tailieunhanh - Synthesis of some derivatives of n-(2,3,4,6-tetra-o-acetyl-õ-d-glucopyranosyl)-n’-(benzothiazole-2’-yl) thioureas

Some compounds of N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-N -(benzothiazole-2 - yl)thioureas have been synthesized from corresponding 2,3,4,6-tetra-O-acetyl- -Dglucopyranosyl isothiocyanate and the substituted derivatives of 2-aminobenzothiazoles executing in home microwave oven. Their spectroscopic properties have been recorded and the relationships between their structures and spectral properties (IR, 1 H- and 13C-NMR) have been discussed. | Journal of Chemistry, Vol. 47 (5), P. 603 - 607, 2009 SYNTHESIS OF SOME DERIVATIVES OF N-(2,3,4,6-TETRA-OACETYL-β-D-GLUCOPYRANOSYL)-N’-(BENZOTHIAZOLE-2’-YL) THIOUREAS Received 5 January 2009 Nguyen Dinh Thanh, Pham Hong Lan, Nguyen Thu Huyen Faculty of Chemistry, Hanoi University of Science, VNU Abstract Some compounds of N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-N -(benzothiazole-2 yl)thioureas have been synthesized from corresponding 2,3,4,6-tetra-O-acetyl- -Dglucopyranosyl isothiocyanate and the substituted derivatives of 2-aminobenzothiazoles executing in home microwave oven. Their spectroscopic properties have been recorded and the relationships between their structures and spectral properties (IR, 1H- and 13C-NMR) have been discussed. I - INTRODUCTION II - EXPERIMENT Certain sugars perform important biological function [1]. They can control various gene expressions to adjust the upgrowth, development and reaction of organs. Glycosyl isothiocyanates have been widely used as valuable intermediates in the synthesis of glycosyl derivatives [2]. The isothiocyanates and glycosyl isothiocyanates have been the focus of synthetic attention during recent years because of their potential pharmacological properties [3]. They have also attracted considerable interest due to the antiHIV activity shown by 1-deoxyno-jirimycin, castanospermine and some of their derivatives [4]. Many biologically important products have a sugar unit joined by an atom (O, S, N or C) or a group of atom [5]. In the present study, we reported on the synthesis of various peracetated glucosylthioureas containing thiazole ring executing in microwave oven. This method is becoming an increasingly popular method of heating which replaces the classical one because it proves to be a clean, cheap, and convenient method [6]. Melting points of the synthesized compounds were measured on STUART SMP3 (BIBBY STERILIN-UK). The FTIS-spectra was recorded on Magna 760 FT-IR Spectrometer (Nicolet, USA) in .