Title of article
Dimroth-type rearrangement of 1-benzyl- and 1-glycosyl-5-aminoimidazoles to 4-(N-substituted amino)imidazoles
Author/Authors
Costanzi، نويسنده , , Stefano and Rouse، نويسنده , , Sean P.N. and Vanbaelinghem، نويسنده , , Laurence and Prior، نويسنده , , Timothy J. and Ewing، نويسنده , , David F. and Boa، نويسنده , , Andrew N. and Mackenzie، نويسنده , , Grahame، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2012
Pages
4
From page
412
To page
415
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.
Keywords
Exocyclic nucleoside , Imidazole , Dimroth rearrangement
Journal title
Tetrahedron Letters
Serial Year
2012
Journal title
Tetrahedron Letters
Record number
1880001
Link To Document