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Synthesis of an Azide-Tagged Library of 2,3-Dihydro-4-quinolones

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journal contribution
posted on 05.03.2010, 00:00 authored by Hajoong Lee, Masato Suzuki, Jiayue Cui, Sergey A. Kozmin
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.