632
TUROV, DRACH
Table 2. (Contd.)
Comp.
no.
1H NMR spectrum, δ, ppm (DMSO-d6)
2.34 s (6Н, 2CН3), 2.46 s (3Н, CН3), 7.17–7.22 m (4Нarom), 7.33–7.43 m (6Нarom), 7.84–7.86 m (2Нarom
3.07 s [12Н, 2N(CH3)2], 7.40–7.42 m (2Нarom), 7.79–7.81 m (2Нarom
1.57 s (6Нpiperid), 1.64 с (6Нpiperid), 3.44–3.47 м (8Нpiperid), 7.39–7.41 м (2Нarom), 7.79–7.81 m (4Нarom
)
VIIIb
IXa
)
)
IXb
IXf
4.39 m (2Н, СН2), 4.54–5.55 m (2Н, СН2), 7.04 m (1Н, NH), 7.20–7.27 m (10Нarom), 7.46–7.48 m (2Нarom), 7.74–7.76 m (2Нarom),
8.95 br.s (1Н, NH)
7.03–7.05 m (2Нarom), 7.19–7.23 m (1Нarom), 7.33–7.41 m (5Нarom), 7.49–7.53 m (2Нarom), 7.63–7.65 m (2Нarom), 7.95–7.97 m
Xa
Xb
Xc
(2Нarom
2.34 s (3Н, СН3), 2.38 s (3Н, СН3), 6.89–6.91 m (2Нarom), 7.13–7.21 m (4Нarom), 7.27–7.29 m (2Нarom), 7.61–7.63 m (2Нarom),
7.92–7.94 m (2Нarom
7.06–7.08 m (2Нarom), 7.34–7.39 m (4Нarom), 7.47–7.49 m (2Нarom), 7.63–7.65 m (2Нarom), 7.94–7.96 m (2Нarom
3.77 s (3Н, ОСН3), 3.81 s (3Н, ОСН3), 6.86–7.01 m (6Нarom), 7.24–7.26 m (2Нarom), 7.62–7.65 m (2Нarom), 7.93–7.95 m (2Нarom
2.32 s (3Н, СН3), 6.95–7.10 m (4Нarom), 7.45–7.60 m (14Нarom), 7.70–7.85 m (3Нarom), 8.00–8.15 m (2Нarom
1.48 c (6H, 2CH3), 2.45 s (3Н, СН3), 3.22 s (3Н, NCH3), 5.78 c (1Н, СН), 6.75–6.81 m (2Нarom), 7.13–7.15 m (2Нarom), 7.41–7.43
m (2Нarom), 7.68–7.78 m (4Нarom), 8.08–8.10 m (2Нarom
)
)
)
)
Xd
XI
)
XII
)
methods. Synthetic value of substrates II, IV will be
considered in future.
of THF was added with stirring over the course of 1 h.
The mixture was allowed to stand for 30 h at 5°C. The
precipitate that formed was filtered off and washed
with ethanol.
EXPERIMENTAL
2-(Benzenesulfonyl)-5-(p-chlorobenzenesulfonyl)-
4-tosyl-1,3-thiazole (IV). To a solution of 0.02 mol of
compound III in 50 ml of boiling trifluoroacetic acid,
5 ml of 30% aqueous hydrogen peroxide was added.
The mixture was refluxed for 1 h, treated with the
same amount of hydrogen peroxide, refluxed for 2.5 h,
and poured into 100 ml of water. The precipitate that
formed was filtered off and crystallized from ethanol–
acetonitrile, 5:1.
Spectral parameters of compounds II–XII are
listed in Table 2. The H NMR spectra were taken on
a Varian Mercury-400 spectrometer in DMSO-d6
against internal TMS.
1
2-(Benzenesulfonyl)-5-chloro-4-tosyl-1,3-thiazole
(II). To a solution of 0.08 mol of compound I [1] in
150 ml of benzene cooled to 0°C, 0.08 mol of thio-
phenol was added and then 0.08 mol of pyridine was
added with stirring for 1 h. The reaction mixture was
stirred for 8 h at 15°C, the solvent was removed in a
vacuum. The residue was washed with water and
ethanol and then dissolved in 200 ml of boiling acetic
acid. After that 15 ml of 30% aqueous hydrogen
peroxide was added, the mixture was refluxed for 1 h,
and then again was treated with the same amount of
hydrogen peroxide and refluxed for 2.5 h. After
cooling 10°C, a precipitate formed and was filtered off
and crystallized from ethanol.
2-(Arylsulfanyl)-5-(p-chlorobenzenesulfonyl)-4-
tosyl-1,3-thiazoles (Va, Vb). A solution of 0.5 mmol
of compound IV in 10 ml of THF was cooled to 0°C,
and a solution of 0.5 mmol of the corresponding thiol
and 0.5 mmol of pyridine in 10 ml of THF was added
dropwise with stirring. The mixture was stirred for 3 h
at 0°C, the solvent was removed in a vacuum, and the
residue was treated with 3 ml of etanol. The precipitate
that formed was filtered off and crystallized from
ethanol.
2-(Benzenesulfonyl)-5-(p-chlorophenylsulfanyl)-
4-tosyl-1,3-thiazole (III). To a solution of 0.06 mol of
compound II in 120 ml of THF, cooled to 0°C, a
solution 0.06 mol of p-chlorothiophenol was added,
and then a solution of 0.06 mol of triethylamine in 15 ml
2-Amino(benzylamino, dimethylamino, methyl-
amino, morpholino, piperidino)-5-(p-chloroben-
zenesulfonyl)-4-tosyl-1,3-thiazoles VIa–VIf. To a
solution of 0.5 mmol of compound IV in 10 ml of
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 78 No. 4 2008
Turov
