ruthenium-catalyzed selective hydrogenation of bis-arylidene tetramic acids. application to the synthesis of novel structurally diverse pyrrolidine-2,4-dionesruthenium-catalyzed选择性加氢的bis-arylidene tetramic酸。.pdfVIP
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ruthenium-catalyzed selective hydrogenation of bis-arylidene tetramic acids. application to the synthesis of novel structurally diverse pyrrolidine-2,4-dionesruthenium-catalyzed选择性加氢的bis-arylidene tetramic酸。
Molecules 2011, 16, 6116-6128; doi:10.3390/molecule
OPEN ACCESS
molecules
ISSN 1420-3049
/journal/molecules
Article
Ruthenium-Catalyzed Selective Hydrogenation of bis-Arylidene
Tetramic Acids. Application to the Synthesis of Novel
Structurally Diverse Pyrrolidine-2,4-diones
Christos S. Karaiskos 1, Dimitris Matiadis 1, John Markopoulos 2,* and
Olga Igglessi-Markopoulou 1,*
1 Laboratory of Organic Chemistry, Department of Chemical Engineering, National Technical
University of Athens, Zografos Campus, Athens 15773, Greece;
E-Mails: chriskarsp@ (C.S.K.); matiadis@mail.ntua.gr (D.M.)
2 Laboratory of Inorganic Chemistry, Department of Chemistry, University of Athens, Panepistimio-
polis, Athens 15771, Greece; E-Mail: jmmarko@chem.uoa.gr
* Author to whom correspondence should be addressed; E-Mail: ojmark@chemeng.ntua.gr;
Tel.: +30-210-772-3079; Fax: +30-210-772-3072.
Received: 1 April 2011; in revised form: 5 July 2011 / Accepted: 11 July 2011 /
Published: 20 July 2011
Abstract: 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.
Keywords: hydrogenatio
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