Chemical Studies on Amino—Carbonyl Reaction

Abstract

When N-n-butyl-D-xylosylamine was heated with acetic acid in methanol at 55~70°G, it decomposed to N-n-butyIpyrrole-2-aldehyde,** through 3-deoxy-d-pentosulose as an intermediate. d-Xylose and methylamine in neutralized aqueous solution at 65~100°C also formed N-methylpyrrole-2-aldehyde. N-n-Butyl-l-rhamnosylamine, in a mixture of methanol and acetic acid, formed the corresponding pyrrolealdehyde, l-n-butyl-5-methylpyrrole-2- aldehyde, at the almost same rate as did N-xyloside. On the contrary, N-n-butyl-d-glucosylamine, under the same condition, did not form any detectable amount of the corresponding pyrrolealdehyde, but formed complicated products. A formation mechanism of the pyrrolealdehydes from 3-deoxyosulose and amine was proposed.