title: Copper(II)-Catalyzed Alkoxyhalogenation of Alkynyl Ureas and Amides as a Route to Haloalkylidene-Substituted Heterocycles.
abstract: A highly effective synthesis of haloalkylidene-substituted heterocycles by copper(II)-catalyzed cyclization of alkynyl ureas and secondary amides has been developed. The reaction, which involves a catalytic amount of CuCl2 and a stoichiometric amount of N-halosuccinimide, occurs selectively through an alkoxyhalogenation process. Alternatively, alkoxychlorination and alkoxybromination reactions can be performed working solely with stoichiometric CuCl2 and CuBr2, respectively.
authors.affiliation: †Dipartimento di Scienza e Alta Tecnologia, Università dell'Insubria, via Valleggio 11, 22100 Como, Italy.
authors.forename: Silvia
authors.initials: S
authors.lastname: Gazzola
authors.affiliation: ‡DISFARM, Sezione di Chimica Generale e Organica "A. Marchesini", Università degli Studi di Milano, via Venezian 21, 20133 Milano, Italy.
authors.forename: Egle M
authors.initials: EM
authors.lastname: Beccalli
authors.affiliation: †Dipartimento di Scienza e Alta Tecnologia, Università dell'Insubria, via Valleggio 11, 22100 Como, Italy.
authors.forename: Tea
authors.initials: T
authors.lastname: Borelli
authors.affiliation: §Dipartimento di Chimica, Università degli Studi di Milano, via Golgi 19, 20133 Milano, Italy.
authors.forename: Carlo
authors.initials: C
authors.lastname: Castellano
authors.affiliation: ∥Dipartimento di Scienze del Farmaco, Università di Catania, Viale Andrea Doria 6, 95125 Catania, Italy.
authors.forename: Maria Assunta
authors.initials: MA
authors.lastname: Chiacchio
authors.affiliation: †Dipartimento di Scienza e Alta Tecnologia, Università dell'Insubria, via Valleggio 11, 22100 Como, Italy.
authors.forename: Daria
authors.initials: D
authors.lastname: Diamante
authors.affiliation: †Dipartimento di Scienza e Alta Tecnologia, Università dell'Insubria, via Valleggio 11, 22100 Como, Italy.
authors.forename: Gianluigi
authors.initials: G
authors.lastname: Broggini
mesh_terms: D000577:Amides / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D054879:Halogenation; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D014508:Urea / Q000737:chemistry*
chemical_list: D000577:Amides; D006571:Heterocyclic Compounds; D003300:Copper; D014508:Urea; C029892:cupric chloride