Abstract
3, 5-Dibromocomanic acid (3, 5-dibromo-γ -pyrone -2-carboxylic acid) VI and its ethyl ester, hitherto not described in the literature, are synthesized by the following route: diethyl acetonedioxalate (I) → diethyl dibromochelidonate (III) → (mono) ethyl dibromochelidonate (IV) → diethyl 3, 5-dibromocomanate (V) → VI. Direct bromination of diethyl bromochelidonate gives the ester III. 6-Bromocomenic acid and its ethyl ester are prepared, as well as 2-bromo-3-hydroxy -γ -pyrone. Bromocomanic acid (x-bromo-γ-pyrone-2-carboxylic acid) XVI is synthesized by the following route: I → (mono) ethyl chelidonate → ethyl comanate → comanic acid XVI. Oxonium salts are obtained: acid sulfates of comanic acid and ethyl comanate.
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For Part VII [1].
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Garkusha, G.A., Khutornenko, G.A. γ-Pyrone derivatives. Chem Heterocycl Compd 2, 245–247 (1967). https://doi.org/10.1007/BF00742356
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DOI: https://doi.org/10.1007/BF00742356