title: Synthesis of differentially substituted 2-aminoimidazolidines via a microwave-assisted tandem Staudinger/aza-Wittig cyclization.
abstract: A new route for the construction of 2-aminoimidazolidines including analogues of the α2 adrenergic agonist drug clonidine is elaborated. The key step is an intramolecular microwave-assisted Staudinger/aza-Wittig cyclization of an in situ generated urea intermediate (formed by the reaction of β-amino azide and isocyanate) upon treatment with Bu3P or polymer-supported phosphine reagent, allowing the introduction of various substituents at the N1 and the 2-amino function. Furthermore, a useful one-pot Staudinger/aza-Wittig/Buchwald-Hartwig protocol leading to bicyclic guanidines has been elaborated.
authors: Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, University of Leuven (KU Leuven), Celestijnenlaan 200F, B-3001 Leuven, Belgium.
authors: Rakesh
authors: R
authors: Kumar
authors: Denis S
authors: DS
authors: Ermolat'ev
authors: Erik V
authors: EV
authors: Van der Eycken
mesh_terms: D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D006146:Guanidines / Q000138:chemical synthesis* / Q000737:chemistry; D048288:Imidazolines / Q000737:chemistry*; D008872:Microwaves; D015394:Molecular Structure
chemical_list: D001643:Bridged Bicyclo Compounds; D006146:Guanidines; D048288:Imidazolines