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Synthesis of [1]benzothienonaphthyridines
Author(s) -
Kudo Hirotaka,
Takahashi Kazufumi,
Castle Raymond N.,
Lee Milton L.
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.5570240421
Subject(s) - chemistry , ring (chemistry) , stereochemistry , lactam , thiophene , chloride , medicinal chemistry , organic chemistry
3‐Chlorobenzo[ b ]thiophene‐2‐carbonyl chloride reacted readily with 2‐amino‐, 3‐amino‐, or 4‐aminopyridine to give the corresponding amides. Photocyclization of the amides afforded the following lactams: [1]ben‐zothieno[2,3‐ c ][1,5]naphthyridin‐6(5 H )‐one ( 14 ), [1]benzothieno[2,3‐ c ][1,6]naphthyridin‐6(5 H )‐one ( 7 ), [1]benzo‐thieno[2,3‐ c ][1,7]naphthyridin‐6(5 H )‐one ( 11 ), and [1]benzothieno[2,3‐ c ][1,8]naphthyridin‐6(5 H )‐one ( 3 ). These lactams have been converted to other derivatives including in two instances the unsubstituted ring system.