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Benzo[ b ]thiophene derivatives. XXVII. 5‐methoxy‐6‐halo‐3‐β‐acetamidoethylbenzo[ b ]thiophenes, blocked analogs of melatonin
Author(s) -
Campaigne E.,
Kim Chung S.
Publication year - 1983
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.5570200651
Subject(s) - chemistry , thiophene , acetic acid , derivative (finance) , stereochemistry , chlorine , medicinal chemistry , organic chemistry , economics , financial economics
The preparation of the 6‐fluoro and 6‐chloro analogs of the title compound is described, in a seven‐step synthesis giving 30‐40% overall yields. All intermediates have been isolated and characterized, including important by‐products, such as the corresponding benzo[ b ]thienyl‐3‐acetic acids, and 3‐methylbenzo[ b ]thiophenes. Cyclization of the 3‐halo‐4‐methoxyphenylthioacetoacetic esters gave more ortho ‐cyclization in the chlorine case than was observed for the fluorine derivative. The title compounds were shown to have weak antiovulatory action, with the fluoro analog most active.