Expedient Synthesis of Quinazoline Analogues through Direct Nucleophilic Arylation/Alkylation of 2-Chloroquinazoline

A practical approach was developed for the synthesis of 4-arylquinazoline compounds through a one-pot nucleophilic arylation/alkylation of 2-chloroquinazoline with aryl lithium compounds generated in situ, followed by ring oxidation. The obtained 2-chloro-4-arylquinazoline adducts were further used as versatile intermediates that undergo a variety of synthetic transformations to provide functionalized quinazoline compounds. The arylation intermediate dihydroquinazoline was also elaborated to the tricyclic dihydroimidazo[2,1-b]quinazolinone.