N−H Insertion Reactions of Boc-Amino Acid Amides: Solution- and Solid-Phase Synthesis of Pyrazinones and Pyrazines
Organic Letters2004Vol. 6(24), pp. 4627–4629
Citations Over TimeTop 17% of 2004 papers
Hana Matsushita, Sang‐Hyeup Lee, Kazuhiro Yoshida, Bruce Clapham, Guido Koch, J. Zimmermann, Kim D. Janda
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]
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