
4d
94
86
83
68
CH3
O
NNHCCH3
3a
4a
5a
3b
4b
5b
89
86
66
CH3
S
88
75
81
78
N
N
Se
5d
N
N
[Cpd*] is compound
RESULTS AND DISCUSSION
New five-membered heterocyclic compounds 4a-d and
5a-d containing two 1,2,3-thiadiazole or selenadiazole
rings that are separated by different alkyl spacers were
synthesized and characterized. The synthesis of comp-
ounds 4a-d and 5a-d was carried out in a multi-step
procedure starting from the corresponding diketones 2a-d
by applying the Hurd-Mori or the Lalezari methods
respectively. The diketones 2a-d have all been prepared in
high chemical yield using a unique method starting from
the corresponding dibromoalkanes 1a-d. All the comp-
ounds 4a-d and 5a-d were obtained in a high chemical
yield. The compounds 4a-d and 5a-d exhibit aromatic
character and have the ability to eliminate molecules of
nitrogen with ring opening if heated above 140 °C to form
new heterocycles. Therefore, these compounds can be
used for crosslinking of polymers to prepare negative
photoresist material and they can be used as nucleus for
2,9-Decandione (2a). This compound was obtained as colorless
crystals (acetone), mp 53-54°; ir (potassium bromide): 2931,
1
2845 (C-H), 1696 (C=O), 1457, 1393, 1346, 1155 cm-1; H nmr
(deuteriochloroform): ꢁ 1.25 (s, 4H, CH2), 1.53-1.57 (m, 4H,
CH2), 2.21 (s, 6H, CH3), 2.43 (t, 4H, -CH2-CO-); 13C nmr
(deuteriochloroform): ꢁ 23.91 (CH3), 29.16-29.81 (CH2), 43.75
(-CH2-CO-), 209.33 (C=O); ms: (5 kV, fd) m/z (%) 170 (100).
Anal. Calcd. for C10H18O2: C, 70.55; H, 10.66. Found: C, 70.28;
H, 10.81.
2,11-Dodecandione (2b). This compound was obtained as pale
yellow powder, mp 62-63°; ir (potassium bromide): 2933, 2847
(C-H), 1697 (C=O), 1456, 1394, 1348, 1155 cm-1. 1H nmr
(deuteriochloroform): ꢁ 1.24 (s, 8H, CH2), 1.51-1.55 (m, 4H,
CH2), 2.18 (s, 6H, CH3), 2.41 (t, 4H, -CH2-CO-); 13C nmr
(deuteriochloroform): ꢁ 23.89 (CH3), 29.13-29.78 (CH2), 43.76
(-CH2-CO-), 209.35 (C=O); ms: (5 kV, fd) m/z (%) 198 (100).

Jul-Aug 2007
Synthesis of New Heterocycles containing more than one 1,2,3-Thia or Selenadiazole Rings
917
Anal. Calcd. for C12H22O2: C, 72.68; H, 11.18. Found: C, 72.36;
H, 11.48.
2,15-Hexadecandione disemicarbazone (3d). This compound
was obtained as white powder, mp 223-224°; ir (potassium
bromide): 3417 (NH2), 3262 (NH), 2948 (C-H), 1698 (C=O),
2,13-Tetradecandione (2c). This compound was obtained as
colorless powder, m.p 71-72°; ir (potassium bromide): 2927,
2843 (C-H), 1695 (C=O), 1453, 1393, 1349, 1157 cm-1. 1H nmr
(deuteriochloroform): ꢀ 1.23 (s, 12H, CH2), 1.52-1.57 (m, 4H,
CH2), 2.17 (s, 6H, CH3), 2.39 (t, 4H, -CH2-CO-); 13C nmr
(deuteriochloroform): ꢀ 23.88 (CH3), 29.19-29.84 (CH2), 43.77
(-CH2-CO-), 209.36 (C=O); ms: (5kV, fd) m/z (%) 226 (100).
Anal. Calcd. for C14H26O2: C, 74.29; H, 11.58. Found: C, 74.07;
H, 11.29.
2,15-Hexadecandione (2d). This compound was obtained as
colorless powder, m.p 78-79; ir (potassium bromide): 2928,
2841 (C-H), 1692 (C=O), 1450, 1396, 1348, 1156 cm-1. 1H nmr
(deuteriochloroform): ꢀ 1.22 (s, 16H, CH2), 1.51-1.55 (m, 4H,
CH2), 2.15 (s, 6H, CH3), 2.38 (t, 4H, -CH2-CO-); 13C nmr
(deuteriochloroform): ꢀ 23.86 (CH3), 29.16-29.81 (CH2), 43.79
(-CH2-CO-), 209.38 (C=O); ms: (5kV, fd) m/z (%) 254 (100).
Anal. Calcd. for C16H30O2: C, 75.54; H, 11.88. Found: C, 75.33;
H, 11.59.
1
1579, 1429, 1291 cm-1; H nmr (dimethyl sulfoxide-d6): ꢀ 1.29
(s, 16H, CH2), 1.57-1.69 (m, 4H, CH2), 2.21 (s, 6H, CH3), 2.43
(t, 4H, -CH2-CO-), 6.51 (s, 4H, NH2), 9.85 (s, 2H, NH); 13C nmr
(dimethyl sulfoxide-d6): ꢀ 23.91 (CH3), 29.16-29.81 (CH2),
43.79 (-CH2-CO-), 144.30 (C=N), 158.98 (C=O); ms: (5 kV, fd)
m/z (%) 368 (100). Anal. Calcd. for C18H36N6O2: C, 58.67; H,
9.84; N, 22.80. Found: C, 58.46; H, 9.67; N, 22.71.
General procedure for preparation of Di-1,2,3-Thiadiazoles
(4a-d). Semicarbazones 3a or 3b or 3c or 3d respectively (0.36
mmol) was dissolved in thionyl chloride (25 mL) with vigorous
stirring and cooling 0 °C. The mixture was allowed to warm up to
room temperature with continuous stirring. Monitoring of reaction
progress with TLC showed that the reaction was completed in 10
hours at which time the solvent was removed under vacuum. The
crude product was washed with diethyl ether and recrystallized
from chloroform and petroleum ether when necessary.
1,6-Bis(1,2,3-thiadiazole-4-yl)hexane (4a). This compound was
obtained as pale-yellow powder, mp 85-86°; ir (potassium
General procedure for the preparation of Disemicarbazones
(3a-d). Semicarbazide hydrochloride (4.44 g, 40.00 mmol) and
sodium acetate (3.33 g, 40.00 mmol) were dissolved in absolute
ethanol (50 mL). The obtained mixture was heated for 20 min
under reflux. The resulting mixture was filtered while hot to
remove precipitated sodium chloride. The filtrate was mixed
with diketones 2a, 2b, 2c, 2d (18.50 mmol), respectively. The
reaction mixture was heated till refluxing then two drops of
concentrated hydrochloric acid were added. The mixture was
heated under reflux overnight with continuous removal of the
water generated. Finally, the solvent was removed under
vacuum and the residue was washed with diethyl ether.
2,9-Decandione disemicarbazone (3a). This compound was
obtained as white powder, mp 211-212°; ir (potassium bromide):
3408 (NH2), 3243 (NH), 2944 (C-H), 1688 (C=O), 1574, 1418,
1
bromide): 2958, 2908, 1576, 1468, 1433, 1223, 982 cm-1; H
nmr (deuteriochloroform): ꢀ 1.38 (s, 4H, CH2), 2.74-2.77 (m,
4H, CH2), 3.21 (t, 4H, CH2), 8.26 (s, 2H, CHS); 13C nmr
(deuteriochloroform): ꢀ 28.31-29.64 (CH2), 37.45 (CH2), 131.29
(C5), 164.32 (C4); ms: (5 kV, fd) m/z (%) 254 (100). Anal.
Calcd. For C10H14N4S2: C, 47.22; H, 5.54; N, 22.02; S, 25.21.
Found: C, 47.13; H, 5.25; N, 22.20; S, 25.36.
1,8-Bis(1,2,3-thiadiazole-4-yl)octane (4b). This compound was
obtained as yellow-orange solid, mp 88-89°; ir (potassium
1
bromide): 2959, 2879, 1580, 1477, 1424, 1229, 971 cm-1; H
nmr (deuteriochloroform): ꢀ 1.37 (s, 8H, CH2), 2.74-2.78 (m,
4H, CH2), 3.18 (t, 4H, CH2), 8.21 (s, 2H, CHS); 13C nmr
(deuteriochloroform): ꢀ 28.29-29.66 (CH2), 37.43 (CH2), 131.27
(C5), 164.30 (C4); ms: (5 kV, fd) m/z (%) 282 (100). Anal.
Calcd. For C12H18N4S2: C, 51.03; H, 6.42; N, 19.84; S, 22.71.
Found: C, 51.18; H, 6.38; N, 19.59; S, 22.83.
1
1279 cm-1; H nmr (dimethyl sulfoxide-d6): ꢀ 1.23 (s, 4H, CH2),
1.53-1.57 (m, 4H, CH2), 2.16 (s, 6H, CH3), 2.39 (t, 4H, -CH2-
CO-), 6.50 (s, 4H, NH2), 9.15 (s, 2H, NH); 13C nmr (dimethyl
sulfoxide-d6): ꢀ 23.91 (CH3), 29.16-29.81 (CH2), 43.75 (-CH2-
CO-), 144.00 (C=N), 158.70 (C=O); ms: (5 kV, fd) m/z (%) 284
(100). Anal. Calcd. for C12H24N6O2: C, 50.69; H, 8.51; N, 29.55.
Found: C, 50.38; H, 8.29; N, 29.41.
1,10-Bis(1,2,3-thiadiazole-4-yl)decane (4c). This compound
was obtained as pale yellow solid, mp 91-92°; ir (potassium
1
bromide): 2966, 2877, 1583, 1475, 1433, 1224, 976 cm-1; H
nmr (deuteriochloroform): ꢀ 1.32 (s, 12H, CH2), 2.70-2.75 (m,
4H, CH2), 3.15 (t, 4H, CH2), 8.17 (s, 2H, CHS); 13C nmr
(deuteriochloroform): ꢀ 28.26-29.63 (CH2), 37.39 (CH2), 131.24
(C5), 164.27 (C4); ms: (5kV, fd) m/z (%) 310 (100). Anal.
Calcd. For C14H22N4S2: C, 54.16; H, 7.14; N, 18.04; S, 20.66.
Found: C, 54.04; H, 7.35; N, 18.31; S, 20.48.
2,11-Dodecandione disemicarbazone (3b). This compound
was obtained as white powder, mp 215-216°; ir (potassium
bromide): 3410 (NH2), 3249 (NH), 2946 (C-H), 1693 (C=O),
1
1579, 1425, 1283 cm-1; H nmr (dimethyl sulfoxide-d6): ꢀ 1.26
(s, 8H, CH2), 1.52-1.55 (m, 4H, CH2), 2.18 (s, 6H, CH3), 2.40 (t,
4H, -CH2-CO-), 6.53 (s, 4H, NH2), 9.91 (s, 2H, N-H); 13C nmr
(dimethyl sulfoxide-d6): ꢀ 23.89 (CH3), 29.13-29.78 (CH2),
43.76 (-CH2-CO-), 144.11 (C=N), 158.90 (C=O); ms: (5 kV, fd)
m/z (%) 312 (100). Anal. Calcd. for C14H28N6O2: C, 53.82; H,
9.03; N, 26.90. Found: C, 53.63; H, 8.89; N, 26.75.
1,12-Bis(1,2,3-thiadiazole-4-yl)dodecane (4d). This compound
was obtained as beige powder, mp 93-94°; ir (potassium
1
bromide): 2962, 2875, 1580, 1472, 1435, 1220, 972 cm-1; H
nmr (deuteriochloroform): ꢀ 1.30 (s, 16H, CH2), 2.71-2.74 (m,
4H, CH2), 3.12 (t, 4H, CH2), 8.13 (s, 2H, CHS); 13C nmr
(deuteriochloroform):
ꢀ 28.27-29.64 (CH2), 37.38 (CH2),
2,13-Tetradecandione disemicarbazone (3c). This compound
was obtained as white powder, mp 219-220°; ir (potassium
bromide): 3413 (NH2), 3251 (NH), 2947 (C-H), 1696 (C=O),
131.21(C5), 164.25(C4); ms: (5kV, fd) m/z (%) 338 (100).
Anal. Calcd. For C16H26N4S2: C, 56.77; H, 7.74; N, 16.55; S,
18.94. Found: C, 56.71; H, 7.63; N, 16.41; S, 18.83.
General procedure for preparation of Di-1,2,3-
Selenadiazoles (5a-d). Semicarbazones 3a or 3b or 3c or 3d
respectively (0.36 mmol) was dissolved in glacial acetic acid (35
mL) with vigorous stirring and gentle heating 40-44 °C. The
solution was treated with selenium dioxide powder (0.84 mmol)
and the mixture was kept under gentle heating with vigorous
stirring. After 2 min, the color of the mixture becomes red.
1
1577, 1421, 1282 cm-1; H nmr (dimethyl sulfoxide-d6): ꢀ 1.27
(s, 12H, CH2), 1.55-1.59 (m, 4H, CH2), 2.19 (s, 6H, CH3), 2.38
(t, 4H, -CH2-CO-), 6.54 (s, 4H, NH2), 9.17 (s, 2H, NH); 13C nmr
(dimethyl sulfoxide-d6): ꢀ 23.87 (CH3), 29.15-29.79 (CH2),
43.78 (-CH2-CO-), 144.13 (C=N), 158.93 (C=O); ms: (5 kV, fd)
m/z (%) 340 (100). Anal. Calcd. for C16H32N6O2: C, 56.44; H,
9.47; N, 24.68. Found: C, 56.17; H, 9.27; N, 24.34.

918
M. Al-Smadi
Vol 44
Monitoring reaction progress using TLC showed that the
reaction was completed in 30 hours at which time the mixture
was filtered and the filtrate was poured over ice water and
extracted with chloroform (3 ꢀ 60 mL). The combined organic
layers were washed with saturated sodium hydrogen carbonate
solution and dried using magnesium sulphate. The solvent was
removed under vacuum. The crude product was chromato-
graphed using ethyl acetate as eleuent. The recrystalization was
followed from chloroform/hexane.
Technology for financial support. Also, we thank Prof. H. Meier
from Mainz University-Germany for help and worthful
discussion.
REFERENCES AND NOTES
[1] a) Litvinov, V. P.; Dyachenko, V. D. Russian Chem. Rev.
1997, 66, 923. b) Bakulev, V. A.; Dehaen, W. The Chemistry of 1,2,3-
Thiadiazoles, John Wiley & Sons, New York, NY, 2004, pp 222-233.
[2] Zhou, Y.; Heimgartner, H. Helvetica Chemica Acta. 2000,
83, 539.
1,6-Bis(1,2,3-selenadiazole-4-yl)hexane (5a). This compound
was obtained as pale yellow-brown solid, mp 70-71°; ir
1
(potassium bromide): 2938, 2858, 1686, 1428, 1233 cm-1; H
[3] Petrov, M. L.; Abramov, M. A.; Dehaen, W.; Toppet, S.
Tetrahedron Lett. 1999, 40, 3903.
nmr (deuteriochloroform): ꢁ 1.28 (s, 4H, CH2), 2.55-2.59 (m,
4H, CH2), 3.12 (t, 4H, CH2), 8.79 (s, 2H, CHSe); 13C nmr
(deuteriochloroform): ꢁ 27.31-28.64 (CH2), 36.45 (CH2), 133.29
(C5), 162.31 (C4); ms: (5 kV, fd) m/z (%) 348 (100). Anal.
Calcd. For C10H14N4Se2: C, 34.50; H, 4.05; N, 16.09; Se, 45.36.
Found: C, 34.33; H, 4.15; N, 16.20.
[4] Detert, H.; Meier, H. Liebigs. Ann. 1997 1557.
[5] Katritzky, A. R.; Rees, C. W. Comprehensive Heterocyclic
Chemistry, Pergamon Press, Oxford, 1984, 6, pp 447-471.
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of Heterocyclic Compounds. 2002, 38, 1437.
1,8-Bis(1,2,3-selenadiazole-4-yl)octane (5b). This compound
was obtained as yellow-brown solid, mp 72-73°; ir (potassium
bromide): 2939, 2859, 1690, 1427, 1234 cm-1; 1H nmr (deuterio-
chloroform): ꢁ 1.29 (s, 8H, CH2), 2.56-2.60 (m, 4H, CH2), 3.13
(t, 4H, CH2), 8.79 (s, 2H, CHSe); 13C nmr (deuteriochloroform):
ꢁ 27.29-28.56 (CH2), 36.44 (CH2), 133.26 (C5), 162.30 (C4);
ms: (5 kV, fd) m/z (%) 376 (100). Anal. Calcd. For C12H18N4Se2:
C, 38.31; H, 4.82; N, 14.89; Se, 41.97. Found: C, 38.11; H, 4.62;
N, 14.59.
1,10-Bis(1,2,3-selenadiazole-4-yl)decane (5c). This compound was
obtained as light brown solid, mp 74-75°; ir (potassium bromide):
2936, 2857, 1693, 1425, 1233 cm-1; 1H nmr (deuteriochloroform): ꢁ
1.25 (s, 12H, CH2), 2.54-2.58 (m, 4H, CH2), 3.09 (t, 4H, CH2), 8.78
(s, 2H, CHSe); 13C nmr (deuteriochloroform): ꢁ 27.26-28.53 (CH2),
36.43 (CH2), 133.24 (C5), 162.27 (C4); ms: (5kV, fd) m/z (%) 404
(100). Anal. Calcd. For C14H22N4Se2: C, 41.59; H, 5.49; N, 13.86;
Se, 39.06. Found: C, 41.26; H, 5.25; N, 13.61.
[8] a) Wendel, A. Selenium in Biology and Medicine, Springer
Verlag, Berlin, 1989, pp 83-97. b) Bruk, R. F. Selenium in Biology and
Human Health, Springer Verlag, New York, 1994, pp 67-85. c)
Klayman, D. L.; Guenter, W. H. Organic Selenium Compounds: Their
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1,12-Bis(1,2,3-selenadiazole-4-yl)dodecane (5d). This compound
was obtained as brown solid, mp 76-77°; ir (potassium
bromide): 2923, 2846, 1696, 1423, 1230 cm-1; 1H nmr (deuterio-
chloroform): ꢁ 1.21 (s, 16H, CH2), 2.51-2.56 (m, 4H, CH2), 3.04
(t, 4H, CH2), 8.76 (s, 2H, CHSe); 13C nmr (deuteriochloroform):
ꢁ 27.23-28.54 (CH2), 36.41 (CH2), 133.21(C5), 162.25 (C4); ms:
(5kV, fd) m/z (%) 432 (100). Anal. Calcd. For C16H26N4Se2: C,
44.45; H, 6.06; N, 12.96; Se, 36.53. Found: C, 44.71; H, 6.14; N,
12.69.
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Acknowledgement. We are grateful to the Deanship of
Scientific Research of the Jordan University of Science and
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