title: Behavior of free sugar thiosemicarbazones toward heterocyclization reactions.
abstract: 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.
authors.affiliation: CIHIDECAR (CONICET)-Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Argentina.
authors.forename: M A
authors.initials: MA
authors.lastname: Alho
authors.forename: N B
authors.initials: NB
authors.lastname: D'Accorso
mesh_terms: D000107:Acetylation; D000995:Antitubercular Agents / Q000737:chemistry; D002247:Carbon Isotopes; D006571:Heterocyclic Compounds / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D011522:Protons; D013237:Stereoisomerism; D013882:Thiosemicarbazones / Q000737:chemistry*
chemical_list: D000995:Antitubercular Agents; D002247:Carbon Isotopes; D006571:Heterocyclic Compounds; D011522:Protons; D013882:Thiosemicarbazones