1028
DEMCHENKO et al.
XIX XXI. The structure of compounds VII XIX was
confirmed by spectral data and elemental analyses.
The 1H NMR spectra of acetanilides XIII XVIII
contain a two-proton singlet from the SCH2 group in
the region 4.0 4.5 ppm and a two-proton singlet
from the amino group in the region 5.8 6.3 ppm.
The amide NH proton appears as a broadened singlet
Excess POCl3 was evaporated under reduced pressure,
and 50 ml of a 10% solution of KOH was added to
the oily residue. After crystallization, the precipitate
was filtered off, washed with water, and recrystallized
from ethanol DMF.
6-Arylamino-3-methyl-7H-[1,2,4]triazolo[3,4-b]-
[1,3,4]thiadiazine hydrochlorides XXg and XXl.
A mixture of 10 mmol of acetanilide XIVg or XIVl
and 20 30 ml of POCl3 was heated for 2 3 h under
reflux. Excess POCl3 was evaporated under reduced
pressure, and the oily residue was ground with 50 ml
of diethyl ether. After crystallization, the precipitate
was filtered off and recrystallized from ethanol DMF.
at
9.8 10.3 ppm. The chemical shifts of protons
in the alkyl substituents on C5 and substituents in the
anilide moiety have their usual values. Unlike anilides
XIII XVIII, the 1H NMR spectra of compounds
XIX XXI lack amino group signal, and signals from
the amide and aromatic protons are slightly displaced
downfield. The yields, melting points, and elemental
analyses of compounds VII XXI are given in Table 1,
and Table 2 contains their 1H NMR parameters.
REFERENCES
1. Hosur, M.C., Talawar, M.B., Laddi, U.V., Ben-
nur, R.S., and Bennur, S.C., Indian J. Chem., 1995,
p. 707.
EXPERIMENTAL
1
The H NMR spectra were recorded on a Bruker-
300 spectrometer (300 MHz) using DMSO-d6 as sol-
vent and TMS as internal reference.
2. Eweiss, N.F. and Bahajaj, A.A., J. Heterocycl.
Chem., 1987, vol. 24, p. 1173.
3. Zhang Zi-Yi and Sun Xiao-Wen, Heterocycles, 1998,
3-Alkyl-6-aryl-7H-[1,2,4]triazolo[3,4-b][1,3,4]-
thiadiazine hydrobromides VII XII. A mixture of
10 mmol of 5-alkyl-4-amino-4H-1,2,4-triazole-3-thiol
I VI and 10 mmol of the corresponding substituted
phenacyl bromide in 20 30 ml of ethyl acetate was
heated for 2 3 h under reflux. It was then cooled, and
the colorless precipitate was filtered off and recrystal-
lized from ethanol or ethanol dimethylformamide.
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Tumkevicius, S., Monatsh. Chem., 2001, vol. 132,
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(5-Alkyl-4-amino-4H-1,2,4-triazol-3-ylsulfanyl)-
acetanilides XIII XVIII. A solution of 10 mmol of
2-chloroacetanilide in 20 ml of ethanol was added to
a solution of 10 mmol of 5-alkyl-4-amino-4H-1,2,4-
triazole-3-thiol I VI and 10 mmol of KOH in 40 ml
of aqueous ethanol. The mixture was heated for
30 min under reflux, cooled, and diluted with 50
60 ml of water, and the colorless precipitate was fil-
tered off, washed with water, and recrystallized from
ethanol.
3-Alkyl-6-arylamino-7H-[1,2,4]triazolo[3,4-b]-
[1,3,4]thiadiazines XIXn, XXc, and XXIl. A mixture
of 10 mmol of (5-alkyl-4-amino-4H-1,2,4-triazol-3-yl-
sulfanyl)acetamide XIIIn, XIVc, or XVIIIl and 20
30 ml of POCl3 was heated for 2 3 h under reflux.
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va, E.Yu., Korshunov, S.P., and Zyong Van Tue,
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ko, K.G., and Lozinskii, M.O., Azotistye geterotsikly
i alkaloidy (Nitrogen-Containing Heterocycles and
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RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 39 No. 7 2003
Demchenko
