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The synthesis of monomethoxy[1]benzothieno[2,3‐ c ]quinolines
Author(s) -
Castle Steven L.,
Buckhaults Phillip J.,
Baldwin Larry J.,
McKenney J. Dew,
Castle Raymond N.
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.5570240435
Subject(s) - quinoline , chemistry , iodide , medicinal chemistry , methyl iodide , thiophene , stereochemistry , organic chemistry
A series of monomethoxy[1]benzothieno[2,3‐ c ]quinolines 24‐28 were prepared by photocylization of the appropriate 3‐chloro‐ N ‐phenylbenzo[ b ]thiophene‐2‐carboxamides 9–13 to [1]benzothieno[2,3‐ c ]quinolin‐6( 5H )‐ones 14‐18 followed by chlorination to 6‐chloro[1]benzothieno[2,3‐ c ]quinolines 19‐23 then dechlorination resulting in the title compounds except for 25 which was achieved by direct reduction of 15 . Reaction of 24‐28 with methyl iodide provided the corresponding N ‐methyl quaternary salts 29‐33 . Also, conversion of 4‐meth‐oxy[1]benzothieno[2,3‐ c ]quinolin‐6( 5H )‐one 16 to 4‐methoxy‐6‐methylthio[1]benzothieno[2,3‐ c ]quinoline 35 and 4,6‐dimethoxy[1]benzothieno[2,3‐ c ]quinoline 36 is described.