Title: Synthesis of 5-(phenyisulfanyl)-1,4-dihydropyrazine-2,3-diones via an unexpected microwave-assisted cascade reaction
Authors: Sharma, Anuj ×
Mehta Pravinchandra, Vaibhav
Van Hecke, Kristof
Van Meervelt, Luc
Van der Eycken, Erik #
Issue Date: Aug-2008
Publisher: Pergamon-elsevier science ltd
Series Title: Tetrahedron letters vol:49 issue:34 pages:4993-4996
Abstract: An unprecedented route for the synthesis of N-1 substituted 5-(phenylsulfanyl)-1,4-dihydropyrazine2,3-diones is disclosed starting from 5-chloro-3-(phenylsulfanyl)pyrazin-2(1H)-ones. The method comprises treatment of various 5-chloro-3-(phenylsulfanyl)pyrazin-2(1H)-ones with Na2CO3 in water under microwave irradiation providing the respective 5-(phenylsulfanyl)-1,4-dihydropyrazine-2,3-diones in good yields, via hydrolysis of the thioether bond and subsequent nucleophilic displacement of the chlorine by the in situ generated thiophenol. The obtained compounds are excellent precursors for the diversity oriented synthesis of pharmacologically active alpha,beta-dicarbonyl compounds. (c) 2008 Elsevier Ltd. All rights reserved.
ISSN: 0040-4039
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Molecular Design and Synthesis
Biochemistry, Molecular and Structural Biology Section
× corresponding author
# (joint) last author

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