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 Citations (Scopus)

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

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Isoxazoles
Nitriles
Cycloaddition
Oxides
Alkenes
Alkynes
Ethers
Derivatives

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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.

A facile synthesis of furo[3,4-c]isoxazoles : Precursors to 3,4-disubstituted isoxazoles. / Kim, Hyung Jin; Lee, Jae Hyun; Olmstead, Marilyn M.; Kurth, Mark J.

In: Journal of Organic Chemistry, Vol. 57, No. 24, 1992, p. 6513-6519.

Research output: Contribution to journalArticle

Kim, HJ, Lee, JH, Olmstead, MM & Kurth, MJ 1992, 'A facile synthesis of furo[3,4-c]isoxazoles: Precursors to 3,4-disubstituted isoxazoles', Journal of Organic Chemistry, vol. 57, no. 24, pp. 6513-6519.
Kim, Hyung Jin ; Lee, Jae Hyun ; Olmstead, Marilyn M. ; Kurth, Mark J. / A facile synthesis of furo[3,4-c]isoxazoles : Precursors to 3,4-disubstituted isoxazoles. In: Journal of Organic Chemistry. 1992 ; Vol. 57, No. 24. pp. 6513-6519.
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