Abstract
Abstract Five new Δ4-1,2,4-thiadiazolines (TDZ), IIa,b, IIIa,b, and IV, were easily prepared by the reaction of potassium methyl cyanoiminodithiocarbonate (I) with N-chloro compounds of O-alkylisoureas, guanidines, and guanylurethane. 2-Methoxyimidoyl-3-imino-5-methylthio-TDZ (IIa), with a reactive imidoether group, was converted into the 2-carbamoyl-TDZ derivative (V) by treatment with excess dry hydrogen chloride. The reaction of IIa with aliphatic amines gave 2-amidino-TDZ derivatives (IIIc–e) in good yields in the presence of both free amines and amine hydrochlorides (molar ratio, 2:1). The mechanism of this amidination was discussed.
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