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 was written by Ohba, Masashi;Shinbo, Yoko;Ohashi, Takako;Toda, Mitsuhiro;Fujii, Tozo. And the article was included in Heterocycles in 1992.Application of 2328-12-3 This article mentions the following:
A formal synthesis of 2,3-dimethoxydibenzo[a,h]quinolizidine (I) 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 with 3,4-dimethoxyphenacyl bromide and proceeded through the amino ketone, amino alc. II, lactam alc., and the lactam III. A parallel sequence of reactions concluded a formal synthesis of the 2,3,11,12-tetramethoxy analog. In the mercuric acetate-edetic acid oxidations of the amino alcs. II under acidic or alk. conditions gave oxazoloisoquinoline derivatives besides the desired lactam alcs. In the experiment, the researchers used many compounds, for example, 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3Application of 2328-12-3).
6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3) belongs to tetrahydroisoquinoline derivatives. There has been increasing research interest and speculation since 1968 in the potential formation of tetrahydroisoquinoline (TIQ) alkaloids in mammalian cells via such interactions, and in the role such TIQs may have in alcohol dependence. An efficient CuCl2-catalyzed coupling of nonfunctionalized tetrahydroisoquinolines with organozinc reagents under aerobic conditions proceeds in high yields under mild reaction conditions and is broadly applicable to a wide range of substrates. The reaction involves an iminium ion intermediate that is formed via a SET process.Application of 2328-12-3
Referemce:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem