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Paper | Special issue | Vol 97, No. 2, 2018, pp.785-792
Published online, 11th May, 2018
DOI: 10.3987/COM-18-S(T)51
Construction of Azaisoflavone Derivatives by Hypervalent Iodine Reagent-Mediated Oxidative Rearrangement of 2’-Nitrochalcone

Akira Nakamura, Reo Takane, Junki Tanaka, Junya Morimoto, and Tomohiro Maegawa*

*School of Pharmaceutical Sciences, Kindai University, 3-4-1 Kowakae, Higashi-Osaka, Osaka 577-8502, Japan

Abstract

Fabrication of a synthetic azaisoflavone skeleton from 2’-nitrochalcone was done using oxidative rearrangement with a hypervalent iodine reagent. A key intermediate compound, aminoacetal, was prepared from readily available 2’-nitrochalcone via a PhI(OH)OTs-mediated rearrangement, followed by reduction of the nitro group. A variety of azaisoflavones were obtained in moderate to high yields by treatment of the intermediate compound under acidic conditions.