Synthesis and characterization of new aromatic aldehyde/ketone 4-(beta-D-glucopyranosyl)thiosemicarbazones.
A series of 22 aromatic aldehyde/ketone 4-(beta-D-glucopyranosyl)thiosemicarbazones have been synthesized by condensation of 4-(per-O-acetylated-beta-D-glucopyranosyl)thiosemicarbazide with an aldehyde or a ketone, and then, deacetylation of the resulting product. The compounds were fully characterized by spectroscopic techniques, elemental analysis, and for two derivatives by X-ray analysis. The data indicate the beta configuration, and the E configuration pertaining to the stereochemistry of the C=N bond. However, a partial conversion of the E-form into the Z-form is possible in solution after several hours.
Tenchiu Deleanu
Alia-Cristina
AC
National Hellenic Research Foundation, Institute of Organic and Pharmaceutical Chemistry, Vas. Constantinou 48, 116 35 Athens, Greece.
Kostas
Ioannis D
ID
Kovala-Demertzi
Dimitra
D
Terzis
Aris
A
D000447:Aldehydes / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013882:Thiosemicarbazones / Q000138:chemical synthesis* / Q000737:chemistry
D000447:Aldehydes; D007659:Ketones; D013882:Thiosemicarbazones