Article ID Journal Published Year Pages File Type
5268754 Tetrahedron Letters 2012 4 Pages PDF
Abstract

An efficient route is described to an unusual exocyclic 4-β-d-ribofuranosyl-aminoimidazole nucleoside, related 4-N-benzylaminoimidazoles and imidazole analogues of precursors in the de novo biosynthesis of purines, via a regiospecific and stereoselective base-catalysed Dimroth-type rearrangement of 1-ribofuranosyl and 1-benzyl-5-aminoimidazoles. Use of a 15N labelled precursor showed the unequivocal endo- to exocyclic translocation of the nitrogen atom during the rearrangement.

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Related Topics
Physical Sciences and Engineering Chemistry Organic Chemistry