Ruthenium-Catalyzed Selective Hydrogenation of bis-Arylidene Tetramic Acids. Application to the Synthesis of Novel Structurally Diverse Pyrrolidine-2,4-diones

Catalytic hydrogenation of 3,5-bis-arylidenetetramic acids, known for their biological activity, has been developed. The chemoselective ruthenium-catalyzed reduction of the exocyclic carbon-carbon double bonds on pyrrolidine-2,4-dione ring system, containing other reducible functions, has been inves...

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Main Authors: Olga Igglessi-Markopoulou, John Markopoulos, Dimitris Matiadis, Christos S. Karaiskos
Format: Article
Language:English
Published: MDPI AG 2011-07-01
Series:Molecules
Subjects:
Online Access:http://www.mdpi.com/1420-3049/16/7/6116/
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author Olga Igglessi-Markopoulou
John Markopoulos
Dimitris Matiadis
Christos S. Karaiskos
author_facet Olga Igglessi-Markopoulou
John Markopoulos
Dimitris Matiadis
Christos S. Karaiskos
author_sort Olga Igglessi-Markopoulou
collection DOAJ
description Catalytic hydrogenation of 3,5-bis-arylidenetetramic acids, known for their biological activity, has been developed. The chemoselective ruthenium-catalyzed reduction of the exocyclic carbon-carbon double bonds on pyrrolidine-2,4-dione ring system, containing other reducible functions, has been investigated. Depending on the substrate the yield of the hydrogenation process can reach up to 95%. The structural elucidation has been established using NMR and HRMS spectral data.
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spelling doaj.art-36662e33e0f24099becb6a26055406fa2022-12-22T03:24:06ZengMDPI AGMolecules1420-30492011-07-011676116612810.3390/molecules16076116Ruthenium-Catalyzed Selective Hydrogenation of bis-Arylidene Tetramic Acids. Application to the Synthesis of Novel Structurally Diverse Pyrrolidine-2,4-dionesOlga Igglessi-MarkopoulouJohn MarkopoulosDimitris MatiadisChristos S. KaraiskosCatalytic hydrogenation of 3,5-bis-arylidenetetramic acids, known for their biological activity, has been developed. The chemoselective ruthenium-catalyzed reduction of the exocyclic carbon-carbon double bonds on pyrrolidine-2,4-dione ring system, containing other reducible functions, has been investigated. Depending on the substrate the yield of the hydrogenation process can reach up to 95%. The structural elucidation has been established using NMR and HRMS spectral data.http://www.mdpi.com/1420-3049/16/7/6116/hydrogenationhomogeneous catalysisruthenium catalystsBINAParylidenetetramic acid
spellingShingle Olga Igglessi-Markopoulou
John Markopoulos
Dimitris Matiadis
Christos S. Karaiskos
Ruthenium-Catalyzed Selective Hydrogenation of bis-Arylidene Tetramic Acids. Application to the Synthesis of Novel Structurally Diverse Pyrrolidine-2,4-diones
Molecules
hydrogenation
homogeneous catalysis
ruthenium catalysts
BINAP
arylidenetetramic acid
title Ruthenium-Catalyzed Selective Hydrogenation of bis-Arylidene Tetramic Acids. Application to the Synthesis of Novel Structurally Diverse Pyrrolidine-2,4-diones
title_full Ruthenium-Catalyzed Selective Hydrogenation of bis-Arylidene Tetramic Acids. Application to the Synthesis of Novel Structurally Diverse Pyrrolidine-2,4-diones
title_fullStr Ruthenium-Catalyzed Selective Hydrogenation of bis-Arylidene Tetramic Acids. Application to the Synthesis of Novel Structurally Diverse Pyrrolidine-2,4-diones
title_full_unstemmed Ruthenium-Catalyzed Selective Hydrogenation of bis-Arylidene Tetramic Acids. Application to the Synthesis of Novel Structurally Diverse Pyrrolidine-2,4-diones
title_short Ruthenium-Catalyzed Selective Hydrogenation of bis-Arylidene Tetramic Acids. Application to the Synthesis of Novel Structurally Diverse Pyrrolidine-2,4-diones
title_sort ruthenium catalyzed selective hydrogenation of bis arylidene tetramic acids application to the synthesis of novel structurally diverse pyrrolidine 2 4 diones
topic hydrogenation
homogeneous catalysis
ruthenium catalysts
BINAP
arylidenetetramic acid
url http://www.mdpi.com/1420-3049/16/7/6116/
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