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: 554-561. doi:10.1016/j.tet.2010.10.042


Author Gordon, Christopher P.
Young, Kelly A.
Robertson, Mark J.
Hill, Timothy A.
McCluskey, Adam
Title An Ugi-intramolecular Diels-Alder route to highly substituted tetrahydroepoxyisoindole carboxamides
Journal name Tetrahedron   Check publisher's open access policy
ISSN 0040-4020
1464-5416
Publication date 2011-01-14
Sub-type Article (original research)
DOI 10.1016/j.tet.2010.10.042
Open Access Status Not yet assessed
Volume 67
Issue 2
Start page 554
End page 561
Total pages 8
Place of publication Kidlington, Oxford, United Kingdom
Publisher Pergamon Press
Language eng
Formatted 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.
Keyword Diels-Alder addition
Medicinal chemistry scaffold
Tricyclic lactams
Ugi condensation
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status Non-UQ

Document type: Journal Article
Sub-type: Article (original research)
Collection: Institute for Molecular Bioscience - Publications
 
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