Journal of Organic Chemistry 2010-03-05

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

Hajoong Lee, Masato Suzuki, Jiayue Cui, Sergey A Kozmin

Index: J. Org. Chem. 75(5) , 1756-9, (2010)

Full Text: HTML

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.