A 1,3-Diaza-Claisen rearrangement that affords guanidines.
[reaction: see text] N-Alkyl-N'-tosylthioureas activated by EDCI react with azanorbonenes at room temperature through a 1,3-diaza-Claisen rearrangement, affording highly substituted, bicyclic guanidines in moderate to good yields.
Bowser
Amy M
AM
Department of Chemistry, University of Vermont, Burlington, Vermont 05405, USA.
Madalengoitia
José S
JS
D001372:Aza Compounds / Q000737:chemistry*; D002384:Catalysis; D006146:Guanidines / Q000032:analysis / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D015394:Molecular Structure; D009636:Norbornanes / Q000737:chemistry
D001372:Aza Compounds; D006146:Guanidines; D007202:Indicators and Reagents; D009636:Norbornanes