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

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