Isoxazolinoisoquinoline Heterocycles via Solid-Phase Reissert and Suzuki Reactions

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 n...

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Veröffentlicht in:Journal of organic chemistry 1998-04, Vol.63 (7), p.2244-2250
Hauptverfasser: Lorsbach, Beth A., Bagdanoff, Jeffrey T., Miller, R. Bryan, Kurth, Mark J.
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo9720142