title: Synthesis of Highly Substituted Quinolines via a Tandem Ynamide Benzannulation/Iodocyclization Strategy.
abstract: A two-stage "tandem strategy" for the regiocontrolled synthesis of very highly substituted quinolines is described. Benzannulation based on the reaction of cyclobutenones or diazo ketones with N-propargyl-substituted ynamides proceeds via a cascade of several pericyclic reactions to generate multiply substituted aniline derivatives. In the second stage of the tandem strategy, triflate derivatives of the phenolic benzannulation products undergo Larock cyclization upon exposure to iodine to form products that are further elaborated by methods such as palladium-catalyzed coupling to generate quinolines that can be substituted at every position of the bicyclic system.
authors.affiliation: Department of Chemistry Massachusetts Institute of Technology Cambridge, Massachusetts 02139, United States.
authors.forename: Thomas P
authors.initials: TP
authors.lastname: Willumstad
authors.affiliation: Department of Chemistry Massachusetts Institute of Technology Cambridge, Massachusetts 02139, United States.
authors.forename: Paul D
authors.initials: PD
authors.lastname: Boudreau
authors.affiliation: Department of Chemistry Massachusetts Institute of Technology Cambridge, Massachusetts 02139, United States.
authors.forename: Rick L
authors.initials: RL
authors.lastname: Danheiser
mesh_terms: D001555:Benzene Derivatives / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D001555:Benzene Derivatives; D011804:Quinolines