Stefano Costanzi
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
Sean P.N. Rouse
Laurence Vanbaelinghem
Dr Timothy Prior T.Prior@hull.ac.uk
Lecturer in Inorganic Chemistry
David F. Ewing
Dr Andrew Boa A.N.Boa@hull.ac.uk
Senior Lecturer
Grahame Mackenzie G.Mackenzie@hull.ac.uk
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.
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
Journal Article Type | Article |
---|---|
Acceptance Date | Nov 11, 2011 |
Online Publication Date | Nov 22, 2011 |
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 |
DOI | https://doi.org/10.1016/j.tetlet.2011.11.058 |
Keywords | Exocyclic nucleoside; Dimroth rearrangement; Imidazole |
Public URL | https://hull-repository.worktribe.com/output/423568 |
Publisher URL | https://www.sciencedirect.com/science/article/pii/S004040391101999X?via%3Dihub |
This file is under embargo due to copyright reasons.
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