Behavior of free sugar thiosemicarbazones toward heterocyclization reactions Original Research Article

The heterocyclization reaction on thiosemicarbazones having the d-galacto, d-gluco and d-manno configuration was studied. We applied two different acetylating conditions, and the reaction products obtained were identified, spectroscopically characterized, and conformationally analyzed. Using experimental data, we discuss a possible mechanistic pathway for heterocyclization and evaluate the influence of several factors, including starting material configuration, pH of reaction medium, and reaction time.