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Synfacts 2009(6): 0608-0608  
DOI: 10.1055/s-0029-1216711
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Gold-Catalyzed Synthesis of Tetrahydrobenz[b]azepin-4-ones

Contributor(s): Victor Snieckus, Josefine Karlsson
L. Cui, G. Zhang, Y. Peng, L. Zhang*
University of Nevada, Reno, USA
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Publication History

Publication Date:
25 May 2009 (online)

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Significance

Described here is an efficient, two-step, one-pot synthesis of tetrahydro[b]azepin-4-ones from tertiary N-(but-3-ynyl)anilines. The reaction needs either a gold catalyst or, for substrates bearing an electron-withdrawing group at the alkyne terminus, no catalyst at all. The oxygen from the N-oxide formed by MCPBA treatment is relayed to a tethered C-C triple bond, which is inert under the mild reaction conditions.