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Hydroxylamine as an ammonia equivalent: access to NH-tetrahydroisoquinolonic derivatives from aldoximes by the Castagnoli–Cushman reaction followed by reduction

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A novel synthetic protocol towards trans-NH-tetrahydroisoquinolonic acid esters is based on the Castagnoli–Cushman reaction between aromatic aldehyde oximes and homophthalic anhydride, followed by esterification and TiCl3-promoted reduction. The scope of… Click to show full abstract

A novel synthetic protocol towards trans-NH-tetrahydroisoquinolonic acid esters is based on the Castagnoli–Cushman reaction between aromatic aldehyde oximes and homophthalic anhydride, followed by esterification and TiCl3-promoted reduction. The scope of the method with respect to the aromatic portion (both electron-rich and electron-deficient) is broader compared to the earlier described approaches, which makes it a suitable synthetic strategy for the structure–activity exploration.

Keywords: cushman reaction; ammonia equivalent; reduction; hydroxylamine ammonia; castagnoli cushman

Journal Title: Mendeleev Communications
Year Published: 2019

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