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 Citations (Scopus)

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

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Nitriles
Cycloaddition
Alkylation
Alkenes
Oxides
Hydrolysis
5-iodoisoquinolin-1-one

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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.

Isoxazolinoisoquinoline Heterocycles via Solid-Phase Reinsert and Suzuki Reactions. / Lorsbach, Beth A.; Bagdanoff, Jeffrey T.; Bryan Miller, R.; Kurth, Mark J.

In: Journal of Organic Chemistry, Vol. 63, No. 7, 03.04.1998, p. 2244-2250.

Research output: Contribution to journalArticle

Lorsbach, BA, Bagdanoff, JT, Bryan Miller, R & Kurth, MJ 1998, 'Isoxazolinoisoquinoline Heterocycles via Solid-Phase Reinsert and Suzuki Reactions', Journal of Organic Chemistry, vol. 63, no. 7, pp. 2244-2250.
Lorsbach BA, Bagdanoff JT, Bryan Miller R, Kurth MJ. Isoxazolinoisoquinoline Heterocycles via Solid-Phase Reinsert and Suzuki Reactions. Journal of Organic Chemistry. 1998 Apr 3;63(7):2244-2250.
Lorsbach, Beth A. ; Bagdanoff, Jeffrey T. ; Bryan Miller, R. ; Kurth, Mark J. / Isoxazolinoisoquinoline Heterocycles via Solid-Phase Reinsert and Suzuki Reactions. In: Journal of Organic Chemistry. 1998 ; Vol. 63, No. 7. pp. 2244-2250.
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