Syntheses with ketones,sulfur, and ammonia or amines at room temperature

A large number of preparatively interesting compounds have become readily available by the simultaneous action of sulfur and ammonia or amines on ketones. Direct syntheses of Δ³-thiazolines, Δ³-imidazoline-5-thiones, 5,6-dihydro-4H-1,4-thiazines, and the 1,2,3,4,5,6-hexathiocane system from ketones, sulfur, and ammonia or amines, and further possibilities for the synthesis of these heterocyclic systems have been proposed. Other heterocycles containing N or N and S (thiazoles, thiophenes, thiazolidines, tetrahydrothiazolo2,3-c]-1,4-thiazines, thiomorpholines, 4-amino-2H-imidazoles, etc.) are readily obtainable by further reactions of these compounds. Hydrolysis of the Δ³-thiazolines yields α-mercapto ketones, which are the starting materials for other syntheses. Most of the syntheses described proceed at room temperature and at normal pressure.