Preparation of 3-hydroxyquinolines from direct oxidation of dihydroquinolinium salts

A series of functionalized 3,4-dihydroquinolinium salts were prepared from the reaction of aryldiazonium salt with alkene in a nitrile solution. Further oxidation yielding either 3-hydroxyquinoline or quinoline products was investigated. A one-pot process from aryldiazonium salts, alkenes and nitriles leading to 3-hydroxyquinolines was also developed. Furthermore, an intramolecular trapping of an N-arylnitrilium ion with a vinyl group at the ortho position leading to 2-substituted quinolines was revealed.

3-Hydroxyquinoline derivatives can be prepared by a cascade cyclization of aryldiazonium salts with nitriles and alkenes followed by oxygenation.