Versatile Synthetic Approach for Selective Diversification of Bicyclic Aza-Diketopiperazines

Herein, we report a convenient synthesis of unprecedented aza-diketopiperazines (aza-DKPs). The strategy is based on selective diversification of bicyclic aza-DKP scaffolds by click reaction, N-acylation, and/or N-alkylation. These scaffolds containing either azido or amino groups were obtained by a...

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Published inACS omega Vol. 3; no. 11; pp. 15182 - 15192
Main Authors Péron, Florent, Riché, Stéphanie, Lesur, Brigitte, Hibert, Marcel, Breton, Philippe, Fourquez, Jean-Marie, Girard, Nicolas, Bonnet, Dominique
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 30.11.2018
ACS Publications
Subjects
Chemical Sciences
Organic chemistry
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Summary:Herein, we report a convenient synthesis of unprecedented aza-diketopiperazines (aza-DKPs). The strategy is based on selective diversification of bicyclic aza-DKP scaffolds by click reaction, N-acylation, and/or N-alkylation. These scaffolds containing either azido or amino groups were obtained by a key Rh­(I)-catalyzed hydroformylative cyclohydrocarbonylation reaction of allyl-substituted aza-DKP. The methodology is readily amenable to the parallel synthesis of original aza-DKPs to enlarge the chemical diversity of aza-heterocycles.
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PMCID: PMC6643515
ISSN:2470-1343
2470-1343
DOI:10.1021/acsomega.8b01752