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Synfacts 2006(10): 1073-1073
DOI: 10.1055/s-2006-949299
DOI: 10.1055/s-2006-949299
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York
Rapid Synthesis of Diketopiperazine Macroarrays
Q. Lin, H. E. Blackwell*
University of Wisconsin-Madison, USA
Further Information
Publication History
Publication Date:
21 September 2006 (online)
Significance
Rapid generation of diketopiperazine libraries was achieved. Thus, Ugi four-component reactions (Ugi 4CRs) of the supported amine building block 1 with aldehydes, 1-isocyanocyclohexene, and N-Fmoc amino acids in H2O gave the Ugi products 2. Methyl esters 3 were formed by microwave (MW)-assisted methanolysis of 2. Deprotection from the N-Fmoc group and subsequent cyclization provided the supported piperazines 4 cleanly. After capping unreacted amines with acetic anhydride, photo-cleavage from the support gave the desired piperazines 5 with high purity (up to 91% purity).