Solid-Phase Synthesis of Isoxazoles and Isoxazolines: En Route to a New Class of Ionophores

Eric J. Kantorowski, Mark J. Kurth

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Solid-phase organic synthesis (SPOS) was employed in the construction of isoxazole and/or isoxazoline polyheterocyclic systems. The [3 + 2] cycloaddition reactions of nitrile oxides generated from the corresponding primary nitro compounds, with resin-bound alkynes or alkenes were highly efficient both chemically and with regard to purification. A parallel solution-phase synthesis was carried out which compared the synthetic efficiency in both media. SPOS of isoxazole/isoxazoline 11, employing a functionalized polystyrene resin, was found to be more efficient than the solution-phase approach. Three other oligoisoxazoles were prepared with average yields per step being 82, 84, and 89%.

Original languageEnglish (US)
Pages (from-to)6797-6803
Number of pages7
JournalJournal of Organic Chemistry
Issue number20
StatePublished - 1997


ASJC Scopus subject areas

  • Organic Chemistry

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