- 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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