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Versatile Synthetic Approach for Selective Diversification of Bicyclic Aza-Diketopiperazines.


ABSTRACT: 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.

SUBMITTER: Peron F 

PROVIDER: S-EPMC6643515 | biostudies-literature | 2018 Nov

REPOSITORIES: biostudies-literature

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Versatile Synthetic Approach for Selective Diversification of Bicyclic Aza-Diketopiperazines.

Péron Florent F   Riché Stéphanie S   Lesur Brigitte B   Hibert Marcel M   Breton Philippe P   Fourquez Jean-Marie JM   Girard Nicolas N   Bonnet Dominique D  

ACS omega 20181109 11


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 c  ...[more]

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