title: Thermolysis of Geminal Diazides: Reagent-Free Synthesis of 3-Hydroxypyridines.
abstract: An operationally simple protocol for the rapid and efficient construction of highly substituted 3-hydroxypyridines is presented. The thermally induced cyclization of easily constructed geminal diazides derived from β-ketoesters having an additional olefin moiety affords the title compounds in yields up to 97% under reagent-free conditions. The new method allows for the synthesis of preparative quantities of material. Additionally, the synthetic utility of the pyridine products for the synthesis of valuable heterocycles is described.
authors.affiliation: Organic Chemistry, Bergische Universität Wuppertal , Gaußstraße 20, 42119 Wuppertal, Germany.
authors.forename: Hellmuth
authors.initials: H
authors.lastname: Erhardt
authors.affiliation: Organic Chemistry, Bergische Universität Wuppertal , Gaußstraße 20, 42119 Wuppertal, Germany.
authors.forename: Kevin A
authors.initials: KA
authors.lastname: Kunz
authors.affiliation: Organic Chemistry, Bergische Universität Wuppertal , Gaußstraße 20, 42119 Wuppertal, Germany.
authors.forename: Stefan F
authors.identifier: 0000-0003-2628-8703
authors.initials: SF
authors.lastname: Kirsch