The formation of thiazolidinethiones 3 and/or imidazolidinedithiones 5 from cyanothioformanilides and aryl isothiocyanates is found to be dependent upon the type of bases used, reaction temperature and the nature and position of substituents on cyanothioformanilides. Examples are presented.
oxide (7). Diether dioxide 5 was converted to the dibromide 6 by using the procedure described for 2. The crude product, isolated in 94% yield, was used without purification. The cyclization of 6 to form 7 was carried out in a manner analogous to the preparation of 3, except the dibromide-bis (phenol) solution did not contain (CH2)40. Chromatographic purification was accomplished by eluting the product from the silica gel column with 0-10% EtOH in EtOAc. The yield from 225 mg of 6 was 59 mg (23%) of light yellow solid, which was the monohydrate of 7: mp 160-290 °C (gradual decomposition);
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