Fluorous Mixture Synthesis of Two Libraries with Hydantoin-, and Benzodiazepinedione-fused Heterocyclic Scaffolds

Overview

Journal J Comb Chem

Publisher American Chemical Society

Specialty Chemistry

Date 2006 Sep 12

PMID 16961407

Citations 7

Authors

Wei Zhang

Yimin Lu

Christine Hiu-Tung Chen

Lu Zeng

Daniel B Kassel

Affiliations

Soon will be listed here.

Abstract

Diversity-oriented synthesis (DOS) and fluorous mixture synthesis (FMS) are two aspects of combinatorial chemistry. DOS generates library scaffolds with skeletal, substitution, and stereochemistry variations, whereas FMS is a highly efficient tool for library production. The combination of these two aspects in solution-phase synthesis of two novel heterocyclic compound libraries is presented in this paper. Mixtures of different fluorous amino acids undergo [3 + 2] cycloadditions followed by postcondensation reactions. The mixtures are then demixed by fluorous HPLC. Fluorous tags are removed by cyclization to afford hydantoin- and benzodiazepinedione-fused heterocyclic compounds as individual, pure, and structurally defined molecules. The application of MS-directed HPLC purification and parallel four-channel LC/MS analysis further increases the efficiency of FMS.

Citing Articles

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One-Pot Synthesis of Triazolobenzodiazepines Through Decarboxylative [3 + 2] Cycloaddition of Nonstabilized Azomethine Ylides and Cu-Free Click Reactions.

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Solid-phase synthesis of a library of amphipatic hydantoins. Discovery of new hits for TRPV1 blockade.

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Fluorous parallel synthesis of a piperazinedione-fused tricyclic compound library.

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