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Paper | Regular issue | Vol 41, No. 2, 1995, pp.309-314
Published online, 1st January, 1970
DOI: 10.3987/COM-94-6936
Regiocontrolled Syntheses of Benzo[b]quinolizinium and Heteroisoquinolinium Cations

William G. Earley*, John A. Dority Jr., Virendra Kumar, and John P. Mallamo

*Sterling Winthrop Pharmaceuticals Research Division, Department of Medicinal Chemistry, 1250 S. Collegeville Rd., Collegeville, PA 19426-0900, U.S.A.

Abstract

A regiocontrolled synthesis of 10-alkoxy and alkyl substituted benzo[b]quinolizinium salts is described. Synthesis of a novel 9-alkoxythiazolo[3,2-b]isoquinolinium cation is reported. In addition the synthesis of several new N-alkylimidazo[1,2-b]isoquinolin-4-ium cations is described. Condensation of dianions (1) with heteroaromatic aldehydes and ketones provides diols in 35-85% yield. Cyclization of diols (2) with POCl3 gives previously unreported 10-substituted benzo[b]quinolizinium cations and heteroisoquinolinium cations (3) in 35-90% yield.