Iodination/Amidation of the N-Alkyl (Iso)quinolinium Salts

The NaIO4-mediated sequential iodination/amidation reaction of N-alkyl quinolinium iodide salts has been first developed. This cascade process provides an efficient way to rapidly synthesize 3-iodo-N-alkyl quinolinones with high regioselectivity and good functional group tolerance. This protocol was also amenable to the isoquinolinium salts, thus providing a complementary method for preparing the 4-iodo-N-alkyl isoquinolinones.

Automated summary

The developed method provides an efficient way to synthesize 3-iodo-N-alkyl quinolinones and 4-iodo-N-alkyl isoquinolinones with high regioselectivity and good functional group tolerance. The protocol is applicable to both quinolinium salts and isoquinolinium salts, offering a complementary method for preparation.