<原報>Thiazolidine 誘導体の研究〔IX〕 : 3-Thiocarbamoyl-2-iminothiazolidine, 3-Thiocarbamoyl-2-oxothiazolidine, 2-(Alkylthiocarbamoylimino)-3-methylthiazolidines の合成
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As shown in Chart I, when Dithiobiuret [I] was treated in ab. ethanol with one equivalent of 1,2-Dibromoethane [II], condensation product was obtained for which five possible structures [III]-[VII] might be conceivable. However, this condensation product was thought to be structure [III] or [IV] by Elemental analysis, Mass spectrum (MS), Infrared spectrum (IR) and no chelate formation with Cu^<++> ion. The same reaction in H_2O gave another main product having a sharp absorption band around 1680(cm)^<-1> indicative carbonyl group in IR (KBr-disk). It is suggested that the latter product originate from the hydrolysis of 3-Carbamoyl-2-iminothiazolidine [III], because acid hydrolysis of the former product lead to the formation of carbonyl compound [VIII]. The identity of the product is confirmed by Elemental analysis, Urtraviolet absorption spectrum (UV), MS and IR. On the other hand, NMR spectra (DMSO-d_6) showed A_2 X_2 triplet-triplet pattern at first due to two methylenes between the nitrogen and the sulfur atoms. They changed into the group of new signals centered at about δ 3.74 with time. [III] heated in H_2O about 1 hr or in benzene about several hours was decomposed 2-Amino-2-thiazoline and H. SCN, these were comfirmed by IR and its picrate. Now structure of [III] and [VIII] were decided by the above reaction. As another samples, reaction of 3-Methyl-2-iminothiazolidine [IX] with Alkyl isothiocyanate [Xa-c] performed to synthesize 2-(Alkylthiocarbamoylimino)-3-methylthiazolidines having 2-Alkylthiocarbamoyl radical in 2-iminothiazolidine ring as shown in Chart [III].
- 共立薬科大学の論文
- 1973-12-25
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