Studies of heterocyclic compounds. VII. The reactions of 5,6-dihydrothiazolo(2,3-b)thiazolium salts with carbanions.

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The reaction of 5, 6-dihydrothiazolo [2, 3-b] thiazolium salt (1) with the sodium salt of acetylacetone furnished 3-(2-thiazolyl)-acetylacetone (2) with elimination of thiirane and 2-acetonylidene-3-acetylthioethyl-4-thiazoline (3). The reaction of 1 with the sodium salt of ethyl acetoacetate gave ethyl 2-(2-thiazolyl)-acetoacetate (12) and the reaction of 1 with the sodium salts of ethyl cyanoacetate and malononitrile gave 2-substituted thiazole (16), 3-(2-mercaptoethyl)-thiazoline (17) and/or its disulfide (18). The tautomeric forms of 2, 12 and 16 are discussed on the basis of the structures of the methylated products and of their spectrophotometric properties.

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