What question did this study set out to answer?

This research aims to explore the synthesis of cyclobutane-fused quinolizine frameworks from Reissert compounds using photocatalysis.

May 27, 2026

Construction of Cyclobutane‐Fused Quinolizine Frameworks Through Intramolecular 2 + 2 Cycloaddition of Reissert Compounds from Isoquinolines Catalyzed by an Iridium Visible‐Light Photocatalyst

Key Points

This research aims to explore the synthesis of cyclobutane-fused quinolizine frameworks from Reissert compounds using photocatalysis.
Used irradiation of Reissert compounds with blue light at 455 nm
Employed an iridium-based photocatalyst with a loading of 0.5 mol%
Mechanistic studies indicate a stepwise [2 + 2] cycloaddition pathway
Achieved high yields of cyclobutane-fused benzo[b]quinolizinone derivatives
Observed moderate to high stereoselectivity in the reaction
Completion of reactions occurred within 1 hour under specified conditions.

Abstract

Irradiation of 2‐(ω‐alkenoyl)‐1,2‐dihydroisoquinoline‐1‐carbonitriles (Reissert compounds) with blue light‐emitting diodes ( λ = 455 nm) in the presence of an iridium‐based photocatalyst efficiently afforded cyclobutane‐fused benzo b quinolizinone derivatives in high yields and with moderate to high stereoselectivity. A catalyst loading as low as 0.5 mol% was sufficient to drive the reaction to completion within 1 h in many cases. Mechanistic studies suggest that the transformation proceeds via a stepwise 2 + 2 cycloaddition pathway involving a triplet biradical intermediate.

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