Reaction of N,N'‐dimethyl‐2‐nitroethene‐1, 1‐diamine with α,ß‐unsaturated acyl isothiocyanates: Preparation of 1,3‐thiazin‐4‐one and 4‐nitro‐1,2‐thiazol‐5(2H)‐imine derivatives

The reaction of N,N-dimethyl-2-nitroethene-1,1-diamine (8) with alpha,beta-unsaturated acyl isothiocyanates 9 affords 3,3-diamino-2-nitroacrylthioamides 10 (Scheme 2) in moderate-to-good yields. Cyclization of 10 under acidic conditions gives 1,3-thiazin-4-one derivatives of type 11. Oxidative cyclization of 10 with diethyl azodicarboxylate leads to 4-nitro-1,2-thiazol-5(2H)-imlne derivatives 12.

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