Dimroth-type rearrangement of 1-benzyl- and 1-glycosyl-5-aminoimidazoles to 4-(N-substituted amino)imidazoles |
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| Authors: | Stefano Costanzi Sean PN Rouse Laurence Vanbaelinghem Timothy J Prior David F Ewing Andrew N Boa Grahame Mackenzie |
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| Institution: | Department of Chemistry, University of Hull, Cottingham Road, Kingston upon Hull HU6 7RX, UK |
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| 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. |
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