Dimroth-type rearrangement of 1-benzyl-and 1-glycosyl-5-aminoimidazoles to 4-(N-substituted amino) imidazoles

S Costanzi, SPN Rouse, L Vanbaelinghem, TJ Prior…

文献索引：Costanzi, Stefano; Rouse, Sean P.N.; Vanbaelinghem, Laurence; Prior, Timothy J.; Ewing, David F.; Boa, Andrew N.; MacKenzie, Grahame Tetrahedron Letters, 2012 , vol. 53, # 4 p. 412 - 415

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被引用次数: 4

摘要

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 ...