title: N-h insertion reactions of Boc-amino acid amides: solution- and solid-phase synthesis of pyrazinones and pyrazines.
abstract: A series of alpha-diazo-beta-ketoesters were reacted with Boc amino acid amides in the presence of rhodium octanoate catalyst. The resulting N-H insertion products were treated with acid, providing the 1,4-azine intermediates, which were oxidized by air to form the corresponding pyrazine-6-one products. The pyrazine-6-ones were further derivatized by N-alkylation or by conversion to the arylpyrazines using sequential bromination and Suzuki coupling reactions. [reaction: see text]
authors.affiliation: Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA.
authors.forename: Hana
authors.initials: H
authors.lastname: Matsushita
authors.forename: Sang-Hyeup
authors.initials: SH
authors.lastname: Lee
authors.forename: Kazuhiro
authors.initials: K
authors.lastname: Yoshida
authors.forename: Bruce
authors.initials: B
authors.lastname: Clapham
authors.forename: Guido
authors.initials: G
authors.lastname: Koch
authors.forename: Jürg
authors.initials: J
authors.lastname: Zimmermann
authors.forename: Kim D
authors.initials: KD
authors.lastname: Janda
mesh_terms: D000596:Amino Acids / Q000737:chemistry; D004952:Esters / Q000737:chemistry; D005563:Formic Acid Esters; D011719:Pyrazines / Q000138:chemical synthesis*; D012238:Rhodium
chemical_list: D000596:Amino Acids; D004952:Esters; D005563:Formic Acid Esters; D011719:Pyrazines; C000345:t-butyloxycarbonyl group; D012238:Rhodium