Novel triazinium-imidothioate zwitterions: intermediates in the reaction of [1,3,4]thiadiazolo[2,3-d][1,2,4]triazolo[1,5-a][1,3,5]triazinium cations with amines

摘要: Abstract Starting with bis([1,3,4]thiadiazolo)[1,3,5]triazinium halides 1 , a novel class of heterocyclic compounds, the [1,3,4]thiadiazolo[2,3-d][1,2,4]triazolo[1,5-a][1,3,5]triazinium 5 were prepared. The reaction between and primary or secondary amines 6 yielded highly substituted guanidines 8 fused tricyclic bis([1,2,4]triazolo)[1,5-a:1′,5′-d][1,3,5]triazinium 9 . formation reactive triazinium-imidothioate zwitterions 7 which is controlled by influence negative hyperconjugation, was proven NMR data X-ray structure 7c subsequent ring-closure/ring-opening steps can be understood in terms an S N (ANRORC) process accompanied intramolecular proton-transfer reactions. reacted EtI forming cationic derivatives 10 hydrolyzed at pH 6–7 to give ethanethioamides 11