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

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 o...

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Bibliographic Details
Published in:Tetrahedron letters 2012-01, Vol.53 (4), p.412-415
Main Authors: Costanzi, Stefano, Rouse, Sean P.N., Vanbaelinghem, Laurence, Prior, Timothy J., Ewing, David F., Boa, Andrew N., Mackenzie, Grahame
Format: Article
Language:English
Subjects:
Biosynthesis
Dimroth rearrangement
Exocyclic nucleoside
Imidazole
Nitrogen atoms
Nucleosides
Precursors
Purines
Tetrahedrons
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Summary: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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2011.11.058