title: Microwave-assisted fluorination of 2-acylpyrroles: synthesis of fluorohymenidin.
abstract: Treatment of mono- and nonbrominated 2-acylpyrroles with Selectfluor under microwave conditions leads to fluorination of the pyrrole ring in the 5-position. In particular, 2-trichloroacetylated pyrrole can be fluorinated. As an example, dihydrofluorohymenidin was synthesized and dehydrogenated to fluorohymenidin as the first fluorinated pyrrole-imidazole alkaloid. Introduction of the vinyl double bond was achieved by chlorination of the 2-aminoimidazole moiety, followed by dehydrochlorination at 100 °C in DMF.
authors.affiliation: TU Braunschweig, Institute of Organic Chemistry, Hagenring 30, 38106 Braunschweig, Germany.
authors.forename: Benjamin
authors.initials: B
authors.lastname: Troegel
authors.forename: Thomas
authors.initials: T
authors.lastname: Lindel
mesh_terms: D054879:Halogenation; D007093:Imidazoles / Q000737:chemistry*; D008872:Microwaves; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011758:Pyrroles / Q000737:chemistry*; D014753:Vinyl Compounds / Q000737:chemistry
chemical_list: D007093:Imidazoles; D011758:Pyrroles; D014753:Vinyl Compounds; C571230:fluorohymenidin; C014973:2-aminoimidazole