REACTIONS OF BENZIMIDAZOLE-2-THIOL
1553
N-tert-Butyl-2-trimethylsilyl-4H-[1,3]thiazino[3,2-a]-
benzimidazole-4-amine (III) was obtained similarly.
133.28, 140.15, 142.28, 145.17. Found, %: С 65.6; Н
6.4; N 11.4. C20H23N3SSi. Calculated, %: С 65.7; Н
6.3; N 11.5.
1
Yield 78%, mp 166°C. Н NMR spectrum, δ, ppm:
3
0.29 s (9Н), 1.17 s (9Н), 1.85 d (1Н, JНН 10.18 Hz),
2-Phenyl-4H-[1,3]thiazino[3,2-a]benzimidazole-
4-ol (VIII). 50 mL of distilled water preheated to 70°C
was added to a solution of 0.0024 mol of compound I
in 50 mL of ethanol under reflux. The resulting mix-
ture was heated at 70°C during 2 min, slowly cooled to
room temperature over 2 h and left at 4°C overnight.
The obtained crystals were filtered off, washed with
3
5.94–5.99 m (1Н), 6.46 d (1Н, JНН 5.09 Hz), 7.24–
7.27 m (2Н), 7.48–7.50 m (1Н), 7.67–7.69 m (1Н). 13С
NMR spectrum, δС, ppm: 2.26, 30.40, 50.02, 62.85,
110.61, 117.35, 120.75, 121.70, 128.19, 129.62, 133.30,
142.53, 145.36. Found, %: С 61.4; Н 7.5; N 11.7.
C17H25N3SSi. Calculated, %: С 61.5; Н 7.6; N 11.6.
1
water, and dried. Yield 90%, mp 240°C. Н NMR
N-Cyclohexyl-2-tert-butyl-4H-[1,3]thiazino[3,2-a]-
benzimidazole-4-amine (IV) was obtained similarly.
3
spectrum, δ, ppm: 6.42 d (1H, JHН 4.4 Hz), 6.65 d. d
3
3
3
(1H, JHН 8.7, JHН 4.4 Hz), 7.04 d (1H, JHН 8.7 Hz),
7.22–7.24 m (2H), 7.46–7.70 m (7H). 13С NMR spec-
trum, δС, ppm: 73.47, 110.88, 116.60, 117.51, 121.45,
122.40, 126.08, 128.86, 129.40, 130.12, 133.30,
136.05, 142.74, 143.77. Found, %: С 68.5; Н 4.4; N
9.9. C16H12N2OS. Calculated, %: С 68.6; Н 4.3; N 10.0.
1
Yield 65%, mp 128°C. Н NMR spectrum, δ, ppm:
0.76–1.65 m (10Н), 1.31 s (9Н), 2.40 br.s (1Н), 2.61
3
br.s (1Н), 5.95 d (1Н, JНН 5.09 Hz), 6.10 m (1Н),
7.10–7.18 m (2Н), 7.47–7.50 m (1Н), 7.61–7.64 m
(1Н). Found, %: С 70.3; Н 7.9; N 12.4. C20H27N3S.
Calculated, %: С 70.3; Н 8.0; N 12.3.
2-tert-Butyl-4H-[1,3]thiazino[3,2-a]benzimidazole-
4-ol (IX) was obtained similarly. Yield 80%, mp 210°C.
1Н NMR spectrum, δ, ppm: 1.36 s (9H), 6.01 d (1H,
3JHН 4.4 Hz), 6.40–6.50 m (1H), 6.78 d (1H, 3JHН 7.3 Hz),
7.14–7.23 m (2H), 7.47–7.55 m (1H), 7.59–7.67 m
(1H). 13С NMR spectrum, δС, ppm: 29.27, 36.57,
73.12, 110.64, 112.74, 117.30, 121.10, 122.15, 133.25,
141.07, 142.80, 144.55. Found, %: С 64.5; Н 6.1; N
10.8. C14H16N2OS. Calculated, % : С 64.6; Н 6.2; N 10.8.
N-Cyclohexyl-2-trimethylsilyl-4H-[1,3]thiazino-
[3,2-a]benzimidazole-4-amine (V) was obtained
1
similarly. Yield 70%, mp 130°C. Н NMR spectrum,
δ, ppm: 0.76–1.65 m (10Н), 0.30 s (9Н), 2.39 br.s
3
(1Н), 2.70 br.s (1Н), 6.13 m (1Н), 6.21 d (1Н, JНН
4.36 Hz), 7.10–7.19 m (2Н), 7.47–7.50 m (1Н), 7.62–
7.65 m (1Н). 13С NMR spectrum, δС, ppm: 1.62, 23.86,
24.59, 24.88, 25.32, 30.22, 30.73, 31.19, 32.57, 109.30,
120.35, 121.80, 168.00. Found, %: С 63.7; Н 7.7; N
11.7. C19H27N3SSi. Calculated, %: С 63.8; Н 7.6; N 11.8.
ACKNOWLEDGMENTS
This work was financially supported by the
Government of the Russian Federation (project
no. 14.B25.310013).
N-Benzyl-2-tert-butyl-4H-[1,3]thiazino[3,2-a]benz-
imidazole-4-amine (VI) was obtained similarly. Yield
1
70%, mp 148°C. Н NMR spectrum, δ, ppm: 1.25 s
(9Н), 2.39 br.s (1Н), 3.30–3.33 m (1Н), 3.50–3.53 m
(1Н), 3.57 br.s (1Н), 5.90 d (1Н, 3JНН 5.09 Hz), 6.22 m
(1Н), 7.10–7.21 m (7Н), 7.49–7.51 m (1Н), 7.69–7.71
m (1Н). 13С NMR spectrum, δС, ppm: 29.19, 36.58,
45.47, 65.33, 110.43, 112.45, 117.35, 121.02, 121.90,
126.20, 127.35, 127.60, 133.25, 140.23, 141.80, 142.85,
145.73. Found, %: С 72.8; Н 6.9; N 12.1. C21H23N3S.
Calculated, %: С 72.8; Н 6.8; N 12.0.
REFERENCES
1. Stadnichuk, M.D., Khramchikhin, A.V., Piterskaya, Yu.L.,
and Suvorova, I.V., Russ. J. Gen. Chem., 1999, vol. 69,
no. 4, p. 593.
2. Karpov, M.V., Khramchikhin, A.V., and Stadnichuk, M.D.,
Russ. J. Gen. Chem., 2005, vol. 75, no. 3, p. 487. DOI:
10.1007/s11176-005-0257-3.
3. Shimizu, M., Hachiya, I., and Mizota, I., Chem. Comm.,
N-Benzyl-2-trimethylsilyl-4H-[1,3]thiazino[3,2-a]-
benzimidazole-4-amine (VII) was obtained similarly.
2009, p. 874. DOI: 10.1039/B814930E.
4. Karpov, M.V., Eremin, A.V., Fisher, A.I., Belyaev, A.N.,
and Stadnichuk, M.D., Russ. J. Gen. Chem., 2011,
vol. 81, no. 1, p. 128. DOI: 10.1134/S1070363211010208.
5. Racharlawar, S.S., Shankar, D., Karkhelikar, M.V.,
Sridhar, B., and Likhar, P.R., J. Organomet. Chem.,
2014, no. 757, p. 14. DOI: 10.1016/j.jorganchem.-
2014.01.028.
1
Yield 70%, mp 158°C. Н NMR spectrum, δ, ppm:
0.25 s (9Н), 3.27–3.34 m (1Н), 3.49–3.65 m (2Н), 6.15
d (1Н, 3JНН 4.36 Hz), 6.23–6.26 m (1Н), 7.11–7.19 m
(7Н), 7.49–7.51 m (1Н), 7.69–7.72 m (1Н). 13С NMR
spectrum, δС, ppm: 2.23, 45.55, 65.82, 110.48, 117.35,
121.04, 121.99, 124.90, 126.22, 127.40, 127.60, 130.53,
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 84 No. 8 2014