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Preparation of benzo[c][2,7]naphthyridin‐5(1 H )‐ones as analogs of benzopyrano[3,4‐ c ]pyridin‐5‐one bronchodilators
Author(s) -
Unangst Paul C.,
Connor David T.,
Carethers Mary E.,
Schwender Charles S.,
Brown Richard E.,
Puchalski Chester
Publication year - 1986
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.5570230355
Subject(s) - chemistry , amination , reductive amination , ketone , ring (chemistry) , alkylation , medicinal chemistry , stereochemistry , methyl vinyl ketone , combinatorial chemistry , organic chemistry , catalysis
Abstract A series of 2,3,4,6‐tetrahydro‐8,9‐dimethoxybenzo[ c ][2,7]naphthyridin‐5(1 H )‐ones was prepared as potential anticholinergic bronchodilators. The naphthyridine ring system was constructed by cyclization of a 3‐amido‐4‐piperidone. Alkylation with alkylaminoethyl chlorides or reductive amination of an intermediate methyl ketone yielded the final target compounds.