8 H-Isoquino [2, 1-b][2, 7] naphthyridin-8-ones: synthesis of the Alangium alkaloids, alangimaridine and alangimarine

Jahangir, MA Brook, DB MacLean…

Index: Brook, Jahangir Michael A.; MacLean, David B.; Holland, Herbert L. Canadian Journal of Chemistry, 1987 ,  vol. 65, p. 2362 - 2368

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Abstract

It is shown that 3, 4-dihydroisoquinolines are activated toward nucleophilic attack by reaction with trimethylsilyl trifluoromethanesulfonate. The complex so formed reacts readily with the lithio derivative of 3-cyano-4-methyl-5-vinylpyridine, affording in a single step a tetracyclic amidine from which a lactam is obtained by hydrolysis. These reactions have been applied to the synthesis of the Alangium alkaloids,(±)-alangimaridine and ...