2-Alkylthio-および2-Ethoxy-6-amino-4H-,3,5-thiadiazin4-imineの合成と反応

抄録

It was clarified that 2-alkylthio-6-amino-4 H-1, 3, 5-thiadiazin-4-imine [4] iodide was obtained by reaction of 4, 6-diamino-2 H-1, 3, 5-thiadiazine-2-thione [1] with alkyl iodide. Compound [4] was unstable and its free base was immediately rearranged into 4-amino-6alkylthio-1, 3, 5-triazine-2-thiol [2]. In boiling water, hydroiodide of compound [4] was hydrolyzed to form 6-amino-4-mercapto-1, 3, 5-triazin-2(1H)-one [6] and amidinothiourea [7]. When hydroiodide of [4] was treated with alkyl iodide in the pres ence of alkali, N-(N²-cyanoamidino)carbonimidodithioate [8] was formed. Hydroiodide of [4] was reacted with amines at room temperature to give 4, 6-diamino-1, 3, 5-triazine-2(1H)-thiones [3]. The reactivities of 2-ethoxy-6-amino-4 H-1, 3, 5-thiadiazin-4-imine [5] prepared by ring closure of O-ethyl N-(N²-cyanoamidino)carbonimidothioate [9] were also investigated.