A facile synthesis of furo[3,4-c]isoxazoles: Precursors to 3,4-disubstituted isoxazoles

Hyung Jin Kim, Jae Hyun Lee, Marilyn M. Olmstead, Mark J. Kurth

Research output: Contribution to journalArticle

15 Scopus citations

Abstract

Nitrile oxide-olefin cycloaddition reactions deliver heterocyclic products with a wide variety of functionality and provide a particularly powerful means of preparing substituted isoxazoles by the intermolecular 1,3-dipolar cycloaddition of a nitrile oxide with a monosubstituted alkyne to give a preponderance of the 3,5-disubstituted isoxazole. In this study, an extension of the intramolecular nitrile oxide-olefin cycloaddition reaction is reported for the facile synthesis of furo[3,4-c]isoxazoles (5) which are in turn shown to be useful precursors to 3,4-disubstituted or 3,4,5-trisubstituted isoxazole derivatives (6). The method consists of a high-yield preparation of a broad spectrum of furo[3,4-c]isoxazoles by intramolecular nitrile oxide-alkyne cycloaddition of acetylenic nitro ethers (3), in turn prepared by Michael addition of various propargylic alkoxides (2) to appropriate nitro olefins (1).

Original languageEnglish (US)
Pages (from-to)6513-6519
Number of pages7
JournalJournal of Organic Chemistry
Volume57
Issue number24
StatePublished - 1992

ASJC Scopus subject areas

  • Organic Chemistry

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    Kim, H. J., Lee, J. H., Olmstead, M. M., & Kurth, M. J. (1992). A facile synthesis of furo[3,4-c]isoxazoles: Precursors to 3,4-disubstituted isoxazoles. Journal of Organic Chemistry, 57(24), 6513-6519.