A method was developed for the synthesis of 1-oxo-1H-isothiochromenes from 2-benzofuran-1(3H)-one (phthalide). 3-Bromo-6-chloro- and 3,6-dibromo-2-benzofuran-1(3H)-ones were prepared by the bromination of 6-chloro- and 6-bromo-2-benzofuran-1(3H)-ones and were converted by hydrolysis into 5-chloro- or 5-bromo-2-formylbenzoic acids. The condensation of these acids with rhodanine followed by recyclization gave 7-chloro- and 7-bromo-1-oxo-1H-isothiochromene-3-carboxylic acids.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 173-179, February, 2010.
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Pokhodylo, N.T., Matiychuk, V.S. & Obushak, M.D. Synthesis of isothiocoumarin derivatives. Chem Heterocycl Comp 46, 140–145 (2010). https://doi.org/10.1007/s10593-010-0484-3
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DOI: https://doi.org/10.1007/s10593-010-0484-3