Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Studies on Organic Sulfur Compounds. IX. The Reaction of Ethoxycarbonyl Isothiocyanate with 4, 5-Substituted 2-Aminothiazoles
長野 光男松井 孝飛塚 淳三小山田 浩三
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1972 年 20 巻 12 号 p. 2626-2633

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The Reactions of ethoxycarbonyl isothiocyanate (23) with 4, 5-substituted 2-amino-thiazoles (24) afforded thiazolo [3, 2-a]-s-triazine-4-thio-2-ones (25), N-alkoxycarbonyl-N'-(2-thiazolyl)thioureas (26), alkyl-N-(2-thiazolyl)carbamates (27), ethyl-N-ethoxycarbonyl thiocarbamate (28) and thiocyanic acid (7). However, in the cases of the amines whose pKa values were smaller than that of 2-aminothiazole (24-a) or the amines which had some substituents on the 4-position of 24, the corresponding cyclic compounds (25) could not be obtained. A series of these phenomena was discussed in connection with basicities of 2-aminothiazoles (24) and the steric hindrance of the substituents on the 4-position of 24.
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