title: One-Pot Conversion of Carbohydrates into Pyrrole-2-carbaldehydes as Sustainable Platform Chemicals.
abstract: A practical conversion method of carbohydrates into N-substituted 5-(hydroxymethyl)pyrrole-2-carbaldehydes (pyrralines) was developed by the reaction with primary amines and oxalic acid in DMSO at 90 °C. Further cyclization of the highly functionalized pyrralines afforded the pyrrole-fused poly-heterocyclic compounds as potential intermediates for drugs, food flavors, and functional materials. The mild Maillard variant of carbohydrates and amino esters in heated DMSO with oxalic acid expeditiously produced the pyrrole-2-carbaldehyde skeleton, which can be concisely transformed into the pyrrole alkaloid natural products, 2-benzyl- and 2-methylpyrrolo[1,4]oxazin-3-ones 8 and 9, lobechine 10, and (-)-hanishin 11 in 23-32% overall yields from each carbohydrate.
authors.affiliation: †Department of Energy Science and Technology and ‡Department of Chemistry, Myong Ji University, Myongji-Ro 116, Cheoin-Gu, Yongin, Gyeonggi-Do 449-728, Korea.
authors.forename: Nirmal Das
authors.initials: ND
authors.lastname: Adhikary
authors.affiliation: †Department of Energy Science and Technology and ‡Department of Chemistry, Myong Ji University, Myongji-Ro 116, Cheoin-Gu, Yongin, Gyeonggi-Do 449-728, Korea.
authors.forename: Sunjeong
authors.initials: S
authors.lastname: Kwon
authors.affiliation: †Department of Energy Science and Technology and ‡Department of Chemistry, Myong Ji University, Myongji-Ro 116, Cheoin-Gu, Yongin, Gyeonggi-Do 449-728, Korea.
authors.forename: Wook-Jin
authors.initials: WJ
authors.lastname: Chung
authors.affiliation: †Department of Energy Science and Technology and ‡Department of Chemistry, Myong Ji University, Myongji-Ro 116, Cheoin-Gu, Yongin, Gyeonggi-Do 449-728, Korea.
authors.forename: Sangho
authors.initials: S
authors.lastname: Koo
mesh_terms: D002087:Butyrates / Q000737:chemistry; D002241:Carbohydrates / Q000737:chemistry*; D002384:Catalysis; D004121:Dimethyl Sulfoxide / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D002087:Butyrates; D002241:Carbohydrates; D006571:Heterocyclic Compounds; D011758:Pyrroles; C511000:hanishin; C561629:lobechine; C051266:pyrrole-2-carboxaldehyde; D004121:Dimethyl Sulfoxide