Synthesis Of Nitrogen-containing Heterocyclic C-glycoside Compounds From Ribose

This paper,based on the progress of the research on nitrogen heterocyclic and carbonoglycoside compounds,a series of ribose modified nitrogen heterocyclic derivatives were designed and synthesized with ribose as original material.The main contents are as follows:1.The ?,?-unsaturated keto-glycoside compounds(compounds 2-8)were obtained by glycosylation with acetylacetone and ribose then reacting with different substituted benzaldehydes by Claisen-Schmidt condensation reaction.After that,?,?-unsaturated keto-glycoside was modified through the addition of bromine.At last,hydrazine hydrate,phenylhydrazine,hydroxylamine hydrochloride cyclized to form pyrazole glycoside,N-phenyl pyrazole glycoside and isoxazole glycoside compounds.2.In order to avoid the use of highly toxic liquid bromine,the synthesis route is further optimized.The ?,?-unsaturated keto carbonyl compounds(compound 2-8)were obtained from the above steps using ribose as original material.After reacting with p-toluenesulfonyl hydrazide,Phenylhydrazine,hydroxylamine hydrochloride and semicarbazide hydrochloride respectively,pyrazole glycoside,N-phenylpyrazole glycoside,isoxazolyl glycoside and ?,?-unsaturated semicarbazide compounds were obtained.3.30 compounds were synthesized by the above two methods.The structures of the synthesized compounds were identified by NMR,IR and HR-MS.All of them were new compounds.Several types reactions mechanism of pyrazolium carbonyl compounds were suggested.