Formal nitrogen-to-carbon replacement in isoindolines to form indenes via N-alkyl tetrahydroisoquinolines
Ryan T Steele1, Julius Domack1, Richmond Sarpong1
1Department of Chemistry, University of California Berkeley CA 94720 USA rsarpong@berkeley.edu.
Abstract:
Herein, we report a Stevens rearrangement ring expansion of isoindolines to N-alkyl-2-aroyl-tetrahydroisoquinolines, followed by a photochemical nitrogen atom extruding ring contraction and elimination to give indene derivatives. By combining the ring expansion and ring contraction in a one-pot procedure, a net single-atom nitrogen-to-carbon replacement was realized. Factors that guide the stability of the immediate amino-indane products that are formed through photochemical ring contraction were studied. Reaction of the amino-indane intermediates with anhydrides yielded stable and isolable functionalized amino-indane derivatives in some cases.
Related Concept Videos
Diazonium Group Substitution: –OH and –H
Electrophilic Aromatic Substitution: Nitration of Benzene
Preparation of Nitriles
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3


