Formal nitrogen-to-carbon replacement in isoindolines to form indenes via N-alkyl tetrahydroisoquinolines

Ryan T. Steele; Julius Domack; Richmond Sarpong

doi:10.1039/d6sc03487j

January 1, 2026Chemical ScienceOpen Access

Formal nitrogen-to-carbon replacement in isoindolines to form indenes via N-alkyl tetrahydroisoquinolines

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Key Points

The aim is to demonstrate a method for transforming isoindolines into indene derivatives through a series of chemical reactions.
Employs Stevens rearrangement ring expansion of isoindolines to form N-alkyl-2-aroyl-tetrahydroisoquinolines.
Utilizes photochemical nitrogen atom extrusion for subsequent ring contraction and elimination.
Combines multiple synthetic steps to achieve indene derivatives from isoindolines.
Successfully synthesizes a variety of indene derivatives from isoindolines.
Demonstrates the feasibility of nitrogen atom extrusion in complex organic transformations.
Shows potential for diverse applications in synthetic chemistry.

Implication

Report describes a novel reaction converting isoindolines to indene derivatives, highlighting synthetic flexibility.

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...

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Cite This Study

Steele et al. (2026) studied this question.

synapsesocial.com/papers/6a338cf6630953a74978e109 https://doi.org/10.1039/d6sc03487j

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Formal nitrogen-to-carbon replacement in isoindolines to form indenes via N-alkyl tetrahydroisoquinolines

Key Points

Implication

Abstract

Discussion

Cite This Study

Formal nitrogen-to-carbon replacement in isoindolines to form indenes via N-alkyl tetrahydroisoquinolines

Key Points

Implication

Abstract

Discussion

Cite This Study

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