Benzo[b]thiophene derivatives. XXVII. 5-methoxy-6-halo-3-β-acetamidoethylbenzo[b]thiophenes,blocked analogs of melatonin |
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Authors: | E Campaigne Chung S Kim |
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Abstract: | 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 benzob]thienyl-3-acetic acids, and 3-methylbenzob]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. |
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