An Ugi-intramolecular Diels-Alder route to highly substituted tetrahydroepoxyisoindole carboxamides

Christopher P. Gordon, Kelly A. Young, Mark J.. Robertson, Timothy A. Hill, Adam McCluskey

    Research output: Contribution to journalArticlepeer-review

    22 Citations (Scopus)

    Abstract

    The four component Ugi reaction of 2-furaldehyde, an alkenoic acid (three examples), an isonitrile (eight examples) and an amine (eight examples) affords rapid access to a family of acetylenic furan analogues, which on heating undergo an intramolecular Diels-Alder (IMDA) reaction yielding highly substituted tricyclic lactams (17 examples) in good to excellent yields (38-72% two-steps). This Ugi-IMDA reaction proved to be highly substituent tolerant across both the isonitriles and amines examined. In one instance, with N,N- dimethylaminopropylamine, a second equivalent of alkynoic acid was required to afford a good yield of the desired tricyclic lactam.
    Original languageEnglish
    Pages (from-to)554-561
    Number of pages8
    JournalTetrahedron
    Volume67
    Issue number2
    DOIs
    Publication statusPublished - 2011

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