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Preparative synthesis of ethyl 5-acyl-4-pyrone-2-carboxylates and 6-aryl-, 6-alkyl-, and 5-acylcomanic acids on their basis

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Abstract

A simple and efficient method for the synthesis of ethyl 5-alkanoyl- and 5-aroyl-4-pyrone-2-carboxylates was developed, which is based on the condensation of 1-R-2-(dimethyl-aminomethylidene)butane-1,3-diones, obtained from 1,3-diketones and dimethylformamide dimethyl acetal, with diethyl oxalate in the presence of NaH in THF. Ethyl 5-acyl-4-pyrone-2-carboxylates were used in the synthesis of 6-R- and 5-RCO-comanic acids.

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Authors and Affiliations

  1. Institute of Natural Sciences of the Ural Federal University named after the first President of Russia B. N. Yeltsin, 51 prosp. Lenina, 620000, Ekaterinburg, Russian Federation

    D. L. Obydennov, A. O. Goncharov & V. Ya. Sosnovskikh

Authors
  1. D. L. Obydennov
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  2. A. O. Goncharov
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  3. V. Ya. Sosnovskikh
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Correspondence to D. L. Obydennov.

Additional information

Based on the materials of the International Congress on the Heterocyclic Chemistry "KOST-2015" (October 17—23, 2015, Moscow, Russia).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 2233—2242, September, 2016.

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Obydennov, D.L., Goncharov, A.O. & Sosnovskikh, V.Y. Preparative synthesis of ethyl 5-acyl-4-pyrone-2-carboxylates and 6-aryl-, 6-alkyl-, and 5-acylcomanic acids on their basis. Russ Chem Bull 65, 2233–2242 (2016). https://doi.org/10.1007/s11172-016-1574-x

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  • DOI: https://doi.org/10.1007/s11172-016-1574-x

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