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Synthesis of substituted benzofurans by condensation of arylglyoxals with enols and phenols

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Abstract

A convenient method for the synthesis of previously unknown substituted 3-hydroxy-5,5- dimethyl-2-(2-arylbenzofuran-3-yl)cyclohex-2-enones, 4-hydroxy-6-methyl-3-(2-arylbenzofuran- 3-yl)-2H-pyran-2-ones, and 2-hydroxy-3-(2-arylbenzofuran-3-yl) naphthoquinones was developed based on the reaction of 3,4-methylenedioxyphenol or 2-naphthol with pyridinium salts obtained by multicomponent condensation of arylglyoxals with carbo- or heterocyclic enols and 4-dimethylaminopyridine.

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References

  1. M. Asif, J. An. & Pharm. Res., 2016, 3, 50.

    Google Scholar 

  2. H. Khanam, S. Uzzaman, Eur. J. Med. Chem., 2014, 97, 483.aaa

    Article  CAS  PubMed  Google Scholar 

  3. K. R. More, J. Chem. Pharm. Res., 2017, 9, 210.

    CAS  Google Scholar 

  4. M. M. Heravi, V. Zadsirjan, H. Hamidi, P. H. T. Amiri, RCS Adv., 2017, 7, 24470.

    Google Scholar 

  5. Yu. O. Gorbunov, V. G. Melekhina, V. S. Mityanov, M. M. Krayushkin, Russ. Chem. Bull., 2018, 67, 304.

    Article  CAS  Google Scholar 

  6. G.-H. He, J.-M. Yuan, H.-M. Zhu, K. Wei, L.Y. Wang, S.-L. Kong, D.-L. Mo, C.-X. Pan, G.-F. Su, Bioorganic Medicinal Chem. Lett., 2017, 26, 1660.

    Google Scholar 

  7. H. Wei, B. Li, G. Wang, K. Van Hecke, O. P. Pereshivko, V. A. Peshkov, Synthesis, 2016, 48, 1734.

    Article  CAS  Google Scholar 

  8. E. Fillion, E. Beaton, Y. Nguyen, A. Wilsily, G. Bondarenko, J. Jacq, Adv. Synth. Catal., 2016, 358, 3422.

    Article  CAS  Google Scholar 

  9. F. A. Leibfarth, Y. Schneider, N. A. Lynd, A. Schultz, B. Moon, E. J. Kramer, G. C. Bazan, C. J. Hawker, J. Am. Chem. Soc., 2010, 132, 14706.

    Article  CAS  PubMed  Google Scholar 

  10. K. Sweidan, Q. Abu-Salemb, A. Al-Sheikhc, G. Abu Sheikhaa, Lett. Org. Chem., 2009, 6, 669.

    Article  CAS  Google Scholar 

  11. M. Zia-Ebrahimi, G. W. Huffman, Synthesis, 1995, 215.

    Google Scholar 

  12. D. R. Zitsane, E. Yu. Gudriniece, I. A. Rijkure, U. O. Kalejs, Chem. Heterocycl. Compd., 2000, 36, 101.

    Article  CAS  Google Scholar 

  13. P. Wang, W.-J. Tao, X.-L. Sun, S. Liao, Y. Tang, J. Am. Chem. Soc., 2013, 135, 16849.

    Article  CAS  PubMed  Google Scholar 

  14. Y. Kutsunugi, S. Kawai, T. Nakashima, T. Kawai, New J. Chem., 2009, 33, 1368.

    Article  CAS  Google Scholar 

  15. A. Tafelska-Kaczmarek, A. Prewysz-Kwinto, K. Skowerski, K. Pietrasiak, A. Kozakiewicz, M. Zaidlewicz, Tetrahedron: Asymmetry, 2010, 21, 2244.

    Article  CAS  Google Scholar 

  16. G. M. Sheldrick, Acta Cryst., 2015, C71, 3.

    Google Scholar 

Download references

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    Yu. О. Gorbunov, А. N. Komogortsev, V. S. Mityanov, B. V. Lichitskii, A. A. Dudinov & М. М. Krayushkin

  2. D. I. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya pl., 125047, Moscow, Russian Federation

    V. S. Mityanov

  3. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991, Moscow, Russian Federation

    K. A. Lyssenko

Authors
  1. Yu. О. Gorbunov
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  2. А. N. Komogortsev
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  3. V. S. Mityanov
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  4. B. V. Lichitskii
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  5. A. A. Dudinov
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  6. K. A. Lyssenko
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  7. М. М. Krayushkin
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Corresponding author

Correspondence to М. М. Krayushkin.

Additional information

Dedicated to Academician of the Russian Academy of Sciences I. P. Beletskaya.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 0504—0509, March, 2018.

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Gorbunov, Y.О., Komogortsev, А.N., Mityanov, V.S. et al. Synthesis of substituted benzofurans by condensation of arylglyoxals with enols and phenols. Russ Chem Bull 67, 504–509 (2018). https://doi.org/10.1007/s11172-018-2101-z

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  • DOI: https://doi.org/10.1007/s11172-018-2101-z

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