Ruthenium-catalyzed selective hydrogenation of bis-arylidene tetramic acids. Application to the synthesis of novel structurally diverse pyrrolidine-2,4-diones

Christos S Karaiskos; Dimitris Matiadis; John Markopoulos; Olga Igglessi-Markopoulou

doi:10.3390/molecules16076116

Ruthenium-catalyzed selective hydrogenation of bis-arylidene tetramic acids. Application to the synthesis of novel structurally diverse pyrrolidine-2,4-diones

Molecules. 2011 Jul 20;16(7):6116-28. doi: 10.3390/molecules16076116.

Authors

Christos S Karaiskos¹, Dimitris Matiadis, John Markopoulos, Olga Igglessi-Markopoulou

Affiliation

¹ Laboratory of Organic Chemistry, Department of Chemical Engineering, National Technical University of Athens, Zografos Campus, Athens 15773, Greece.

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Hydrogenation
Pyrrolidines / chemistry*
Pyrrolidinones / chemistry*
Ruthenium / chemistry*
Stereoisomerism

Substances

Pyrrolidines
Pyrrolidinones
tetramic acid
Ruthenium
pyrrolidine