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A Multicomponent aza‐Prins Strategy for the Diastereoselective Synthesis of Piperidine‐Fused Dihydroquinazolinones

Year: 2025

Type: article

Abstract: Dihydroquinazolinones (DHQs) and piperidines are widely acknowledged as privileged structures and are of significant interest for the development of new drug candidates. Herein, a novel aza‐Prins strategy is presented for the synthesis of piperidine‐fused DHQs through a domino multicomponent reaction. Homoallylic ammonium halide salts are found to react with bifunctional aldehydes under acidic conditions to give halide‐substituted fused piperidines in a diastereoselective fashion. The reaction can be extended to the incorporation of alcohol nucleophiles via fine tuning of the reaction conditions. Finally, the utility of the substituted compounds is demonstrated by performing a variety of functionalization reactions on the scaffold.

Source: European Journal of Organic Chemistry

DOI: 10.1002/ejoc.202500368

Authors: Lovisa Dybeck, Morgane Baudoin, Luke R. Odell

Institution: Uppsala University

Language: English

Topic: Quinazolinone synthesis and applications

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,330

Funders: Imperial College London, Cancerfonden, Vetenskapsrådet, Uppsala Universitet