title: Synthesis of N-styrenyl amidines from α,β-unsaturated nitrones and isocyanates through CO2 elimination and styrenyl migration.
abstract: A mild, metal-free, and modular route for the preparation of N-styrenyl amidines from N-aryl-α,β-unsaturated nitrones and isocyanates has been developed that accesses an initial oxadiazolidinone intermediate that can undergo CO(2) elimination and styrenyl migration. The use of a migration event to install N-styrenyl amidine substituents circumvents a limitation of traditional Pinner-type methods for amidine synthesis that require the use of amine nucleophiles. The modularity of the nitrone and isocyanate reagents provides access to a variety of differentially substituted N-styrenyl amidines. The scope and tolerance of the method are presented, and preliminary mechanistic data for the transformation are discussed.
authors.affiliation: Department of Chemistry, University of Illinois at Chicago , Chicago, Illinois 60607, United States.
authors.forename: Dong-Liang
authors.initials: DL
authors.lastname: Mo
authors.forename: Wiktoria H
authors.initials: WH
authors.lastname: Pecak
authors.forename: Meng
authors.initials: M
authors.lastname: Zhao
authors.forename: Donald J
authors.initials: DJ
authors.lastname: Wink
authors.forename: Laura L
authors.initials: LL
authors.lastname: Anderson
mesh_terms: D000578:Amidines / Q000138:chemical synthesis* / Q000737:chemistry; D002245:Carbon Dioxide / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D007202:Indicators and Reagents; D017953:Isocyanates / Q000737:chemistry*; D015394:Molecular Structure; D009589:Nitrogen Oxides / Q000737:chemistry*; D013343:Styrenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000578:Amidines; D007202:Indicators and Reagents; D017953:Isocyanates; D009589:Nitrogen Oxides; D013343:Styrenes; C015388:nitrones; D002245:Carbon Dioxide