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A facile synthesis of benzo[ b ]thiophene derivatives
Author(s) -
Watanabe Mitsuaki,
Date Mutsuhiro,
Kawanishi Kenji,
Akiyoshi Ryuji,
Furukawa Sunao
Publication year - 1991
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.5570280130
Subject(s) - chemistry , thiophene , formic acid , medicinal chemistry , organic chemistry
Lithiation of S ‐(2‐methylphenyl) N,N,N',N' ‐tetramethylphosphorodiamidothioate with sec ‐BuLi at ‐105° gave the corresponding benzylic anion which was acylated with various aromatic esters to give various deoxybenzoin derivatives in moderate to high yields. Acidic treatment of these products in refluxing formic acid gave 2‐arylbenzo[ b ]thiophene derivatives. 2‐Methylbenzo[ b ]thiophene and benzo[ b ]thiophen‐2(3 H )‐one were also prepared using the similar procedure.