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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

DOI: 10.1039/P19800001038

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 1038 - 1044 (1980)

Update date:2022-08-05

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Authors:

Howes, P.D.Howes, P.D.

Payne, J.J.Payne, J.J.

Pianka, M.Pianka, M.

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Article abstract of DOI:10.1039/P19800001038

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-cyano-1-ethoxycarbonyl)methylene>-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).

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