title: Diversity-Oriented Synthesis of a Library of Star-Shaped 2H-Imidazolines.
abstract: A library of star-shaped 2H-imidazolines has been synthesized via Debus-Radziszewski condensation from 1,2-diketones and ketone starting materials. Selective reduction of one imine group of the 2H-imidazole intermediate with LiAlH4 or catalytic flow hydrogenation furnished 2H-imidazolines, which could be conveniently diversified by reacting the amine N with electrophiles, resulting in a set of 21 amide-, carbamate-, urea-, and allylamine-containing products. In total, five points of diversification could be used, which allow the production of a set of functionally diverse compounds. The synthesis of acylated 2H-imidazolidines resulted in intrinsically labile compounds, which spontaneously degraded to acyclic derivatives, as shown for the reaction of 2H-imidazolidine with hexylisocyanate.
authors.affiliation: Institute of Organic Chemistry, Graz University of Technology , A-8010 Graz, Austria.
authors.forename: Xuepu
authors.initials: X
authors.lastname: Yu
authors.affiliation: Institute of Organic Chemistry, Graz University of Technology , A-8010 Graz, Austria.
authors.forename: Nikolaus
authors.initials: N
authors.lastname: Guttenberger
authors.affiliation: Institute of Organic Chemistry, Graz University of Technology , A-8010 Graz, Austria.
authors.forename: Elisabeth
authors.initials: E
authors.lastname: Fuchs
authors.affiliation: Institute of Organic Chemistry, Graz University of Technology , A-8010 Graz, Austria.
authors.forename: Martin
authors.initials: M
authors.lastname: Peters
authors.affiliation: Institute of Organic Chemistry, Graz University of Technology , A-8010 Graz, Austria.
authors.forename: Hansjörg
authors.initials: H
authors.lastname: Weber
authors.affiliation: Institute of Organic Chemistry, Graz University of Technology , A-8010 Graz, Austria.
authors.forename: Rolf
authors.initials: R
authors.lastname: Breinbauer
mesh_terms: D020650:Combinatorial Chemistry Techniques; D048288:Imidazolines / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D015394:Molecular Structure; D054852:Small Molecule Libraries / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D048288:Imidazolines; D007659:Ketones; D054852:Small Molecule Libraries
keywords: 1,2-diketones; Birch reduction; aminal; diversity elements; heterocycles; imidazolines; imine reduction; protein−protein interaction