Synthesis of an azide-tagged library of 2,3-dihydro-4-quinolones.
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.
Lee
Hajoong
H
Department of Chemistry, University of Chicago, 5735 S. Ellis Ave., Chicago, Illinois 60637, USA.
Suzuki
Masato
M
Cui
Jiayue
J
Kozmin
Sergey A
SA
D042462:4-Quinolones / Q000138:chemical synthesis* / Q000737:chemistry; D001386:Azides / Q000138:chemical synthesis* / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques / Q000379:methods; D003500:Cyclization; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D012996:Solutions / Q000737:chemistry; D013237:Stereoisomerism
D042462:4-Quinolones; D001386:Azides; D012996:Solutions