title: Regioselective synthesis of isochromenones by iron(III)/PhSeSePh-mediated cyclization of 2-alkynylaryl esters.
abstract: A series of 4-Se-(Te, S)-isochromenones and 3-substituted isochromenones were synthesized in good yields via FeCl(3)-mediated cyclization of alkynylaryl esters with different diorganyl dichalcogenides. This methodology was carried out at room temperature, using inexpensive and environmentally friendly iron salts as metallic source and under air atmosphere. The reaction showed to be tolerant to a range of substituents bonded into the aromatic ring of the diorganyl dichalcogenides as well as to alkyl groups directly bonded to the chalcogen atom. Alternatively, the cyclization reaction of 2-alkynylaryl esters with FeCl(3), in the absence of diorganyl dichalcogenide, gave the isochromenones without the chalcogen moiety in the structure. This approach proved to be highly regioselective, providing only six-membered ring products, once the possible five-membered products were not observed in any experiments.
authors: Laboratório de Síntese, Reatividade, Avaliação Farmacológica e Toxicológica de Organocalcogênios, CCNE, UFSM, Santa Maria, Rio Grande do Sul 97105-900, Brazil.
authors: Adriane
authors: A
authors: Sperança
authors: Benhur
authors: B
authors: Godoi
authors: Simone
authors: S
authors: Pinton
authors: Davi F
authors: DF
authors: Back
authors: Paulo H
authors: PH
authors: Menezes
authors: Gilson
authors: G
authors: Zeni
mesh_terms: D001578:Benzopyrans / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D018011:Chalcogens / Q000737:chemistry*; D003500:Cyclization; D004952:Esters; D005290:Ferric Compounds / Q000737:chemistry*; D007501:Iron / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D001578:Benzopyrans; D018011:Chalcogens; D004952:Esters; D005290:Ferric Compounds; D007501:Iron