Isoxazolinoisoquinoline Heterocycles via Solid-Phase Reissert and Suzuki Reactions

A traceless solid-phase synthesis strategy has been developed that delivers novel isoxazolinoisoquinoline heterocycles. The process consists of solid-phase Reissert formation (isoquinoline → I), Suzuki coupling lithiation, and subsequent C1-alkylation (I → II), and exo-olefin selective 1,3-dipolar nitrile oxide cycloaddition followed by Reissert hydrolysis (II → III) to liberate the targeted heterocycle.