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Title: Synthesis of alpha-carbolines and beta-carbolinones via intramolecular Diels-Alder reactions of 2(1H)-pyrazinones
Authors: Tahri, A ×
Buysens, KJ
Van der Eycken, Erik
Vandenberghe, DM
Hoornaert, GJ #
Issue Date: Oct-1998
Publisher: Pergamon-elsevier science ltd
Series Title: Tetrahedron vol:54 issue:43 pages:13211-13226
Abstract: 2(1H)-Pyrazinones bearing a X-(o-C6H4)-C=C-R moiety (X=NH, NAc) are shown to undergo an intramolecular cycloaddition-elimination reaction on thermolysis in refluxing bromobenzene yielding alpha-caarbolines or beta-carbolinones. The product distribution depends strongly on the substitution pattern of the pyrazinone precursors and the solvent used for thermolysis. A high yield and selective formation of beta-carbolinones is possible when heating in tetrahydronaphthalene at reflux. Use of acetic anhydride as solvent facilitated the reaction and made it possible to realise a carbolin(on)e unaccessible by thermolysis in the previously mentioned solvents. (C) 1998 Elsevier Science Ltd. All rights reserved.
URI: 
ISSN: 0040-4020
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Molecular Design and Synthesis
× corresponding author
# (joint) last author

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