2774
SINENKO et al.
2-(1,3-Dioxolan-2-yl)-4-[(methylsulfanyl)methyl]-
from 2-(1,3-dioxolan-2-yl)-4-[(methylsulfanyl)methyl]-
1,3-thiazole (26b) was prepared similarly to com-
pound 23b from 2-(1,3-dioxolan-2-yl)-4-(chloro-
methyl)-1,3-thiazole 22.
1,3-thiazole 26b.
REFERENCES
5-[(Dimethylamino)methyl]-1,3-thiazole-2-carbal-
dehyde (27a). To a solution of 0.005 mol of compound
23a in 15 mL of tetrahydrofuran was added a solution
of 0.006 mol of conc. sulfuric acid in 15 mL of water.
The mixture was refluxed for 8 h, and then cooled to
20°C. A solution of 0.012 mol of sodium hydroxide in
10 mL of water was added. The resulting mixture was
extracted with ethyl acetate. The organic layer was
separated, washed with water, and dried with sodium
sulfate. The solvent was removed at a reduced pressure
and the residue was chromatographed.
1. Chalopin, T., Alvarez Dorta, D., Sivignon, A., Caudan, M.,
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5-[(Methylsulfanyl)methyl]-1,3-thiazole-2-carbal-
dehyde (27b). To a solution of 0.01 mol of compound
23b in 15 mL of acetonitrile and 6 mL of water was
added 0.001 mol of p-toluenesulfonic acid. The
mixture was refluxed for 12 h. After cooling to 20°C,
30 mL of ethyl acetate was added. The organic layer
was separated, washed with a saturated aqueous
solution of sodium bicarbonate, and dried with sodium
sulfate. The solvent was removed at a reduced
pressure, the residue was chromatographed.
4. Murphy, J.M., Armijo, Aman L., Nomme, J., Lee, C.H.,
Smith, Q.A., Li, Z., Campbell, D.O., Liao, H.-I.,
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p. 3179. doi 10.1021/acschembio.6b00609
2-[(Dimethylamino)methyl]-1,3-thiazole-5-carbal-
dehyde (28a) was prepared similarly to compound 27a
from 1-[5-(1,3-dioxolan-2-yl)-1,3-thiazol-2-yl]-N,N-
dimethylmethanamine 24a.
6. Sznaidman, M.L., Haffner, C.D., Maloney, P.R.,
Fivush, A., Chao, E., Goreham, D., Sierra, M.L.,
LeGrumelec, C., Xu, H.E., Montana, V.G., Lambert, M.H.,
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10.1016/S0960-894X(03)00207-5
2-[(Methylsulfanyl)methyl]-1,3-thiazole-5-carbal-
dehyde (28b) was prepared similarly to compound 27b
from 5-(1,3-dioxolan-2-yl)-2-[(methylsulphanyl)methyl]-
1,3-thiazole 24b.
7. Wei, Z. and Kozikowski, A.P., J. Org. Chem., 2003,
2-[(Dimethylamino)methyl]-1,3-thiazole-4-carbal-
dehyde (29a) was prepared similarly to compound 27a
from 1-[4-(1,3-dioxolan-2-yl)-1,3-thiazol-2-yl]-N,N-di-
methylmethanamine 25a.
vol. 68, p. 9116. doi 10.1021/jo035140g
8. Louvel, J., Guo, D., Soethoudt, M., Mocking, T.,
Lenselink, E.B., Mulder-Krieger, T., Heitman, L.H., and
Ijzerman, A.P., Eur. J. Med. Chem., 2015, vol. 101,
p. 681. doi 10.1016/j.ejmech.2015. 07.023
2-[(Methylsulfanyl)methyl]-1,3-thiazole-4-carbal-
dehyde (29b) was prepared similarly to compound 27b
from 4-(1,3-dioxolan-2-yl)-2-[(methylsulfanyl)methyl]-
1,3-thiazole 25b.
9. Brunschweiger, A., Koch, P., Schlenk, M., Rafehi, M.,
Radjainia, H., Küppers, P., Hinz, S., Pineda, F., Wiese, M.,
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10.1016/j.bmc.2016.09.003
4-[(Dimethylamino)methyl]-1,3-thiazole-2-carbal-
dehyde (30a) was prepared similarly to compound 27a
from 1-[2-(1,3-dioxolan-2-yl)-1,3-thiazol-4-yl]-N,N-di-
methylmethanamine 26a.
10. Siegrist, R., Pozzi, D., Jacob, G., Torrisi, C., Colas, K.,
Braibant, B., Mawet, J., Pfeifer, T., De Kanter, R.,
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acs.jmedchem.6b01356
4-[(Methylsulfanyl)methyl]-1,3-thiazole-2-carbal-
dehyde (30b) was prepared similarly to compound 27b
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 87 No. 12 2017