Additionsreaktion von 1,3‐Thiazol‐5(4H)‐thionen und inaminen; Bildung von Thioamiden und Thioketonen

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Abstract
Addition Reaction of 1,3‐Thiazole‐5(4H)‐thiones and Ynamines; Formation of Thioamides and ThioketonesYnamines and 1,3‐thiazole‐5(4H)‐thiones of type 1 undergo an addition reaction on heating in toluene yielding mainly α,β‐unsaturated 2‐(4,5‐dihydro‐1,3‐thiazol‐5‐yliden)thioamides of type 7 (Scheme 2 and Table). In some cases, 1‐diethylamino‐1‐(4,5‐dihydro‐1,3‐thiazol‐5‐yliden)‐2‐alkanethiones 8 have been isolated as minor products. In analogy to other reactions of ynamines with CO and CS bonds, a [2 + 2] cycloaddition to thiete intermediates, followed by an electrocyclic ring opening is suggested as reaction mechanism.