New multi-1,2,3-selenadiazole aromatic derivatives

Article abstract of DOI:10.3390/10091126

The aromatic polyketones 3a-d are versatile compounds for the synthesis of the multi-1,2,3-selenadiazole aromatic derivatives 1a-d. The preparation starts with the reaction between the multi-bromomethylene benzene derivatives 2a-d and 4-hydroxy-acetophenone to give compounds 3a-d which are transformed through the reaction with semicarbazide hydrochloride or ethyl hydrazine carboxylate into the corresponding semicarbazones derivatives 4a-d or hydrazones 5a-d. The reaction with selenium dioxide leads to regiospecific ring closure of semicarbazones or hydrazones to give the multi-1,2,3-selenadiazole aromatic derivatives in high yield.

Full text of DOI:10.3390/10091126

Molecules 2005, 10, 1126-1134
molecules
ISSN 1420-3049
http://www.mdpi.org
New Multi-1,2,3-Selenadiazole Aromatic Derivatives
Mousa Al-Smadi* and Samer Ratrout
Department of Applied Chemical Sciences, Jordan University of Science and Technology, P.O. Box
3030, Irbid 22110, Jordan
* Author to whom correspondence should be addressed; e-mail: mariam10@just.edu.jo
Received: 23 April 2005 / Published: 30 September 2005
Abstract: The aromatic polyketones 3a-d are versatile compounds for the synthesis of
the multi-1,2,3-selenadiazole aromatic derivatives 1a-d. The preparation starts with the
reaction between the multi-bromomethylene benzene derivatives 2a-d and 4-hydroxy-
acetophenone to give compounds 3a-d which are transformed through the reaction with
semicarbazide hydrochloride or ethyl hydrazine carboxylate into the corresponding
semicarbazones derivatives 4a-d or hydrazones 5a-d. The reaction with selenium dioxide
leads to regiospecific ring closure of semicarbazones or hydrazones to give the multi-
1,2,3-selenadiazole aromatic derivatives in high yield.
Keywords: 1,2,3-Selenadiazoles; semicarbazones; aromatic derivatives
Introduction
Heterocyclic systems with multi-arm 1,2,3-thiadiazoles were recently prepared by Meier et. al [1-
2] and heterocyclic systems containing two 1,2,3-selenadiazole rings were also recently prepared by
Reddy et. al [3-4], but multi-arm 1,2,3-selenadiazoles are still unknown. Therefore depending on the
previous experience of the principal investigator in synthesizing multi-arm 1,2,3-thiadiazoles, the
analogous multi-arm selenadiazoles were prepared following the method that was first reported by
Lalezari et. al [5-7], through reaction in the presence of acetic acid of selenium dioxide with α-
ketomethylene semicarbazones or hydrazones which contain aminocarbonyl or ethoxycarbonyl groups
as good leaving groups. NOE measurements showed that the (E)-configuration largely predominated
around the CN double bond.

Molecules 2005, 10
1127
Selenium containing heterocycles are of increasing interest because of their interesting chemical
properties [8-13] and varied biological activities [14-16]. Remarkable differences are known to exist
between Se- and S-containing compounds. Due to the larger size of the Se-atom, selenium compounds
show an increased polarizability and therefore they are, in general, less stable than the corresponding
S-analogues [17-20]. We report herein on our efforts to generate the multi-branched benzene
derivatives 1a, 1b, 1c and 1d, in which the 1,2,3-selenadiazole rings are linked to the central benzene
core via phenoxymethylene spacers.
Scheme 1
O
O
O
HO
Br
CH3
CH3
n
K2CO3, Acetone
n
3a-3d
2a-2d
O
Z
NH
N
O
O
SeO2
H2N NH C
Z
CH3
AcOH
n
(Z=NH or OC H )
2
2 5
4a-4d
Se
O
N
N
n
1a-1d
Series
n
6
4
3
2
a
b
c
d
Results and Discussion
Our synthetic procedure (see Scheme 1) started from the commercially available bromomethyl-
benzene derivatives 2a-2d. Multiple substitution with 4-hydroxyacetophenone gave the corresponding
polyketones 3a-3d, which were transformed into the target compounds 1a-1d by the reaction of the

Molecules 2005, 10
1128
corresponding semicarbazones 4a-4d or ethoxycarbonyl hydrazones 5a-5d, essentially as described by
Lalezari et. al. [5-7]. The yields of all three steps were optimized, so that the total overall yields for the
sequences 2a → 1a, 2b → 1b, 2c → 1c and 2d → 1d amounted to 90%, 85%, 89% and 85%,
respectively (Table 1).
Table 1
R
R
R
R
R
R
R
Ring system
R
R
R
R
R
R
R
R
R
Cpd.
2a
Yield
Cpd.
2b
Yield
Cpd.
2c
Yield
Cpd.
2d
Yield
Br
―
―
―
―
O
3a
87
3b
90
3c
95
3d
89
O
O
N
NH
4a
91
4b
81
4c
96
4d
98
NH2
O
O
N
NH
O
5a
1a
92
96
5b
1b
87
92
5c
1c
85
87
5d
1d
91
60
OCH2CH3
Se
N
O
N
Acknowledgements
We are grateful to the Deanship of Scientific Research of the Jordan University for Science and
Technology for financial support. Also, we thank Prof. H. Meier from Mainz University-Germany for
helpful discussions.
Experimental
General
The solvents were purified by standard procedures. The melting points (m.p.) were determined on
an Electrothermal digital melting point apparatus and are uncorrected. Infrared (IR) spectra of pure
substances were recorded as KBr-pellets using a Nicolet 410 FT-IR spectrometer (ν in cm-1). The 1H-
and 13C-NMR spectra were recorded on Bruker AM400 and AC200 spectrometers in CDCl3 or
DMSO-d6 using TMS as internal standard. The spectral data are reported in delta (δ) units relative to

Molecules 2005, 10
1129
the TMS reference peak. The mass spectra were recorded using a Finnigan MAT95 field desorption
(FD, 5 kV ionizing energy) instrument. The signals are given as m/z with the relative intensity between
brackets. Elemental analyses were performed in the Analytical Laboratory of the Institute of Organic
Chemistry of University of Mainz, Germany. Bromo compounds 2a-2d (1,2,3,4,5,6-hexakis-, 1,2,4,5-
tetrakis-, 1,3,5-tri- and 1,4-dibromomethylbenzene, respectively), ethyl hydrazine carboxylate,
semicarbazide hydrochloride and sodium acetate were obtained from Aldrich.
General Procedure for the Preparation of Multi-Ketones 3a-d [1]
A mixture of 4-hydroxyacetophenone (1 equivalent) and 2a (0.14 equivalents), 2b (0.21
equivalents), 2c (0.3 equivalents) or 2d (0.45 equivalents), potassium carbonate (1 equivalent) and
potassium iodide (in the same equivalent amount as the bromo compound used) plus a few drops of
Aliquat 336 were refluxed in dry acetone (100 mL) for 48 hours. The reaction was followed by TLC
(eluent: chloroform) till completion. After cooling, the reaction mixture was diluted with water (50
mL) and extracted with dichloromethane (3 × 40 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 recrystalization from acetone or chloroform was performed.
1-{4-[2,3,4,5,6-Penta(4-acetylphenoxymethyl)benzyloxy]phenyl}-1-ethanone (3a).
1
Colorless powder (87% yield), m.p. 234-235°C; IR: ν 1675, 1604, 1508, 1239, 1002, 832 cm-1; H-
13
NMR (CDCl3): 2.50 (s, 3H, CH3), 5.26 (s, 2H, CH2O), 6.89, 7.83 (d, d, 2H, 2H, AA′BB′); C-NMR
(CDCl3): 26.20 (CH3), 63.60 (CH2O), 137.70 (central benzene ring Cq), 114.21 and 130.70 (side chain
benzene CH), 131.30, 161.80 (side chain benzene Cq), 196.40 (C=O); MS: 967 (M+, 100); Anal. %
Calcd. for C60H54O12: C, 74.52; H, 5.63. Found: C, 74.27; H, 5.54.
1-{4-[2,4,5-Tri(4-acetylphenoxymethyl)benzyloxy]phenyl}-1-ethanone (3b).
Colorless powder (90% yield); m.p. 224-226°C; IR: ν 1665, 1590, 1502, 1250, 1170, 830 cm-1; 1H-
NMR (CDCl3): 2.53 (s, 3H, CH3), 5.23 (s, 2H, CH2O), 6.94, 7.89 (d, d, 2H, 2H, AA′BB′), 7.65 (s,
benzene ring central CH); 13C-NMR (CDCl3): 26.30 (CH3), 67.70 (CH2O), 129.80 (central benzene
ring CH), 135.10 (central benzene ring Cq), 114.41 and 130.60 (side chain benzene CH), 131.10,
162.10 (side chain benzene Cq), 196.50 (C=O); MS: 670 (M+, 100); Anal. % Calcd. for C42H38O8: C,
75.21; H, 5.71. Found: C, 75.13; H, 5.59.
1-{4-[3,5-Di(4-acetylphenoxymethyl)benzyloxy]phenyl}-1-ethanone (3c).
Pale yellow powder (100% yield); m.p. 82-83°C; IR: ν 2910, 1670, 1591, 1500, 1250, 1172, 836 cm-1.
1H-NMR (DMSO-d6): 2.49 (-s, 3H, CH3), 5.22 (s, 2H, CH2O), 7.09, 7.90 (d, d, 2H, 2H, AA′BB′), 7.53
(s, benzene ring central CH); 13C-NMR (DMSO-d6): 26.30 (CH3), 69.20 (CH2O), 126.60 (central
benzene ring CH), 137.20 (central benzene ring Cq), 114.61 and 130.50 (side chain benzene CH),
130.10, 162.00 (side chain benzene Cq), 196.30 (C=O); MS: 523 (M+, 100); Anal. % Calcd. for
C33H30O6: C, 75.84; H, 5.79. Found: C, 75.81; H, 5.68.

Molecules 2005, 10
1130
1-{4-[4-Mono-(4-acetylphenoxymethyl) benzyloxy] phenyl}-1-ethanone (3d).
1
Colorless crystals (89% yield); m.p. 181-182°C; IR: ν 1668, 1591, 1239, 996, 823 cm-1; H-NMR
(CDCl3): 2.53 (s, 3H, CH3), 5.12 (s, 2H, CH2O), 7.00, 7.90 (d, d, 2H, 2H, AA′BB′), 7.44 (d, benzene
13
ring central CH); C-NMR (CDCl3): 26.40 (CH3), 69.70 (CH2O), 127.80 (central benzene ring CH),
136.20 (central benzene ring Cq), 114.50 and 130.60 (side chain benzene CH), 130.60, 162.40 (side
chain benzene Cq), 196.70 (C=O); MS: 374 (M+, 100); Anal. % Calcd. for C24H22O4: C, 76.99; H,
5.92. Found: C, 76.78; H, 5.81.
General procedure for the preparation of multiple semicarbazones 4a-d
A mixture of semicarbazide hydrochloride (1 equivalent) and sodium acetate (1 equivalent) was
dissolved in absolute ethanol (40 mL). The mixture was heated for 15 min under reflux, then filtered
while hot to remove precipitated sodium chloride. The filtrate was mixed with ketone 3a (0.14
equivalents), ketone 3b (0.21 equivalents), ketone 3c (0.30 equivalents) or ketone 3d (0.45
equivalents), respectively. The reaction mixture was heated to reflux then two drops of concentrated
hydrochloric acid were added. The mixture was heated under reflux for overnight with continuously
removal of generated water. After that the solvent was removed under vacuum and the residue was
washed with diethyl ether.
1-{4-[2,3,4,5,6-Penta(4-acetylphenoxymethyl) benzyloxy]phenyl}-1-ethanone-N-aminocarbonyl semi-
carbazone (4a).
White powder (91% yield), m.p. 300°C (dec.); IR: ν 3417, 3212, 1687, 1597, 1431, 1239, 1014, 829
1
cm-1; H-NMR (DMSO-d6): 2.08 (s, 3H, CH3-C=N)), 5.37 (s, 2H, CH2O), 6.41 (s, 2H, NH2), 6.93,
7.70 (d, d, 2H, 2H, AA′BB′), 9.18 (s, 1H, N-H); 13C-NMR (DMSO-d6): 13.29 (CH3-C=N), 63.90
(CH2O), 137.60 (central benzene ring Cq), 114.30 and 127.50 (side chain benzene CH), 130.40,
159.60 (side chain benzene Cq), 143.90 (C=N), 157.40 (C=O); MS: 1309.4 (M+, 100); Anal. % Calcd.
for C66H72N18O12: C, 60.54; H, 5.54; N, 19.25, Found: C, 60.35; H, 5.54; N, 19.30.
1-{4-[2,4,5-Tri(4-acetylphenoxymethyl)benzyloxy]phenyl}-1-ethanone-N-aminocarbonylsemi-
carbazone (4b).
White powder (81% yield); m.p. 250°C (dec.); IR: ν 3429, 3180, 1670, 1599, 1418, 1258, 836 cm-1;
1H-NMR (DMSO-d6): 2.12 (s, 3H, CH3-C=N)), 5.34 (s, 2H, CH2O), 5.99 (s, 2H, NH2), 7.06, 7.86 (d,
d, 2H, 2H, AA′BB′), 7.71 (s, central benzene ring CH), 9.19 (s, 1H, N-H); 13C-NMR (DMSO-d6):
13.38 (CH3-C=N), 67.08 (CH2O), 129.10 (central benzene ring CH), 134.80 (central benzene ring Cq),
114.70 and 127.50 (side chain benzene CH), 130.50, 159.70 (side chain benzene Cq), 144.00 (C=N),
157.50 (C=O); MS: 899 (M+, 100); Anal. % Calcd. for C46H50N12O8: C, 62.33; H, 5.67; N, 18.17,
Found: C, 62.29; H, 5.61; N, 18.05.

Molecules 2005, 10
1131
1-{4-[3,5-Di(4-acetylphenoxymethyl)benzyloxy]phenyl}-1-ethanone-N-aminocarbonyl semicarbazone
(4c).
Pale yellow powder (100% yield); m.p. 240°C (dec.); IR: ν 3417, 3250, 1681, 1579, 1508, 1470, 1226,
829 cm-1; 1H-NMR (DMSO-d6): 2.13 (s, 3H, CH3-C=N)), 5.15 (s, 2H, CH2O), 6.55 (s, 2H, NH2), 6.98,
7.76 (d, d, 2H, 2H, AA′BB′), 7.49 (s, central benzene ring CH), 9.25 (s, 1H, N-H); 13C-NMR (DMSO-
d6): 13.38 (CH3-C=N), 69.15 (CH2O), 126.44 (central benzene ring CH), 137.76 (central benzene ring
Cq), 114.54 and 127.50 (side chain benzene CH), 131.20, 158.73 (side chain benzene Cq), 144.11
(C=N), 157.90 (C=O); MS: 693.77 (M+, 100); Anal. % Calcd. for C36H39N9O6: C, 61.46; H, 5.61; N,
18.70, Found: C, 63.32; H, 5.51; N, 18.63.
1-{4-[4-(4-acetylphenoxymethyl)benzyloxy]phenyl}-1-ethanone-N-aminocarbonyl semicarbazone (4d).
White powder (100% yield); m.p. 300°C (dec.); IR: ν 3417, 3212, 1681, 1604, 1502, 1418, 1239,
1
1014, 829 cm-1; H-NMR (DMSO-d6): 2.12 (s, 3H, CH3-C=N)), 5.20 (s, 2H, CH2O), 5.90 (s, 2H,
13
NH2), 7.08, 7.89 (d, d, 2H, 2H, AA′BB′), 7.45 (d, central benzene ring CH), 9.21 (s, 1H, N-H); C-
NMR (DMSO-d6): 13.30 (CH3-C=N), 69.30 (CH2O), 127.80 (central benzene ring CH), 136.41
(central benzene ring Cq), 114.50 and 128.00 (side chain benzene CH), 131.17, 159.70 (side chain
benzene Cq), 143.00 (C=N), 158.70 (C=O); MS: 488.5 (M+, 100); Anal. % Calcd. for C26H28N6O4: C,
63.92; H, 5.78; N, 17.20, Found: C, 63.71; H, 5.72; N, 17.15.
General procedure for the preparation of multiple hydrazones 5a-d [1].
A solution of di- or tri- or tetra- or hexaketone 3a-d (1 equivalent), a few drops of concentrated
hydrochloric acid and 6, 9, 12 or 18 equivalents of ethyl hydrazinecarboxylate in dry chloroform (50
mL) was heated under reflux overnight with continuously removal of generated water. The solution
was concentrated and the residue was washed with diethyl ether and chloroform.
1-{4-[2,3,4,5,6-Penta(4-acetylphenoxymethyl)benzyloxy]phenyl}-1-ethanone-N-ethoxycarbonyl
hydrazone (5a).
White solid powder (92% yield); m.p. 293°C (dec.); IR: ν 3231, 1719, 1610, 1502, 1233, 1047, 829
1
cm-1; H-NMR (DMSO-d6): 1.23 (t, 3H, CH3CH2), 2.12 (s, 3H, CH3-C=N)), 4.13 (q, 2H, CH3CH2),
5.29 (s, 2H, CH2O), 6.95, 7.58 (d, d, 2H, 2H, AA′BB′), 9.96 (s, 1H, N-H); 13C-NMR (DMSO-d6):
14.23 (CH3CH2), 15.01 (CH3-C=N), 60.95 (CH3CH2O), 64.36 (CH2O-ph), 138.09 (central benzene
ring Cq), 114.86 and 127.94 (side chain benzene CH), 131.93, 159.41 (side chain benzene Cq), 149.25
(C=N), 154.76 (CO2); MS: 1484 (M+,100); Anal. % Calcd. for C78H90N12O18: C, 63.15; H, 6.11; N,
11.33, Found: C, 62.79; H, 6.27; N, 11.44.

Molecules 2005, 10
1132
1-{4-[2,4,5-Tri-(4-acetylphenoxymethyl)benzyloxy]phenyl}-1-ethanone-N-ethoxycarbonyl hydrazone
(5b).
White powder (87% yield), m.p. 211-213°C; IR: ν 3200, 3045, 1700, 1596, 1492, 1235, 1040, 828
1
cm-1; H-NMR (DMSO-d6): 1.24 (t, 3H, CH3CH2), 2.16 (s, 3H, CH3-C=N)), 4.16 (q, 2H, CH3CH2),
5.27 (s, 2H, CH2O), 7.03, 7.65 (d, d, 2H, 2H, AA′BB′), 7.71 (s, central benzene ring CH), 9.98 (s, 1H,
13
N-H); C-NMR (DMSO-d6): 14.28 (CH3CH2), 15.19 (CH3-C=N), 60.98 (CH3CH2O), 67.40 (CH2O-
ph), 129.37 (central benzene ring CH), 135.43 (central benzene ring Cq), 115.08 and 128.00 (side
chain benzene CH), 131.76, 159.33 (side chain benzene Cq), 148.70 (C=N), 154.80 (CO2); MS: 1015
(M+, 100); Anal. % Calcd. for C54 H62N8O12: C, 63.89; H, 6.16; N, 11.04, Found: C, 63.58; H, 6.09; N,
10.97.
1-{4-[3,5-Di(4-acetylphenoxymethyl)benzyloxy]phenyl}-1-ethanone-N-ethoxycarbonyl hydrazone (5c).
Pale yellow powder (85% yield), m.p. 202-204°C; IR: ν 3200, 3035, 1705, 1600, 1503, 1238, 1040,
1
830 cm-1; H-NMR (DMSO-d6): δ 1.24 (t, 3H, CH3CH2), 2.17 (s, 3H, CH3-C=N)), 4.15 (q, 2H,
CH3CH2), 5.18 (s, 2H, CH2O), 7.03, 7.67 (d, d, 2H, 2H, AA′BB′), 7.52 (s, central benzene ring CH),
13
9.99 (s, 1H, N-H); C-NMR (DMSO-d6): δ 14.30 (CH3CH2), 15.20 (CH3-C=N), 60.90 (CH3CH2O),
69.60 (CH2O-ph), 126.90 (central benzene ring CH), 138.06 (central benzene ring Cq), 115.10 and
128.00 (side chain benzene CH), 131.60, 159.50 (side chain benzene Cq), 148.70 (C=N), 154.20
(CO2); MS: 781 (M+, 100); Anal. % Calcd. for C42H48N6O9: C, 64.60; H, 6.20; N, 10.76, Found: C,
64.48; H, 6.13; N, 10.50.
1-{4-[4-Mono(4-acetylphenoxymethyl)benzyloxy]phenyl}-1-ethanone-N-ethoxycarbonyl hydrazone
(5d).
1
White powder (91% yield); m.p. 259-260°C; IR: ν 3205, 3035, 1705, 1600, 1500, 1230, 822 cm-1; H-
NMR (DMSO-d6): δ 1.22 (t, 3H, CH3CH2), 2.15 (s, 3H, CH3-C=N)), 4.16 (q, 2H, CH3CH2), 5.10 (s,
2H, CH2O), 6.99, 7.87 (d, d, 2H, 2H, AA′BB′), 7.43 (d, central benzene ring CH), 9.99 (s, 1H, N-H);
13C-NMR (DMSO-d6): δ 13.60 (CH3CH2), 14.70 (CH3-C=N), 60.80 (CH3CH2O), 67.80 (CH2O-Ph),
127.60 (central benzene ring CH), 136.30 (central benzene ring Cq), 114.50 and 127.60 (side chain
benzene CH), 130.50, 160.10 (side chain benzene Cq), 148.81 (C=N), 154.30 (CO2); MS: 547 (M+,
100); Anal. % Calcd. for C30H34N4O6: C, 65.92; H, 6.27; N, 10.25, Found: C, 65.99; H, 6.18; N, 10.15.
General procedure for preparation of multiple 1,2,3-selenadiazoles 1a-d
Hydrazone 5a (0.47 mmol) or 5b (0.59 mmol) or 5c (0.9 mmol) or 5d (0.27 mmol) was dissolved
in glacial acetic acid (30 mL) with vigorous stirring and gentle heating to 40-45°C. The solution was
treated with selenium dioxide powder (8.46 mmol, 7.08 mmol, 8.1 mmol or 0.81 mmol, respectively)
and the mixture was kept under gentle heating with vigorous stirring. After 2 min, the color of the
mixture becomes red. Monitoring of the reaction by TLC showed that the reaction was complete in
two days. The mixture was filtered and the filtrate was poured into ice water and extracted with
chloroform (3 × 50 mL). The combined organic layers were washed with saturated sodium hydrogen

Molecules 2005, 10
1133
carbonate solution and dried using magnesium sulphate. The solvent was removed under vacuum. The
crude product was purified by chromatography using methanol or ethyl acetate as eluents, followed by
recrystallization from chloroform/hexane.
4-(4-{2,3,4,5,6-Penta[4-(1,2,3-selenadiazole-4-yl)phenoxymethyl]benzyloxy}phenyl)-1,2,3-
selenadiazole (1a).
Yellow-orange solid (100%); m.p. 77-78°C; IR: ν 3096, 2975, 1739, 1611, 1527, 1469, 1220, 989, 841
1
cm-1; H-NMR (CDCl3): 5.27 (s, 2H, CH2O), 7.06, 7.17 (d, d, 2H, 2H, AA′BB′), 9.68 (s, 1H, CHSe);
13C-NMR (CDCl3): 63.62 (CH2O), 128.50 (central benzene ring Cq), 115.36 and 130.20 (side chain
benzene CH), 119.20, 152.40 (side chain benzene Cq), 159.61 (C=N), 137.70 (CHSe); MS: 1500 (M+,
100); Anal. % Calcd. For C60H42N12O6Se6: C, 48.01; H, 2.82; N, 11.20; Se, 31.57, Found: C, 47.91; H,
2.74; N, 11.11.
4-(4-{2,4,5-Tri[4-(1,2,3-selenadiazole-4-yl)phenoxymethyl]benzyloxy}phenyl)-1,2,3-selenadiazole
(1b).
Yellow-orange solid (92% yield); m.p. 87-88°C; IR: ν 3096, 2930, 1725, 1611, 1527, 1469, 1245,
1
1040, 822 cm-1; H-NMR (CDCl3): 5.25 (s, 2H, CH2O), 7.12, 7.22 (d, d, 2H, 2H, AA′BB′), 7.70 (s,
benzene central ring CH), 9.71 (s, 1H, CHSe); 13C-NMR (CDCl3): 67.70 (CH2O), 124.00 (central
benzene ring CH), 129.80 (central benzene ring Cq), 115.89 and 130.12 (side chain benzene CH),
118.80, 152.60 (side chain benzene Cq), 159.92 (C=N), 136.40 (CHSe); MS: 1026 (M+, 100); Anal. %
Calcd. For C42H30N8O4Se4: C, 49.13; H, 2.95; N, 10.91; Se, 30.77, Found: C, 49.10; H, 2.75; N, 10.71.
4-(4-{3,5-Di[4-(1,2,3-selenadiazole-4-yl)phenoxymethyl]benzyloxy} phenyl)-1,2,3-selenadiazole (1c).
Yellow-orange solid (87% yield); m.p.100-102°C; IR: ν 3096, 2917, 1738, 1610, 1534, 1450, 1239,
1
1046, 835 cm-1; H-NMR (CDCl3): 5.15 (s, 2H, CH2O), 7.11, 7.20 (d, d, 2H, 2H, AA′BB′), 7.49 (s,
central benzene ring CH), 9.72 (s, 1H, CHSe); 13C-NMR (CDCl3): 69.69 (CH2O), 126.00 (central
benzene ring CH), 129.70 (central benzene ring Cq), 115.99 and 130.03 (side chain benzene CH),
118.80, 149.15 (side chain benzene Cq), 160.15 (C=N), 137.60 (CHSe); MS: 789 (M+, 100); Anal. %
Calcd. For C33H24N6O3Se3: C, 50.20; H, 3.06; N, 10.64; Se, 30.01, Found: C, 50.10; H, 3.00; N, 10.59.
1,4-Bis[4-(1,2,3-selenadiazol-4-yl)phenoxymethyl]benzene (1d).
Yellow-orange solid (60% yield); m.p. 160-162°C; IR: ν 3077, 2911, 1732, 1610, 1533, 1456, 1239,
1008, 822 cm-1; 1H-NMR (DMSO-d6): 5.15 (s, 2H, CH2O), 7.12, 7.21 (d, d, 2H, 2H, AA′BB′), 7.47 (d,
13
benzene central ring CH), 9.72 (s, 1H, CHSe); C-NMR (DMSO-d6): 70.00 (CH2O), 127.89 (central
benzene ring CH), 129.18 (central benzene ring Cq), 116.10 and 130.00 (side chain benzene CH),
121.00, 152.00 (side chain benzene Cq), 160.00 (C=N), 138.00 (CHSe); MS: 552 (M+, 100); Anal. %
Calcd. For C24H18N4O2Se2: C, 52.18; H, 3.28; N, 10.14; Se, 28.60, Found: C, 52.03; H, 3.25; N, 10.20.

Molecules 2005, 10
1134
References
1. Al-Smadi, M.; Meier, H. Liebigs Ann. 1997, 2357.
2. Al-Smadi, M.; Hanold, N.; Meier, H. J. Heterocycl. Chem. 1997, 34, 605.
3. Reddy, D. B.; Babu, N. C.; Padmavathi, V.; Padmaja, A. Tetrahedron 1997, 53, 17351.
4. Bhaskar Reddy, D.; Somasekhar Reddy, A.; Padmavathi, V. Synth. Commun. 2001, 31, 3429.
5. Lalezari, I.; Shafiee, A. Tetrahedron Lett. 1969, 5105.
6. Lalezari, I.; Shafiee, A. J. Org. Chem. 1971, 36, 2836.
7. Lalezari, I.; Shafiee, A.; Yalpani, M. J. Org. Chem. 1973, 38, 338.
8. Zhou, Y.; Heimgartner, H. Helv. Chem. Acta 2000, 83, 539.
9. Petrov, M. L.; Abramov, M. A.; Dehaen, W.; Toppet, S. Tetrahedron Lett. 1999, 40, 3903.
10. Detert, H.; Meier, H. Liebigs Ann. 1997, 1557.
11. Zhou, Y.; Heimgartner, H. Helv. Chem. Acta 2000, 83, 539.
12. Nishiyama, Y.; Hada, Y.; Anjiki, M.; Hanita, S.; Sonoda, N. Tetrahedron Lett. 1999, 40, 6293.
13. Arsenyan, P.; Oberte, K.; Pudova, O.; Lukevics, E. Chem. Heterocycl. Comp. 2002, 38, 1437.
14. Burling, F. T.; Goldenstein, B. M. J. Am. Chem.Soc. 1992, 114, 2313.
15. Jalilian, A. R.; Sattari, S.; Bineshmarvasti, M.; Daneshtalab, M.; Shafiee, A. Farmaco 2003, 58,
63.
16. Lalezari, I.; Shafiee, A.; Khorrami, J.; Soltani, A. J. Pharm. Sci. 1987, 67, 1336.
17. Abramov, M. A.; Dehaen, W.; D’Hooge, B.; Petrov, M. L.; Smeets, S.; Toppet, S.; Voets, M.
Tetrahedron, 2000, 56, 3933.
18. D’ Hooge, B.; Smeets, S.; Toppet, S.; Dehaeam, S. J. Chem. Soc. Chem. Commun. 1997, 1753.
19. L’Abbe, G.; Haelterman, B.; Dehaen, W. J. Chem. Soc. Perkin Trans. 1 1994, 2203.
20. Malek-Yazdi, F.; Yalpani, M. Synthesis 1977, 328.
Sample availability: Contact the author.
© 2005 by MDPI (http://www.mdpi.org). Reproduction is permitted for noncommercial purposes.