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Reductive rearrangement of 2-aroyl-2,3-dihydrobenzofurans into 2-hydroxydihydrochalcones and flav-2-enes

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Chemistry of Heterocyclic Compounds Aims and scope

A two-step procedure was proposed for the synthesis of 2-aryl- and 2,4-diaryl-substituted 4H-chromenes by the formal [4+1] cycloaddition reaction of o-quinone methides and pyridinium ylides followed by reductive rearrangement of 2-aroyl-2,3-dihydrobenzofurans by the action of zinc in acetic acid or samarium and trimethylchlorosilane in 1,4-dioxane. The reduction of 3-unsubstituted 2-aroyl-2,3-dihydrobenzofurans by the action of zinc in acetic acid leads mainly to 2-hydroxydihydrochalcones.

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References

  1. (a) Costa, M.; Dias, T. A.; Brito, A.; Proenca, F. Eur. J. Med. Chem. 2016, 123, 487. (b) Patil, S. A.; Patil, R.; Pfeffer, L. M.; Miller, D. D. Future Med. Chem. 2013, 5, 1647. (c) Parthiban, A.; Muthukumaran, J.; Priya, A. M.; Jayachandran, S.; Krishna, R.; Rao, H. S. P. Med. Chem. Res. 2014, 23, 642. (d) Patil, S. A.; Patil, S. A.; Patil, R. Future Med. Chem. 2015, 7, 893. (e) Raj. V.; Lee, J. Front. Chem. 2020, 8, 623.

  2. (a) Gramshaw, J. W.; Johnson, A. W.; King, T. J. J. Chem. Soc. 1958, 4040. (b) Valla, С.; Baeza, A.; Menges, F.; Pfaltz, A. Synlett 2008, 3167.

  3. (a) Porzel, A.; Lien, T. P.; Schmidt, J.; Drosihn, S.; Wagner, C.; Merzweiler, K.; Sung, T. V.; Adam, G. Tetrahedron 2000, 56, 865. (b) Okwu, D. E.; Ukanwa, N. Chemica Sinica 2010, 1, 21. (c) Nakashima, K.-i.; Abe, N.; Kamiya, F.; Ito, T.; Oyama, M.; Iinuma, M. Helv. Chim. Acta 2009, 92, 1999. (d) Ogata, T.; Yahara, S.; Hisatsune, R.; Konishi, R.; Nohara, T. Chem. Pharm. Bull. 1990, 38, 2750.

  4. Demidov, M. R. Cand. Sci. (Chem.) Dissertation; Samara, 2019. http://d21221705.samgtu.ru/sites/d21221705.samgtu.ru/files/dissertaciya_demidov.pdf

  5. Jurd, L.; Roitman, J. N. Tetrahedron 1978, 34, 57.

    Article  CAS  Google Scholar 

  6. (a) Osyanin, V. A.; Lukashenko, A. V.; Osipov, D. V. Russ. Chem. Rev. 2021, 90, 324. [Usp. Khim. 2021, 90, 324.] (b) Osipov, D. V.; Osyanin, V. A.; Klimochkin, Yu. N. Russ. Chem. Rev. 2017, 86, 625. [Usp. Khim. 2017, 86, 625.]

  7. (a) Osyanin, V. A.; Osipov, D. V.; Klimochkin, Yu. N. J. Org. Chem. 2013, 78, 5505. (b) Osyanin, V. A.; Osipov, D. V.; Klimochkin, Yu. N. Chem. Heterocycl. Compd. 2012, 48, 993. [Khim. Geterotsikl. Soedin. 2012, 1069.]

  8. Stompor, M.; Broda, D.; Bajek-Bil, A. Molecules 2019, 24, 4468.

    Article  CAS  Google Scholar 

  9. (a) Banik, B. K. Eur. J. Org. Chem. 2002, 2431. (b) Banik, B. K. Mod. Chem. Appl. 2017, 5(3). DOI: https://doi.org/10.4172/2329-6798.1000227. (c) Matsukawa, S.; Hinakubo, Y. Org. Lett. 2003, 5, 1221. (d) Liu, Y.; Li, Y.; Qi, Y.; Wan, J. Synthesis 2010, 4188. (e) Concellón, J. M.; Rodríguez-Solla, H.; Simal, C. Org. Lett. 2007, 9, 2685.

  10. Demidov, M. R.; Osipov, D. V.; Korol'kov, K. A.; Osyanin, V. A. Adv. Synth. Catal. 2021, 363, 3737.

    Article  CAS  Google Scholar 

  11. Löwenbein, A. Chem. Ber. 1924, 57, 1517.

    Article  Google Scholar 

  12. Bird, T. G. C.; Brown, B. R.; Stuart, I. A.; Tyrrell, A. W. R. J. Chem. Soc., Perkin Trans. 1 1983, 1831.

    Article  Google Scholar 

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The study was carried out with the financial support of the Russian Foundation for Basic Research within the framework of the scientific project No. 19-03-01024 using the scientific equipment of the Center for Collective Use "“Investigation of the physico-chemical properties of substances and materials" of the Samara State Technical University.

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  1. Samara State Technical University, 244 Molodogvardeyskaya St, Samara, 443100, Russia

    Dmitry V. Osipov, Maxim R. Demidov, Vitaly А. Osyanin & Yuri N. Klimochkin

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  1. Dmitry V. Osipov
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  2. Maxim R. Demidov
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  3. Vitaly А. Osyanin
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  4. Yuri N. Klimochkin
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Correspondence to Vitaly А. Osyanin.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2021, 57(12), 1170–1175

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Osipov, D.V., Demidov, M.R., Osyanin, V.А. et al. Reductive rearrangement of 2-aroyl-2,3-dihydrobenzofurans into 2-hydroxydihydrochalcones and flav-2-enes. Chem Heterocycl Comp 57, 1170–1175 (2021). https://doi.org/10.1007/s10593-021-03039-6

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  • DOI: https://doi.org/10.1007/s10593-021-03039-6

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