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

Costanzi, Stefano; Rouse, Sean P.N.; Vanbaelinghem, Laurence; Prior, T.J.; Ewing, David F.; Boa, Andrew N.; Mackenzie, Grahame

Authors

Stefano Costanzi

Sean P.N. Rouse

Laurence Vanbaelinghem

David F. Ewing



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.

Journal Article Type Article
Publication Date Jan 25, 2012
Journal Tetrahedron Letters
Print ISSN 0040-4039
Electronic ISSN 1873-3581
Publisher Elsevier
Peer Reviewed Peer Reviewed
Volume 53
Issue 4
Pages 412-415
APA6 Citation Rouse, S., Vanbaelinghem, L., Ewing, D., Boa, A., MacKenzie, G., Costanzi, S., …Mackenzie, G. (2012). Dimroth-type rearrangement of 1-benzyl- and 1-glycosyl-5-aminoimidazoles to 4-(N-substituted amino)imidazoles. Tetrahedron letters; the international organ for the rapid publication of preliminary communications in organic chemistry, 53(4), 412-415. https://doi.org/10.1016/j.tetlet.2011.11.058
DOI https://doi.org/10.1016/j.tetlet.2011.11.058
Keywords Exocyclic nucleoside; Dimroth rearrangement; Imidazole
Publisher URL https://www.sciencedirect.com/science/article/pii/S004040391101999X?via%3Dihub
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