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Synthesis of an azide-tagged library of 2,3-dihydro-4-quinolones.

ABSTRACT: We describe the assembly of a 960-member library of tricyclic 2,3-dihydro-4-quinolones using a combination of solution-phase high-throughput organic synthesis and parallel chromatographic purification. The library was produced with high efficiency and complete chemo- and diastereoselectivity by diversification of an azide-bearing quinolone via a sequence of [4 + 2] cycloadditions, N-acylations, and reductive aminations. The azide-functionalization of this library is designed to facilitate subsequent preparation of fluorescent or affinity probes, as well as small-molecule/surface conjugation.

SUBMITTER: Lee H

PROVIDER: S-EPMC2830352 | biostudies-literature | 2010 Mar

REPOSITORIES: biostudies-literature

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Synthesis of an azide-tagged library of 2,3-dihydro-4-quinolones.

Lee Hajoong H Suzuki Masato M Cui Jiayue J Kozmin Sergey A SA

The Journal of organic chemistry 20100301 5

We describe the assembly of a 960-member library of tricyclic 2,3-dihydro-4-quinolones using a combination of solution-phase high-throughput organic synthesis and parallel chromatographic purification. The library was produced with high efficiency and complete chemo- and diastereoselectivity by diversification of an azide-bearing quinolone via a sequence of [4 + 2] cycloadditions, N-acylations, and reductive aminations. The azide-functionalization of this library is designed to facilitate subseq ...[more]

PMID: 20141224

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