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

Gordon, Christopher P., Young, Kelly A., Robertson, Mark J., Hill, Timothy A., and McCluskey, Adam (2011) An Ugi-intramolecular Diels–Alder route to highly substituted tetrahydroepoxyisoindole carboxamides. Tetrahedron, 67 (2). pp. 554-561.

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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.

Item ID: 36828
Item Type: Article (Research - C1)
ISSN: 1464-5416
Keywords: Ugi condensation, Diels-Alder addition, tricyclic lactams, medicinal chemistry scaffold
Funders: Australian Research Council (ARC)
Date Deposited: 10 Dec 2014 07:31
FoR Codes: 03 CHEMICAL SCIENCES > 0305 Organic Chemistry > 030503 Organic Chemical Synthesis @ 100%
SEO Codes: 97 EXPANDING KNOWLEDGE > 970103 Expanding Knowledge in the Chemical Sciences @ 100%
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