Isoxazolinoisoquinoline Heterocycles via Solid-Phase Reinsert and Suzuki Reactions

Beth A. Lorsbach, Jeffrey T. Bagdanoff, R. Bryan Miller, Mark J. Kurth

Research output: Contribution to journalArticle

73 Scopus citations

Abstract

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.

Original languageEnglish (US)
Pages (from-to)2244-2250
Number of pages7
JournalJournal of Organic Chemistry
Volume63
Issue number7
StatePublished - Apr 3 1998

ASJC Scopus subject areas

  • Organic Chemistry

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    Lorsbach, B. A., Bagdanoff, J. T., Bryan Miller, R., & Kurth, M. J. (1998). Isoxazolinoisoquinoline Heterocycles via Solid-Phase Reinsert and Suzuki Reactions. Journal of Organic Chemistry, 63(7), 2244-2250.