SYNTHESIS OF HETEROCYCLIC-SYSTEMS WITH A CARBOHYDRATE FRAGMENT .1. STEREOSELECTIVE SYNTHESIS OF AZOLOANHYDROSUGARS VIA THE ADDITION OF AZOLES TO LEVOGLUCOSENONE

Levoglucosenone, the alpha,beta-unsaturated ketone obtained by the pyr olysis of cellulose, reacts with NH-azoles in the presence of bases. I n this process not only normal Michael adducts are formed, but in some cases their hydrates (gem-diols) are also formed. In all cases the ad dition proceeds stereospecifically and with good yields. 3-Nitro-s-tri azole, 3-nitro-and 4-nitropyrazoles, 3-methyl-4-nitropyrazole, 5-nitro tetrazole, 4,5-dicarbomethoxy-nu-triazole, 3,4-dinitropyrazole, 3(5)-m ethylpyrazole, pyrazole, and imidazole have been studied in this react ion. All of the adducts are characterized by NMR- and IR-spectroscopy.