REACTION OF tert-BUTYLIMINE OF PHENYLPROPIOLIC ALDEHYDE
767
regioisomers is possible, which is due to the position
of the phenyl group in the original imidazole-2-tione.
C24H18N2OS. Calculated, %: С 75.4; Н 4.7; N 7.3; O
4.2; S 8.4.
2,7-Diphenyl-5H-imidazolo[2,1-b][1,3]thiazin-5-
ol (IVc) was prepared analogously. The yield 50%, mp
195°С (dec.). The H NMR spectrum (400 MHz,
It has earlier been shown on the ground of DFT-
calculations that in the reaction of 1-aza-1, 3-enynes
with adenine-8-tiol a single regioisomer forms from
two possible: the one whose formation in the course of
the reaction meets minimal steric hindrances [4].
Because of that, the structures of 2,7-diphenylimidazo-
[2,1-b][1,3]tiazine-5-tert-butylamine and 2,7-diphenyl-
5H-imidazo[2,1-b][2,3]thiazin-5-ol, respectively, should
be attributed to compounds IIIc and IVc.
1
DMSO-d6), δ, ppm: 7.94 s (1H), 7.80 d (2Н, J 7.2 Hz),
7.70–7.59 m (2H), 7.57–7.45 m (3H), 7.39 t (2Н, J
7.7 Hz), 7.25 d.d (2Н, J 11.6, 5.5 Hz), 6.44 d.t (2Н, J
13.1, 4.3 Hz). The 13C NMR spectrum (101 MHz,
DMSO-d6), δС, ppm: 130.14, 129.64, 129.08, 127.29,
126.63, 124.81, 116.80, 115.63, 75.83. Found, %: С
70.0; Н 4.9; N 9.3. C18H14N2OS. Calculated, %: С
70.6; Н 4.6; N 9.1; O 5.2; S 10.5.
1H NMR spectra were registered on a spectrometer
Bruker 400 [400 (1H), 100 MHz (13С)], solvent
DMSO-d6. The elemental analysis was carried out
using the CHN-analyzer Perkin-Elmer 2400. Melting
points were determined on the Koeffler heating block.
2,3-Dimethyl-7-phenyl-5H-imidazo[2,1-b][1,3]-
thiazin-5-ol (IVa). 4,5-Dimethylimidazole-2-thione
(0.005 mol) was added to the solution of 5 mmol of
tert-butylimine of phenylpropiolic aldehyde in 25 mL
of methanol at stirring. In 30 min the reaction mixture
was heated to 60°С and water (3 mL) was added. After
cooling the residue was filtered off and recrystallized
from aqueous methanol. The yield is 70%, colorless
crystals, mp 215°C (dec.). 1H NMR spectrum
(400 MHz, DMSO-d6), δ, ppm: 7.57 d (2H, J 6.3 Hz),
7.51–7.32 m (3H), 6.66 d (1H, J 8.8 Hz), 6.26 d (1H, J
4.9 Hz), 6.16 d.d (1H, J 8.8, 4.9 Hz), 2.27 s (3H), 2.09
(3H). 13C NMR spectrum (101 MHz, DMSO-d6), δС,
ppm: 136.84, 133.97, 132.44, 131.35, 129.94, 129.53,
126.53, 122.80, 116.17, 73.31, 12.82, 8.73. Found, %:
С 64.8; Н 5.9; N 10.3. C14H14N2OS. Calculated, %: С
65.1; Н 5.5; N 10.8; O 6.2; S 12.4.
ACKNOWLEDGMENTS
The work was carried out with the financial support
of the Government of the Russian Federation in the
framework of the state support of scientific research
(project no. 14.B25.310013).
REFERENCES
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no. 1, p. 128. DOI: 10.1134/S1070363211010208.
3. Karpov, M.V., Garabadzhiu, A.V., Davidovich, P.B.,
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2,3,7-Triphenyl-5Н-imidazolo[2,1-b][1,3]thiazin-
5-ol (IVb) was prepared analogously. Yield 65%, mp
228°С. The 1H NMR spectrum (400 MHz, DMSO-d6),
δ, ppm: 7.68–7.59 m (2H), 7.58–7.44 m (8H), 7.39 d
(2H, J 7.3 Hz), 7.20 d.t (3H, J 24.2, 7.1 Hz), 6.81 d
(1H, J 9.0 Hz), 6.49 d (1H, J 5.4 Hz), 6.04 d.d (1H, J
8.9, 5.5 Hz). The 13C NMR spectrum (101 MHz,
DMSO-d6), δС, ppm: 138.36, 136.46, 131.85, 131.48,
130.15, 129.62, 129.37, 128.64, 128.26, 127.12,
126.75, 116.87, 73.20.Found, %: С 74.9; Н 5.0; N 7.5.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 85 No. 3 2015