複素環化合物のチオシアノ化反応に関する研究(第4報)Imidazo[2,1-b]-1,3,4-thiadiazoleおよびThiazolo[3,2-b]-s-triazole誘導体の合成とそれらのチオシアノ化およびブロム化反応

概要

論文の詳細を見る
6-Methylimidazo [2,1-b]-1,3,4-thiadiazoles (III_<1,2>) were prepared in a good yield by treatment of 2-amino-1,3,4-thiadiazoles (I_<1,2>) with bromoacetone in H_2O for 1 hr at 95-100°. Six kinds of 6-phenylimidazo [2,1-b]-1,3,4-thiadiazoles (VI_<1-6>) were obtained in a good yield by treatment of 2-imino-3-phenacyl-△^4-1,3,4-thiadiazoles (V_<1-6>) with polyphosphoric acid (PPA) for 2 hr at 135-140°. Thiocyanation of III_<1,2> and VI_<1-6> was carried out by the bromine method and the urea method, and the corresponding 5-thiocyanato derivatives (VII_<1-8>) were obtained in a good yield. The preparation of 5-methylthiazolo [3,2-b]-s-triazoles (XII_<1,2>) was effected in a good yield by treatment of 3-(2-propynylthio)-1,2,4-triazole hydrobromides (X_<1,2>) with two equivalents of sodium ethoxide in ethanol, and XII_2 was also obtained by treatment of 3-acetonylthio-5-methyl-1,2,4-triazole (XII_2') with PPA for 2 hr at 140-145°. Six kinds of 5-phenylthiazolo [3,2-b]-s-triazoles (XIV_<1-6>) were prepared in a good yield by treatment of 3-phenacylthio-1,2,4-triazoles (XIII_<1-6>) with PPA for 2 hr at 150-160°. Thiocyanation of XII and XIV did not proceed, whereas the corresponding 6-bromo derivatives (XV_<1-8>) were obtained in a good yield by bromination of XII_<1,8> and XIV_<1-6>.
公益社団法人日本薬学会の論文
1972-08-25