Synthetic Protocols Mutually Applicable to 4-Oxoquinolines and 4-Oxo-1,8- naphthyridines: Synthesis of 1-Aryl-2-substituted and 1-Aryl-3-fluoro-4-oxo-quinolines and 4-Oxo-1,8-naphthyridines

摘要

We have achieved the synthesis of 1-aryl-2-substituted 4-oxoquinoline and 4-oxo-1,8-naphthyridine derivatives, which cannot be synthesized by known methods, via two useful synthons, 2-formyl-4-oxoquinoline and 2-methylsulfonyl-4-oxo-1,8-naph-thyridine. We also succeeded in the synthesis of l-aryl-3-fluoro-4- oxoquinoline by fluorocyclization of N-arylenaminone with Select-fluor and potassium carbonate in DMF in a one-pot procedure. To the best of our knowledge, this is the first synthesis of 3-fluoro-4- oxoquinoline derivatives. We confirmed that these protocols were mutually applicable to the synthesis of 4-oxoquinoline and 4-oxo1,8-naphthyridine derivatives.