Preparation of N-Arylquinazolinium Salts via a Cascade Approach

J Org Chem. 2019 Jun 7;84(11):7459-7467. doi: 10.1021/acs.joc.9b00601. Epub 2019 May 22.

Abstract

An easy manipulation method for the preparation of N-arylquinazolinium salts is described from readily available aryldiazonium salts, nitriles, and 2-aminoarylketones in a one-pot operation. This method relies on the in situ generation of the N-arylnitrilium intermediate from the reaction of aryldiazonium salt with nitrile, which undergoes amination/cascade cyclization/aromatization, leading to N-arylquinazolinium salts in excellent yields. Nucleophilic addition of alkoxide to these N-arylquinazolinium salts provides functionalized dihydro- N-arylquinazoline.