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

Title: An Ugi-intramolecular Diels-Alder route to highly substituted tetrahydroepoxyisoindole carboxamides
Creator: Gordon, Christopher P.; Young, Kelly A.; Robertson, Mark J.; Hill, Timothy A.; McCluskey, Adam
Relation: Tetrahedron Vol. 67, Issue 2, p. 554-561
Publisher Link: http://dx.doi.org/10.1016/j.tet.2010.10.042
Publisher: Elsevier
Resource Type: journal article
Date: 2011
Description: 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.
Subject: Ugi condensation; Diels–Alder addition; tricyclic lactams; medicinal chemistry scaffold
Identifier: http://hdl.handle.net/1959.13/937190
Identifier: uon:12523
Identifier: ISSN:0040-4020
Language: eng
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