Use of Phenacyl Thiosalicylates for the Preparation of 3-Hydroxybenzo[b]thiophene Derivatives

Abstract In this work, we attempted to synthesize thioflavonols using rearrangement of phenacyl thiosalicylates prepared by two different approaches and subjected to cyclization under acidic conditions. Contrary to our expectations, the isolated products were identified as (3-hydroxybenzo[ b ]thioph...

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Bibliographic Details
Published in:Synlett 2018-04, Vol.29 (6), p.810-814
Main Authors: Trapani, Patricia, Kvapil, Lubomír, Hradil, Pavel, Soural, Miroslav
Format: Article
Language:English
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Summary:Abstract In this work, we attempted to synthesize thioflavonols using rearrangement of phenacyl thiosalicylates prepared by two different approaches and subjected to cyclization under acidic conditions. Contrary to our expectations, the isolated products were identified as (3-hydroxybenzo[ b ]thiophen-2-yl)(phenyl)methanones. The detailed reaction mechanism was elucidated by characterization of all reaction intermediates with HPLC and NMR spectroscopy. The applicability of the reaction using different phenacyl esters was tested.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0036-1591875