Reactions of Zamino-2-deoxy-D-glucose and its N-butyl derivative with lethoxy-Znitroethene produced 2-deoxy-2-[(2-nitrovinyl)amino]-D-glucose ( 6) and its N-butyl derivative (8), respectively, in high yields. The spectra of these compounds indicated that they were cu,p-anomeric mixtures, and also that 6 existed as equilibrium mixtures of the Zand E-geometrical isomers, the proportions of which depended on the polarity of the medium. Acetylation of 6 and 8 afforded the corresponding tetra-acetates 7 and 9. The reaction of P-D-glucopyranosylamine with lethoxy-2-nitroethene yielded syrupy l-(fl-D-glucopyranosylamino)-2-nitroethene, which was characterised as the crystalline tetra-0-acetyl derivative. Compounds 6 and 8 cyclised readily to give the 4-nitro-2-(D-arubino-tetritol-1-yl)pyrroles 12 and 14, which could also be obtained by treatment of 2-amino-2-deoxy-D-glucose and its N-butyl derivative with l-ethoxy-2-nitroethene in boiling methanol. Similar reactions with l-amino-l-deoxy-D-fructose and its N-methyl, N-butyl, and N-p-tolyl derivatives afforded the respective 4-nitro-3-(D-arubino-tetritol-1-yl)pyrroles.
A series of 4-nitro-3-and -2-pyrrolecarbaldehydes was obtained by periodate oxidation of the 2-and 3-(alditol-1-yl)&nitropyrroles.
INTRODUCIION l-Amino-2-nitroalkenes ("nitroenamines") have attracted interest because of their pharmacological properties2v3 and utility as precursors of heterocyclic com-pounds4. We have described1*5 the synthesis and properties of 1-alkyl(aryl)amino-2nitroalkenes and their conversion into imidazoles. Furthermore, cY-aminoketones (e.g., 1) react with l-ethoxy-2-nitroethene (ENE, 2) and with cr-nitroketones to afford 3-nitropyrroles (e.g., 4) in high yield@. The reaction has been supposed to proceed via nitroenamine intermediates (e.g., 3), the intramolecular aldehydeenamine condensation of which affords the pyrroles. The similar synthesis of 3-acyl-*