Reactions of chlorodinitroand dichlorodinitrobenzofuroxans with 4-[(4-aminophenyl)sulfonyl]aniline

Full text of DOI:10.1134/S1070363212090289

ISSN 1070-3632, Russian Journal of General Chemistry, 2012, Vol. 82, No. 9, pp. 1599–1600. © Pleiades Publishing, Ltd., 2012.
Original Russian Text © E.A. Chugunova, R.E. Timasheva, E.M. Gibadullina, A.R. Burilov, A.D. Voloshina, V.V. Zobov, M.A. Pudovik, 2012, published in
Zhurnal Obshchei Khimii, 2012, Vol. 82, No. 9, pp. 1565–1566.
LETTERS
TO THE EDITOR
Reactions of Chlorodinitro-
and Dichlorodinitrobenzofuroxans
with 4-[(4-Aminophenyl)sulfonyl]aniline
a,b
b
a,b
b
E. A. Chugunova , R. E. Timasheva , E. M. Gibadullina , A. R. Burilov ,
a
a
a
A. D. Voloshina , V. V. Zobov , and M. A. Pudovik
a
Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center,
Russian Academy of Sciences, ul. Arbuzova 8, Kazan, Tatarstan, 420088 Russia
e-mail: elena-chugunova@list.ru
b
Kazan State Technological University, Kazan, Tatarstan, Russia
Received April 26, 2012
DOI: 10.1134/S1070363212090289
Aiming to synthesize compounds possessing bio-
logical activity, we studied the reaction of 4,6-di-
chloro-5-nitrobenzofuroxan I and 5,7-dichloro-4,6-
dinitrobenzofuroxan II with 4-[(4-aminophenyl)sul-
fonyl]aniline III. Both benzofuroxan derivatives and
diamine III (known as dapsone) have antibacterial and
antifungal activity [1, 2]. We presumed that the
combination of the structural fragments of these two
classes of compounds in a single molecule may lead to
materials with high biological activity.
aniline can lead to the formation of the products of 1:1
and 1:2 composition [3]. We isolated only the product
IV of 1:1 composition in the reaction of benzofuroxan
I and diamine III.
The reaction of benzofuroxan II with diamine III
occurs including both chlorine atoms of the benzo-
furoxan ring to give compound V.
The structure of the compounds was confirmed by
1
the H NMR and IR spectra, the composition, by the
elemental analysis data.
Depending on the solvent nature and the reactants
ratio, the reaction of furoxan I with the aromatic di-
amine like 4,4'-methylenedianiline or 4,4'-ethylenedi-
The obtained compounds IV and V were found to
possess the bacteriostatic action at concentrations of
2
O
−
O
3
+
N
Cl
N
9
1
O N
O
S
O
S
2
8
N
H
4
7
O + H N
NH2
H N
N
2
2
+
6
N
Cl
−
O
III
O
5
O
O N
Cl
2
I
IV
−
O
O
+
N
N
O
S
H
NO2
O N
N
NH
2
2
Cl
O
S
N
O
O + III
H N
2
NH
NO2
+
N
−
O N
2
O
O
Cl
II
V
1
599

1
600
CHUGUNOVA et al.
–
1
5
00–15.6 mg l . The activity of compound IV is much
Ar), 6.92–6.98 m (2Н, Ar), 7.27–7.35 m (2Н, Ar),
7.41–7.48 m (2Н, Ar), 7.51–7.57 m (2Н, Ar), 7.64–
.67 m (2Н, Ar), 7.74–7.77 m (2Н, Ar), 11.32 s (1Н,
NH), 11.36 s (1Н, NH). Found, %: C 50.35; H 2.99; N
5.62; S 9.02. C H N O S . Calculated, %: C 50.14;
higher than that of compound V.
7
4
-[4-(4-Aminophenyl)sulfonylphenyl]amino-6-
chloro-5-nitrobenzo[с]-1,2,5-oxadiazole 1-oxide (IV).
To a solution of 0.125 g of benzofuroxan I in 5 ml of
DMSO was added dropwise 0.21 g of diamine III in
1
3
0
22
8
10 2
H 3.09; N 15.59; S 8.92.
5
ml of DMSO at 20°C. The reaction mixture was kept
The IR spectra were registered on a Vector 22
–
1
for 30 min and then poured into the distilled water.
The precipitate was separated, washed with water, and
dried in a vacuum at 40°C to the constant weight.
Yield 0.18 g (78 %), mp 116–117°С (hexane). IR
Bruker spectrometer in the range of 400–3600 cm .
1
The Н NMR spectra were recorded on an Avance-600
instrument operating at 600.13 MHz and reported
relative to the residual protons of the deuterated sol-
vents (acetone-d , DMSO-d ).
–
1
spectrum, ν, cm : 1146 (SO ), 1359 (NO , s), 1561
2
2
6
6
1
(NO , as), 1612 (furoxan), 3096 (ArH), 3306 (NH). Н
2
ACKNOWLEDGMENTS
NMR spectrum (acetone-d ), δ, ppm (J, Hz): 5.92 s
6
7
3
(
2Н, NН ), 7.14 s (1Н, СH ), 7.17 d (2Н, Ar, J 8.5),
This work was supported by The Russian Founda-
tion for Basic Research (grant no 12-03-97041).
2
HH
3
3
7
8
.32 d (2Н, Ar, J 8.5), 8.05 d (2Н, Ar, J 8.5),
.14 d (2Н, Ar, JHH 8.5), 8.40 s (1Н, NH). Found, %:
HH HH
3
REFERENCES
C 46.56; H 2.42; Cl 7.08; N 15.31; S 7.05.
C H ClN O S. Calculated, %: C 46.81; H 2.62; Cl
7
1
.
Jorge, S.D., Masunari, A., Rangel-Yagui, C.O.,
Pasqualotoa, K.F.M., and Tavares, L.C., Bioorg. Med.
Chem., 2009, no. 17, p. 3028.
Mashkovskii, M.D., Lekarstvennye sredstva (Drugs),
Moscow: Novaya Volna, 2012.
1
8
12
5
6
.68; N 15.16; S 6.94.
,7-Bis{[4-(4-aminophenyl)sulfonylphenyl]amino}-
,6-dinitrobenzo[с]-1,2,5-oxadiazol 1-oxide (V) was
5
2
3
.
.
4
obtained similarly from 0.125 g of compound II and
.42 g of diamine III. Yield 0.32 g (89%), mp 90–92°С
Chugunova, Е.А., Burilov, A.R., and Sazykina, M.A.,
0
Benzofuroksany. Sintez, khimicheskie svoistva
biologicheskaya aktivnost’ (Benzofuroxans. Synthesis,
chemical properties and biological activity),
i
–
1
(
hexane). IR spectrum, ν, cm : 1148 (SO ), 1360
2
(
NO , s), 1559 (NO as), 1636 (furoxan), 3315 (NH).
2
2,
1
Saarbrücken: LAP LAMBERT Academic Publishing
GmbH&Co KG, 2011.
Н NMR spectrum (DMSO-d ), δ, ppm (J, Hz): 5.94
6
br. s (2Н, NН ), 6.07 s (2Н, NН ), 6.56–6.63 m (4Н,
2
2
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 82 No. 9 2012