KCS

Abstract: Readily available carbohydrates (biomass) were converted into N-substituted 5-(hydroxymethyl)pyrrole-2-carbaldehydes (pyrralines) by the reaction with primary amines and oxalic acid in DMSO at 90 °C. Efficient production of pyrrolefused poly-heterocyclic compounds as potential intermediates for drugs, food flavors, and functional materials were achieved by further cyclization of the highly functionalized pyrralines. The mild Maillard variant of carbohydrates and amino esters in heated DMSO with oxalic acid expeditiously produced the pyrrole-2-carbaldehyde skeletons, which were concisely transformed into the pyrrole alkaloid natural products, 2-benzyl- and 2- methylpyrrolo[1,4]oxazin-3-ones and , lobechine , and (−)-hanishin