Synthesis Of Quinoxaline C-glycosides

In this thesis, C-glycosides from monosaccharide have been investigated based on the review of C-glycosides compounds including application of heterocyclic quinoxaline, the synthetic methods of C-glycoside and the synthetic methods for quinoxalines. A series of quinoxalines C-glycosides have been synthesized using the new method. In consideration of the experimental results, we concluded the mechanism. In addition, the regioselective acylation in carbon glycoside was studied by dibutyltin oxide. The main results obtained are as follows:1. The new quinoxaline C-glycosides have been synthesized started from simple sugar by five steps, including acetyl acetone change, acylation, bromination, catalytic reaction with 1,2-Diaminebenzene. The mechanism has been concluded.The C-glycosides of the heterocyclic quinoxaline ring on the carbon chain have been synthesized started from Glucose, Galactose and Ribose. The C-glycoside of the heterocyclic quinoxaline ring on the inside of the carbon chain has been obtained with mannose as raw material. Two kinds of heterocyclic quinoxaline C-glycoside compounds have been synthesized started from Xylose and Arabinose. The investigation of antibacterial bioactive indicated that the above derivatives possessed moderate antibacterial biological activity.2. The regioselective acylation in carbon glycoside was studied by dibutyltin oxide in the process of synthesis of C-glycosides.β-C-glycosides could be regioselective single acylated with dibutyltin oxide. In the thesis,29 compounds were synthesized, and 20 compounds are new compounds. All the new compounds were characterized by MS,1H NMR, 13C NMR, IR spectra. The test of antibacterial biological activity of these new compouds indicated that most of the compounds have certain antimicrobial activity.