Behavior of free sugar thiosemicarbazones toward heterocyclization reactions.
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.
Alho
M A
MA
CIHIDECAR (CONICET)-Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Argentina.
D'Accorso
N B
NB
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*
D000995:Antitubercular Agents; D002247:Carbon Isotopes; D006571:Heterocyclic Compounds; D011522:Protons; D013882:Thiosemicarbazones