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SYNTHESIS OF PER‐O‐ACETYL‐β‐D‐GLUCOPYRANOSYL THIOUREAS CONTAINING THIAZOLE RING
Published: 31 October 2009 by MDPI in The 13th International Electronic Conference on Synthetic Organic Chemistry session Symposium on Microwave Assisted Synthesis
Abstract: N‐(2,3,4,6‐tetra‐O‐acetyl‐β‐D‐glucopyranosyl)‐N'‐(thiazol‐2'‐yl)thioureas have been synthesized from corresponding 2,3,4,6‐tetra‐O‐acetyl‐β‐D‐glucopyranosyl isothiocyanate and the substituted derivatives of 2‐aminothiazoles executing in domestic microwave oven. The 1H and 13CNMR spectra of some derivatives of N‐(2,3,4,6‐tetra‐O‐acetyl‐β‐D‐glucopyranosyl)‐N'‐(4'‐arylthiazole‐2'‐ yl)thiourea have been recorded. The magnetic signals in their NMR spectra show the relationships between the structure and positions of the substituted groups. It's also indicated that the substitution in the thiazole ring influenced on the chemical shift of proton on thiourea group. 2‐Iminothiazolidin‐4‐ones have been synthesized from ethyl bromoacetate and substituted N‐(2,3,4,6‐tetra‐O‐acetyl‐β‐Dglucopyranosyl)‐ N'‐(phenylthiazole‐2'‐yl)thioureas. The presence of 2‐iminothiazolidin‐4‐one isomers were confirmed by NMR spectroscopies.