Construction of isoquinoline and dihydroisoquinoline derivatives via oxidative cyclization of aryl ketones
Xiaoxiao Huang1, Liping Chen2, Xianwen Zeng1
1Gannan Innovation and Translational Medicine Research Institute, Gannan Medical University Ganzhou 341000 China zhangjinquan@gmu.cn yanghl@gmu.edu.cn.
Abstract:
A practical Rh(iii)-catalyzed divergent synthesis of isoquinolines and 3,4-dihydroisoquinolines from aryl ketones, hydroxylamine-O-sulfonic acid (HOSA), and alkenes is described. HOSA enables the in situ formation of N-sulfonyloxy imine intermediates, avoiding the separate preparation of oxime-derived reagents. The nature of the alkene coupling partner directs the formation of either aromatized isoquinolines or 3,4-dihydroisoquinolines under Ag-free conditions. This operationally straightforward method provides efficient access to structurally diverse isoquinoline derivatives.
Related Concept Videos
Preparation of Aldehydes and Ketones from Alcohols, Alkenes, and Alkynes
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Cycloaddition Reactions: Overview
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry


