Title: Diastereoselective intramolecular hetero Diels-Alder approach towards polycyclic heterocycles
Authors: Ceulemans, E ×
Voets, M
Emmers, S
Uytterhoeven, Koen
Van Meervelt, Luc
Dehaen, Wim #
Issue Date: Jan-2002
Publisher: Pergamon-elsevier science ltd
Series Title: Tetrahedron vol:58 issue:3 pages:531-544
Abstract: Several different heterocyclic aldehydes, derived from pyrazole. pyrimidine, pyridine, indole and thiazole, were converted to polyheterocyclic compounds containing four to seven rings. The key steps in the sequence were a Knoevenagel condensation of the aldehyde and a heterocyclic carbonyl compound, such as pyrazolone and isoxazolone, followed by an intramolecular hetero Diets-Alder reaction. Most final products were isolated with high yield and diastereoselecivity. The isoxazolo fused cycloadducts formed interesting spiro-adducts upon heating. The cis nature of the bridging hydrogens of the heterocycles was evidenced by X-ray diffraction analysis.(dagger) (C) 2002 Elsevier Science Ltd. All rights reserved.
ISSN: 0040-4020
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Tutorial services, Faculty of Science
Biochemistry, Molecular and Structural Biology Section
Molecular Design and Synthesis
× corresponding author
# (joint) last author

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