Simultaneously Electrogenerated Cycloaddition Partners for Regiospecific Inverse-Electron-Demand Diels−Alder Reactions: A Route for Polyfunctionalized 1,4-Benzoxazine Derivatives

Citations Over Time

Abstract

A multistep one-pot electrochemical synthesis of a variety of complex 2-alkylamino-1,4-benzoxazine derivatives is described. The reactions are regiospecific and diastereospecific in the case of heterocyclic annulation. This cascade sequence, wherein both cycloaddition partners are generated in situ, at room temperature, under metal-free conditions, allows the inverse-electron-demand Diels-Alder reaction of an o-iminoquinone diene and a secondary alkylenamine dienophile, two chemically nonaccessible unstable entities. To increase the molecular diversity, a variant in which the enamine is separately prepared completes the aforementioned procedure. The extension of this reaction should be useful to generate libraries of heterocycles.

Related Papers

• → Transannular [6 + 4] and Ambimodal Cycloaddition in the Biosynthesis of Heronamide A(2015)90 cited
• → Asymmetric Cycloaddition/Annulation Reactions by Chiral Phosphoric Acid Catalysis: Recent Advances(2022)20 cited
• → Regiospecific synthesis of mitosenes by a new bromoquinone-enamine annulation reaction(1992)30 cited
• → Stereoselective Synthesis of (±)-Dihydrocorynantheol via Enamine Annelation(1980)12 cited
• → Studies on the syntheses of heterocyclic compounds. Part 878. Synthesis of (±)-camptothecin and (±)-10-methoxycamptothecin via enamine annulation(1981)14 cited