Synthesis of heterocyclic systems with a carbohydrate fragment

Levoglucosenone, the ,ß-unsaturated ketone obtained by the pyrolysis of cellulose, reacts with NH-azoles in the presence of bases. In this process not only normal Michael adducts are formed, but in some cases their hydrates (gem-diols) are also formed. In all cases the addition proceeds stereospecifically and with good yields. 3-Nitro-s-triazole, 3-nitro- and 4-nitropyrazoles, 3-methyl-4-nitropyrazole, 5-nitrotetrazole, 4,5-dicarbomethoxy-v-triazole, 3,4-dinitropyrazole, 3(5)-methylpyrazole, pyrazole, and imidazole have been studied in this reaction. All of the adducts are characterized by NMR- and IR-spectroscopy.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1135–1140, June, 1994.