Electrochemically-generated basic species from the reduction of acetonitrile assisted the condensation of carbon disulfide, primary arylmethylamines and chloroacetone to yield the corresponding N-substituted-4-hydroxy-4-methylthiazolidine-2-thione derivatives. In some cases, dehydration reaction led to the N-substituted-4-methylthiazole-2(3H)-thione analogues. The effect of the electrogenerated base amount on the reaction yield was also studied.
FotouhiL., HeraviM. M., FatehiA., and BakhtiariK., Tetrahedron Lett., 2007, 48, 5379.
6.
FerociM., CasadeiM. A., OrsiniM., PalombiL., and InesiA., J. Org. Chem., 2003, 68, 1548.
7.
FerociM., OrsiniM., SotguiG., RossiL., and InesiA., J. Org. Chem., 2005, 70, 7795.
8.
UtleyJ.H. P., and NielsenM. F., Organic electrochemistry, 4th edn, eds. LundH., and HammerichO., Marcel Dekker, New York, 2001, pp. 1227–1257.
9.
WagenknechtJ.H., and BaizerM. M., J. Org. Chem., 1966, 31, 3885.
10.
MatthewsW.S., BaresJ. E., BartmessJ. E., BordwellF. G., CornforthF. J., DruckerG. E., MargolinZ., McCallumR. J., McCollumG. J., and VanierN. R., J. Am. Chem. Soc., 1975, 97, 7006.
11.
MichidaT., and YamaokaY., Chem. Pharmaceut. Bull, 1998, 46, 207.