Affiliation:
1. Scientific Technological Centre of Organic and Pharmaceutical Chemistry NAS RA
Abstract
By the reaction of 1-(3,4-dimethoxy)phenylcycloalkanmethan- and 4-(3,4-dimethoxyphenyl)tetrahydropyran-4-methanamines with benzo[ d ][1,3]dioxol-5-carbonyl chloride corresponding N -substituted benzo[ d ][1,3]dioxol-5-carboxamides were synthesized. Cyclization of the latter with phosphorus oxychloride gave dihydroisoquinolines reduced with sodium borohydride to the corresponding spiro-substituted tetrahydroisoquinolines, whose methylation according to Eschweiler-Clark reaction gave N -methyl derivatives. By condensation abovementioned amines with benzo[ d ][1,3]dioxol-5-carbaldehyde Schiff bases were synthesized. The reduction of the latter with sodium borohydride gave the corresponding secondary amines - non-cyclic analogues of tetrahydroisoquinolines, which undergo cyclization under the conditions of the Eschweiler-Clark reaction to form N -benzodioxolmethyl-substituted tetrahydroisoquinolines.
Publisher
The Russian Academy of Sciences
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