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Communication | Regular issue | Vol 78, No. 5, 2009, pp.1183-1190
Published online, 28th January, 2009
DOI: 10.3987/COM-08-11629
Regiospecific Synthesis of Unsubstituted Basic Skeletons of Heterocycles Containing Nitrogen Neighboring an Aromatic Ring by the Reductive Ring Expansion Reaction Using Diisobutylaluminum Hydride

Hidetsura Cho,* Yusuke Iwama, Kenji Sugimoto, Eunsang Kwon, and Hidetoshi Tokuyama*

*Department of Chemistry, Graduate School of Science, Tohoku University, Aoba-ku, Sendai 980-8578, Japan

Abstract

A systematic investigation of reductive ring expansion reaction of oximes with diisobutylaluminum hydride (DIBAH) was performed. The reaction regiospecifically provided a variety of unsubstituted bicyclic heterocycles 3a-3g or tricyclic heterocycles 3h, 3j-3l that contained nitrogen attached to an aromatic ring.