Repozytorium publikacji - Politechnika Gdańska

In our recent project we focused on reactivity of2,2-dimethyl-4,6-dioxane-1,3-dione carbamoilo- and thiocarbamoylo- derivatives as a ketenesource. Meldrum`s acid derivatives after thermal decomposition gives substituted keteneswith stoichiometric yield, that can be trapped with various spectrum of nucleophiles likealcohols, thiols, amine, imines etc. In case of5-[3-(dimethylamino)-sulfanyl-propyliden]-2,2-dimethyl-1,3-dioxane-4,6-dione after heatingin the presence of various amines we isolated main unexpected product2,2-dimethyl-5-[1,3-thiazolidin-2-ylidene)-1,3-dioxane-4,6-dione. The compound that weobtained, indicates that in this reaction instead of thermal decomposition to ketene, occurssubstitution of dimethylamine by sulfanyl group, resulting in closure of 1,3-thiazolidin ring.We are dealing here with unusual case in which secondary amine in basic conditions works asa leaving group. This exclude compound as a ketene source, however phenomenon is ancurious case of irregular behavior of secondary amine group.

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