74598-48-4Relevant articles and documents
Synthesis of 5,6-Dihydro-4H-1,3,5-dithiazines, 2,3-Dihydro-6-thioxo-6H-1,3-thiazine, and 6-Amino-1,3-dithiins
Howes, P.D.,Payne, J.J.,Pianka, M.
, p. 1038 - 1044 (2007/10/02)
Dithiolates (1) or (2), derived from compounds containing an active methylene or a sulphonamido-group, carbon disulphide and sodium or potassium hydroxide, underwent a Mannich reaction with formaldehyde and a primary amine to form 5,6-dihydro-1,3,5-dithiazines (3) or (4).The dithiolate (12), derived from ethyl acetoacetate, cyclised under the above conditions to ethyl 2,3-dihydro-3,4-dimethyl-6-thioxo-6H-1,3-thiazine-5-carboxylate (18).The dithiolates (20), derived from cyanoacetic ester, or (10), derived from acetophenone, interacted with formaldehyde and cyanoacetic esters or with 2-cyanoacrylates to form 6-amino-1,3-dithiins (26) or iminodithians (28).Methyl 6-amino-2--1,3-dithiin-5-carboxylate (26; R1=Et, R2=Me) formed N-acyl derivatives with aliphatic acid chlorides.On oxidation the dithiin (26; R1=Et, R2=Me) contracted to ethyl 2-cyano-2-(4-cyano-1,3-dithiolan-5-ylidene)acetate (31).
