Synthesis of β-nitropyrroles from amino sugars and nitroacetone

Abstract

Reactions of 2-amino-2-deoxy-d-glucose and 1-amino-1-deoxy-d-fructose with nitroacetone produced 2-methyl-3-nitro-5-(d-arabino-tetritol-1-yl)pyrrole (7) and 2-methyl-3-nitro-4-(d-arabino-tetritol-1-yl)pyrrole (11), respectively, in good yields. The reactions take place through the intermediacy of the unstable 2-nitrovinylamino sugars 5 and 13, the former compound having been isolated as its 1,3,4,6-tetra-O-acetyl derivative 9. Acetylation of 7 and 11 afforded the corresponding tetra-acetates 8 and 12. Periodate oxidation of 7 and 11 gave 5-methyl-4-nitro-2-pyrrolecarbaldehyde and 5-methyl-4-nitro-3-pyrrolecarbaldehyde, respectively, in good yields.