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First example of the synthesis of S,O-macroheterocycle based on 2(5H)-furanone and 2,2´-oxydiethanethiol

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Abstract

A base-catalyzed reaction of 3,4-dichloro-5-methoxy- and 3,4-dichloro-5-ethoxy-2(5H)-furanones with 2,2´-oxydiethanethiol gave thiols and bis-thioethers of 2(5H)-furanone series. A new S,O-macroheterocyclic compound containing a 18-membered oxathiamacrocycle and two 2(5H)-furanone fragments was synthesized based on the thiols in an aqueous solution of potassium hydroxide, which was characterized by X-ray diffraction.

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Authors and Affiliations

  1. A. M. Butlerov Institute of Chemistry of Kazan (Volga Region) Federal University, 18 ul. Kremlevskaya, 420008, Kazan, Russian Federation

    A. R. Kurbangalieva, L. T. Hoang, M. Yu. Kuzmicheva, K. Tanaka & G. A. Chmutova

  2. A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center of the Russian Academy of Sciences, 8 ul. Akad. Arbuzova, 420088, Kazan, Russian Federation

    O. A. Lodochnikova

  3. Biofunctional Synthetic Chemistry Laboratory, RIKEN, 2-1, Hirosawa, Wako-shi, Saitama, 351-0198, Japan

    A. R. Pradipta & K. Tanaka

Authors
  1. A. R. Kurbangalieva
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  2. L. T. Hoang
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  3. O. A. Lodochnikova
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  4. M. Yu. Kuzmicheva
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  5. A. R. Pradipta
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  6. K. Tanaka
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  7. G. A. Chmutova
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Corresponding author

Correspondence to A. R. Kurbangalieva.

Additional information

Dedicated to Academician of the Russian Academy of Sciences O. G. Sinyashin on the occasion of his 60th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 1278–1284, May, 2016.

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Kurbangalieva, A.R., Hoang, L.T., Lodochnikova, O.A. et al. First example of the synthesis of S,O-macroheterocycle based on 2(5H)-furanone and 2,2´-oxydiethanethiol. Russ Chem Bull 65, 1278–1284 (2016). https://doi.org/10.1007/s11172-016-1448-2

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  • DOI: https://doi.org/10.1007/s11172-016-1448-2

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