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Synthesis of novel 1,2,3,4‐tetrahydrobenzo[ c ]‐1,5‐naphthyridines from pyrrolo[1,2‐ b ]isoquinolines
Author(s) -
Martin Lawrence L.,
Scott Susan J.,
Setescak Linda L.,
Van Engen Donna
Publication year - 1987
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570240609
Subject(s) - chemistry , isoquinoline , oxime , stereochemistry , combinatorial chemistry , medicinal chemistry
1,2,3,4‐Tetrahydrobenzo[ c ]‐1,5‐naphthyridine ( 5a ) was prepared by a novel synthetic route involving the rearrangement of (±)‐( Z )‐1,10a‐dihydropyrrolo[1,2‐ b ]isoquinoline‐3,10(2 H ,5 H )‐dione oxime to afford 1,4‐dihydrobenzo[ c ]‐1,5‐naphthyridin‐2(3 H )‐one, which was reduced to 5a. The cholinomimetic activity observed with 5a prompted the synthesis and biological evaluation of additional analogues.