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Paper | Regular issue | Vol 34, No. 9, 1992, pp.1857-1870
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6123
■ Quinolizidines. XXXI. A Synthesis of the Dibenzo[a,h]quinolizidine Ring System: An Application of the Mercuric Acetate-Edetic Acid Oxidation Method to 1,2,3,4-Tetrahydroisoquinoline

Masashi Ohba, Yoko Shinbo, Takako Ohashi, Mitsuhiro Toda, and Tozo Fujii*

*Faculty of Pharmaceutical Sciences, Kanazawa University, Takara-machi, Kanazawa 920, Japan

Abstract

A formal synthesis of 2,3-dimethoxydibenzo[a,h]quinolizidine (25a) has been achieved through a route including mercuric acetate-edetic acid oxidation of a benzene-fused piperidine. The route started with an initial condensation of 1,2,3,4-tetrahydroisoquinoline (3a) with 3,4-dimethoxyphenacyl bromide (7) and proceeded through the amino ketone (8a), amino alcohol (9a), lactam alcohol (10a), and the lactam (15a). A parallel sequence of reactions starting with 1,2,3,4-tetrahydro-6,7-dimethoxyisoquinoline (3b) and 7 concluded a formal synthesis of the 2,3,11,12-tetramethoxy analogue (25b) of the tetracycle (25a). In the mercuric acetate-edetic acid oxidations of the amino alcohols (9a,b) under acidic or alkaline conditions, the oxazoloisoquinoline derivatives (11a,b) were obtained besides the desired lactam alcohols (10a,b).