AZINES AND AZOLES: CXXII.
145
EXPERIMENTAL
primary amine, and 15 ml of DMF was refluxed until
reaction completion (1 2 h, TLC control). Excess
DMF was removed in a vacuum ( 10 20 mm Hg).
The residue was recrystallized from ethanol or
butan-1-ol.
The UV spectra in 96.5% ethanol were obtained
on a Shimadzu UV-mini spectrophotometer. The 1H
and 13C NMR spectra in DMSO-d were recorded
6
on a Bruker AM-500 spectrometer (500 and 125 MHz,
respectively). The IR spectra in KBr were taken on an
FSM-1201 Fourier spectrometer. The reaction prog-
ress and the purity of products were controlled by
TLC on Sorbfil plates. Quantum-chemical calculations
were performed by the semiempirical PM3 method
with the GAMESS program package [16].
c. A solution of 1 g of 4-hydroxy-5-[1-alkyl(aryl)-
iminoethyl]-3,6-dihydro-2H-1,3-thiazine-2,6-dione
IIa IIc in 15 ml of DMF was refluxed until reaction
completion (TLC control). The solvent was removed
in a vacuum ( 10 20 mm Hg). The residue was re-
crystallized from ethanol or butan-1-ol.
ACKNOWLEDGMENTS
5
-Acetyl-4-hydroxy-2H-1,3-thiazine-2,6(3H)-
dione (Ia) was prepared as described in [7]. Acetic
anhydride, 45 ml, was added to a solution of 21 g of
malonic acid in 100 ml of acetic acid. The solution
was stirred for 15 min at 20 25 C, after which 19 g of
KSCN was added in one portion, and stirring was
continued for 1 h at 18 25 C. The transparent yellow
solution was left to stand for 48 h at 20 C. The re-
action mixture crystallized and was diluted with
The work was financially supported by the Prog-
ram for Support of Basic Research in Natural and
Exact Sciences of the Ministry of Education of the
Russian Federation (project no. E02-5.0-384, 2003
2
004).
REFERENCES
3
00 ml of water, filtered off, dried in air, and recrys-
1
2
. Kvasha, V.V., Fedorova, E.V., Studentsov, E.P.,
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2
1
98 200 C.
-Hydroxy-5-[1-alkyl(aryl)iminoethyl]-3,6-di-
hydro-2H-1,3-thiazine-2,6-diones IIa IIs (Tables 1
. Mironova, G.A., Kuklin, V.N., Kirilova, E.N., and
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4
4). A mixture of 1 g of 5-acyl-4-hydroxy-1,3-thiazine-
2
,6-dione Ia Ic and 5.5 mmol of primary amine was
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already within 10 min. After cooling, the crystals
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in air. Pure compounds not requiring recrystallization
were obtained almost always. When required, the
products may be recrystallized from ethanol, propan-
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4
. Ryabukhin, Yu.I., Korzhavina, O.B., and Suzda-
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6
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and 10 15 ml of primary amine was refluxed until re-
action completion (15 60 min, TLC control). Excess
amine was removed in a vacuum ( 10 20 mm Hg).
The residue was recrystallized from ethanol or butan-
7
. Yuskovets, V.N., Moskvin, A.V., and Ivin, B.A., Zh.
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1
-ol.
9
. Gunar, V.I. and Zav’yalov, S.I., Dokl. Akad. Nauk
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With aliphatic primary amines, the residue was
poured with 20 ml of 0.5 N aqueous NaOH, the mix-
ture was stirred for 15 min at 18 25 C, and undis-
silved 1,3-disubstituted urea was filtered off. The
filtrate was neutralized with HCl, the uracil that pre-
cipitated was filtered off, washed with water, and re-
crystallized from ethanol or butan-1-ol.
1
0. Kato, T., Chiba, T., Shimuzu, T., and Takahashi, H.,
Chem. Pharm. Bull., 1981, vol. 29, no. 3, p. 862.
11. Singh, H., Singh, P., Aggarwal, P., and Kumar, S.,
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1
2. Findeisen, K. and Goerdeler, J., Methoden der orga-
nischen Chemie (Houben-Weyl), E4: Kohlensaure
b. A mixture of 1 g of thiazine Ia Ic, 5.5 mmol of
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 75 No. 1 2005