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

Jahangir Jahangir | Zendy; Michael A. Brook | Zendy; David B. MacLean | Zendy; Herbert L. Holland | Zendy

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

Author(s) -

Jahangir Jahangir,

Michael A. Brook,

David B. MacLean,

Herbert L. Holland

Publication year - 1987

Publication title -

canadian journal of chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.323

H-Index - 68

eISSN - 1480-3291

pISSN - 0008-4042

DOI - 10.1139/v87-394

Subject(s) - chemistry , amidine , derivative (finance) , trimethylsilyl , trifluoromethanesulfonate , hydrolysis , nucleophile , trimethylsilyl trifluoromethanesulfonate , medicinal chemistry , stereochemistry , organic chemistry , catalysis , financial economics , economics

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 alangimarine.

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