Proton-Induced Ring Transformation of 2-Imino-3-thiocarbamoyl-4-thiazoline

概要

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The reaction of 4-methyl-2-methylaminothiazole (1a) and N, N-dimethylthiocarbamoyl chloride (2a) in a nonpolar solvent gave four products, 4-methyl-2-methylimino-3-(N, N-dimethylthiocarbamoyl)-4-thiazoline (3a), 1,1,3-trimethyl-3-(4-methyl-2-thiazolyl) thiourea (4a), 4-methyl-2-methylamino-5-(N, N-dimethylthiocarbamoyl) thiazole (5a), and 1,1-dimethyl-3-(3,4-dimethyl-2 (3H)-thiazolyidene) thiourea (6a). The 2-phenylamino analog of 1a (1b) gave the corresponding phenyl compounds (3b-6b) on reaction with 2a. Compounds 3a and 3b were isomerized to 6a and 6b, respectively, in dioxane with a drop of hydrochloric acid. From studies with ^<15>N-labeled compounds, a mechanism is proposed involving a proton-induced ring transformation of 3,via protonation of 3,cleavage of the 3,4-bond, and bond formation between the imino nitrogen and 4-carbon atoms. A similar ring transformation took place with 3-N, N-dimethylcarbamoyl analogs of 3a and 3b, but not with a thiazolidine analog of 3b.
公益社団法人日本薬学会の論文
1984-11-25