TY - JOUR
T1 - An Ugi-intramolecular Diels-Alder route to highly substituted tetrahydroepoxyisoindole carboxamides
AU - Gordon, Christopher P.
AU - Young, Kelly A.
AU - Robertson, Mark J..
AU - Hill, Timothy A.
AU - McCluskey, Adam
PY - 2011
Y1 - 2011
N2 - 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.
AB - 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.
UR - http://handle.uws.edu.au:8081/1959.7/546867
U2 - 10.1016/j.tet.2010.10.042
DO - 10.1016/j.tet.2010.10.042
M3 - Article
SN - 1464-5416
VL - 67
SP - 554
EP - 561
JO - Tetrahedron
JF - Tetrahedron
IS - 2
ER -