Reactivity of the Biheterocyclic Betaine with the para-Substituted Phenacyl Bromides for the Ring Transformation Reaction

摘要

7-Dithiocarboxy-3-phenyl-5,6-dihydro imidazo[2,1-b]thiazolium-betaine (2) was prepared by treatment of 3-phenyl-5,6-dihydro imidazo[2,1-b]thiazole (1) with carbon disulfide in acetone at room temperature. On the reaction of 2 with para-substituted phenacyl bromides (4) having the electron withdrawing property by virtue of (+) resonance (R) < (-) inductive (グ) or (-) resonance (R), (-) inductive (グ) effect, ring transformation product p-substituted-2-[2-[7-(p-substituted benzoyl)-5-thioxo-2,3-dihydro-1H-imidazo[1,2-c] thiazol-1-yl]-2-phenylvinylthio] acetophenone (6) was obtained; however, when R is electron donating grops with (+) resonance (R) > (-) inductive (グ) effect the quarternary ammonium salt 7-(p-substituted phenyl) carbonyl methyl-3-phenyl-5,6-dihydro imidazo [2,1-b] thiazolium bromide (8) is formed. The reaction of 2 with unsubstituted-phenacyl bromide (R = H), on the other hand, gives 6a and 8a to the similar ratio, respectively.