title: Solid Phase Synthesis of (Benzannelated) Six-Membered Heterocycles via Cyclative Cleavage of Resin-Bound Pseudo-Oxazolones.
abstract: A solid supported procedure for the synthesis of benzoxazinones, dihydropyrazinones, quinoxalinones, and dihydrooxazinones using immobilized oxazolones in combination with difunctional nucleophiles as cleavage agent is presented. The scope of the novel method has been demonstrated through subsequent modification of the parent oxazolone scaffold on solid supports using conversions with electrophiles or CuAAC reactions to give functionalized pyrazin-2-ones. The described method allows the synthesis of the target heterocycles in good yields via three to five steps on solid phases with only one chromatographic purification step.
authors.affiliation: Institute of Toxicology and Genetics, Karlsruhe Institute of Technology , Hermann-von-Helmholtz-Platz 1, 76344 Eggenstein-Leopoldshafen, Germany.
authors.forename: Simone
authors.initials: S
authors.lastname: Gräßle
authors.affiliation: Institute of Organic Chemistry, Karlsruhe Institute of Technology , Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany.
authors.forename: Sylvia
authors.initials: S
authors.lastname: Vanderheiden
authors.affiliation: Institute of Toxicology and Genetics, Karlsruhe Institute of Technology , Hermann-von-Helmholtz-Platz 1, 76344 Eggenstein-Leopoldshafen, Germany.
authors.forename: Patrick
authors.initials: P
authors.lastname: Hodapp
authors.affiliation: Institute of Toxicology and Genetics, Karlsruhe Institute of Technology , Hermann-von-Helmholtz-Platz 1, 76344 Eggenstein-Leopoldshafen, Germany.
authors.forename: Bekir
authors.initials: B
authors.lastname: Bulat
authors.affiliation: Laboratory of Inorganic Chemistry, Department of Chemistry, University of Helsinki , P.O Box 55, A. I. Virtasen aukio 1, 00014 Helsinki, Finland.
authors.forename: Martin
authors.initials: M
authors.lastname: Nieger
authors.affiliation: Institute of Toxicology and Genetics, Karlsruhe Institute of Technology , Hermann-von-Helmholtz-Platz 1, 76344 Eggenstein-Leopoldshafen, Germany.|Institute of Organic Chemistry, Karlsruhe Institute of Technology , Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany.
authors.forename: Nicole
authors.initials: N
authors.lastname: Jung
authors.affiliation: Institute of Toxicology and Genetics, Karlsruhe Institute of Technology , Hermann-von-Helmholtz-Platz 1, 76344 Eggenstein-Leopoldshafen, Germany.|Institute of Organic Chemistry, Karlsruhe Institute of Technology , Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany.
authors.forename: Stefan
authors.initials: S
authors.lastname: Bräse