REGIOCONTROLLED SYNTHESES OF BENZO[B]QUINOLIZINIUM AND HETEROISOQUINOLINIUM CATIONS

A regiocontrolled synthesis of 10-alkoxy and alkyl substituted benzo[b ]quinolizinium salts is described. Synthesis of a novel 9-alkoxythiazo lo[3,2b]isoquinolinium cation is reported. In addition the synthesis o f several new N-alkylimidazo[1,2-b]isoquinolin-4-ium cations is descri bed. Condensation of dianions (1) with heteroaromatic aldehydes and ke tones provides diols in 35-85% yield. Cyclization of diols (2) with PO Cl3 gives previously unreported 10-substituted benzo[b]quinolizinium c ations and heteroisoquinolinium cations (3) in 35-90% yield.